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LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T1 99967-99970 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762
T2 104376-104379 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762
T3 113619-113622 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762
T4 117218-117221 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762
T5 119713-119723 Body_part denotes nucleotide http://purl.org/sig/ont/fma/fma82740
T6 119794-119800 Body_part denotes genome http://purl.org/sig/ont/fma/fma84116
T7 122555-122560 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T8 122583-122588 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T9 122774-122779 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T10 122954-122958 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T11 123053-123057 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T12 123130-123135 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T13 123237-123242 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T14 123265-123270 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T15 123548-123553 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T16 123615-123620 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T17 123810-123815 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T18 123869-123874 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T19 124069-124074 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T20 124128-124133 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T21 124174-124179 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T22 124202-124207 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T23 124352-124357 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T24 124418-124422 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T25 124492-124496 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T26 124660-124665 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T27 124727-124732 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T28 124922-124927 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T29 124981-124986 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T30 125181-125186 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T31 125240-125245 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T32 125314-125317 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T33 125873-125878 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T34 126009-126013 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T35 126064-126068 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T36 126540-126548 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T37 126819-126827 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T38 127269-127278 Body_part denotes cellulose http://purl.org/sig/ont/fma/fma82748
T39 127553-127560 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T40 128166-128175 Body_part denotes cellulose http://purl.org/sig/ont/fma/fma82748
T41 128497-128504 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T42 129160-129169 Body_part denotes cellulose http://purl.org/sig/ont/fma/fma82748
T43 129448-129455 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T44 130040-130049 Body_part denotes cellulose http://purl.org/sig/ont/fma/fma82748
T45 130220-130223 Body_part denotes v 2 http://purl.org/sig/ont/fma/fma13443|http://purl.org/sig/ont/fma/fma68615
T47 130343-130350 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T48 130838-130847 Body_part denotes cellulose http://purl.org/sig/ont/fma/fma82748
T49 131138-131145 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T50 131922-131929 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T51 132172-132176 Body_part denotes body http://purl.org/sig/ont/fma/fma256135
T52 133297-133301 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T66277 372-379 Body_part denotes genomes http://purl.org/sig/ont/fma/fma84116
T35139 472-480 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T8747 694-701 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T54374 1189-1206 Body_part denotes respiratory tract http://purl.org/sig/ont/fma/fma265130
T26446 1360-1366 Body_part denotes Genome http://purl.org/sig/ont/fma/fma84116
T37694 1929-1935 Body_part denotes genome http://purl.org/sig/ont/fma/fma84116
T78312 2065-2073 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T72980 2179-2187 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T62636 2354-2362 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T24320 2869-2877 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T27359 3154-3162 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T53411 3241-3248 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T16702 4454-4462 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T24397 4904-4914 Body_part denotes Amino acid http://purl.org/sig/ont/fma/fma82739
T35749 5058-5068 Body_part denotes Amino acid http://purl.org/sig/ont/fma/fma82739
T62413 6176-6184 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T55817 7585-7594 Body_part denotes glutamine http://purl.org/sig/ont/fma/fma82752
T4591 7787-7795 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T6474 7912-7919 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T1473 7920-7928 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T69470 8367-8374 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T53161 11090-11100 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T58451 12998-13001 Body_part denotes CsF http://purl.org/sig/ont/fma/fma20935
T56425 14144-14147 Body_part denotes CsF http://purl.org/sig/ont/fma/fma20935
T49380 14566-14574 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T87686 16756-16764 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T47943 16834-16837 Body_part denotes C–S http://purl.org/sig/ont/fma/fma284995
T89780 16955-16963 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T71020 17498-17506 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T29395 18048-18053 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T77718 18120-18125 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T39660 18221-18226 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T54465 18297-18301 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T44584 18302-18307 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T80152 18501-18507 Body_part denotes plasma http://purl.org/sig/ont/fma/fma62970
T12289 19706-19713 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T15026 19935-19942 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T44316 20103-20108 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T16632 20457-20464 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T93878 20804-20808 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T88519 20948-20952 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T52556 21266-21274 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T92468 21831-21839 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T63397 23553-23557 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T53789 23781-23786 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T46 23808-23814 Body_part denotes kidney http://purl.org/sig/ont/fma/fma7203
T40778 23846-23850 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T47080 23851-23867 Body_part denotes epithelial cells http://purl.org/sig/ont/fma/fma66768
T52254 23862-23867 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T65361 24006-24010 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T97321 24172-24184 Body_part denotes glycoprotein http://purl.org/sig/ont/fma/fma62925
T89000 25413-25417 Body_part denotes hand http://purl.org/sig/ont/fma/fma9712
T53 26861-26866 Body_part denotes liver http://purl.org/sig/ont/fma/fma7197
T54 26867-26877 Body_part denotes microsomes http://purl.org/sig/ont/fma/fma67438
T55 27953-27961 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T56 28027-28030 Body_part denotes C–S http://purl.org/sig/ont/fma/fma284995
T57 28098-28106 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T58 29090-29098 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T59 29211-29219 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T60 29552-29560 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T61 29608-29615 Body_part denotes leucine http://purl.org/sig/ont/fma/fma82757
T62 29923-29931 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T63 30154-30161 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T64 31272-31281 Body_part denotes leukocyte http://purl.org/sig/ont/fma/fma62852
T65 31412-31415 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T66 31419-31422 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T67 31966-31969 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T68 32009-32013 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T69 32203-32208 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T70 32216-32220 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T71 32414-32417 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T72 33075-33079 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T73 33278-33290 Body_part denotes glycoprotein http://purl.org/sig/ont/fma/fma62925
T74 33707-33711 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T75 33726-33731 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T76 33744-33756 Body_part denotes glycoprotein http://purl.org/sig/ont/fma/fma62925
T77 33896-33901 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T78 33960-33964 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T79 34023-34027 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T80 34028-34033 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T81 34048-34054 Body_part denotes tissue http://purl.org/sig/ont/fma/fma9637
T82 34180-34184 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T83 34185-34190 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T84 34733-34739 Body_part denotes plasma http://purl.org/sig/ont/fma/fma62970
T85 37135-37142 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T86 37308-37317 Body_part denotes alaninate http://purl.org/sig/ont/fma/fma82749
T87 38575-38582 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T88 38993-38998 Body_part denotes joint http://purl.org/sig/ont/fma/fma7490
T89 40130-40134 Body_part denotes neck http://purl.org/sig/ont/fma/fma7155
T90 40289-40298 Body_part denotes alaninate http://purl.org/sig/ont/fma/fma82749
T91 41979-41986 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T92 44108-44111 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762
T93 49001-49004 Body_part denotes CsF http://purl.org/sig/ont/fma/fma20935
T94 84488-84491 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762
T95 98278-98281 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762

LitCovid-PD-UBERON

Id Subject Object Predicate Lexical cue uberon_id
T1 1189-1206 Body_part denotes respiratory tract http://purl.obolibrary.org/obo/UBERON_0000065
T2 16392-16397 Body_part denotes scale http://purl.obolibrary.org/obo/UBERON_0002542
T3 18297-18301 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T4 23808-23814 Body_part denotes kidney http://purl.obolibrary.org/obo/UBERON_0002113
T5 23846-23850 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T6 25413-25417 Body_part denotes hand http://purl.obolibrary.org/obo/UBERON_0002398
T7 26861-26866 Body_part denotes liver http://purl.obolibrary.org/obo/UBERON_0002107
T8 32216-32220 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T9 33707-33711 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T10 34023-34027 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T11 34048-34054 Body_part denotes tissue http://purl.obolibrary.org/obo/UBERON_0000479
T12 34180-34184 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T13 35630-35634 Body_part denotes tube http://purl.obolibrary.org/obo/UBERON_0000025
T14 40130-40134 Body_part denotes neck http://purl.obolibrary.org/obo/UBERON_0000974

LitCovid-PD-MONDO

Id Subject Object Predicate Lexical cue mondo_id
T1 118-126 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T2 167-175 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T3 220-224 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T4 277-281 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T5 300-333 Disease denotes severe acute respiratory syndrome http://purl.obolibrary.org/obo/MONDO_0005091
T6 335-339 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T7 355-359 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T8 818-822 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T9 1131-1139 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T10 1189-1216 Disease denotes respiratory tract infection http://purl.obolibrary.org/obo/MONDO_0024355
T11 1207-1216 Disease denotes infection http://purl.obolibrary.org/obo/MONDO_0005550
T12 1294-1298 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T13 1420-1424 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T14 1460-1493 Disease denotes severe acute respiratory syndrome http://purl.obolibrary.org/obo/MONDO_0005091
T15 1495-1499 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T16 1523-1527 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T17 1596-1600 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T18 1723-1727 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T19 1771-1775 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T20 1846-1856 Disease denotes infections http://purl.obolibrary.org/obo/MONDO_0005550
T21 1918-1922 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T22 2229-2233 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T23 2423-2427 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T24 2460-2464 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T25 2475-2479 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T26 2718-2722 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T27 2774-2778 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T28 3746-3750 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T29 3814-3818 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T30 5298-5302 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T31 5909-5913 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T32 5987-5991 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T33 6080-6084 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T34 6314-6318 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T35 6489-6493 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T36 6715-6719 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T37 6930-6934 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T38 7283-7287 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T39 7610-7614 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T40 8072-8076 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T41 8442-8446 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T42 9143-9147 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T43 9244-9248 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T44 9391-9399 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T45 9471-9475 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T46 9845-9853 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T47 9961-9965 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T48 10182-10190 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T49 14296-14300 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T50 15062-15066 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T51 15335-15339 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T52 15410-15414 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T53 16166-16170 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T54 16513-16517 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T55 17691-17695 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T56 17977-17981 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T57 19261-19265 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T58 19300-19304 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T59 19917-19921 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T60 20809-20818 Disease denotes infection http://purl.obolibrary.org/obo/MONDO_0005550
T61 20953-20962 Disease denotes infection http://purl.obolibrary.org/obo/MONDO_0005550
T62 21153-21157 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T63 21675-21679 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T64 22295-22299 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T65 22839-22843 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T66 24581-24585 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T67 27066-27070 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T68 27479-27483 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T69 27650-27654 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T70 27665-27669 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T71 28509-28513 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T72 29640-29644 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T73 30048-30052 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T74 30263-30267 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T75 31008-31012 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T76 31142-31146 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T77 31181-31185 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T78 31682-31686 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T79 31940-31956 Disease denotes immunodeficiency http://purl.obolibrary.org/obo/MONDO_0021094
T80 32317-32321 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T81 32723-32727 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T82 32911-32915 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T83 33228-33232 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T84 33444-33448 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T85 34059-34063 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T86 34068-34076 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T87 34140-34144 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T88 34344-34348 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T89 34406-34410 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T90 34547-34551 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T91 34617-34621 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T92 34882-34886 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T93 35008-35016 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T94 119052-119056 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T95 119226-119230 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T96 119695-119699 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T97 119768-119772 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T98 121010-121014 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T99 121112-121116 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T100 121213-121217 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T101 121274-121278 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T102 121708-121712 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T103 121911-121915 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T104 122472-122476 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T105 122818-122822 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T106 123377-123379 Disease denotes OD http://purl.obolibrary.org/obo/MONDO_0017178
T107 125554-125558 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T108 125590-125594 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T109 125612-125616 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T110 131813-131817 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T111 132087-132091 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T112 132198-132202 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T113 133278-133282 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T1 98829-98830 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T2 99673-99681 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T3 99673-99681 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T4 99954-99955 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T5 99967-99970 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T6 100571-100573 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T7 100607-100612 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T8 100617-100626 http://purl.obolibrary.org/obo/CLO_0007923 denotes N-{(1S)-1
T9 100769-100771 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T10 100776-100777 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T11 100993-100997 http://purl.obolibrary.org/obo/CL_0000784 denotes Pd/C
T12 101353-101354 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T13 101679-101681 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T14 101716-101721 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T15 102176-102177 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T16 102325-102326 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T17 102340-102343 http://purl.obolibrary.org/obo/CLO_0001310 denotes 351
T18 102348-102350 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T19 102632-102634 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T20 102640-102642 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T21 102673-102678 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T22 103180-103181 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T23 103331-103332 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T24 103792-103794 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T25 103831-103836 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T26 104359-104360 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T27 104376-104379 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T28 104997-104999 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T29 105033-105038 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T30 105693-105694 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T31 105849-105850 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T32 106212-106214 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T33 106249-106254 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T34 106964-106965 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T35 107120-107121 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T36 107539-107541 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T37 107574-107579 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T38 108313-108314 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T39 108465-108466 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T40 108848-108850 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T41 108883-108888 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T42 109209-109211 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T43 109478-109479 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T44 109553-109556 http://purl.obolibrary.org/obo/CLO_0001000 denotes 3–5
T45 110056-110058 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T46 110091-110096 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T47 110710-110711 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T48 110956-110957 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T49 111261-111265 http://purl.obolibrary.org/obo/CLO_0001527 denotes 9, 4
T50 111365-111367 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T51 111400-111405 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T52 111937-111938 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T53 111984-111985 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T54 112255-112256 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T55 112657-112659 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T56 112685-112688 http://purl.obolibrary.org/obo/CLO_0001360 denotes 412
T57 112690-112695 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T58 113388-113389 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T59 113574-113576 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T60 113604-113605 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T61 113619-113622 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T62 113630-113631 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T63 114015-114017 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T64 114048-114053 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T65 114263-114265 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T66 114267-114268 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T67 114645-114647 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T68 114664-114665 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69 114943-114944 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T70 115527-115529 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T71 115562-115567 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T72 116050-116051 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T73 116625-116627 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T74 116664-116669 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T75 117204-117205 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T76 117218-117221 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T77 117381-117383 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T78 117727-117729 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T79 117763-117768 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T80 118415-118416 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T81 118569-118570 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T82 119006-119008 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T83 119042-119047 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T84 119108-119116 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T85 119163-119164 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T86 119431-119438 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T87 119458-119459 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T88 119894-119895 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T89 120058-120064 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T90 120082-120089 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T91 120156-120163 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T92 120303-120304 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T93 120576-120577 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T94 120601-120602 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T95 120774-120775 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T96 121070-121078 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T97 121143-121144 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T98 121250-121258 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T99 121308-121309 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T100 121342-121349 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T101 121418-121419 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T102 121430-121437 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T103 121479-121486 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T104 121541-121542 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T105 121578-121579 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T106 121610-121617 http://purl.obolibrary.org/obo/OBI_0000968 denotes Devices
T107 121636-121642 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T108 121686-121687 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T109 121833-121840 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T110 122001-122009 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T111 122091-122099 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T112 122105-122106 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T113 122144-122152 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T114 122188-122189 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T115 122440-122448 http://purl.obolibrary.org/obo/CLO_0001658 denotes Activity
T116 122547-122554 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T117 122555-122560 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T118 122583-122588 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T119 122774-122779 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T120 122850-122851 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T121 122954-122958 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T122 123053-123057 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T123 123130-123135 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T124 123237-123242 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T125 123265-123270 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T126 123405-123409 http://purl.obolibrary.org/obo/CLO_0001550 denotes a 10
T127 123512-123518 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T128 123548-123553 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T129 123570-123576 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T130 123615-123620 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T131 123773-123779 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T132 123810-123815 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T133 123869-123874 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T134 124030-124036 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T135 124069-124074 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T136 124128-124133 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T137 124168-124179 http://purl.obolibrary.org/obo/CLO_0052043 denotes MRC-5 cells
T138 124168-124179 http://purl.obolibrary.org/obo/CLO_0052044 denotes MRC-5 cells
T139 124168-124179 http://purl.obolibrary.org/obo/CLO_0052045 denotes MRC-5 cells
T140 124202-124207 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T141 124352-124357 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T142 124418-124422 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T143 124492-124496 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T144 124624-124630 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T145 124660-124665 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T146 124682-124688 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T147 124727-124732 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T148 124885-124891 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T149 124922-124927 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T150 124981-124986 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T151 125142-125148 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T152 125181-125186 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T153 125240-125245 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T154 125575-125580 http://purl.obolibrary.org/obo/OGG_0000000002 denotes Genes
T155 125736-125741 http://purl.obolibrary.org/obo/OGG_0000000002 denotes Genes
T156 125759-125760 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T157 125795-125796 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T158 125873-125878 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T159 126009-126013 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T160 126064-126068 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T161 126135-126136 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T162 126220-126224 http://purl.obolibrary.org/obo/CLO_0001387 denotes 4 °C
T163 126261-126262 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T164 126332-126333 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T165 126400-126401 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T166 126513-126514 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T167 126574-126575 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T168 126585-126587 http://purl.obolibrary.org/obo/CLO_0003797 denotes hp
T169 126585-126587 http://purl.obolibrary.org/obo/PR_000008725 denotes hp
T170 126585-126587 http://purl.obolibrary.org/obo/UBERON_0000007 denotes hp
T171 126670-126671 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T172 126753-126754 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T173 127060-127063 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T174 127122-127125 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T175 127169-127172 http://purl.obolibrary.org/obo/CLO_0001577 denotes a 3
T176 127209-127211 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T177 127217-127221 http://purl.obolibrary.org/obo/CLO_0001387 denotes 4 °C
T178 127259-127260 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T179 127446-127449 http://purl.obolibrary.org/obo/CLO_0050644 denotes w/v
T180 127581-127582 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T181 127801-127802 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T182 127822-127823 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T183 127956-127959 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T184 128018-128021 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T185 128065-128068 http://purl.obolibrary.org/obo/CLO_0001577 denotes a 3
T186 128106-128108 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T187 128114-128118 http://purl.obolibrary.org/obo/CLO_0001387 denotes 4 °C
T188 128156-128157 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T189 128344-128347 http://purl.obolibrary.org/obo/CLO_0050644 denotes w/v
T190 128525-128526 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T191 128745-128746 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T192 128766-128767 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T193 128947-128950 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T194 129012-129015 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T195 129059-129062 http://purl.obolibrary.org/obo/CLO_0001577 denotes a 3
T196 129100-129102 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T197 129108-129112 http://purl.obolibrary.org/obo/CLO_0001387 denotes 4 °C
T198 129150-129151 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T199 129338-129341 http://purl.obolibrary.org/obo/CLO_0050644 denotes w/v
T200 129476-129477 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T201 129693-129694 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T202 129714-129715 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T203 129939-129942 http://purl.obolibrary.org/obo/CLO_0001577 denotes a 3
T204 129980-129982 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T205 129988-129992 http://purl.obolibrary.org/obo/CLO_0001387 denotes 4 °C
T206 130030-130031 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T207 130268-130271 http://purl.obolibrary.org/obo/CLO_0050644 denotes w/v
T208 130355-130356 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T209 130598-130599 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T210 130619-130620 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T211 130727-130730 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T212 130782-130785 http://purl.obolibrary.org/obo/CL_0000784 denotes DC2
T213 130828-130829 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T214 131065-131068 http://purl.obolibrary.org/obo/CLO_0050644 denotes w/v
T215 131161-131162 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T216 131163-131166 http://purl.obolibrary.org/obo/CLO_0053733 denotes 1:1
T217 131178-131179 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T218 131329-131331 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T219 131412-131413 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T220 131561-131562 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T221 131582-131583 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T222 132792-132803 http://purl.obolibrary.org/obo/UBERON_0000473 denotes testing was
T223 132828-132829 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T224 133112-133123 http://purl.obolibrary.org/obo/UBERON_0000473 denotes testing was
T225 133199-133203 http://purl.obolibrary.org/obo/CLO_0009609 denotes wish
T226 133297-133306 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell line
T227 133321-133328 http://purl.obolibrary.org/obo/UBERON_0000473 denotes testing
T228 133342-133346 http://purl.obolibrary.org/obo/CLO_0009609 denotes wish
T56090 214-219 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T55568 462-466 http://purl.obolibrary.org/obo/CLO_0053943 denotes a 3C
T24614 502-503 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T12954 626-633 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T9960 712-713 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T99506 735-742 http://purl.obolibrary.org/obo/CLO_0009985 denotes focused
T95582 993-994 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T83605 1384-1389 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T83875 1399-1400 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T73484 1734-1737 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T36915 1791-1792 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T8644 2055-2059 http://purl.obolibrary.org/obo/CLO_0053943 denotes a 3C
T48219 2254-2255 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T88436 2572-2578 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T85651 2586-2587 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T20594 2677-2685 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T55317 3142-3148 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T10101 3171-3172 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T44241 3310-3316 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T14318 3322-3325 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T44972 3410-3411 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T86707 3456-3457 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T48673 3764-3772 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T59338 3832-3840 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T84522 3964-3970 http://purl.obolibrary.org/obo/CLO_0007225 denotes labels
T52983 4084-4092 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T93599 4274-4280 http://purl.obolibrary.org/obo/CLO_0007225 denotes labels
T17152 4296-4297 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T88872 4510-4511 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T65970 4642-4644 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T92074 4836-4838 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T85061 4904-4923 http://purl.obolibrary.org/obo/CHEBI_33708 denotes Amino acid residues
T26767 4904-4923 http://purl.obolibrary.org/obo/PR_000036907 denotes Amino acid residues
T20668 5017-5019 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T60323 5058-5077 http://purl.obolibrary.org/obo/CHEBI_33708 denotes Amino acid residues
T37975 5058-5077 http://purl.obolibrary.org/obo/PR_000036907 denotes Amino acid residues
T19619 5154-5156 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T13145 5234-5240 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T6787 5313-5314 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T62466 5394-5399 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T96017 5535-5536 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T76689 5562-5564 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T22773 5849-5850 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69827 5900-5901 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T68342 6128-6129 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T24689 6205-6206 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T30229 6228-6234 http://purl.obolibrary.org/obo/UBERON_0000473 denotes tested
T25588 6410-6416 http://purl.obolibrary.org/obo/UBERON_0000473 denotes tested
T99633 6417-6419 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T58385 6420-6422 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T89484 6460-6462 http://purl.obolibrary.org/obo/CLO_0008337 denotes P4
T40961 6528-6532 http://purl.obolibrary.org/obo/CLO_0001236 denotes 2, a
T60248 6585-6587 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T5489 6656-6658 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T9645 6659-6662 http://purl.obolibrary.org/obo/CLO_0007437 denotes M–1
T53142 6659-6662 http://purl.obolibrary.org/obo/CLO_0007448 denotes M–1
T23219 6659-6662 http://purl.obolibrary.org/obo/CLO_0007449 denotes M–1
T80219 6659-6662 http://purl.obolibrary.org/obo/CLO_0050175 denotes M–1
T91123 6659-6662 http://purl.obolibrary.org/obo/CLO_0052399 denotes M–1
T26503 6663-6666 http://purl.obolibrary.org/obo/CLO_0050050 denotes s–1
T80373 7316-7317 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T21360 7369-7370 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T91275 7395-7396 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T85006 7512-7514 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T17731 7582-7584 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T91390 7657-7659 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T31378 7674-7675 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T58086 7863-7865 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T31518 7887-7888 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T61341 8316-8322 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T92676 8607-8608 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T73055 8609-8616 http://purl.obolibrary.org/obo/CLO_0009985 denotes focused
T20789 8684-8686 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T9121 9216-9217 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T13335 9410-9417 http://purl.obolibrary.org/obo/UBERON_0000473 denotes testing
T88691 9418-9421 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T27161 9445-9446 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T90807 9514-9515 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T52020 9556-9562 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T76337 9568-9571 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T86009 9794-9795 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T73832 9878-9885 http://purl.obolibrary.org/obo/CLO_0009985 denotes focused
T49922 10089-10090 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T8217 10471-10472 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T52201 10513-10514 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T96491 10557-10558 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T72259 10645-10647 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T79057 10844-10846 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T4510 10943-10945 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T19787 11432-11435 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T8586 11572-11574 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T41909 11610-11612 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T84353 11637-11640 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T64722 11799-11800 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T21026 12004-12006 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T93676 12007-12008 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T62552 12121-12124 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T38138 12159-12162 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T5895 12270-12271 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T91690 12351-12352 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T7075 12407-12414 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T97610 12434-12437 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T35533 12478-12491 http://purl.obolibrary.org/obo/UBERON_0002329 denotes epimerization
T32370 12679-12681 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T64601 13169-13171 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T24049 13290-13292 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T15952 13317-13318 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T58065 13338-13351 http://purl.obolibrary.org/obo/UBERON_0002329 denotes epimerization
T75772 13359-13361 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T70942 13456-13458 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T27962 13492-13495 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T47002 13516-13518 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T84592 13868-13870 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T16252 14118-14122 http://purl.obolibrary.org/obo/CL_0000784 denotes Pd/C
T28229 14361-14363 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T30736 14463-14466 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T42783 14806-14807 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T59953 15027-15028 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T67520 15095-15096 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69080 15233-15235 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T29047 15243-15244 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T27082 15452-15455 http://purl.obolibrary.org/obo/CLO_0007437 denotes M–1
T89112 15452-15455 http://purl.obolibrary.org/obo/CLO_0007448 denotes M–1
T44311 15452-15455 http://purl.obolibrary.org/obo/CLO_0007449 denotes M–1
T11842 15452-15455 http://purl.obolibrary.org/obo/CLO_0050175 denotes M–1
T68824 15452-15455 http://purl.obolibrary.org/obo/CLO_0052399 denotes M–1
T53118 15456-15459 http://purl.obolibrary.org/obo/CLO_0050050 denotes s–1
T18679 15503-15505 http://purl.obolibrary.org/obo/CLO_0007653 denotes Me
T64538 15616-15618 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T67844 15622-15624 http://purl.obolibrary.org/obo/CLO_0007653 denotes Me
T54087 15690-15692 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T91151 15707-15709 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T73065 15715-15720 http://purl.obolibrary.org/obo/CLO_0002488 denotes (Cl)2
T12274 15751-15755 http://purl.obolibrary.org/obo/CLO_0002972 denotes (F)2
T81297 15787-15789 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T26335 15854-15856 http://purl.obolibrary.org/obo/CLO_0007653 denotes Me
T57513 15873-15875 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T77214 15926-15927 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T43067 16131-16132 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T17773 16195-16197 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T88669 16453-16454 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T51542 16539-16540 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T17790 16547-16548 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T86458 16597-16605 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T80470 16744-16750 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T34478 16787-16788 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T81268 16832-16833 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T15335 16996-16997 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T62436 17122-17123 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T40750 17233-17234 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T8354 17268-17269 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75567 17475-17476 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T94234 17534-17535 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T35747 17928-17930 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T36376 18040-18047 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T60100 18048-18053 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T41307 18112-18119 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T44344 18120-18125 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T95747 18163-18171 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T41737 18216-18220 http://purl.obolibrary.org/obo/CLO_0009524 denotes Vero
T58120 18216-18220 http://purl.obolibrary.org/obo/CLO_0050515 denotes Vero
T23029 18221-18226 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T96607 18291-18296 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T31340 18297-18301 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T79444 18297-18301 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T79987 18302-18307 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T84247 18347-18349 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T92769 18495-18500 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T56673 18501-18507 http://purl.obolibrary.org/obo/UBERON_0001969 denotes plasma
T32052 18525-18527 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T59638 18537-18539 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T18074 18549-18550 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T19548 18561-18569 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T94580 18823-18824 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T9015 18984-18986 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T67341 18992-18993 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T16805 19129-19131 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T11594 19162-19164 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T58796 19381-19382 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T39597 19732-19733 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T24511 20033-20036 http://purl.obolibrary.org/obo/CLO_0007437 denotes M–1
T12434 20033-20036 http://purl.obolibrary.org/obo/CLO_0007448 denotes M–1
T28200 20033-20036 http://purl.obolibrary.org/obo/CLO_0007449 denotes M–1
T54715 20033-20036 http://purl.obolibrary.org/obo/CLO_0050175 denotes M–1
T71311 20033-20036 http://purl.obolibrary.org/obo/CLO_0052399 denotes M–1
T97946 20037-20040 http://purl.obolibrary.org/obo/CLO_0050050 denotes s–1
T96800 20086-20094 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T32450 20098-20102 http://purl.obolibrary.org/obo/CLO_0009524 denotes Vero
T14088 20098-20102 http://purl.obolibrary.org/obo/CLO_0050515 denotes Vero
T54297 20103-20108 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T91837 20191-20193 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T99824 20679-20684 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T45488 20712-20720 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T66631 20740-20741 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T29691 20761-20766 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T82549 20804-20808 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T68545 20873-20881 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T85347 20948-20952 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T59256 21436-21437 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T19419 21575-21581 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T18919 21777-21778 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T36051 21819-21825 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T23602 22084-22086 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T57314 22084-22086 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T18914 22097-22098 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T63101 22186-22187 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T52927 22235-22237 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T52376 22327-22329 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T57943 22354-22355 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T83388 22356-22357 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T97788 22540-22541 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T22715 22583-22584 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T17416 22647-22649 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T390 22647-22649 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T74194 22678-22679 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T29295 22744-22746 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T38768 22754-22756 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T2687 22778-22780 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T76472 22899-22901 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T47677 22975-22977 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T57536 23159-23161 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T68663 23177-23178 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75668 23486-23487 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75637 23553-23557 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T94133 23687-23693 http://purl.obolibrary.org/obo/CLO_0002172 denotes Caco-2
T56692 23687-23693 http://purl.obolibrary.org/obo/CLO_0051943 denotes Caco-2
T24243 23687-23693 http://purl.obolibrary.org/obo/CLO_0051958 denotes Caco-2
T87690 23687-23693 http://purl.obolibrary.org/obo/CLO_0051960 denotes Caco-2
T229 23773-23780 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T230 23781-23786 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T231 23801-23807 http://purl.obolibrary.org/obo/NCBITaxon_9479 denotes monkey
T232 23808-23814 http://purl.obolibrary.org/obo/UBERON_0002113 denotes kidney
T233 23808-23814 http://www.ebi.ac.uk/efo/EFO_0000927 denotes kidney
T234 23808-23814 http://www.ebi.ac.uk/efo/EFO_0000929 denotes kidney
T235 23840-23845 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T236 23846-23867 http://purl.obolibrary.org/obo/CL_0000082 denotes lung epithelial cells
T237 23998-24005 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T238 24006-24015 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell line
T239 24091-24092 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T240 24141-24147 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T241 24609-24610 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T242 24753-24755 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T243 24777-24778 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T244 24811-24812 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T245 24900-24901 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T246 25027-25028 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T247 25282-25283 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T248 25339-25340 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T249 25496-25497 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T250 25635-25636 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T251 25811-25813 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T252 26015-26017 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T253 26035-26037 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T254 26352-26353 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T255 26411-26412 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T256 26855-26860 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T257 26861-26866 http://purl.obolibrary.org/obo/UBERON_0002107 denotes liver
T258 26861-26866 http://www.ebi.ac.uk/efo/EFO_0000887 denotes liver
T259 26895-26897 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T260 27112-27114 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T261 27172-27173 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T262 27174-27175 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T263 27358-27359 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T264 27401-27402 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T265 27529-27530 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T266 27911-27912 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T267 27941-27947 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T268 27989-27990 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T269 28025-28026 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T270 28156-28157 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T271 28195-28201 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T272 28732-28738 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T273 28835-28837 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T274 28842-28844 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T275 28842-28844 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T276 28877-28879 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T277 28912-28913 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T278 29182-29184 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T279 29310-29312 http://purl.obolibrary.org/obo/CLO_0002105 denotes C2
T280 29310-29312 http://purl.obolibrary.org/obo/CLO_0051742 denotes C2
T281 29365-29367 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T282 29421-29422 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T283 29460-29462 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T284 29508-29510 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T285 29520-29521 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T286 29671-29673 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T287 29671-29673 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T288 29827-29828 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T289 30015-30016 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T290 30401-30402 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T291 30428-30433 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T292 30637-30638 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T293 30797-30798 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T294 30799-30802 http://purl.obolibrary.org/obo/NCBITaxon_9596 denotes pan
T295 30826-30833 http://purl.obolibrary.org/obo/UBERON_0000473 denotes Testing
T296 31031-31032 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T297 31132-31133 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T298 31221-31222 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T299 31224-31229 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T300 31258-31263 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T301 31292-31297 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T302 31322-31327 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T303 31346-31351 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T304 31370-31375 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T305 31396-31401 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T306 31483-31488 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T307 31508-31509 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T308 31675-31676 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T309 31793-31794 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T310 31804-31811 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T311 31836-31844 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T312 31869-31875 http://purl.obolibrary.org/obo/UBERON_0000473 denotes tested
T313 31888-31893 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T314 31934-31939 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T315 31957-31962 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T316 31977-31982 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T317 32009-32013 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T318 32125-32133 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T319 32140-32141 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T320 32166-32171 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T321 32197-32208 http://purl.obolibrary.org/obo/CLO_0052043 denotes MRC-5 cells
T322 32197-32208 http://purl.obolibrary.org/obo/CLO_0052044 denotes MRC-5 cells
T323 32197-32208 http://purl.obolibrary.org/obo/CLO_0052045 denotes MRC-5 cells
T324 32210-32215 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T325 32216-32220 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T326 32216-32220 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T327 32287-32292 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T328 32303-32304 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T329 32315-32316 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T330 32481-32482 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T331 32741-32748 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T332 32852-32859 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T333 33012-33018 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T334 33057-33062 http://purl.obolibrary.org/obo/CLO_0007865 denotes MRC-5
T335 33057-33062 http://purl.obolibrary.org/obo/CLO_0050055 denotes MRC-5
T336 33067-33079 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76 cell
T337 33098-33099 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T338 33268-33269 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T339 33314-33315 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T340 33344-33346 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T341 33354-33356 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T342 33360-33361 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T343 33414-33415 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T344 33465-33473 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T345 33566-33567 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T346 33701-33706 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T347 33707-33711 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T348 33707-33711 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T349 33720-33731 http://purl.obolibrary.org/obo/CLO_0052043 denotes MRC-5 cells
T350 33720-33731 http://purl.obolibrary.org/obo/CLO_0052044 denotes MRC-5 cells
T351 33720-33731 http://purl.obolibrary.org/obo/CLO_0052045 denotes MRC-5 cells
T352 33888-33895 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T353 33896-33901 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T354 33960-33969 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell line
T355 34017-34022 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T356 34023-34027 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T357 34023-34027 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T358 34028-34033 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T359 34174-34179 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T360 34180-34184 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T361 34180-34184 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T362 34185-34190 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T363 34733-34739 http://purl.obolibrary.org/obo/UBERON_0001969 denotes plasma
T364 34817-34818 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T365 34900-34903 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T366 34956-34957 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T367 35265-35266 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T368 35303-35304 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T369 35460-35461 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T370 35572-35573 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T371 35621-35622 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T372 35630-35634 http://purl.obolibrary.org/obo/UBERON_0000025 denotes tube
T373 36396-36397 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T374 36449-36450 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T375 37147-37150 http://purl.obolibrary.org/obo/CLO_0001577 denotes A 3
T376 37537-37538 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T377 37583-37584 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T378 37968-37969 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T379 37990-37998 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T380 37990-37998 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T381 38089-38097 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T382 38089-38097 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T383 38198-38199 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T384 38370-38372 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T385 38406-38411 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T386 38505-38506 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T387 38886-38887 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T388 38981-38982 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T389 38993-38998 http://purl.obolibrary.org/obo/UBERON_0000982 denotes joint
T48885 38993-38998 http://purl.obolibrary.org/obo/UBERON_0004905 denotes joint
T391 39046-39047 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T392 39075-39077 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T393 39159-39160 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T394 39541-39544 http://purl.obolibrary.org/obo/CLO_0009952 denotes sat
T395 39640-39641 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T396 39691-39693 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T397 39715-39718 http://purl.obolibrary.org/obo/CLO_0001302 denotes 3–4
T398 39789-39790 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T399 39986-39988 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T400 40122-40123 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T401 40130-40134 http://www.ebi.ac.uk/efo/EFO_0000967 denotes neck
T402 40167-40168 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T403 40303-40308 http://purl.obolibrary.org/obo/CLO_0003431 denotes g, 35
T404 40488-40489 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T405 40534-40535 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T406 40679-40680 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T407 40727-40728 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T408 40980-40988 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T409 40980-40988 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T410 41162-41163 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T411 41331-41332 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T412 41569-41571 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T413 41577-41579 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T414 41811-41814 http://purl.obolibrary.org/obo/CLO_0001577 denotes a 3
T415 42431-42432 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T416 42453-42461 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T417 42453-42461 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T418 42779-42780 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T419 43058-43059 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T420 43099-43100 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T421 43379-43381 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T422 43403-43405 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T423 43726-43728 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T424 44000-44008 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T425 44000-44008 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T426 44093-44094 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T427 44108-44111 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T428 44232-44233 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T429 44436-44438 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T430 44472-44477 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T431 44565-44566 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T432 44821-44822 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T433 45010-45011 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T434 45153-45154 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T435 45351-45353 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T436 45387-45392 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T437 45483-45485 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T438 45487-45488 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T439 45674-45676 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T440 45911-45912 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T441 46140-46142 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T442 46177-46182 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T443 46334-46335 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T444 46589-46590 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T445 46726-46727 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T446 46808-46811 http://purl.obolibrary.org/obo/CLO_0053733 denotes 1:1
T447 47243-47245 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T448 47280-47285 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T449 47289-47290 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T450 47600-47601 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T451 47663-47666 http://purl.obolibrary.org/obo/CLO_0053733 denotes 1:1
T452 47671-47674 http://purl.obolibrary.org/obo/CLO_0009952 denotes sat
T453 47757-47765 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T454 47757-47765 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T455 47856-47857 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T456 47902-47904 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T457 48399-48401 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T458 48436-48441 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T459 48671-48672 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T460 48711-48713 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T461 48741-48742 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T462 49038-49039 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T463 49086-49087 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T464 49257-49264 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T465 49257-49264 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T466 49452-49454 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T467 49482-49483 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T468 49968-49970 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T469 50003-50008 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T470 50505-50506 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T471 51064-51068 http://purl.obolibrary.org/obo/CLO_0050298 denotes 10 H
T472 51071-51073 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T473 51106-51111 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T474 51578-51579 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T475 52104-52106 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T476 52139-52144 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T477 52609-52610 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T478 53254-53256 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T479 53289-53294 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T480 53777-53778 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T481 54402-54404 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T482 54437-54442 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T483 54678-54680 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T484 54932-54933 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T485 55576-55578 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T486 55611-55616 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T487 56104-56105 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T488 56740-56742 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T489 56775-56780 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T490 57263-57264 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T491 57886-57888 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T492 57922-57927 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T493 58418-58419 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T494 59068-59070 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T495 59105-59110 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T496 59352-59354 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T497 59610-59611 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T498 59657-59659 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T499 59714-59717 http://purl.obolibrary.org/obo/CLO_0053001 denotes 114
T500 59752-59753 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T501 60151-60153 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T502 60189-60194 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T503 60750-60751 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T504 60883-60884 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T505 61311-61313 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T506 61348-61353 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T507 61810-61811 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T508 61959-61960 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T509 62366-62368 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T510 62403-62408 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T511 62981-62982 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T512 63110-63112 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T513 63593-63595 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T514 63629-63634 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T515 64188-64189 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T516 64258-64261 http://purl.obolibrary.org/obo/CLO_0001302 denotes 3–4
T517 64719-64721 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T518 64754-64759 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T519 65062-65064 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T520 65321-65322 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T521 65391-65394 http://purl.obolibrary.org/obo/CLO_0001302 denotes 3–4
T522 65922-65924 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T523 65957-65962 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T524 66452-66453 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T525 66550-66561 http://purl.obolibrary.org/obo/CLO_0007698 denotes mg (38%) of
T526 66584-66585 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T527 66979-66981 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T528 67014-67019 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T529 67285-67286 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T530 67566-67567 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T531 67801-67802 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T532 68127-68129 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T533 68348-68349 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T534 68469-68472 http://purl.obolibrary.org/obo/CLO_0001360 denotes 412
T535 68773-68776 http://purl.obolibrary.org/obo/CLO_0053733 denotes 1:1
T536 68781-68784 http://purl.obolibrary.org/obo/CLO_0009952 denotes sat
T537 68875-68883 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T538 68875-68883 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T539 68974-68975 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T540 69020-69022 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T541 69043-69046 http://purl.obolibrary.org/obo/CLO_0001000 denotes 3–5
T542 69206-69207 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T543 69477-69479 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T544 69532-69534 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T545 69569-69574 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T546 70183-70184 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T547 70227-70229 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T548 70328-70329 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T549 70606-70608 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T550 70661-70663 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T551 70699-70704 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T552 71295-71296 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T553 71447-71448 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T554 71771-71773 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T555 71809-71814 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T556 72531-72532 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T557 72601-72604 http://purl.obolibrary.org/obo/CLO_0001302 denotes 3–4
T558 73014-73016 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T559 73052-73057 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T560 73750-73751 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T561 73846-73847 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T562 73963-73964 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T563 74308-74310 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T564 74344-74349 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T565 74890-74891 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T566 75040-75041 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T567 75359-75361 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T568 75396-75401 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T569 75812-75813 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T570 75857-75859 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T571 75956-75957 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T572 76256-76258 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T573 76291-76296 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T574 76453-76455 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T575 76851-76852 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T576 77347-77349 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T577 77382-77387 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T578 77712-77714 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T579 78092-78093 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T580 78684-78686 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T581 78721-78726 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T582 78753-78758 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T583 78936-78938 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T584 79346-79347 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T585 79499-79500 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T586 79514-79516 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T587 79549-79554 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T588 79630-79639 http://purl.obolibrary.org/obo/CLO_0007923 denotes N-{(1S)-1
T589 79992-79993 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T590 80136-80137 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T591 80556-80558 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T592 80591-80596 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T593 81321-81322 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T594 81466-81467 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T595 81899-81901 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T596 81934-81939 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T597 81966-81971 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T598 82148-82149 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T599 82871-82872 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T600 82892-82894 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T601 82927-82932 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T602 82936-82937 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T603 83289-83290 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T604 83875-83877 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T605 83910-83915 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T606 84316-84317 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T607 84479-84480 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T608 84488-84491 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T609 85309-85310 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T610 85458-85459 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T611 85478-85480 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T612 85891-85893 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T613 85899-85901 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T614 85929-85934 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T615 86153-86162 http://purl.obolibrary.org/obo/CLO_0007923 denotes N-{(1S)-1
T616 86520-86521 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T617 86671-86672 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T618 87036-87038 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T619 87044-87046 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T620 87075-87080 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H
T621 87435-87436 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T622 87481-87483 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T623 87583-87584 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T624 87734-87735 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T625 87937-87939 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T626 87974-87979 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T627 88494-88495 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T628 88610-88621 http://purl.obolibrary.org/obo/CLO_0007699 denotes mg (63%) of
T629 88610-88621 http://purl.obolibrary.org/obo/CLO_0050808 denotes mg (63%) of
T630 89051-89053 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T631 89089-89094 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T632 89731-89732 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T633 89852-89854 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T634 89882-89883 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T635 90301-90303 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T636 90336-90341 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T637 90598-90599 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T638 90794-90799 http://purl.obolibrary.org/obo/CLO_0007736 denotes mL, 2
T639 90914-90915 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T640 91171-91172 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T641 91544-91546 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T642 91650-91651 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T643 92043-92044 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T644 92507-92508 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T645 92737-92739 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T646 92745-92747 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T647 92834-92835 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T648 92956-92957 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T649 93250-93258 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T650 93250-93258 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T651 93388-93389 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T652 93623-93625 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T653 93631-93633 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T654 94062-94063 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T655 94240-94242 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T656 94537-94541 http://purl.obolibrary.org/obo/CLO_0007731 denotes m, J
T657 94611-94613 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T658 94619-94621 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES
T659 95191-95192 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T660 95347-95348 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T661 95737-95739 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T662 95774-95779 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T663 96400-96401 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T664 96554-96555 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T665 97002-97004 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T666 97037-97042 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T667 97248-97249 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T668 98037-98045 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T669 98037-98045 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T670 98265-98266 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T671 98278-98281 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T1 13-19 Chemical denotes Ketone http://purl.obolibrary.org/obo/CHEBI_17087
T2 472-480 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T3 694-701 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T4 791-797 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T5 804-814 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T6 846-852 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T7 977-979 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T9 1002-1011 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T10 1042-1056 Chemical denotes pharmaceutical http://purl.obolibrary.org/obo/CHEBI_52217
T11 2065-2073 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T12 2179-2187 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T13 2354-2362 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T14 2792-2802 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T15 2808-2817 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T16 2869-2897 Chemical denotes cysteine protease inhibitors http://purl.obolibrary.org/obo/CHEBI_64152
T17 2869-2877 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T18 2878-2897 Chemical denotes protease inhibitors http://purl.obolibrary.org/obo/CHEBI_37670|http://purl.obolibrary.org/obo/CHEBI_60258
T20 2887-2897 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T21 2913-2922 Chemical denotes aldehydes http://purl.obolibrary.org/obo/CHEBI_17478
T22 2929-2933 Chemical denotes thio http://purl.obolibrary.org/obo/CHEBI_29830
T23 2958-2972 Chemical denotes cyclic ketones http://purl.obolibrary.org/obo/CHEBI_3992
T24 2965-2972 Chemical denotes ketones http://purl.obolibrary.org/obo/CHEBI_17087
T25 2998-3006 Chemical denotes nitriles http://purl.obolibrary.org/obo/CHEBI_18379
T26 3070-3076 Chemical denotes carbon http://purl.obolibrary.org/obo/CHEBI_27594|http://purl.obolibrary.org/obo/CHEBI_33415
T28 3124-3135 Chemical denotes sulfur atom http://purl.obolibrary.org/obo/CHEBI_26833
T29 3131-3135 Chemical denotes atom http://purl.obolibrary.org/obo/CHEBI_33250
T30 3154-3162 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T31 3241-3248 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T32 3249-3255 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T33 3353-3362 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T34 3468-3483 Chemical denotes peptidomimetics http://purl.obolibrary.org/obo/CHEBI_63175
T35 3683-3692 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T36 3917-3927 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T37 3955-3970 Chemical denotes affinity labels http://purl.obolibrary.org/obo/CHEBI_60788
T38 4265-4280 Chemical denotes affinity labels http://purl.obolibrary.org/obo/CHEBI_60788
T39 4434-4444 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T40 4454-4462 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T41 4555-4563 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T42 4625-4630 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T43 4716-4722 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T44 4904-4914 Chemical denotes Amino acid http://purl.obolibrary.org/obo/CHEBI_33704
T45 4910-4914 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T46 4943-4954 Chemical denotes polypeptide http://purl.obolibrary.org/obo/CHEBI_15841
T47 4964-4969 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T49 5017-5019 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T50 5058-5068 Chemical denotes Amino acid http://purl.obolibrary.org/obo/CHEBI_33704
T51 5064-5068 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T52 5154-5156 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T53 5537-5540 Chemical denotes Gln http://purl.obolibrary.org/obo/CHEBI_30011
T54 5562-5564 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T55 5823-5831 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T56 5927-5936 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T57 6005-6014 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T58 6035-6043 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T59 6098-6108 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T60 6130-6138 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T61 6176-6192 Chemical denotes cysteine residue http://purl.obolibrary.org/obo/CHEBI_32460
T62 6176-6184 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T63 6262-6272 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T64 6370-6378 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T65 6417-6419 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T66 6420-6422 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T67 6460-6462 Chemical denotes P4 http://purl.obolibrary.org/obo/CHEBI_35895
T68 6561-6567 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T70 6576-6581 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T71 6585-6587 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T72 7038-7046 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T73 7076-7084 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T74 7085-7091 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T75 7156-7164 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T76 7170-7175 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T77 7216-7224 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T78 7242-7250 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T79 7251-7257 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T80 7273-7275 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T82 7343-7351 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T83 7512-7514 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T84 7582-7584 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T85 7585-7594 Chemical denotes glutamine http://purl.obolibrary.org/obo/CHEBI_28300
T86 7686-7694 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T87 7715-7717 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T89 7725-7731 Chemical denotes lactam http://purl.obolibrary.org/obo/CHEBI_24995
T90 7746-7754 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T91 7796-7802 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T92 7846-7848 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T94 7856-7862 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T96 7863-7865 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T97 7889-7897 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T98 7912-7919 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T99 8136-8145 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T100 8270-8275 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T101 8357-8366 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T102 8367-8374 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T103 8684-8686 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T104 8687-8693 Chemical denotes lactam http://purl.obolibrary.org/obo/CHEBI_24995
T105 8712-8719 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T107 8720-8726 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T109 8735-8740 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T110 8878-8883 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T112 8884-8892 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T113 9046-9051 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T115 9079-9085 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T116 9129-9139 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T117 9454-9463 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T118 9816-9818 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T119 9934-9940 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T120 9947-9957 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T121 9989-9995 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T122 10091-10099 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T123 10264-10270 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T124 10645-10647 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T125 10680-10684 Chemical denotes NaOH http://purl.obolibrary.org/obo/CHEBI_32145
T126 10686-10690 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T127 10733-10746 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T128 10748-10751 Chemical denotes TEA http://purl.obolibrary.org/obo/CHEBI_28621|http://purl.obolibrary.org/obo/CHEBI_35026
T130 10754-10769 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T131 10771-10774 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T134 10789-10794 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T135 10811-10814 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T136 10815-10822 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T137 10848-10851 Chemical denotes HBr http://purl.obolibrary.org/obo/CHEBI_47266
T138 10877-10880 Chemical denotes EDC http://purl.obolibrary.org/obo/CHEBI_27789
T139 10893-10908 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T140 10910-10913 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T141 10928-10930 Chemical denotes Mg http://purl.obolibrary.org/obo/CHEBI_25107
T142 10932-10937 Chemical denotes HgCl2 http://purl.obolibrary.org/obo/CHEBI_31823
T143 10943-10945 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T144 10947-10950 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T147 10976-10983 Chemical denotes lithium http://purl.obolibrary.org/obo/CHEBI_30145
T148 11016-11019 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T151 11045-11050 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T152 11051-11056 Chemical denotes ester http://purl.obolibrary.org/obo/CHEBI_35701
T153 11090-11100 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T154 11090-11095 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T155 11096-11100 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T156 11133-11137 Chemical denotes Acid http://purl.obolibrary.org/obo/CHEBI_37527
T157 11183-11196 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T158 11333-11350 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T159 11346-11350 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T160 11368-11376 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T161 11475-11478 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T162 11576-11579 Chemical denotes HBr http://purl.obolibrary.org/obo/CHEBI_47266
T163 11583-11598 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T164 11678-11690 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T165 11881-11885 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T166 11909-11922 Chemical denotes Weinreb amide http://purl.obolibrary.org/obo/CHEBI_59741
T167 11917-11922 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T169 11978-11984 Chemical denotes benzyl http://purl.obolibrary.org/obo/CHEBI_22744
T170 11998-12003 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T171 12194-12201 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T172 12318-12327 Chemical denotes methylene http://purl.obolibrary.org/obo/CHEBI_29357|http://purl.obolibrary.org/obo/CHEBI_29358|http://purl.obolibrary.org/obo/CHEBI_50728
T175 12329-12331 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T176 12407-12414 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T177 12530-12546 Chemical denotes carboxylic acids http://purl.obolibrary.org/obo/CHEBI_33575
T178 12541-12546 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T179 12566-12572 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T180 12573-12581 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T181 12679-12681 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T182 12686-12691 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T183 12729-12739 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T184 12838-12841 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T185 12842-12845 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T188 12861-12882 Chemical denotes N,N-dimethylformamide http://purl.obolibrary.org/obo/CHEBI_17741
T189 12884-12887 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T190 12911-12914 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T191 12915-12922 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T192 12944-12965 Chemical denotes indolecarboxylic acid http://purl.obolibrary.org/obo/CHEBI_38610
T193 12961-12965 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T194 12972-12975 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T195 13003-13006 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T196 13008-13023 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T197 13019-13023 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T198 13169-13171 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T199 13183-13189 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T200 13219-13224 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T202 13359-13361 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T203 13430-13440 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T204 13551-13555 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T205 13653-13661 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T207 13730-13736 Chemical denotes silver http://purl.obolibrary.org/obo/CHEBI_30512|http://purl.obolibrary.org/obo/CHEBI_9141
T209 13741-13746 Chemical denotes oxide http://purl.obolibrary.org/obo/CHEBI_25741|http://purl.obolibrary.org/obo/CHEBI_29356
T211 13776-13786 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T212 13868-13870 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T213 13875-13880 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T214 13918-13928 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T215 14007-14010 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T216 14011-14018 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T217 14025-14028 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T218 14029-14032 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T221 14048-14051 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T222 14079-14100 Chemical denotes indolecarboxylic acid http://purl.obolibrary.org/obo/CHEBI_38610
T223 14096-14100 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T224 14118-14120 Chemical denotes Pd http://purl.obolibrary.org/obo/CHEBI_33363
T225 14124-14126 Chemical denotes H2 http://purl.obolibrary.org/obo/CHEBI_18276
T226 14128-14132 Chemical denotes EtOH http://purl.obolibrary.org/obo/CHEBI_16236
T227 14149-14152 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T228 14168-14172 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T229 14190-14194 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T230 14196-14199 Chemical denotes cat http://purl.obolibrary.org/obo/CHEBI_32402
T231 14201-14206 Chemical denotes K2CO3 http://purl.obolibrary.org/obo/CHEBI_131526
T232 14223-14227 Chemical denotes CH3I http://purl.obolibrary.org/obo/CHEBI_39282
T233 14235-14238 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T234 14361-14363 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T235 14444-14454 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T236 14566-14574 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T237 14658-14663 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T238 14693-14698 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T239 14848-14861 Chemical denotes electrophiles http://purl.obolibrary.org/obo/CHEBI_59739
T240 14886-14896 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T241 15029-15049 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T242 15128-15134 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T243 15135-15143 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T244 15197-15205 Chemical denotes benzoate http://purl.obolibrary.org/obo/CHEBI_16150
T245 15233-15235 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T246 15528-15534 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T247 15551-15561 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T248 15556-15561 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T249 15578-15580 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T250 15602-15604 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T251 15625-15627 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T252 15648-15650 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T253 15670-15672 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T254 15690-15692 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T255 15693-15695 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T256 15716-15718 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T257 15721-15723 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T258 15756-15758 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T259 15787-15789 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T260 15790-15792 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T261 15823-15825 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T262 15859-15861 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T263 15888-15890 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T264 15912-15914 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T265 16153-16162 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T266 16218-16226 Chemical denotes electron http://purl.obolibrary.org/obo/CHEBI_10545
T267 16237-16245 Chemical denotes benzoate http://purl.obolibrary.org/obo/CHEBI_16150
T268 16369-16379 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T269 16625-16635 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T270 16671-16679 Chemical denotes electron http://purl.obolibrary.org/obo/CHEBI_10545
T271 16756-16764 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T272 16774-16780 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T273 16810-16819 Chemical denotes methylene http://purl.obolibrary.org/obo/CHEBI_29357|http://purl.obolibrary.org/obo/CHEBI_29358|http://purl.obolibrary.org/obo/CHEBI_50728
T276 16820-16826 Chemical denotes carbon http://purl.obolibrary.org/obo/CHEBI_27594|http://purl.obolibrary.org/obo/CHEBI_33415
T278 16856-16862 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T279 16863-16871 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T280 16935-16943 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T281 16964-16966 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T283 17031-17039 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T284 17102-17111 Chemical denotes imidazole http://purl.obolibrary.org/obo/CHEBI_14434|http://purl.obolibrary.org/obo/CHEBI_16069
T286 17124-17132 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T287 17138-17143 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T288 17195-17204 Chemical denotes imidazole http://purl.obolibrary.org/obo/CHEBI_14434|http://purl.obolibrary.org/obo/CHEBI_16069
T290 17205-17213 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T291 17245-17262 Chemical denotes electron acceptor http://purl.obolibrary.org/obo/CHEBI_17654|http://purl.obolibrary.org/obo/CHEBI_39143
T293 17245-17253 Chemical denotes electron http://purl.obolibrary.org/obo/CHEBI_10545
T294 17254-17262 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T295 17281-17286 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T296 17314-17319 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T297 17331-17339 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T298 17363-17368 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T299 17395-17403 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T300 17458-17466 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T301 17489-17497 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T302 17507-17515 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T303 17755-17764 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T304 17876-17881 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T305 17896-17916 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T306 18002-18011 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T307 18153-18162 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T308 18403-18415 Chemical denotes nucleophiles http://purl.obolibrary.org/obo/CHEBI_59740
T309 18424-18435 Chemical denotes glutathione http://purl.obolibrary.org/obo/CHEBI_16856|http://purl.obolibrary.org/obo/CHEBI_57925
T311 18636-18638 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T312 18697-18699 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T313 18761-18771 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T314 18801-18821 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T315 18840-18850 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T316 18884-18889 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T317 18954-18961 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T319 18962-18968 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T321 18994-19007 Chemical denotes benzimidazole http://purl.obolibrary.org/obo/CHEBI_36622|http://purl.obolibrary.org/obo/CHEBI_41275
T323 19026-19035 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T324 19162-19164 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T325 19580-19587 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T327 19588-19594 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T329 19608-19623 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T330 19706-19713 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T331 19935-19942 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T332 20076-20085 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T333 20269-20278 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T334 20330-20332 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T335 20457-20464 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T336 20502-20506 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T337 21089-21099 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T338 21184-21194 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T339 21219-21225 Chemical denotes ethers http://purl.obolibrary.org/obo/CHEBI_25698
T340 21266-21294 Chemical denotes cysteine protease inhibitors http://purl.obolibrary.org/obo/CHEBI_64152
T341 21266-21274 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T342 21275-21294 Chemical denotes protease inhibitors http://purl.obolibrary.org/obo/CHEBI_37670|http://purl.obolibrary.org/obo/CHEBI_60258
T344 21284-21294 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T345 21374-21384 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T346 21445-21453 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T347 21495-21503 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T349 21518-21527 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T350 21587-21590 Chemical denotes Cys http://purl.obolibrary.org/obo/CHEBI_15356|http://purl.obolibrary.org/obo/CHEBI_17561|http://purl.obolibrary.org/obo/CHEBI_29950
T353 21599-21605 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T354 21805-21811 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T355 21831-21839 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T356 21861-21869 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T357 21881-21889 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T358 21949-21956 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T359 22084-22086 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T360 22213-22223 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T361 22235-22237 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T362 22327-22329 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T363 22647-22649 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T364 22778-22780 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T365 22781-22784 Chemical denotes Phe http://purl.obolibrary.org/obo/CHEBI_17295|http://purl.obolibrary.org/obo/CHEBI_29997
T367 22975-22977 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T368 22980-22986 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T370 22987-22990 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T373 22991-23000 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T374 23093-23102 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T375 23103-23109 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T376 23159-23161 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T377 23162-23164 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T379 23179-23187 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T380 23213-23218 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T382 23248-23254 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T384 23327-23334 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T386 23335-23341 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T388 23371-23377 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T389 23385-23393 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T390 23493-23502 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T391 23590-23600 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T392 23748-23757 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T393 23919-23928 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T394 24112-24121 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T395 24172-24184 Chemical denotes glycoprotein http://purl.obolibrary.org/obo/CHEBI_17089
T396 24215-24224 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T397 24362-24365 Chemical denotes PSA http://purl.obolibrary.org/obo/CHEBI_61599
T398 24395-24403 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T399 24645-24652 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T401 24685-24691 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T403 24726-24734 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T405 24753-24755 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T406 24813-24821 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T407 24827-24832 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T408 24873-24881 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T410 24902-24910 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T411 25029-25037 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T412 25043-25048 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T413 25093-25101 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T414 25124-25130 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T415 25257-25266 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T416 25305-25313 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T418 25341-25349 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T419 25355-25363 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T420 25373-25379 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T421 25449-25457 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T422 25467-25475 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T424 25498-25506 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T425 25512-25517 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T426 25525-25533 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T427 25605-25608 Chemical denotes PSA http://purl.obolibrary.org/obo/CHEBI_61599
T428 25613-25621 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T429 25647-25657 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T430 25739-25753 Chemical denotes hydroxyl group http://purl.obolibrary.org/obo/CHEBI_43176
T431 25739-25747 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191
T432 25748-25753 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T433 25811-25813 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T434 25824-25827 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T437 25834-25844 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T438 25839-25844 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T439 25845-25848 Chemical denotes Ala http://purl.obolibrary.org/obo/CHEBI_16977|http://purl.obolibrary.org/obo/CHEBI_46217
T441 25881-25894 Chemical denotes methoxy group http://purl.obolibrary.org/obo/CHEBI_44520
T442 25881-25888 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772
T443 25889-25894 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T444 25904-25910 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T446 25978-25987 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T447 26087-26096 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T448 26288-26290 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T450 26291-26299 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T451 26305-26310 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T452 26326-26332 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T454 26392-26401 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T455 26453-26462 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T456 26556-26561 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T457 26732-26747 Chemical denotes peptidomimetics http://purl.obolibrary.org/obo/CHEBI_63175
T458 27000-27002 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T459 27112-27114 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T460 27603-27609 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T461 27884-27892 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T462 27893-27899 Chemical denotes carbon http://purl.obolibrary.org/obo/CHEBI_27594|http://purl.obolibrary.org/obo/CHEBI_33415
T464 27953-27961 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T465 27971-27977 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T466 28003-28011 Chemical denotes carbinol http://purl.obolibrary.org/obo/CHEBI_17790
T467 28050-28058 Chemical denotes carbinol http://purl.obolibrary.org/obo/CHEBI_17790
T468 28059-28067 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T470 28074-28082 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T471 28107-28109 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T473 28133-28138 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T475 28139-28141 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T477 28167-28172 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T478 28173-28181 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T479 28226-28234 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T480 28252-28267 Chemical denotes primary alcohol http://purl.obolibrary.org/obo/CHEBI_15734
T481 28260-28267 Chemical denotes alcohol http://purl.obolibrary.org/obo/CHEBI_16236|http://purl.obolibrary.org/obo/CHEBI_30879
T483 28400-28409 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T484 28564-28573 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T485 28685-28690 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T486 28777-28785 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T487 28842-28844 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T488 28885-28891 Chemical denotes lactam http://purl.obolibrary.org/obo/CHEBI_24995
T489 28892-28900 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T490 28921-28929 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T491 28976-28982 Chemical denotes lactam http://purl.obolibrary.org/obo/CHEBI_24995
T492 28983-28985 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T494 29000-29008 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T495 29065-29071 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T496 29099-29105 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T497 29220-29228 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T498 29233-29235 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T500 29264-29272 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T501 29303-29305 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T503 29310-29312 Chemical denotes C2 http://purl.obolibrary.org/obo/CHEBI_30083
T504 29313-29321 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T505 29329-29335 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T507 29355-29357 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T509 29365-29367 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T510 29368-29371 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T513 29375-29384 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T514 29423-29431 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T515 29448-29456 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T516 29460-29462 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T517 29463-29466 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T520 29485-29492 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T521 29498-29507 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T522 29508-29510 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T523 29511-29513 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T525 29529-29537 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T526 29561-29569 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T527 29608-29623 Chemical denotes leucine residue http://purl.obolibrary.org/obo/CHEBI_32630
T528 29608-29615 Chemical denotes leucine http://purl.obolibrary.org/obo/CHEBI_25017
T529 29671-29673 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T530 29746-29752 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T532 29793-29795 Chemical denotes S3 http://purl.obolibrary.org/obo/CHEBI_29388
T533 29849-29851 Chemical denotes S3 http://purl.obolibrary.org/obo/CHEBI_29388
T534 29932-29937 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T535 29950-29952 Chemical denotes S3 http://purl.obolibrary.org/obo/CHEBI_29388
T536 30154-30161 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T537 30815-30824 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T538 31744-31753 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T539 31826-31835 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T540 32149-32158 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T541 32420-32422 Chemical denotes RF http://purl.obolibrary.org/obo/CHEBI_73818
T542 32662-32671 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T543 32967-32976 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T544 33239-33248 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T545 33278-33290 Chemical denotes glycoprotein http://purl.obolibrary.org/obo/CHEBI_17089
T546 33301-33310 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T547 33344-33346 Chemical denotes CP http://purl.obolibrary.org/obo/CHEBI_3380|http://purl.obolibrary.org/obo/CHEBI_73461
T549 33384-33393 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T550 33455-33464 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T551 33525-33534 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T552 33606-33615 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T553 33654-33663 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T554 33744-33756 Chemical denotes glycoprotein http://purl.obolibrary.org/obo/CHEBI_17089
T555 33843-33852 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T556 33996-34005 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T557 34109-34118 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T558 34311-34325 Chemical denotes peptidomimetic http://purl.obolibrary.org/obo/CHEBI_63175
T559 34326-34336 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T560 34375-34377 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T561 34529-34539 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T562 34653-34662 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T563 35188-35195 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T564 35595-35603 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T565 35607-35612 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T566 35700-35708 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T567 35811-35817 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T568 35887-35894 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T569 36329-36333 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T570 36338-36344 Chemical denotes iodine http://purl.obolibrary.org/obo/CHEBI_24859
T571 36417-36419 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T572 36563-36580 Chemical denotes tetramethylsilane http://purl.obolibrary.org/obo/CHEBI_85361
T573 36582-36585 Chemical denotes TMS http://purl.obolibrary.org/obo/CHEBI_85361
T574 36588-36590 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T575 36864-36869 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T576 36871-36875 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T577 37061-37063 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T578 37135-37142 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T579 37245-37251 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T581 37255-37274 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T582 37308-37317 Chemical denotes alaninate http://purl.obolibrary.org/obo/CHEBI_32439
T583 37363-37371 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T584 37387-37395 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T585 37425-37429 Chemical denotes NaCl http://purl.obolibrary.org/obo/CHEBI_26710
T586 37436-37440 Chemical denotes NaOH http://purl.obolibrary.org/obo/CHEBI_32145
T587 37458-37463 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T588 37474-37482 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T589 37653-37661 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T590 37721-37738 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T591 37734-37738 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T592 37808-37816 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T593 37856-37869 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T594 37856-37861 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T596 37862-37869 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T598 37909-37926 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T599 37922-37926 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T600 37941-37948 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T601 38044-38057 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T602 38044-38049 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T604 38050-38057 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T606 38133-38138 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T607 38217-38219 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T608 38256-38258 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T609 38294-38296 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T610 38313-38315 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T611 38332-38334 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T612 38370-38372 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T613 38443-38446 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T614 38477-38483 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T616 38484-38490 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T617 38491-38500 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T618 38507-38515 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T619 38522-38541 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T620 38575-38582 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T621 38606-38609 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T624 38653-38655 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T625 38708-38716 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T626 38747-38760 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T627 38849-38856 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T628 39048-39056 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T629 39060-39072 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T630 39097-39110 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T631 39105-39110 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T632 39122-39134 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T633 39244-39246 Chemical denotes AL http://purl.obolibrary.org/obo/CHEBI_73770
T634 39279-39287 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T635 39359-39361 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T636 39412-39424 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T637 39500-39513 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T638 39500-39505 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T640 39506-39513 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T642 39546-39552 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T643 39598-39603 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T644 39691-39693 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T645 39709-39713 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T646 39720-39728 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T647 39729-39739 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T648 39810-39812 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T649 39818-39822 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T650 39839-39841 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T651 39863-39865 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T652 39878-39880 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T653 39892-39894 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T654 39920-39922 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T655 39934-39936 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T656 39948-39950 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T657 39986-39988 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T658 40025-40027 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T659 40060-40063 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T660 40094-40100 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T662 40101-40107 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T663 40108-40117 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T664 40169-40177 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T665 40226-40232 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T667 40236-40255 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T668 40289-40298 Chemical denotes alaninate http://purl.obolibrary.org/obo/CHEBI_32439
T669 40316-40319 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T672 40381-40389 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T673 40446-40449 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T676 40461-40472 Chemical denotes cyclohexane http://purl.obolibrary.org/obo/CHEBI_29005
T677 40681-40688 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T678 40692-40696 Chemical denotes AcOH http://purl.obolibrary.org/obo/CHEBI_15366
T679 40709-40712 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T682 40948-40961 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T683 40948-40953 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T685 40954-40961 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T687 41006-41011 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T688 41028-41034 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T689 41076-41081 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T690 41101-41109 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T691 41230-41243 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T692 41230-41235 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T694 41236-41243 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T696 41285-41298 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T697 41293-41298 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T698 41364-41366 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T699 41381-41385 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T700 41401-41403 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T701 41427-41429 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T702 41460-41462 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T703 41493-41495 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T704 41512-41514 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T705 41531-41533 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T706 41569-41571 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T707 41577-41579 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T708 41614-41616 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T709 41746-41749 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T710 41780-41786 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T712 41787-41793 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T713 41794-41803 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T714 41870-41878 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T715 41926-41945 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T716 41979-41986 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T717 42017-42032 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T718 42051-42059 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T719 42096-42100 Chemical denotes NaCl http://purl.obolibrary.org/obo/CHEBI_26710
T720 42133-42150 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T721 42146-42150 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T722 42151-42155 Chemical denotes salt http://purl.obolibrary.org/obo/CHEBI_24866|http://purl.obolibrary.org/obo/CHEBI_26710
T724 42302-42309 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T725 42336-42344 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T726 42375-42380 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T727 42404-42411 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T728 42493-42510 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T729 42506-42510 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T730 42525-42530 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T731 42547-42553 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T732 42607-42612 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T733 42632-42640 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T734 42675-42685 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T735 42680-42685 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T736 42695-42702 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T738 42703-42709 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T740 42710-42715 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T741 42719-42722 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T742 42753-42759 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T744 42760-42765 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T746 42766-42775 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T747 42812-42814 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T748 42829-42834 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T749 42847-42849 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T750 42873-42875 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T751 42905-42907 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T752 43003-43005 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T753 43022-43024 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T754 43036-43038 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T755 43114-43122 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T756 43168-43177 Chemical denotes magnesium http://purl.obolibrary.org/obo/CHEBI_25107
T757 43244-43249 Chemical denotes HgCl2 http://purl.obolibrary.org/obo/CHEBI_31823
T758 43301-43309 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T759 43322-43325 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T762 43403-43405 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T763 43554-43564 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T764 43559-43564 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T765 43574-43581 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T767 43582-43588 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T769 43589-43594 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T770 43598-43601 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T771 43632-43638 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T773 43639-43644 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T775 43645-43654 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T776 43737-43745 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T777 43856-43861 Chemical denotes NH4Cl http://purl.obolibrary.org/obo/CHEBI_31206
T778 43862-43870 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T779 43888-43895 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T780 43959-43972 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T781 43959-43964 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T783 43965-43972 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T785 44025-44030 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T786 44050-44058 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T787 44175-44183 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T788 44184-44199 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T789 44260-44262 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T790 44277-44282 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T791 44436-44438 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T792 44505-44511 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T793 44523-44539 Chemical denotes pyrrolidin-2-one http://purl.obolibrary.org/obo/CHEBI_36592
T794 44541-44554 Chemical denotes Hydrochloride http://purl.obolibrary.org/obo/CHEBI_17883
T795 44567-44575 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T796 44579-44589 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T797 44584-44589 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T798 44598-44603 Chemical denotes diazo http://purl.obolibrary.org/obo/CHEBI_30105
T799 44606-44609 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T800 44640-44646 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T802 44647-44653 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T803 44655-44664 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T804 44687-44698 Chemical denotes 1,4-dioxane http://purl.obolibrary.org/obo/CHEBI_47032
T805 44691-44698 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T806 44740-44742 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T807 44786-44794 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T808 44823-44831 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T809 44839-44856 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T810 44852-44856 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T811 44860-44871 Chemical denotes 1,4-dioxane http://purl.obolibrary.org/obo/CHEBI_47032
T812 44864-44871 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T813 45082-45095 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T814 45090-45095 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T815 45169-45171 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T816 45177-45181 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T817 45212-45214 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T818 45237-45239 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T819 45262-45264 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T820 45276-45278 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T821 45304-45306 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T822 45318-45320 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T823 45346-45348 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T824 45351-45353 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T825 45424-45427 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T826 45458-45464 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T828 45465-45471 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T829 45472-45481 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T830 45489-45497 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T831 45501-45511 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T832 45506-45511 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T833 45520-45526 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T834 45529-45532 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T835 45563-45569 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T837 45570-45576 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T838 45577-45586 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T839 45609-45624 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T840 45648-45656 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T841 45690-45694 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T842 45803-45808 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T843 45829-45834 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T844 45926-45928 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T845 45943-45947 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T846 45963-45965 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T847 45987-45989 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T848 46012-46014 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T849 46037-46039 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T850 46051-46053 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T851 46079-46081 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T852 46093-46095 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T853 46107-46109 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T854 46140-46142 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T855 46216-46219 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T856 46250-46256 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T858 46257-46263 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T859 46264-46269 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T860 46270-46278 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T861 46280-46293 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T862 46297-46304 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T864 46305-46314 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T865 46305-46307 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T866 46308-46314 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T867 46317-46328 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T869 46336-46344 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T870 46352-46354 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T871 46356-46375 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T872 46388-46394 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T873 46397-46400 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T874 46431-46437 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T876 46438-46444 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T877 46483-46494 Chemical denotes 1,4-dioxane http://purl.obolibrary.org/obo/CHEBI_47032
T878 46487-46494 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T879 46538-46540 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T880 46563-46571 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T881 46591-46599 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T882 46607-46624 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T883 46620-46624 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T884 46628-46639 Chemical denotes 1,4-dioxane http://purl.obolibrary.org/obo/CHEBI_47032
T885 46632-46639 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T886 46812-46819 Chemical denotes ethanol http://purl.obolibrary.org/obo/CHEBI_16236
T887 46820-46831 Chemical denotes 1,4-dioxane http://purl.obolibrary.org/obo/CHEBI_47032
T888 46824-46831 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T889 46888-46894 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T890 46897-46900 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T891 46931-46937 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T893 46938-46944 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T894 46960-46973 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T895 46997-46999 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T896 47005-47009 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T897 47035-47037 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T898 47064-47066 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T899 47092-47094 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T900 47106-47108 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T901 47134-47136 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T902 47148-47150 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T903 47162-47164 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T904 47243-47245 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T905 47291-47299 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T906 47313-47326 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T907 47327-47331 Chemical denotes salt http://purl.obolibrary.org/obo/CHEBI_24866|http://purl.obolibrary.org/obo/CHEBI_26710
T909 47338-47345 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T911 47346-47355 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T912 47346-47348 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T913 47349-47355 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T914 47358-47373 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T915 47369-47373 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T916 47397-47400 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T917 47444-47446 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T918 47484-47492 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T919 47675-47681 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T920 47721-47734 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T921 47721-47726 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T923 47727-47734 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T925 47814-47819 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T926 47902-47904 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T927 47919-47923 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T928 47928-47936 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T929 47937-47947 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T930 48017-48019 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T931 48025-48029 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T932 48046-48048 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T933 48070-48072 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T934 48094-48096 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T935 48108-48110 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T936 48122-48124 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T937 48146-48148 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T938 48170-48172 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T939 48194-48196 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T940 48219-48221 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T941 48244-48246 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T942 48300-48302 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T943 48314-48316 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T944 48328-48330 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T945 48399-48401 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T946 48533-48546 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T947 48533-48535 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T948 48547-48555 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T949 48559-48565 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T951 48566-48571 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T952 48575-48578 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T953 48608-48613 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T46839 48698-48709 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T30029 48705-48709 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T40022 48743-48751 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T92548 48775-48781 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T77046 48784-48787 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T322 48818-48824 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T8 48825-48831 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1448 48832-48837 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T89400 48838-48846 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T86029 48848-48861 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T74561 48865-48872 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T65219 48873-48882 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T44034 48873-48875 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41687 48876-48882 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T75707 48885-48896 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T19 48920-48923 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T75923 48949-48951 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T30381 48970-48978 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T8447 49040-49046 Chemical denotes Teflon http://purl.obolibrary.org/obo/CHEBI_53251
T16308 49182-49187 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T44169 49216-49231 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T72291 49289-49294 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T52737 49409-49417 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T27 49418-49433 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T47188 49497-49499 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T21947 49514-49518 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T62313 49535-49537 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65167 49561-49563 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7414 49587-49589 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29594 49601-49603 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T13853 49627-49629 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11215 49653-49655 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84447 49679-49681 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75855 49705-49707 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35764 49731-49733 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55887 49750-49752 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7116 49821-49823 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T12321 49840-49842 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T67952 49873-49875 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T77336 49968-49970 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T73211 50044-50047 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T65519 50138-50151 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T62787 50138-50140 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2814 50152-50160 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T48 50164-50170 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T39064 50171-50176 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T28301 50180-50183 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T28169 50213-50218 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T28986 50219-50242 Chemical denotes Cyclopropanecarboxylate http://purl.obolibrary.org/obo/CHEBI_36128
T33097 50320-50327 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T33354 50328-50341 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T39869 50328-50330 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T80612 50342-50350 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T99831 50354-50360 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T99405 50361-50366 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T74190 50370-50373 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T23544 50403-50416 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T69104 50403-50408 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T82668 50409-50416 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T47617 50434-50461 Chemical denotes cyclopropanecarboxylic acid http://purl.obolibrary.org/obo/CHEBI_23500
T89669 50457-50461 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T69 50581-50589 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T92205 50590-50605 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T96218 50652-50654 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94620 50669-50673 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T58187 50702-50704 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39205 50728-50730 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91620 50754-50756 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T22421 50768-50770 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65323 50794-50796 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99169 50820-50822 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60504 50839-50841 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19823 50865-50867 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T81 50879-50881 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T77212 50898-50900 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T18933 50969-50971 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91104 50988-50990 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T26339 51007-51009 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70916 51071-51073 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T6246 51147-51150 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T88 51241-51254 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T15293 51241-51243 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91973 51255-51263 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T28576 51267-51273 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T93 51274-51279 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T81514 51283-51286 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T95 51316-51321 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T71989 51408-51415 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T37846 51416-51429 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T86199 51416-51418 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94436 51430-51438 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T72503 51442-51448 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T48336 51449-51454 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T27045 51458-51461 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T19478 51491-51504 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T106 51491-51496 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T86264 51497-51504 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T5769 51522-51534 Chemical denotes pivalic acid http://purl.obolibrary.org/obo/CHEBI_45133
T3867 51530-51534 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T111 51654-51662 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T3238 51663-51678 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T22213 51726-51728 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T114 51743-51747 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T26714 51764-51766 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54523 51790-51792 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10730 51816-51818 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38064 51830-51832 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79920 51844-51846 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99227 51870-51872 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94617 51884-51886 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6524 51910-51912 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T53306 51924-51926 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47671 51943-51945 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T69670 52104-52106 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T41002 52180-52183 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T26484 52272-52285 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T6443 52272-52274 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T129 52286-52294 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T19275 52298-52304 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T132 52305-52310 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T133 52314-52317 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T37457 52347-52352 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T98566 52439-52446 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T62963 52447-52460 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T26567 52447-52449 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T93538 52461-52469 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T44363 52473-52479 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T70419 52480-52485 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T88170 52489-52492 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T54249 52522-52535 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T145 52522-52527 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T146 52528-52535 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T99810 52553-52565 Chemical denotes benzoic acid http://purl.obolibrary.org/obo/CHEBI_30746
T149 52561-52565 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T150 52685-52693 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T37878 52694-52709 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T45619 52757-52759 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60775 52774-52778 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T14819 52795-52797 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95058 52821-52823 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T32231 52847-52849 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T3493 52892-52894 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15212 52911-52913 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87949 52925-52927 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68112 52944-52946 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T92861 52970-52972 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35336 52996-52998 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T49210 53015-53017 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36386 53041-53043 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99513 53055-53057 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47121 53074-53076 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36911 53140-53142 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T168 53159-53161 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40561 53178-53180 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54496 53254-53256 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T27523 53330-53333 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T43551 53422-53435 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T173 53422-53424 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T174 53436-53444 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T66744 53448-53454 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T92090 53455-53460 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T8503 53464-53467 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T19071 53497-53502 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T85874 53598-53605 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T19973 53606-53619 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T27534 53606-53608 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15174 53620-53628 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T24743 53632-53638 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T187 53639-53644 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T44430 53648-53651 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T5710 53681-53694 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T44919 53681-53686 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T28140 53687-53694 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T6107 53712-53733 Chemical denotes 4-methoxybenzoic acid http://purl.obolibrary.org/obo/CHEBI_40813
T79822 53714-53733 Chemical denotes methoxybenzoic acid http://purl.obolibrary.org/obo/CHEBI_25238
T67419 53729-53733 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T53278 53853-53861 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T26216 53862-53877 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T78176 53925-53927 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10398 53942-53946 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T10216 53975-53977 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T201 54001-54003 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31573 54027-54029 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68231 54067-54069 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6450 54093-54095 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52301 54170-54172 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T206 54184-54186 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47282 54203-54205 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T208 54288-54290 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20724 54307-54309 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T210 54326-54328 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T92188 54402-54404 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T8859 54478-54481 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T69992 54487-54490 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T44568 54579-54592 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T68088 54579-54581 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87163 54593-54601 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T47562 54605-54611 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T219 54612-54617 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T220 54621-54624 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T53970 54654-54659 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T44136 54754-54761 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T72315 54762-54775 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T80123 54762-54764 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38371 54776-54784 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T84329 54788-54794 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T18805 54795-54800 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T29990 54804-54807 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T16489 54837-54850 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T52074 54837-54842 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T82193 54843-54850 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T58673 54868-54888 Chemical denotes 4-methylbenzoic acid http://purl.obolibrary.org/obo/CHEBI_36635
T4356 54870-54888 Chemical denotes methylbenzoic acid http://purl.obolibrary.org/obo/CHEBI_25280
T58977 54884-54888 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T76679 55008-55016 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T88844 55017-55032 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T43261 55079-55081 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87223 55096-55100 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T97389 55129-55131 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T63097 55155-55157 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52721 55181-55183 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20525 55221-55223 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70463 55247-55249 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48645 55299-55301 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85643 55318-55320 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T81008 55344-55346 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19507 55358-55360 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T59206 55377-55379 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T17149 55462-55464 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6479 55481-55483 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95796 55500-55502 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T96393 55576-55578 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T60033 55652-55655 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T82823 55661-55664 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T94285 55753-55766 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T78521 55753-55755 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98598 55767-55775 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T78187 55779-55785 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T8644 55786-55791 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T93744 55795-55798 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T10728 55828-55833 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T6645 55927-55934 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T24935 55935-55948 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T51772 55935-55937 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11518 55949-55957 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T90153 55961-55967 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T51491 55968-55973 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T274 55977-55980 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T275 56010-56023 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T1127 56010-56015 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T277 56016-56023 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T90786 56056-56060 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T9344 56180-56188 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T77856 56189-56204 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T282 56252-56254 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T23848 56269-56273 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T17625 56302-56304 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T285 56328-56330 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T76411 56354-56356 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T22480 56406-56408 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20382 56432-56434 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T289 56458-56460 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T23836 56484-56486 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31815 56510-56512 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T292 56536-56538 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87127 56555-56557 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T93964 56626-56628 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91601 56645-56647 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T93656 56664-56666 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T26375 56740-56742 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T77524 56816-56819 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T32873 56910-56923 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T23379 56910-56912 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37336 56924-56932 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T2370 56936-56942 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T73933 56943-56948 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T50653 56952-56955 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T42320 56985-56990 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T81899 56991-57007 Chemical denotes 4-Fluorobenzoate http://purl.obolibrary.org/obo/CHEBI_27893
T9552 57085-57092 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T310 57093-57106 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T32526 57093-57095 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40996 57107-57115 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T9241 57119-57125 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T57936 57126-57131 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T64563 57135-57138 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T79903 57168-57181 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T318 57168-57173 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T27698 57174-57181 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T7101 57199-57219 Chemical denotes 4-fluorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_20364
T51290 57201-57219 Chemical denotes fluorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_24071
T28381 57215-57219 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T46812 57339-57347 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T60273 57348-57363 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T326 57411-57413 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T88966 57428-57432 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T328 57461-57463 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25584 57487-57489 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T53007 57513-57515 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39591 57559-57561 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T22988 57604-57606 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T45786 57630-57632 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T4900 57656-57658 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T97125 57682-57684 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24094 57701-57703 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42946 57772-57774 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56337 57791-57793 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14470 57810-57812 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1882 57886-57888 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T64203 57964-57967 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T20111 57973-57976 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T343 58065-58078 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T36066 58065-58067 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9618 58079-58087 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T51357 58091-58097 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T348 58098-58103 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T2775 58107-58110 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T17738 58140-58145 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T351 58240-58247 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T35648 58248-58261 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T14380 58248-58250 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47527 58262-58270 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T17117 58274-58280 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T89113 58281-58286 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T12500 58290-58293 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T40611 58323-58336 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T53583 58323-58328 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T85901 58329-58336 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T87477 58354-58374 Chemical denotes 4-chlorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_30747
T31167 58356-58374 Chemical denotes chlorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_23134|http://purl.obolibrary.org/obo/CHEBI_51967
T53497 58370-58374 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T3423 58494-58502 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T369 58503-58518 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T64316 58566-58568 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T371 58583-58587 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T372 58616-58618 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9840 58642-58644 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T53167 58668-58670 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48220 58708-58710 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T80277 58760-58762 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57111 58786-58788 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T378 58812-58814 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68385 58838-58840 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89225 58864-58866 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T381 58883-58885 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42226 58954-58956 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T383 58973-58975 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T62942 58992-58994 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T385 59068-59070 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T5217 59148-59151 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T387 59157-59160 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T42290 59249-59262 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T82154 59249-59251 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90421 59263-59271 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T4734 59275-59281 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T76315 59282-59287 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T11391 59291-59294 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T44740 59324-59329 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T80476 59428-59435 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T17330 59436-59449 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T64183 59436-59438 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T400 59450-59458 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T87264 59462-59468 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T76187 59469-59474 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T404 59478-59481 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T46479 59511-59524 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T87387 59511-59516 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T76732 59517-59524 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T409 59542-59566 Chemical denotes 2,6-dichlorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_48623
T96547 59562-59566 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T6862 59657-59659 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T2479 59674-59678 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T15870 59683-59691 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T44525 59692-59702 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T64096 59767-59769 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T21640 59775-59779 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T417 59806-59808 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T76959 59830-59832 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T77251 59854-59856 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24704 59887-59889 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24047 59911-59913 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T21248 59935-59937 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T423 59959-59961 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T76092 59984-59986 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T96814 60009-60011 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70327 60065-60067 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56820 60151-60153 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T20891 60232-60235 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T32179 60389-60402 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T74653 60389-60391 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55010 60403-60411 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T24783 60415-60421 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T80040 60422-60427 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T435 60431-60434 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T436 60464-60469 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T67469 60568-60575 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T6716 60576-60589 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T440 60576-60578 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T27269 60590-60598 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T71057 60602-60608 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T37832 60609-60614 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T445 60618-60621 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T3496 60651-60664 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T29662 60651-60656 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T52526 60657-60664 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T76420 60702-60706 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T6362 60810-60820 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T92016 60821-60834 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T453 60821-60826 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T2923 60827-60834 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T38070 60898-60900 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T80306 60906-60910 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T43354 60937-60939 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70821 60961-60963 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19448 60985-60987 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15280 61018-61020 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T463 61042-61044 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87734 61066-61068 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7633 61090-61092 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55385 61114-61116 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T21941 61139-61141 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6127 61164-61166 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T469 61220-61222 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1610 61311-61313 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T24870 61445-61458 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T472 61445-61447 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T92714 61459-61467 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T474 61471-61477 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T476 61478-61483 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T91368 61487-61490 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T15436 61520-61525 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T58230 61535-61552 Chemical denotes 2-hydroxybenzoate http://purl.obolibrary.org/obo/CHEBI_30762
T82477 61537-61552 Chemical denotes hydroxybenzoate http://purl.obolibrary.org/obo/CHEBI_24675
T47760 61630-61637 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T73517 61638-61651 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T54590 61638-61640 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20498 61652-61660 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T94492 61664-61670 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T81538 61671-61676 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T33480 61680-61683 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T23080 61713-61726 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T88395 61713-61718 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T81533 61719-61726 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T18088 61762-61766 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T5642 61886-61894 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T10616 61895-61910 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T19363 61972-61974 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46759 61980-61984 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T499 62001-62003 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9341 62017-62019 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35490 62041-62043 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T502 62065-62067 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T71559 62089-62091 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73360 62103-62105 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9054 62117-62119 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T506 62169-62171 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24379 62275-62277 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T508 62366-62368 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T35582 62445-62448 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T8877 62454-62459 Chemical denotes CHCl3 http://purl.obolibrary.org/obo/CHEBI_35255
T511 62612-62625 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T512 62612-62614 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25413 62626-62634 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T21736 62638-62644 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T7785 62645-62650 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T84926 62654-62657 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T518 62687-62692 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T519 62701-62717 Chemical denotes 2-fluorobenzoate http://purl.obolibrary.org/obo/CHEBI_27839
T90266 62703-62717 Chemical denotes fluorobenzoate http://purl.obolibrary.org/obo/CHEBI_24070
T99924 62795-62802 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T44253 62803-62816 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T524 62803-62805 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T5357 62817-62825 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T72842 62829-62835 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T85759 62836-62841 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T97580 62845-62848 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T27319 62878-62891 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T531 62878-62883 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T95641 62884-62891 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T26474 62911-62916 Chemical denotes cyano http://purl.obolibrary.org/obo/CHEBI_48819
T55911 62917-62937 Chemical denotes 2-fluorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_19577
T63746 62919-62937 Chemical denotes fluorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_24071
T24776 62933-62937 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T58646 63066-63074 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T73632 63075-63090 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T63056 63161-63163 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94802 63169-63173 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T48046 63200-63202 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90487 63224-63226 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79058 63248-63250 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T27834 63286-63288 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66852 63300-63302 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85913 63324-63326 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T548 63348-63350 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36056 63372-63374 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T62836 63396-63398 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T80609 63421-63423 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89228 63446-63448 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14019 63502-63504 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84653 63593-63595 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T52061 63670-63673 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T29765 63827-63840 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T9348 63827-63829 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25888 63841-63849 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T10525 63853-63859 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T37511 63860-63865 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T67658 63869-63872 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T95557 63902-63907 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T41294 64006-64013 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T27571 64014-64027 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T33797 64014-64016 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19899 64028-64036 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T17127 64040-64046 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T20979 64047-64052 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T24436 64056-64059 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T63617 64089-64102 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T19836 64089-64094 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T62752 64095-64102 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T39717 64120-64144 Chemical denotes 2,6-dimethylbenzoic acid http://purl.obolibrary.org/obo/CHEBI_64827
T86577 64124-64144 Chemical denotes dimethylbenzoic acid http://purl.obolibrary.org/obo/CHEBI_64810
T39212 64140-64144 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T580 64263-64271 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T80380 64272-64287 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T55207 64357-64359 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T74866 64365-64369 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T11716 64396-64398 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83028 64420-64422 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40392 64444-64446 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15135 64458-64460 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2982 64472-64474 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T78888 64496-64498 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52500 64534-64536 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T76687 64558-64560 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40106 64719-64721 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T64937 64794-64797 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T46431 64802-64807 Chemical denotes CHCl3 http://purl.obolibrary.org/obo/CHEBI_35255
T595 64958-64971 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T95039 64958-64960 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T597 64972-64980 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T35315 64984-64990 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T75048 64991-64996 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T12198 65000-65003 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T94741 65033-65038 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T603 65138-65145 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T605 65146-65159 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T11750 65146-65148 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95862 65160-65168 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T35408 65172-65178 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T87533 65179-65184 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T67929 65188-65191 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T35508 65221-65234 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T35794 65221-65226 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T76788 65227-65234 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T58822 65252-65277 Chemical denotes 2,6-dimethoxybenzoic acid http://purl.obolibrary.org/obo/CHEBI_89493
T15516 65273-65277 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T15070 65396-65404 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T64122 65405-65420 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T81298 65490-65492 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54533 65498-65502 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T622 65529-65531 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T623 65553-65555 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46651 65577-65579 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56552 65591-65593 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79428 65634-65636 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65113 65658-65660 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T81511 65682-65684 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T81900 65706-65708 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T78670 65731-65733 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86509 65756-65758 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57101 65831-65833 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T30991 65922-65924 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T72032 65998-66001 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T70397 66007-66012 Chemical denotes CHCl3 http://purl.obolibrary.org/obo/CHEBI_35255
T54206 66101-66114 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T76205 66101-66103 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54283 66115-66123 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T639 66127-66133 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T641 66134-66139 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T2659 66143-66146 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T99382 66176-66181 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T36053 66275-66282 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T84024 66283-66296 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T72558 66283-66285 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73227 66297-66305 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T64769 66309-66315 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T99752 66316-66321 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T76711 66325-66328 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T6710 66358-66371 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T56439 66358-66363 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T87053 66364-66371 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T43272 66404-66408 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T84518 66512-66522 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T25451 66523-66536 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T64172 66523-66528 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T44252 66529-66536 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T46481 66599-66601 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72289 66607-66611 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T666 66628-66630 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89315 66652-66654 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57495 66676-66678 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44704 66690-66692 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T670 66704-66706 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T671 66718-66720 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T27257 66732-66734 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46988 66746-66748 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T674 66770-66772 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T675 66794-66796 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94853 66818-66820 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T63231 66888-66890 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T16286 66979-66981 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T14704 67054-67057 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T680 67216-67221 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T681 67225-67228 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T28223 67258-67263 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T96207 67287-67295 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T684 67299-67309 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T8989 67304-67309 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T686 67318-67323 Chemical denotes bromo http://purl.obolibrary.org/obo/CHEBI_22927|http://purl.obolibrary.org/obo/CHEBI_47265
T45200 67326-67329 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T8478 67360-67366 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T36282 67367-67373 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T83154 67374-67383 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T693 67406-67409 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T46336 67435-67459 Chemical denotes 2,6-dichlorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_48623
T695 67455-67459 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T75958 67491-67497 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T97736 67498-67506 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T90033 67669-67682 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T15643 67669-67674 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T94319 67675-67682 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T39328 67710-67715 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T81342 67759-67764 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T22666 67878-67886 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T74066 67887-67902 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T31384 67973-67975 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85312 67990-67994 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T67067 68038-68040 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72314 68066-68068 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T711 68080-68082 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90477 68094-68096 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98218 68127-68129 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T65368 68169-68171 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T37154 68240-68242 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T37988 68276-68282 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T40575 68285-68288 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T87309 68319-68325 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T15226 68326-68332 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T71708 68350-68358 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T84983 68377-68382 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T723 68385-68391 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T70140 68403-68419 Chemical denotes pyrrolidin-2-one http://purl.obolibrary.org/obo/CHEBI_36592
T48078 68420-68433 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T8628 68457-68460 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T92797 68461-68464 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T24507 68490-68493 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T64579 68535-68537 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T4261 68581-68589 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T97970 68709-68716 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T81782 68793-68799 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T74303 68839-68852 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T61396 68839-68844 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T89842 68845-68852 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T65022 68932-68937 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T8881 69020-69022 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T68823 69037-69041 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T743 69048-69056 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T78694 69057-69067 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T745 69095-69097 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T61338 69099-69118 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T3870 69131-69137 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T57417 69140-69143 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T92113 69174-69180 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T3316 69181-69187 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T18208 69220-69222 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73895 69228-69232 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T54705 69258-69260 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9003 69272-69274 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95148 69296-69298 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46407 69321-69323 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29864 69346-69348 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48792 69360-69362 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T760 69374-69376 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T761 69388-69390 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38397 69402-69404 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72464 69416-69418 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73628 69430-69432 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T33402 69444-69446 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T766 69532-69534 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T68140 69611-69614 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T768 69779-69785 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T46442 69786-69791 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T40784 69795-69798 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T772 69828-69833 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T97390 69917-69919 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T774 69921-69940 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T5508 69953-69959 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T26823 69962-69965 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T2423 69996-70002 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T28917 70003-70009 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T82726 70051-70070 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T80982 70071-70076 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T782 70080-70083 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T77931 70113-70118 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T784 70119-70139 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T36317 70227-70229 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T3451 70244-70248 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T89696 70259-70267 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T41704 70268-70278 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T50597 70349-70351 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T77382 70357-70361 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T2563 70387-70389 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9467 70425-70427 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T26116 70450-70452 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T59212 70475-70477 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83656 70489-70491 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T62470 70503-70505 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36387 70517-70519 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99952 70531-70533 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44278 70545-70547 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11106 70559-70561 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T801 70573-70575 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2297 70661-70663 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T36011 70742-70745 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T96004 70846-70848 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T26145 70896-70902 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T97987 70903-70908 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T16126 70912-70915 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T34684 70945-70950 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T74104 71034-71036 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T73494 71037-71043 Chemical denotes acetyl http://purl.obolibrary.org/obo/CHEBI_40574|http://purl.obolibrary.org/obo/CHEBI_46887
T42703 71056-71068 Chemical denotes chloroacetyl http://purl.obolibrary.org/obo/CHEBI_60669
T73085 71100-71102 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T54639 71103-71109 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T6066 71153-71172 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T33483 71176-71182 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T97706 71183-71188 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T70759 71192-71195 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T56418 71225-71230 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T18623 71231-71251 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T24226 71373-71381 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T27925 71382-71397 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T73984 71461-71463 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T827 71469-71473 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T42368 71499-71501 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99725 71523-71525 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T30893 71567-71569 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T5793 71592-71594 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75720 71606-71608 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66104 71620-71622 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T34056 71648-71650 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85882 71662-71664 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T836 71676-71678 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19325 71771-71773 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T86821 71853-71856 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T3508 71861-71866 Chemical denotes EtOAc http://purl.obolibrary.org/obo/CHEBI_27750
T56900 72009-72011 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99865 72012-72024 Chemical denotes Benzimidazol http://purl.obolibrary.org/obo/CHEBI_36622
T33937 72041-72047 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T96959 72048-72053 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T3582 72057-72060 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T93827 72090-72095 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T56185 72199-72205 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T13156 72208-72211 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T9056 72242-72248 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T66361 72249-72255 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T6884 72256-72261 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T73915 72262-72270 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T16806 72272-72285 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T4138 72289-72296 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T857 72297-72306 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1150 72297-72299 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68704 72300-72306 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T94522 72309-72320 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T73856 72350-72369 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T863 72373-72379 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T23817 72380-72385 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T56409 72389-72392 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T34890 72422-72427 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T868 72428-72448 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T54365 72453-72487 Chemical denotes 1H-benzimidazole-2-carboxylic acid http://purl.obolibrary.org/obo/CHEBI_46117
T58462 72453-72469 Chemical denotes 1H-benzimidazole http://purl.obolibrary.org/obo/CHEBI_41275
T80761 72453-72455 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84904 72456-72469 Chemical denotes benzimidazole http://purl.obolibrary.org/obo/CHEBI_36622
T45612 72472-72487 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T87122 72483-72487 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T875 72606-72614 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T89803 72615-72630 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T51988 72698-72700 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54835 72706-72710 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T33731 72727-72729 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T92838 72751-72753 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T88564 72775-72777 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60324 72799-72801 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T97684 72852-72854 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T80754 72877-72879 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35133 72919-72921 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60607 72947-72949 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65260 73014-73016 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T69025 73249-73264 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T50605 73281-73287 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T10099 73288-73293 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T892 73297-73300 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T87185 73330-73335 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T50783 73433-73440 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T55467 73441-73454 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T26971 73441-73443 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95635 73455-73463 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T46198 73467-73473 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T12400 73474-73479 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T17502 73483-73486 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T68028 73516-73529 Chemical denotes butyl acetate http://purl.obolibrary.org/obo/CHEBI_31328
T79654 73516-73521 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T4229 73522-73529 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T88027 73558-73564 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T908 73567-73570 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T16652 73601-73607 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T19988 73608-73614 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T62244 73618-73624 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T21601 73625-73627 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T90197 73634-73649 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T96677 73682-73706 Chemical denotes 2,6-dichlorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_48623
T23465 73702-73706 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T76208 73860-73864 Chemical denotes MeCN http://purl.obolibrary.org/obo/CHEBI_38472
T43038 73881-73885 Chemical denotes AcOH http://purl.obolibrary.org/obo/CHEBI_15366
T85290 73889-73894 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T76232 73911-73915 Chemical denotes AcOH http://purl.obolibrary.org/obo/CHEBI_15366
T922 73986-73988 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T30289 74003-74007 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T924 74033-74035 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66446 74057-74059 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86069 74071-74073 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T34148 74123-74125 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89634 74142-74144 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70943 74156-74158 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43516 74175-74177 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T76066 74194-74196 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T58831 74232-74234 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87003 74308-74310 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T27881 74386-74389 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T13099 74520-74522 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T68219 74556-74562 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T99043 74565-74568 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T91353 74599-74605 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T62725 74606-74612 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T37317 74616-74622 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T30108 74699-74701 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T11556 74703-74722 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T12506 74735-74741 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T55873 74744-74747 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T74812 74778-74784 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T31730 74785-74791 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T950 74824-74827 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T63866 74831-74838 Chemical denotes t-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T60099 74833-74838 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T54817 74840-74843 Chemical denotes Ala http://purl.obolibrary.org/obo/CHEBI_16977|http://purl.obolibrary.org/obo/CHEBI_46217
T955 74971-74979 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T956 74980-74990 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T957 75054-75056 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T958 75062-75066 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T959 75092-75094 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T960 75106-75108 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T961 75130-75132 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T962 75155-75157 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T963 75180-75182 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T964 75194-75196 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T965 75208-75210 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T966 75232-75234 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T967 75256-75258 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T968 75270-75272 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T969 75284-75286 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T970 75298-75300 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T971 75359-75361 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T972 75431-75434 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T973 75465-75471 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T975 75472-75478 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T976 75480-75482 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T977 75484-75503 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T978 75507-75513 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T980 75590-75600 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T981 75595-75600 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T982 75632-75635 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T983 75666-75672 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T985 75673-75679 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T986 75680-75685 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T987 75708-75718 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T988 75719-75728 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T989 75746-75749 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T990 75753-75760 Chemical denotes t-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T991 75755-75760 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T992 75762-75765 Chemical denotes Ala http://purl.obolibrary.org/obo/CHEBI_16977|http://purl.obolibrary.org/obo/CHEBI_46217
T994 75857-75859 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T995 75874-75878 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T996 75887-75895 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T997 75896-75906 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T998 75977-75979 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T999 75985-75989 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1000 76015-76017 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1001 76029-76031 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1002 76067-76069 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1003 76125-76127 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1004 76139-76141 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1005 76167-76169 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1006 76181-76183 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1007 76195-76197 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1008 76256-76258 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1009 76335-76338 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1010 76369-76375 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1012 76376-76382 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1013 76383-76388 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1014 76389-76397 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1015 76420-76427 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1017 76428-76437 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1018 76428-76430 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1019 76431-76437 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1020 76440-76451 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1022 76547-76550 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1023 76581-76587 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1025 76588-76594 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1026 76595-76600 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1027 76623-76633 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T1028 76637-76644 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1030 76645-76654 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1031 76645-76647 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1032 76648-76654 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1033 76657-76668 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1035 76711-76714 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1036 76745-76751 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1038 76752-76758 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1039 76760-76762 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1040 76764-76783 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1041 76787-76793 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1043 76927-76935 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1044 76936-76946 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1045 77015-77017 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1046 77032-77036 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1047 77053-77055 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1048 77095-77097 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1049 77133-77135 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1050 77157-77159 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1051 77181-77183 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1052 77195-77197 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1053 77239-77241 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1054 77281-77283 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1055 77295-77297 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1056 77309-77311 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1057 77347-77349 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1058 77423-77431 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1059 77437-77440 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T1060 77594-77597 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1061 77628-77634 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1063 77635-77641 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1064 77642-77647 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1065 77648-77656 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1066 77679-77686 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1068 77687-77696 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1069 77687-77689 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1070 77690-77696 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1071 77699-77710 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1073 77793-77799 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1074 77802-77805 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1075 77836-77842 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1077 77843-77849 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1078 77850-77855 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1079 77856-77864 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1080 77866-77879 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1081 77883-77890 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1083 77891-77900 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1084 77891-77893 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1085 77894-77900 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1086 77903-77914 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1088 77932-77934 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1089 77936-77955 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1090 77968-77974 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1091 77977-77980 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1092 78011-78017 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1094 78018-78024 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1095 78028-78034 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1097 78177-78185 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1098 78186-78196 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1099 78265-78267 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1100 78282-78286 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1101 78315-78317 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1102 78341-78343 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1103 78367-78369 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1104 78381-78383 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1105 78407-78409 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1106 78433-78435 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1107 78459-78461 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1108 78485-78487 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1109 78504-78506 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1110 78575-78577 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1111 78594-78596 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1112 78613-78615 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1113 78646-78648 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1114 78684-78686 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1115 78818-78821 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1116 78852-78858 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1118 78859-78865 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1119 78866-78871 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1120 78872-78880 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1121 78903-78910 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1123 78911-78920 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1124 78911-78913 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1125 78914-78920 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1126 78923-78934 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1128 79017-79024 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T1129 79027-79030 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1130 79061-79067 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1132 79068-79074 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1133 79075-79080 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1134 79081-79089 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1135 79091-79104 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1136 79108-79115 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1138 79116-79125 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1139 79116-79118 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1140 79119-79125 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1141 79128-79139 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1143 79177-79183 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1144 79186-79189 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1145 79220-79226 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1147 79227-79233 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1148 79234-79239 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1149 79240-79248 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T17569 79271-79278 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1152 79279-79288 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1153 79279-79281 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1154 79282-79288 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1155 79291-79302 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1157 79430-79438 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1158 79439-79449 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1159 79514-79516 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1160 79670-79677 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T1161 79680-79683 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1162 79714-79720 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1164 79721-79727 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1165 79728-79733 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1166 79735-79745 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T1167 79749-79756 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1169 79757-79766 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1170 79757-79759 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1171 79760-79766 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1172 79769-79780 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1174 79832-79835 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1175 79866-79872 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1177 79873-79879 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1178 79880-79885 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1179 79886-79894 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1180 79917-79924 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1182 79925-79934 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1183 79925-79927 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1184 79928-79934 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1185 79937-79948 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1187 80067-80075 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1188 80076-80086 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1189 80151-80153 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1190 80159-80163 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1191 80180-80182 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1192 80204-80206 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1193 80228-80230 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1194 80242-80244 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1195 80256-80258 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1196 80280-80282 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1197 80304-80306 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1198 80328-80330 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1199 80352-80354 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1200 80366-80368 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1201 80380-80382 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1202 80409-80411 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1203 80438-80440 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1204 80480-80482 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1205 80494-80496 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1206 80508-80510 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1207 80537-80539 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1208 80556-80558 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1209 80631-80634 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T1210 80791-80798 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1212 80801-80804 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1213 80835-80841 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1215 80842-80848 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1216 80849-80854 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1217 80855-80863 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1218 80884-80893 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1219 80884-80886 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1220 80887-80893 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1221 80896-80907 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1223 80972-80979 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1225 81000-81007 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1227 81010-81013 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1228 81044-81050 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1230 81051-81057 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1231 81058-81063 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1232 81064-81072 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1233 81090-81099 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1234 81090-81092 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1235 81093-81099 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1236 81102-81113 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1238 81151-81158 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T1239 81161-81164 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1240 81195-81201 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1242 81202-81208 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1243 81209-81214 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1244 81215-81223 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1245 81246-81253 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1247 81254-81263 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1248 81254-81256 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1249 81257-81263 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1250 81266-81277 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1252 81399-81407 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1253 81408-81418 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1254 81484-81486 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1255 81501-81505 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1256 81522-81524 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1257 81548-81550 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1258 81562-81564 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1259 81576-81578 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1260 81602-81604 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1261 81628-81630 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1262 81654-81656 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1263 81673-81675 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1264 81692-81694 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1265 81711-81713 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1266 81738-81740 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1267 81804-81806 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1268 81823-81825 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1269 81842-81844 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1270 81861-81863 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1271 81899-81901 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1272 82031-82034 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1273 82065-82071 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1275 82072-82078 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1276 82079-82084 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1277 82085-82093 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1278 82095-82108 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1279 82112-82119 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1281 82120-82129 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1282 82120-82122 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1283 82123-82129 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1284 82132-82143 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1286 82150-82158 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1287 82182-82188 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1288 82191-82194 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1289 82225-82231 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1291 82232-82238 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1292 82239-82244 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1293 82245-82253 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1294 82255-82268 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1295 82272-82279 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1297 82280-82289 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1298 82280-82282 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1299 82283-82289 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1300 82292-82303 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1302 82342-82346 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T1303 82369-82372 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T1304 82416-82418 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1305 82443-82451 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1306 82469-82475 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T1307 82476-82484 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T1308 82602-82615 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T1309 82602-82607 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T1311 82608-82615 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1313 82649-82654 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T1314 82703-82708 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T1315 82760-82767 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1317 82768-82781 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T1318 82768-82770 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1319 82782-82790 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1320 82794-82800 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T1322 82801-82806 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1323 82810-82813 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1324 82843-82848 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1325 82849-82867 Chemical denotes oxo(phenyl)acetate http://purl.obolibrary.org/obo/CHEBI_36656
T1326 82849-82852 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1327 82853-82859 Chemical denotes phenyl http://purl.obolibrary.org/obo/CHEBI_30396
T1328 82860-82867 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1330 82892-82894 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1331 82938-82946 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1332 82975-82982 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1334 82983-82996 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T1335 82983-82985 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1336 82997-83005 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1337 83009-83015 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T1339 83016-83021 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1340 83025-83028 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1341 83058-83063 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1342 83064-83082 Chemical denotes oxo(phenyl)acetate http://purl.obolibrary.org/obo/CHEBI_36656
T1343 83064-83067 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1344 83068-83074 Chemical denotes phenyl http://purl.obolibrary.org/obo/CHEBI_30396
T1345 83075-83082 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1347 83086-83094 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1348 83137-83139 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1349 83157-83176 Chemical denotes potassium carbonate http://purl.obolibrary.org/obo/CHEBI_131526
T1350 83157-83166 Chemical denotes potassium http://purl.obolibrary.org/obo/CHEBI_26216
T1351 83167-83176 Chemical denotes carbonate http://purl.obolibrary.org/obo/CHEBI_41609
T1352 83371-83379 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1353 83380-83390 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1354 83460-83462 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1355 83468-83472 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1356 83489-83491 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1357 83513-83515 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1358 83537-83539 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1359 83551-83553 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1360 83565-83567 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1361 83589-83591 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1362 83613-83615 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1363 83637-83639 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1364 83661-83663 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1365 83704-83706 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1366 83733-83735 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1367 83775-83777 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1368 83789-83791 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1369 83803-83805 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1370 83875-83877 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1371 83945-83948 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1372 83979-83985 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1374 83986-83992 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1375 83994-83996 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1376 83998-84017 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1377 84019-84021 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1378 84022-84028 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1380 84100-84110 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T1381 84105-84110 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1382 84142-84145 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1383 84176-84182 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1385 84183-84189 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1386 84190-84195 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1387 84218-84228 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T1388 84229-84238 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T1389 84256-84259 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T1390 84262-84268 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1392 84269-84272 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T1395 84408-84416 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1396 84417-84432 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T1397 84493-84495 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1398 84510-84515 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1399 84548-84550 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1400 84562-84564 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1401 84671-84673 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1402 84792-84795 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1403 84826-84832 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1405 84833-84839 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1406 84840-84845 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1407 84846-84854 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1408 84856-84869 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1409 84873-84880 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1411 84883-84889 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1413 84890-84899 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1414 84890-84892 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1415 84893-84899 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1416 84902-84913 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1418 85004-85007 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1419 85038-85044 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1421 85045-85051 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1422 85052-85057 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1423 85080-85090 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T1424 85094-85101 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1426 85102-85111 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1427 85102-85104 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1428 85105-85111 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1429 85114-85125 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1431 85168-85171 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1432 85202-85208 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1434 85209-85215 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1435 85217-85219 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1436 85221-85240 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1437 85242-85244 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1438 85245-85251 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1440 85401-85409 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1441 85410-85425 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T1442 85483-85485 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1443 85500-85505 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1444 85518-85520 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1445 85532-85534 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1446 85577-85579 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1447 85603-85605 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1824 85617-85619 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1449 85643-85645 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1450 85657-85659 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1451 85676-85678 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1452 85690-85692 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1453 85808-85810 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1454 85853-85855 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1455 85867-85869 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1456 85891-85893 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1457 85899-85901 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T1458 85969-85972 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1459 86003-86009 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1461 86010-86016 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1462 86017-86022 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1463 86023-86031 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1464 86033-86046 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1465 86050-86057 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1467 86060-86066 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1469 86067-86076 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1470 86067-86069 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1471 86070-86076 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1472 86079-86090 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1474 86193-86200 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T1475 86203-86206 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1476 86237-86243 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1478 86244-86250 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1479 86251-86256 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1480 86258-86268 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T1481 86272-86279 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1483 86280-86289 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1484 86280-86282 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1485 86283-86289 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1486 86292-86303 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1488 86355-86358 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1489 86389-86395 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1491 86396-86402 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1492 86403-86408 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1493 86409-86417 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1494 86419-86432 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1495 86436-86443 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1497 86446-86452 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1499 86453-86462 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1500 86453-86455 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1501 86456-86462 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1502 86465-86476 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1504 86614-86622 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1505 86623-86638 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T1506 86697-86699 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1507 86714-86719 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1508 86733-86735 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1509 86747-86749 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1510 86773-86775 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1511 86799-86801 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1512 86825-86827 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1513 86851-86853 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1514 86865-86867 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1515 86884-86886 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1516 86903-86905 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1517 86974-86976 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1518 86993-86995 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1519 87036-87038 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1520 87044-87046 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T1521 87085-87087 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1522 87121-87127 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1523 87130-87133 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1524 87164-87170 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1526 87171-87177 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1527 87253-87255 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1528 87257-87276 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1529 87289-87295 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1530 87298-87301 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1531 87332-87338 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1533 87339-87345 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1534 87378-87381 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T1535 87481-87483 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T1536 87499-87503 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T1537 87514-87522 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1538 87523-87533 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1539 87604-87606 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1540 87612-87616 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1541 87642-87644 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1542 87656-87658 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1543 87680-87682 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1544 87705-87707 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1545 87756-87758 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1546 87763-87765 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1547 87777-87779 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1548 87791-87793 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1549 87805-87807 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1550 87819-87821 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1551 87833-87835 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1552 87847-87849 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1553 87861-87863 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1554 87937-87939 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1555 88013-88016 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1556 88047-88053 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1558 88054-88060 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1559 88061-88066 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1560 88067-88075 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1561 88076-88082 Chemical denotes pentyl http://purl.obolibrary.org/obo/CHEBI_25902
T1562 88086-88093 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1564 88094-88103 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1565 88094-88096 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1566 88097-88103 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1567 88106-88117 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1569 88195-88201 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1570 88204-88207 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1571 88238-88244 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1573 88245-88251 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1574 88252-88257 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1575 88258-88266 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1576 88268-88281 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1577 88285-88292 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1579 88293-88302 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1580 88293-88295 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1581 88296-88302 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1582 88305-88316 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1584 88334-88336 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1585 88338-88357 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1586 88370-88376 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1587 88379-88382 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1588 88413-88419 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1590 88420-88426 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1591 88575-88583 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1592 88584-88594 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1593 88664-88666 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1594 88672-88676 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1595 88693-88695 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1596 88717-88719 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1597 88741-88743 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1598 88755-88757 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1599 88769-88771 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1600 88793-88795 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1601 88817-88819 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1602 88841-88843 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1603 88866-88868 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1604 88891-88893 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1605 88905-88907 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1606 88919-88921 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1607 88961-88963 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1608 88975-88977 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1609 88989-88991 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43246 89051-89053 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1611 89224-89227 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1612 89258-89264 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1614 89265-89271 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1615 89272-89277 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1616 89278-89286 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1617 89287-89293 Chemical denotes pentyl http://purl.obolibrary.org/obo/CHEBI_25902
T1618 89297-89304 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1620 89305-89314 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1621 89305-89307 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1622 89308-89314 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1623 89317-89328 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1625 89411-89418 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T1626 89421-89424 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1627 89455-89461 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1629 89462-89468 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1630 89469-89474 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1631 89475-89483 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1632 89485-89498 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1633 89502-89509 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1635 89510-89519 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1636 89510-89512 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1637 89513-89519 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1638 89522-89533 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1640 89574-89580 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1641 89583-89586 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1642 89617-89623 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1644 89624-89630 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1645 89631-89636 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1646 89637-89645 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1647 89646-89652 Chemical denotes pentyl http://purl.obolibrary.org/obo/CHEBI_25902
T1648 89656-89663 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1650 89664-89673 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1651 89664-89666 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1652 89667-89673 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1653 89676-89687 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1655 89814-89822 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1656 89823-89833 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1657 89896-89898 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1658 89904-89908 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1659 89925-89927 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1660 89949-89951 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1661 89973-89975 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1662 89987-89989 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1663 90001-90003 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1664 90025-90027 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1665 90049-90051 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1666 90073-90075 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1667 90097-90099 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1668 90140-90142 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1669 90169-90171 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1670 90211-90213 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1671 90225-90227 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1672 90239-90241 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1673 90301-90303 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1674 90376-90379 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T1675 90384-90397 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T1676 90384-90389 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T1678 90390-90397 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1680 90537-90569 Chemical denotes (9H-Fluoren-9-ylmethoxy)carbonyl http://purl.obolibrary.org/obo/CHEBI_48605
T1681 90541-90548 Chemical denotes Fluoren http://purl.obolibrary.org/obo/CHEBI_28266
T1682 90561-90569 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1683 90573-90579 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1685 90600-90608 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1686 90615-90647 Chemical denotes (9H-fluoren-9-ylmethoxy)carbonyl http://purl.obolibrary.org/obo/CHEBI_48605
T1687 90639-90647 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1688 90651-90657 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1690 90660-90670 Chemical denotes norleucine http://purl.obolibrary.org/obo/CHEBI_18347|http://purl.obolibrary.org/obo/CHEBI_36405
T1692 90693-90701 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1693 90719-90726 Chemical denotes toluene http://purl.obolibrary.org/obo/CHEBI_17578
T1694 90772-90775 Chemical denotes TMS http://purl.obolibrary.org/obo/CHEBI_85361
T1695 90776-90788 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T1696 90805-90811 Chemical denotes hexane http://purl.obolibrary.org/obo/CHEBI_29021
T1697 90872-90875 Chemical denotes TMS http://purl.obolibrary.org/obo/CHEBI_85361
T1698 90876-90888 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T1699 90999-91003 Chemical denotes AcOH http://purl.obolibrary.org/obo/CHEBI_15366
T1700 91118-91131 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T1701 91118-91123 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T1703 91124-91131 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1705 91132-91138 Chemical denotes hexane http://purl.obolibrary.org/obo/CHEBI_29021
T1706 91199-91201 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1707 91216-91221 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1708 91356-91358 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1709 91401-91403 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1710 91434-91436 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1711 91453-91455 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1712 91472-91474 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1713 91544-91546 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1714 91625-91631 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1716 91652-91660 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1717 91664-91670 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1719 91674-91706 Chemical denotes (9H-fluoren-9-ylmethoxy)carbonyl http://purl.obolibrary.org/obo/CHEBI_48605
T1720 91698-91706 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1721 91710-91716 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1723 91755-91758 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T1724 91777-91779 Chemical denotes KF http://purl.obolibrary.org/obo/CHEBI_73605
T1725 91813-91826 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T1726 91853-91878 Chemical denotes di-tert-butyl dicarbonate http://purl.obolibrary.org/obo/CHEBI_48500
T1727 91856-91866 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T1728 91861-91866 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1729 91900-91907 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1730 92018-92025 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1731 92063-92065 Chemical denotes KF http://purl.obolibrary.org/obo/CHEBI_73605
T1732 92133-92140 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1733 92158-92171 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T1734 92166-92171 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T1735 92200-92206 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T1736 92224-92241 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T1737 92237-92241 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T1738 92255-92261 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T1739 92301-92306 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T1740 92326-92334 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T1741 92452-92467 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T1742 92468-92474 Chemical denotes hexane http://purl.obolibrary.org/obo/CHEBI_29021
T1743 92533-92535 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1744 92550-92555 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1745 92580-92582 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1746 92599-92601 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1747 92632-92634 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1748 92737-92739 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1749 92745-92747 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T1750 92778-92780 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T1751 92811-92817 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1753 92820-92830 Chemical denotes norleucine http://purl.obolibrary.org/obo/CHEBI_18347|http://purl.obolibrary.org/obo/CHEBI_36405
T1755 92836-92844 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1756 92848-92854 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1758 92858-92877 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1759 92881-92887 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1761 92926-92929 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T1764 92958-92966 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1765 92990-92994 Chemical denotes LiOH http://purl.obolibrary.org/obo/CHEBI_33979
T1766 93041-93048 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1767 93173-93190 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T1768 93186-93190 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T1769 93210-93223 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T1770 93210-93215 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T1772 93216-93223 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1774 93303-93308 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T1775 93328-93335 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T1776 93414-93416 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1777 93431-93436 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1778 93461-93463 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1779 93480-93482 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1780 93518-93520 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1781 93537-93539 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1782 93570-93572 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1783 93623-93625 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1784 93631-93633 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T1785 93664-93666 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T1786 93671-93673 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1787 93707-93713 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1788 93716-93719 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1789 93750-93756 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1791 93757-93763 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1792 93767-93773 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1794 93848-93850 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1795 93852-93871 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1796 93884-93890 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1797 93893-93896 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1798 93927-93933 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1800 93934-93940 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1801 93976-93995 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1802 93999-94005 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1804 94008-94018 Chemical denotes norleucine http://purl.obolibrary.org/obo/CHEBI_18347|http://purl.obolibrary.org/obo/CHEBI_36405
T1806 94155-94163 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1807 94164-94179 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T1808 94245-94247 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1809 94262-94266 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1810 94294-94296 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1811 94308-94310 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1812 94334-94336 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1813 94372-94374 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1814 94386-94388 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1815 94412-94414 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1816 94431-94433 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1817 94450-94452 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1818 94469-94471 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1819 94488-94490 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1820 94611-94613 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1821 94619-94621 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T1822 94656-94658 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708
T1823 94692-94695 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T21200 94726-94732 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1826 94733-94739 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1827 94740-94745 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1828 94746-94754 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1829 94774-94781 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1831 94782-94791 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1832 94782-94784 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1833 94785-94791 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1834 94794-94805 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1836 94883-94889 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1837 94892-94895 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1838 94926-94932 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1840 94933-94939 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1841 94940-94945 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1842 94946-94954 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1843 94956-94969 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1844 94973-94980 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1846 94981-94990 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1847 94981-94983 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1848 94984-94990 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1849 94993-95004 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1851 95022-95024 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1852 95026-95045 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T1853 95058-95064 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1854 95067-95070 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1855 95101-95107 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1857 95108-95114 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1858 95118-95124 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1860 95278-95286 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1861 95287-95297 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1862 95362-95364 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1863 95370-95374 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1864 95391-95393 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1865 95415-95417 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1866 95439-95441 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1867 95453-95455 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1868 95467-95469 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1869 95491-95493 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1870 95515-95517 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1871 95539-95541 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1872 95567-95569 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1873 95581-95583 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1874 95623-95625 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1875 95637-95639 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1876 95651-95653 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1877 95737-95739 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1878 95878-95881 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1879 95912-95918 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1881 95919-95925 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T44400 95926-95931 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1883 95932-95940 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1884 95960-95967 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1886 95968-95977 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1887 95968-95970 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1888 95971-95977 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1889 95980-95991 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1891 96074-96081 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T1892 96084-96087 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1893 96118-96124 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1895 96125-96131 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1896 96132-96137 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1897 96138-96146 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1898 96148-96161 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1899 96165-96172 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1901 96173-96182 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1902 96173-96175 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1903 96176-96182 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1904 96185-96196 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1906 96234-96240 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1907 96243-96246 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1908 96277-96283 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1910 96284-96290 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1911 96291-96296 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1912 96297-96305 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1913 96325-96332 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1915 96333-96342 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1916 96333-96335 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1917 96336-96342 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1918 96345-96356 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1920 96485-96493 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1921 96494-96504 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1922 96568-96570 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1923 96576-96580 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1924 96597-96599 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1925 96621-96623 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1926 96645-96647 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1927 96659-96661 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1928 96673-96675 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1929 96697-96699 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1930 96721-96723 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1931 96745-96747 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1932 96769-96771 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1933 96817-96819 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1934 96846-96848 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1935 96888-96890 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1936 96902-96904 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1937 96916-96918 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1938 97002-97004 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1939 97148-97151 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1940 97182-97188 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1942 97189-97195 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1943 97196-97201 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1944 97224-97234 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T1945 97235-97244 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T74760 97250-97258 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T79325 97262-97272 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T98057 97267-97272 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T22604 97295-97298 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T25590 97329-97335 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T71034 97336-97342 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T7146 97343-97352 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T64367 97376-97383 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T97507 97405-97422 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T47345 97418-97422 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T86277 97423-97430 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T33926 97447-97455 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T50802 97522-97530 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T66031 97570-97577 Chemical denotes toluene http://purl.obolibrary.org/obo/CHEBI_17578
T70328 97630-97643 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T42778 97644-97648 Chemical denotes salt http://purl.obolibrary.org/obo/CHEBI_24866|http://purl.obolibrary.org/obo/CHEBI_26710
T49099 97664-97667 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T36941 97684-97692 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T53628 97728-97731 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T38411 97947-97952 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T50847 97970-97977 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T50559 97997-98010 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T93140 98005-98010 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T31300 98062-98067 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T91535 98087-98095 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T36747 98208-98216 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T28856 98217-98232 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T50448 98363-98365 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38103 98380-98385 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1914 98410-98412 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37713 98443-98445 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24526 98469-98471 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44060 98483-98485 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29984 98510-98512 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68855 98537-98539 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36398 98704-98707 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T68180 98738-98744 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T23806 98745-98751 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T43660 98752-98757 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T81179 98780-98790 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T16323 98794-98801 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T59723 98802-98811 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T83326 98802-98804 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54917 98805-98811 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T90295 98814-98825 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T63164 98831-98839 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T59444 98843-98853 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T35775 98848-98853 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T40975 98885-98888 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T93872 98919-98925 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T74567 98926-98932 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T69512 98933-98938 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T20884 98961-98971 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T5959 98972-98981 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T56743 99005-99012 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T53389 99034-99051 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T42433 99047-99051 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T4011 99052-99059 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T75071 99076-99084 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T51684 99151-99159 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T36338 99199-99206 Chemical denotes toluene http://purl.obolibrary.org/obo/CHEBI_17578
T93903 99259-99272 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T66847 99273-99277 Chemical denotes salt http://purl.obolibrary.org/obo/CHEBI_24866|http://purl.obolibrary.org/obo/CHEBI_26710
T48542 99293-99296 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T25345 99313-99321 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T18497 99357-99364 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T14391 99365-99371 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T25234 99374-99389 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T15706 99385-99389 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T72172 99583-99588 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T37051 99606-99613 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T9365 99633-99646 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T51737 99641-99646 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T21849 99699-99704 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T33310 99743-99748 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T79743 99768-99776 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T76543 99897-99905 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T18868 99906-99921 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T41848 100071-100073 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47509 100088-100093 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T15859 100106-100108 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42303 100132-100134 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6599 100177-100179 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38218 100203-100205 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14852 100229-100231 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83387 100248-100250 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79575 100274-100276 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94704 100288-100290 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84391 100302-100304 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T97905 100316-100318 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T3346 100343-100345 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41450 100370-100372 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T49284 100397-100399 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2691 100424-100426 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T53090 100476-100478 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55404 100490-100492 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40430 100528-100530 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20957 100571-100573 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T108 100657-100664 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T75685 100667-100670 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T27382 100701-100707 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T45473 100708-100714 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T41599 100715-100720 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T51393 100722-100732 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T85773 100736-100743 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T55280 100744-100753 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T35054 100744-100746 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86527 100747-100753 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T82746 100756-100767 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T69959 100778-100786 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T89092 100823-100826 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T42124 100857-100863 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T96403 100864-100870 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T85316 100871-100876 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T23127 100899-100909 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T5211 100913-100920 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T66026 100921-100930 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T94179 100921-100923 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T26412 100924-100930 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T6050 100933-100944 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T49337 100967-100971 Chemical denotes EtOH http://purl.obolibrary.org/obo/CHEBI_16236
T58326 100993-100995 Chemical denotes Pd http://purl.obolibrary.org/obo/CHEBI_33363
T68828 101075-101077 Chemical denotes H2 http://purl.obolibrary.org/obo/CHEBI_18276
T7886 101107-101115 Chemical denotes catalyst http://purl.obolibrary.org/obo/CHEBI_35223
T20259 101151-101159 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T52048 101284-101292 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T11858 101293-101308 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T96551 101368-101370 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65169 101402-101404 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6691 101428-101430 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42762 101454-101456 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57781 101480-101482 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T51145 101560-101562 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83196 101579-101581 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72340 101598-101600 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35423 101636-101638 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10973 101679-101681 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T27769 101757-101760 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T21249 101862-101868 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T69136 101871-101874 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T17599 101905-101911 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T9892 101912-101918 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T19230 101922-101939 Chemical denotes phenylalaninamide http://purl.obolibrary.org/obo/CHEBI_21371
T33680 101997-101999 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T87508 102001-102020 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T90688 102033-102039 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T85873 102042-102045 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T13091 102076-102082 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T86710 102083-102089 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T29648 102122-102125 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T47981 102126-102129 Chemical denotes Phe http://purl.obolibrary.org/obo/CHEBI_17295|http://purl.obolibrary.org/obo/CHEBI_29997
T89287 102268-102276 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T5237 102277-102292 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T93823 102353-102355 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90226 102370-102375 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T95940 102388-102390 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91093 102421-102423 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T18151 102447-102449 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T17831 102466-102468 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T81758 102480-102482 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T32769 102556-102558 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56438 102575-102577 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24078 102594-102596 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90628 102632-102634 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T19605 102640-102642 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T65045 102702-102705 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T4382 102736-102742 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T37560 102743-102749 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T78880 102757-102764 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T31050 102765-102778 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T23536 102765-102767 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44895 102779-102787 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T68911 102791-102808 Chemical denotes phenylalaninamide http://purl.obolibrary.org/obo/CHEBI_21371
T85128 102886-102892 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T16482 102895-102898 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T52838 102929-102935 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T7376 102936-102942 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T96266 102943-102948 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T8256 102949-102957 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T60449 102959-102972 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T28806 102976-102983 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T20881 102984-102993 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T98928 102984-102986 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87171 102987-102993 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T83064 102996-103007 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T81926 103028-103047 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T54816 103059-103065 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T52496 103068-103071 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T79162 103102-103108 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T50557 103109-103115 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T73976 103119-103136 Chemical denotes phenylalaninamide http://purl.obolibrary.org/obo/CHEBI_21371
T66397 103274-103282 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T28248 103283-103298 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T23370 103359-103361 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42571 103376-103380 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T80029 103409-103411 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31051 103435-103437 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39463 103461-103463 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73098 103475-103477 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11300 103527-103529 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T22367 103579-103581 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29269 103593-103595 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35866 103619-103621 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T13469 103645-103647 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87006 103659-103661 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56958 103730-103732 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47490 103749-103751 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39016 103768-103770 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44950 103792-103794 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T28369 103861-103864 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T12835 103895-103901 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T80677 103902-103908 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T17859 103916-103923 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T7065 103924-103937 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T92099 103924-103926 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43403 103938-103946 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T51598 103950-103967 Chemical denotes phenylalaninamide http://purl.obolibrary.org/obo/CHEBI_21371
T51479 104050-104057 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T4347 104060-104063 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T40276 104094-104100 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T95406 104101-104107 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T22791 104108-104113 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T65875 104114-104122 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T87134 104124-104137 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T13948 104141-104148 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T99354 104149-104158 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T82374 104149-104151 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T58026 104152-104158 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T74351 104161-104172 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T67119 104200-104206 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T9916 104209-104212 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T4652 104243-104249 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T96724 104250-104256 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T40234 104264-104271 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T30605 104272-104285 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T90926 104272-104274 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79164 104286-104294 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T74733 104298-104315 Chemical denotes phenylalaninamide http://purl.obolibrary.org/obo/CHEBI_21371
T42744 104454-104462 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T26550 104463-104478 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T14781 104544-104546 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83129 104561-104565 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T66087 104594-104596 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T96471 104640-104642 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95809 104685-104687 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T63196 104737-104739 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68027 104763-104765 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38372 104789-104791 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T51455 104815-104817 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T5413 104841-104843 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65537 104855-104857 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28177 104869-104871 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11461 104935-104937 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25377 104954-104956 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7201 104973-104975 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7039 104997-104999 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T78859 105075-105078 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T67263 105175-105178 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T65033 105209-105215 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T43926 105216-105222 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T16887 105223-105228 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T77334 105229-105237 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T58537 105258-105267 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T75975 105258-105260 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T77305 105261-105267 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T12280 105270-105281 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T18482 105359-105365 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T3913 105368-105371 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T17528 105402-105408 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T46489 105409-105415 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T9807 105416-105421 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T48158 105422-105430 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T69723 105432-105445 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T81751 105449-105456 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T16849 105457-105466 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T59070 105457-105459 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70034 105460-105466 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T51068 105469-105480 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T34589 105498-105500 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T45671 105502-105521 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T53546 105534-105540 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T6792 105543-105546 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T23315 105577-105583 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T89825 105584-105590 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T80551 105594-105600 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T63930 105619-105625 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T89213 105628-105643 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T96977 105639-105643 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T25472 105780-105788 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T84236 105789-105799 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T28525 105870-105872 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T18910 105878-105882 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T44223 105899-105901 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52771 105923-105925 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T21993 105947-105949 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14169 105961-105963 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36677 105985-105987 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66878 106009-106011 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T30164 106023-106025 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T69157 106047-106049 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T78349 106071-106073 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72436 106104-106106 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99712 106132-106134 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36064 106146-106148 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T34105 106160-106162 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89514 106174-106176 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86892 106212-106214 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T30542 106292-106297 Chemical denotes CHCl3 http://purl.obolibrary.org/obo/CHEBI_35255
T83745 106456-106459 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T76114 106490-106496 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T3901 106497-106503 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T352 106504-106509 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T80556 106510-106518 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T46890 106539-106548 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T48095 106539-106541 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28241 106542-106548 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T46264 106551-106562 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T50110 106645-106652 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T60530 106655-106658 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T11768 106689-106695 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T89247 106696-106702 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T90294 106703-106708 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T86763 106709-106717 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T366 106719-106732 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T78790 106736-106743 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T43521 106744-106753 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T30776 106744-106746 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9454 106747-106753 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T79856 106756-106767 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T26854 106805-106811 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T22890 106814-106817 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T53600 106848-106854 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T42371 106855-106861 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T84577 106862-106867 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T51575 106868-106876 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T91179 106897-106906 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T27726 106897-106899 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60137 106900-106906 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T83574 106909-106920 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T62945 107051-107059 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T42343 107060-107070 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T10830 107135-107137 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T21346 107143-107147 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T71779 107164-107166 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98102 107188-107190 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T33119 107212-107214 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T71777 107226-107228 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75210 107240-107242 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19469 107264-107266 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79077 107278-107280 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T50738 107302-107304 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65918 107326-107328 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90404 107350-107352 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91939 107364-107366 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44976 107378-107380 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T402 107407-107409 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75011 107436-107438 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20389 107464-107466 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52745 107478-107480 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T50565 107492-107494 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20747 107506-107508 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98778 107539-107541 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T8220 107614-107619 Chemical denotes CHCl3 http://purl.obolibrary.org/obo/CHEBI_35255
T71168 107624-107637 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T37749 107624-107629 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T14874 107630-107637 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T88676 107643-107646 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T61187 107803-107806 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T85968 107837-107843 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T84117 107844-107850 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T83483 107851-107856 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T85382 107857-107865 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T31472 107886-107895 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T24322 107886-107888 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57403 107889-107895 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T51067 107898-107909 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T42070 107974-107981 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T19254 108002-108009 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T21168 108012-108015 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T78288 108046-108052 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T70271 108053-108059 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T30845 108060-108065 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T34779 108066-108074 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T15437 108092-108101 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T15738 108092-108094 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25581 108095-108101 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T22068 108104-108115 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T83442 108153-108160 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T17431 108163-108166 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T41161 108197-108203 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T36519 108204-108210 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T61331 108211-108216 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T47970 108217-108225 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T449 108246-108255 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T17365 108246-108248 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T17081 108249-108255 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T37575 108258-108269 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T80084 108397-108405 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T96119 108406-108416 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T71814 108480-108482 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98352 108488-108492 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T24718 108509-108511 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15447 108591-108593 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57883 108605-108607 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T96176 108629-108631 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T62641 108653-108655 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2200 108667-108669 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20444 108681-108683 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T67451 108706-108708 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T16902 108731-108733 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T78000 108773-108775 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36020 108787-108789 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86594 108801-108803 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57849 108815-108817 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20594 108848-108850 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T80810 108923-108936 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T83883 108923-108928 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T9831 108929-108936 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T5541 108942-108945 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T61982 109101-109104 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T71698 109135-109141 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T56721 109142-109148 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T482 109149-109154 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T53225 109155-109163 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T84487 109184-109193 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T83320 109184-109186 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56115 109187-109193 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T14589 109196-109207 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T46073 109290-109297 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T80362 109300-109303 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T87227 109334-109340 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T56493 109341-109347 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T64530 109348-109353 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T50968 109354-109362 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T34733 109383-109392 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T47522 109383-109385 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86590 109386-109392 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T69646 109395-109406 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T6332 109424-109434 Chemical denotes iodoethane http://purl.obolibrary.org/obo/CHEBI_42487
T40783 109558-109566 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T53959 109567-109577 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T44816 109645-109647 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37387 109653-109657 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T20227 109674-109676 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85360 109698-109700 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28870 109722-109724 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T74091 109775-109777 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90759 109789-109791 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46592 109813-109815 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44815 109837-109839 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52189 109851-109853 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T59283 109865-109867 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T67493 109890-109892 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73043 109915-109917 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25045 109957-109959 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28781 109971-109973 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T93739 109985-109987 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T18825 109999-110001 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10894 110056-110058 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T42644 110180-110183 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T68514 110214-110220 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T21366 110221-110227 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T21526 110231-110237 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T39636 110238-110240 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T13874 110247-110262 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T28717 110368-110374 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T75985 110377-110380 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T93605 110411-110417 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T23417 110418-110424 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T79368 110425-110430 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T99383 110431-110439 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T20650 110441-110454 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T98371 110458-110465 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T11205 110466-110475 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T38417 110466-110468 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2963 110469-110475 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T81836 110478-110489 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T2887 110507-110509 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T82388 110511-110530 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T36552 110543-110549 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T41180 110552-110555 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T25341 110586-110592 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T67454 110593-110599 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T32311 110603-110609 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T33330 110633-110648 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T34206 110651-110666 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T93178 110662-110666 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T50341 110793-110803 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T2028 110825-110833 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T57067 110849-110857 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T40698 110876-110886 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T98231 110977-110979 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T67200 110993-111008 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T89807 111009-111017 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T95015 111020-111022 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56651 111037-111041 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T14914 111067-111069 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86751 111091-111093 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T86812 111105-111107 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T65558 111138-111140 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T50688 111157-111159 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T71028 111185-111187 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41625 111204-111206 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T77264 111223-111225 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56858 111270-111272 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99463 111308-111310 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29043 111365-111367 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T67283 111430-111433 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T52681 111464-111470 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T20921 111471-111477 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T57916 111481-111487 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T48683 111488-111490 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T31075 111497-111512 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T52657 111623-111630 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T24930 111633-111636 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T51196 111667-111673 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T13647 111674-111680 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T65438 111681-111686 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T33389 111687-111695 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T95855 111697-111710 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T96644 111714-111721 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T16002 111722-111731 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T77625 111722-111724 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T63320 111725-111731 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T55463 111734-111745 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T53751 111774-111780 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T51154 111783-111786 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T83834 111817-111823 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T8561 111824-111830 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T37297 111834-111840 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T35855 111841-111843 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T72927 111850-111865 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T5889 112050-112065 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T44322 112066-112074 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T17552 112137-112152 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T67714 112153-112161 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T71126 112188-112203 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T615 112276-112278 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T57191 112293-112308 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T46095 112309-112317 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T57606 112320-112322 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14340 112337-112341 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T45366 112367-112369 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T78885 112391-112393 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79714 112405-112407 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9816 112429-112431 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37063 112448-112450 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94111 112467-112469 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38482 112505-112507 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95396 112524-112526 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25882 112543-112545 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T4649 112581-112583 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15589 112657-112659 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T26178 112879-112882 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T18263 112913-112919 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T6843 112920-112926 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T35904 112930-112936 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T74314 112937-112939 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T92900 112946-112961 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T4349 113054-113061 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T46678 113082-113089 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T95252 113092-113095 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T88190 113126-113132 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T79875 113133-113139 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T3845 113140-113145 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T45787 113146-113154 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T18498 113172-113181 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T69767 113172-113174 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10654 113175-113181 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T64683 113184-113195 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T15598 113224-113231 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T8327 113234-113237 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T34932 113268-113274 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T29171 113275-113281 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T31199 113285-113291 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T661 113292-113294 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T51274 113301-113316 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T73260 113475-113490 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T99798 113491-113499 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T86708 113518-113533 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T38620 113632-113639 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T33106 113658-113660 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T88017 113674-113689 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T76322 113690-113698 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T86006 113701-113703 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T16015 113718-113722 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T2881 113768-113770 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11899 113792-113794 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T17370 113806-113808 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7197 113863-113865 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38393 113887-113889 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89009 113939-113941 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31599 114015-114017 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T89775 114149-114156 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T65814 114159-114162 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T51895 114193-114199 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T17086 114200-114206 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T87780 114207-114212 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T18055 114213-114221 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T38903 114223-114236 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T38323 114238-114247 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T35868 114238-114240 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54851 114241-114247 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T25452 114250-114261 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T96709 114269-114277 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T78225 114301-114308 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T53284 114311-114314 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T68087 114345-114351 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T34247 114352-114358 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T10126 114359-114364 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T17616 114365-114373 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T42313 114375-114388 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T23058 114392-114399 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T46947 114400-114409 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T8538 114400-114402 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48591 114403-114409 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T47040 114412-114423 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T81598 114445-114456 Chemical denotes iodomethane http://purl.obolibrary.org/obo/CHEBI_39282
T54246 114482-114488 Chemical denotes silver http://purl.obolibrary.org/obo/CHEBI_30512|http://purl.obolibrary.org/obo/CHEBI_9141
T62922 114492-114497 Chemical denotes oxide http://purl.obolibrary.org/obo/CHEBI_25741|http://purl.obolibrary.org/obo/CHEBI_29356
T18262 114521-114536 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T55045 114579-114581 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T54261 114684-114695 Chemical denotes iodomethane http://purl.obolibrary.org/obo/CHEBI_39282
T39240 114808-114823 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T37635 114850-114855 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T76936 114901-114906 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T26520 115028-115036 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T88534 115037-115047 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T81841 115116-115118 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79196 115124-115128 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T44195 115145-115147 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55525 115169-115171 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68136 115193-115195 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T33267 115207-115209 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T64544 115221-115223 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48541 115245-115247 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37058 115269-115271 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31005 115293-115295 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94988 115307-115309 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T13706 115321-115323 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85428 115346-115348 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T59647 115371-115373 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85409 115427-115429 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T737 115441-115443 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68386 115455-115457 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T739 115527-115529 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T74801 115663-115666 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T65750 115697-115703 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T3852 115704-115710 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T90185 115711-115716 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T57007 115717-115725 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T12166 115727-115740 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T45877 115742-115751 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T22508 115742-115744 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90512 115745-115751 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T56428 115754-115765 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T54398 115843-115849 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T34240 115852-115855 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T22447 115886-115892 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T32734 115893-115899 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T16199 115900-115905 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T54946 115906-115914 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T29365 115916-115929 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T13674 115933-115940 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T74571 115941-115950 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T80619 115941-115943 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24048 115944-115950 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T3894 115953-115964 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T27297 115982-115988 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T2161 115991-116006 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T56450 116002-116006 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T39246 116144-116152 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T33818 116153-116168 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T20847 116234-116236 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T74007 116251-116255 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T16982 116272-116274 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T63708 116298-116300 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2955 116324-116326 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44220 116369-116371 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9758 116395-116397 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T33550 116409-116411 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T69327 116435-116437 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40756 116511-116513 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90580 116530-116532 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T82858 116549-116551 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T32498 116625-116627 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T7550 116704-116707 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T31924 116738-116744 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T87725 116745-116751 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T46963 116752-116757 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T98839 116758-116766 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T70183 116768-116781 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T31478 116783-116792 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T64949 116783-116785 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46001 116786-116792 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T39824 116795-116806 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T93292 116889-116896 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T39926 116899-116902 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T24479 116933-116939 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T71379 116940-116946 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T38104 116947-116952 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T90466 116953-116961 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T61936 116963-116976 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T7882 116980-116987 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T51027 116988-116997 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T75175 116988-116990 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T17960 116991-116997 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T11063 117000-117011 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T93122 117049-117055 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T56680 117058-117061 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T35692 117092-117098 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T3494 117099-117105 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T53890 117106-117111 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T93081 117112-117120 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T44392 117122-117135 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T6187 117137-117146 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T88828 117137-117139 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T74900 117140-117146 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T24081 117149-117160 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T31330 117296-117304 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T93828 117305-117320 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T71758 117386-117388 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75834 117403-117407 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T43907 117424-117426 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T16037 117495-117497 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83963 117509-117511 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20664 117535-117537 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83646 117561-117563 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T76364 117575-117577 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T45015 117651-117653 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28626 117684-117686 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T25151 117727-117729 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T36103 117804-117807 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377
T39479 117813-117816 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T66045 117913-117916 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T23748 117947-117953 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T43983 117954-117960 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T21455 117961-117966 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T88565 117967-117975 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T21468 117977-117990 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T74384 117992-118001 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T54444 117992-117994 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35349 117995-118001 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T84005 118004-118015 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T81767 118080-118087 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T73828 118108-118115 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T66740 118118-118121 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T76597 118152-118158 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T47584 118159-118165 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T39931 118166-118171 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T28202 118172-118180 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T28596 118198-118207 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T71605 118198-118200 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T32069 118201-118207 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T20286 118210-118221 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T10780 118259-118266 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T6847 118269-118272 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T39595 118303-118309 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T86446 118310-118316 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T75226 118317-118322 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T18936 118323-118331 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T89249 118333-118346 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T39765 118348-118357 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T29747 118348-118350 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T93285 118351-118357 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T15195 118360-118371 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T79362 118512-118520 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T75763 118521-118536 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T15590 118594-118596 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75783 118602-118607 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T40557 118620-118622 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66123 118646-118648 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T87495 118672-118674 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T58676 118704-118706 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T23864 118723-118725 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28515 118749-118751 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38891 118782-118784 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2154 118808-118810 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T8346 118835-118837 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84249 118854-118856 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T36306 118868-118870 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T58223 118963-118965 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T92825 119006-119008 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T35507 119293-119298 Chemical denotes TAMRA http://purl.obolibrary.org/obo/CHEBI_52282
T5777 119330-119335 Chemical denotes TAMRA http://purl.obolibrary.org/obo/CHEBI_52282
T28848 119401-119406 Chemical denotes TAMRA http://purl.obolibrary.org/obo/CHEBI_52282
T2026 119431-119438 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T44479 119569-119574 Chemical denotes HEPES http://purl.obolibrary.org/obo/CHEBI_46756
T46139 119590-119594 Chemical denotes EDTA http://purl.obolibrary.org/obo/CHEBI_42191|http://purl.obolibrary.org/obo/CHEBI_64755
T68206 119619-119623 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T58647 119713-119723 Chemical denotes nucleotide http://purl.obolibrary.org/obo/CHEBI_36976
T40885 119914-119923 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T72511 120082-120089 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T5798 120156-120163 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T910 120262-120271 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T13364 120376-120385 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T20114 120633-120642 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T59232 120685-120695 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T76963 120835-120845 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T70486 121342-121349 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T36781 121430-121437 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T53887 121479-121486 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T22935 121673-121675 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T29474 121695-121704 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T14079 121746-121752 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T17562 121769-121773 Chemical denotes Tris http://purl.obolibrary.org/obo/CHEBI_9754
T5538 121774-121777 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T32012 121795-121799 Chemical denotes NaCl http://purl.obolibrary.org/obo/CHEBI_26710
T47682 121806-121810 Chemical denotes EDTA http://purl.obolibrary.org/obo/CHEBI_42191|http://purl.obolibrary.org/obo/CHEBI_64755
T12616 121817-121821 Chemical denotes TCEP http://purl.obolibrary.org/obo/CHEBI_63213
T32778 121833-121840 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T46679 122449-122453 Chemical denotes Base http://purl.obolibrary.org/obo/CHEBI_18282|http://purl.obolibrary.org/obo/CHEBI_22695
T9229 122604-122614 Chemical denotes phenol red http://purl.obolibrary.org/obo/CHEBI_31991
T16403 122604-122610 Chemical denotes phenol http://purl.obolibrary.org/obo/CHEBI_15882
T61020 122898-122900 Chemical denotes MT http://purl.obolibrary.org/obo/CHEBI_73614
T87606 123001-123012 Chemical denotes neutral red http://purl.obolibrary.org/obo/CHEBI_86370
T53163 123093-123095 Chemical denotes WI http://purl.obolibrary.org/obo/CHEBI_141448
T16600 123106-123117 Chemical denotes neutral red http://purl.obolibrary.org/obo/CHEBI_86370
T42830 123208-123219 Chemical denotes neutral red http://purl.obolibrary.org/obo/CHEBI_86370
T67130 123315-123321 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T31728 123322-123330 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T31154 123336-123340 Chemical denotes EtOH http://purl.obolibrary.org/obo/CHEBI_16236
T66158 123345-123356 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T49097 123352-123356 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T82790 123485-123496 Chemical denotes neutral red http://purl.obolibrary.org/obo/CHEBI_86370
T16617 123746-123757 Chemical denotes neutral red http://purl.obolibrary.org/obo/CHEBI_86370
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T57484 124223-124233 Chemical denotes phenol red http://purl.obolibrary.org/obo/CHEBI_31991
T51593 124223-124229 Chemical denotes phenol http://purl.obolibrary.org/obo/CHEBI_15882
T86896 124536-124539 Chemical denotes dye http://purl.obolibrary.org/obo/CHEBI_37958
T37376 124597-124608 Chemical denotes neutral red http://purl.obolibrary.org/obo/CHEBI_86370
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T54614 126589-126591 Chemical denotes GE http://purl.obolibrary.org/obo/CHEBI_73801
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T95650 126819-126827 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
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T979 127489-127492 Chemical denotes DTT http://purl.obolibrary.org/obo/CHEBI_18320
T98660 127553-127560 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
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T98387 128371-128379 Chemical denotes chloride http://purl.obolibrary.org/obo/CHEBI_17996
T56005 128387-128393 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
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T72082 128432-128436 Chemical denotes TCEP http://purl.obolibrary.org/obo/CHEBI_63213
T12102 128497-128504 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
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T63926 129084-129086 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T62765 129160-129177 Chemical denotes cellulose acetate http://purl.obolibrary.org/obo/CHEBI_145232
T26566 129170-129177 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T67725 129342-129345 Chemical denotes PEG http://purl.obolibrary.org/obo/CHEBI_46793
T1016 129358-129361 Chemical denotes MES http://purl.obolibrary.org/obo/CHEBI_39005|http://purl.obolibrary.org/obo/CHEBI_39010
T39607 129378-129386 Chemical denotes glycerol http://purl.obolibrary.org/obo/CHEBI_17754
T30005 129448-129455 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T15551 129491-129497 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T1021 129657-129665 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
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T72200 129743-129751 Chemical denotes glycerol http://purl.obolibrary.org/obo/CHEBI_17754
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T94758 129964-129966 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T61922 130040-130057 Chemical denotes cellulose acetate http://purl.obolibrary.org/obo/CHEBI_145232
T47664 130050-130057 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T10990 130240-130251 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T1034 130247-130251 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T35805 130272-130275 Chemical denotes PEG http://purl.obolibrary.org/obo/CHEBI_46793
T86928 130343-130350 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T1037 130369-130375 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
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T95323 130626-130632 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T67189 130648-130656 Chemical denotes glycerol http://purl.obolibrary.org/obo/CHEBI_17754
T94315 130670-130672 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
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T35251 130838-130855 Chemical denotes cellulose acetate http://purl.obolibrary.org/obo/CHEBI_145232
T19137 130848-130855 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T67659 131018-131027 Chemical denotes potassium http://purl.obolibrary.org/obo/CHEBI_26216
T82330 131028-131034 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
T33318 131035-131043 Chemical denotes tartrate http://purl.obolibrary.org/obo/CHEBI_132950|http://purl.obolibrary.org/obo/CHEBI_30929|http://purl.obolibrary.org/obo/CHEBI_50562
T22599 131069-131072 Chemical denotes PEG http://purl.obolibrary.org/obo/CHEBI_46793
T31946 131138-131145 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T26094 131185-131191 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T77705 131335-131337 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T76569 131356-131360 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T55351 131361-131369 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T99825 131525-131533 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T70082 131589-131595 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T1062 131611-131619 Chemical denotes glycerol http://purl.obolibrary.org/obo/CHEBI_17754
T984 131703-131705 Chemical denotes ID http://purl.obolibrary.org/obo/CHEBI_17754|http://purl.obolibrary.org/obo/CHEBI_141439
T19989 131852-131854 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T25872 131922-131929 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T1067 132128-132130 Chemical denotes PF http://purl.obolibrary.org/obo/CHEBI_74795|http://purl.obolibrary.org/obo/CHEBI_90284
T57084 132256-132262 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T47707 132782-132791 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T63365 132992-132994 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T1072 133022-133027 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T8339 133182-133184 Chemical denotes AL http://purl.obolibrary.org/obo/CHEBI_73770
T52863 133249-133251 Chemical denotes MT http://purl.obolibrary.org/obo/CHEBI_73614

LitCovid-PD-GO-BP

Id Subject Object Predicate Lexical cue
T1 124418-124428 http://purl.obolibrary.org/obo/GO_0008219 denotes cell death
T2 126958-126965 http://purl.obolibrary.org/obo/GO_0051235 denotes storage
T30304 509-522 http://purl.obolibrary.org/obo/GO_0006412 denotes translational
T75111 1650-1659 http://purl.obolibrary.org/obo/GO_0007585 denotes breathing
T3 2205-2222 http://purl.obolibrary.org/obo/GO_0019079 denotes viral replication
T4 2205-2222 http://purl.obolibrary.org/obo/GO_0019058 denotes viral replication
T5 5225-5240 http://purl.obolibrary.org/obo/GO_0008233 denotes protease active
T6 9640-9657 http://purl.obolibrary.org/obo/GO_0019079 denotes viral replication
T7 9640-9657 http://purl.obolibrary.org/obo/GO_0019058 denotes viral replication
T8 14974-14985 http://purl.obolibrary.org/obo/GO_0006508 denotes proteolysis
T9 18181-18192 http://purl.obolibrary.org/obo/GO_0006412 denotes translation
T10 18244-18250 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T11 18244-18250 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T12 20613-20624 http://purl.obolibrary.org/obo/GO_0006508 denotes proteolysis
T13 23650-23656 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T14 23650-23656 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T15 23738-23744 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T16 23738-23744 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T17 23984-23990 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T18 23984-23990 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T19 24131-24137 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T20 24131-24137 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T21 24141-24160 http://purl.obolibrary.org/obo/GO_0015291 denotes active transporters
T22 24170-24184 http://purl.obolibrary.org/obo/GO_0008559 denotes P-glycoprotein
T23 24512-24518 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T24 24512-24518 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T25 25214-25225 http://purl.obolibrary.org/obo/GO_0006508 denotes proteolysis
T26 32116-32133 http://purl.obolibrary.org/obo/GO_0008233 denotes protease activity
T27 33012-33030 http://purl.obolibrary.org/obo/GO_0015291 denotes active transporter
T28 33194-33200 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T29 33194-33200 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T30 33276-33290 http://purl.obolibrary.org/obo/GO_0008559 denotes P-glycoprotein
T31 33291-33300 http://purl.obolibrary.org/obo/GO_0006810 denotes transport
T32 33599-33605 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T33 33599-33605 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T34 33742-33756 http://purl.obolibrary.org/obo/GO_0008559 denotes P-glycoprotein
T35 33763-33774 http://purl.obolibrary.org/obo/GO_0006810 denotes transporter
T36 33929-33935 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T37 33929-33935 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T38 44997-45006 http://purl.obolibrary.org/obo/GO_0009058 denotes formation
T39 46713-46722 http://purl.obolibrary.org/obo/GO_0009058 denotes formation

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T1 0-126 Sentence denotes Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19
T2 128-136 Sentence denotes Abstract
T3 137-349 Sentence denotes The novel coronavirus disease COVID-19 that emerged in 2019 is caused by the virus SARS CoV-2 and named for its close genetic similarity to SARS CoV-1 that caused severe acute respiratory syndrome (SARS) in 2002.
T4 350-584 Sentence denotes Both SARS coronavirus genomes encode two overlapping large polyproteins, which are cleaved at specific sites by a 3C-like cysteine protease (3CLpro) in a post-translational processing step that is critical for coronavirus replication.
T5 585-711 Sentence denotes The 3CLpro sequences for CoV-1 and CoV-2 viruses are 100% identical in the catalytic domain that carries out protein cleavage.
T6 712-942 Sentence denotes A research effort that focused on the discovery of reversible and irreversible ketone-based inhibitors of SARS CoV-1 3CLpro employing ligand-protease structures solved by X-ray crystallography led to the identification of 3 and 4.
T7 943-1140 Sentence denotes Preclinical experiments reveal 4 (PF-00835231) as a potent inhibitor of CoV-2 3CLpro with suitable pharmaceutical properties to warrant further development as an intravenous treatment for COVID-19.
T8 1142-1154 Sentence denotes Introduction
T9 1155-1253 Sentence denotes In late 2019, cases of an unknown respiratory tract infection were first reported in Wuhan, China.
T10 1254-1708 Sentence denotes By February 2020, the novel coronavirus SARS CoV-2 was identified as the causative agent for COVID-19.1,2 Genome analysis of this virus revealed a high similarity to SARS CoV-1, the coronavirus that caused severe acute respiratory syndrome (SARS) in 2002–2003.2−4 Like SARS CoV-1, which resulted in 799 deaths among the 8464 probable cases,5 SARS CoV-2 can induce fever, coughing, and difficulty breathing that rapidly becomes more serious in some cases.
T11 1709-2092 Sentence denotes The spread of SARS CoV-2 has been more extensive than that of SARS CoV-1, causing a global pandemic with the current number of worldwide infections surpassing eight million and deaths surpassing 400,000.6 The SARS CoV-1 genome encodes for two large polyproteins pp1a (∼450 kDa) and pp1ab (∼750 kDa) that contain overlapping sequences and include a 3C-like cysteine protease (3CLpro).
T12 2093-2441 Sentence denotes The function of this internally encoded 3CLpro is integral to the processing of these proteins and critical for viral replication.7 The SARS CoV-1 3CLpro shares a high degree of structural homology and similar substrate specificity with the coronavirus 3C-like cysteine proteases of hCoV 229E and TGEV8 but is most similar to the SARS CoV-2 3CLpro.
T13 2442-2827 Sentence denotes Specifically, the SARS CoV-1 and SARS CoV-2 share 96% identity between their respective 3CLpro sequences and 100% identity in the active site.8 A recent report by Dai et al. demonstrates that crystallographic information and structure–activity relationships obtained with the SARS CoV-1 3CLpro could facilitate the design of potent SARS CoV-2 3CLpro inhibitors with antiviral potency.9
T14 2828-3210 Sentence denotes There are numerous reports of reversible cysteine protease inhibitors, which include aldehydes,10−13 thio- or oxymethylketones,14 cyclic ketones,15 amidomethylketones,16 nitriles,17,18 or various 1,2-dicarbonyl motifs.19,20 The electrophilic carbon of these chemotypes reacts reversibly with the sulfur atom of an active-site cysteine forming a covalently bound tetrahedral complex.
T15 3211-3624 Sentence denotes Stabilization of this charged protein–ligand transition state by an “oxyanion hole” present in the active site has been observed with certain inhibitor classes by X-ray crystallography and NMR.21,22 A recent report describes the optimization of a series of peptidomimetics designed with an α-ketoamide warhead, which achieves broad-spectrum inhibition against the Mpro for several coronaviruses and enteroviruses.
T16 3625-3843 Sentence denotes Importantly, the reported protease potencies correlate to antiviral potencies, and the authors suggest that the reported SARS CoV-1 3CLpro activity of their lead could be predictive of the SARS CoV-2 3CLpro activity.23
T17 3844-3928 Sentence denotes Alternative modes of enzyme inhibition are covalently bound irreversible inhibitors.
T18 3929-4571 Sentence denotes While chemically reactive affinity labels such as chloromethylketones (CMKs) have demonstrated potent protease inhibition and in certain instances in vivo activity, their inherent chemical reactivity precludes development as clinical agents due to safety concerns.24 However, acyloxymethylketones first reported by Krantz as “quiescent affinity labels” for cathepsin B have demonstrated potent levels of enzyme inhibition with relatively low chemical reactivity.25,26 Mechanistic studies of this class of inhibitors with the cysteine protease caspase-1 support the intermediacy of a thiohemiketal arising from the initial 1,2-carbonyl attack.
T19 4572-4838 Sentence denotes Orientation and stabilization of the acyloxy leaving group within the S1′ domain (Figure 1) of the protease can facilitate SN2 displacement via sulfur migration, resulting in irreversible or bimodal (reversible inhibition followed by slow inactivation) inhibition.27
T20 4839-4903 Sentence denotes Figure 1 Subsite nomenclature for proteolytic enzymes is shown.
T21 4904-5057 Sentence denotes Amino acid residues to the left of the polypeptide scissile amide bond are numbered sequentially, beginning with P1 and increasing toward the N-terminus.
T22 5058-5195 Sentence denotes Amino acid residues to the right of the scissile bond are numbered sequentially, beginning with P1′ and increasing toward the C-terminus.
T23 5196-5283 Sentence denotes Complimentary regions of the protease active site employ the corresponding S numbering.
T24 5284-5565 Sentence denotes Following the SARS outbreak, a CoV-1 3CLpro homology model was published in 2003 with comparisons made to the human rhinovirus (HRV) 3Cpro.28 Although these two proteases share very little sequence conservation, the substrate consensus sequences have a Gln residue in common at P1.
T25 5566-5787 Sentence denotes Analysis of the HRV 3Cpro crystal structure with 1 (rupintrivir; Figure 2) revealed binding interactions that are like those observed for 1 bound to TGEV 3CLpro, which was used in the construction of their homology model.
T26 5788-5937 Sentence denotes The authors concluded that Michael acceptor 1 would serve as a starting point to expedite the identification of a potent SARS CoV-1 3CLpro inhibitor.
T27 5938-6193 Sentence denotes Figure 2 HRV clinical candidate rupintrivir and SARS CoV-1 3CLpro inhibitor 2 employing Michael acceptor-based warheads along with optimized SARS CoV-1 3CLpro inhibitors 3 and 4 containing a carbonyl designed for attack by the catalytic cysteine residue.
T28 6194-6343 Sentence denotes Performing a similar analysis, we tested 1 and additional HRV 3Cpro inhibitors that displayed very weak to unmeasurable SARS CoV-1 3CLpro inhibition.
T29 6344-6518 Sentence denotes Concurrently, new Michael acceptor derivatives were designed that tested P1/P2 alterations and truncation of the P3/P4 binding motif to optimize SARS CoV-1 3CLpro inhibition.
T30 6519-6908 Sentence denotes Compound 2, a derivative that contains an indole capping group at P2, displayed modest levels of irreversible inhibition (kobs/I = 586 ± 11 M–1 s–1) that enabled cocrystallization in complex with SARS CoV-1 3CLpro (PDB code 6XHO).29 Comparison of this structure with the complex of 1 in HRV 3Cpro helped to rationalize the poor performance of the warhead, which had been successful in HRV.
T31 6909-7058 Sentence denotes The structure of the SARS CoV-1 3CLpro complex revealed an eclipsed torsion about the resulting sp3 α,β-carbons from the Michael acceptor (Figure 3).
T32 7059-7197 Sentence denotes Furthermore, the carbonyl oxygen sp2 lone pair electrons are not aligned well with either 3CLpro hydrogen bond donor of the oxyanion hole.
T33 7198-7432 Sentence denotes Specifically, the hydrogen bond between the carbonyl oxygen and the Gly143 NH in the SARS CoV-1 3CLpro complex is 3.4 Å, while the corresponding hydrogen bond distance is a much more favorable 2.8 Å in the complex of 1 with HRV 3Cpro.
T34 7433-7710 Sentence denotes In contrast to these unfavorable interactions, the constrained lactam30 at the P1 site, which was designed to be isosteric with the highly conserved P1 glutamine present in all SARS CoV substrates, is well positioned in the S1 pocket making a favorable hydrogen bond to His163.
T35 7711-7827 Sentence denotes The NH of the lactam is within the hydrogen bond distance to Glu166 and the backbone oxygen of Phe140 in the 3CLpro.
T36 7828-8004 Sentence denotes Additionally, the NH of the indole P2 capping moiety makes a hydrogen bond with the protein backbone while it extends across an otherwise lipophilic surface over the P3 pocket.
T37 8005-8106 Sentence denotes Figure 3 Cocrystal structure of the covalent adduct of 2 bound to SARS CoV-1 3CLpro (PDB code 6XHO).
T38 8107-8178 Sentence denotes The Connolly surface for the inhibitor binding pocket is shown in gray.
T39 8179-8276 Sentence denotes The bonds are represented as the dashed lines, with the bond length measured between heavy atoms.
T40 8277-8397 Sentence denotes The views are centered on warhead with active-site interactions and of complete inhibitor–protein interactions depicted.
T41 8398-8593 Sentence denotes Although the structure of 2 in complex with SARS CoV-1 3CLpro is the final product, the above analysis is expected to apply similarly to the more relevant and structurally close transition state.
T42 8594-8791 Sentence denotes Accordingly, a focused design strategy aimed at replacing the warhead while retaining the P1 lactam and utilizing the methoxy indole capping group in the early rounds of optimization was initiated.
T43 8792-8983 Sentence denotes Specifically, an ideal electrophilic warhead would be bioisosteric, with the scissile amide carbonyl of peptidyl substrates ensuring proper alignment within the oxyanion hole of the protease.
T44 8984-9188 Sentence denotes To better mimic the tetrahedral intermediate generated in the amide bond cleavage, we designed ketone-based covalent reversible and irreversible inhibitors of SARS CoV-1 3CLpro, as illustrated by 3 and 4.
T45 9189-9376 Sentence denotes Compound 4 was selected as a development candidate for SARS CoV-1 but with the successful public health response that ended the 2003 pandemic, the clinical advancement of 4 was suspended.
T46 9377-9584 Sentence denotes Following the COVID-19 outbreak, testing has demonstrated that 4 is a potent inhibitor of the SARS CoV-2 3CLpro (Ki = 0.27 ± 0.1 nM) and a cocrystal structure with 4 bound in the active site has been solved.
T47 9585-9854 Sentence denotes In addition to the potent inhibition of the 3CLpro and viral replication of several coronaviruses, 4 possesses solubility as well as metabolic and chemical stability characteristics, which are consistent with a continuous infusion IV therapeutic treatment for COVID-19.
T48 9855-10191 Sentence denotes We report the research focused on the discovery of reversible and irreversible ketone-based inhibitors of SARS CoV-1 3CLpro employing ligand-protease structures solved by X-ray crystallography, which led to the identification of 4 as a molecule warranting further evaluation for its potential to treat coronaviruses, including COVID-19.
T49 10193-10215 Sentence denotes Results and Discussion
T50 10217-10226 Sentence denotes Chemistry
T51 10227-10400 Sentence denotes Central to our strategy of examining ketone-based thiophiles was the preparation of an array of intermediates containing diverse methylketone moieties and protecting groups.
T52 10401-10619 Sentence denotes The preparation of halomethylketone intermediates was accomplished in a two-step procedure by the generation of a diazoketone intermediate31 or directly by a modified Kowalski–Haque reaction,32 as depicted in Scheme 1.
T53 10620-10671 Sentence denotes Scheme 1 Preparation of P1 Synthetic Intermediates
T54 10672-11026 Sentence denotes (i) 3 M NaOH, MeOH (95%), (ii) isobutylchloroformate (IBCF), triethylamine (TEA), tetrahydrofuran (THF), (iii) CH2N2/ether (92%), (iv) 4 M HCl/dioxane (83%), (v) 1.0 equiv 48% HBr (83%), (vi) HNCH3(OCH3), EDC, HOBt, NMM, dichloromethane (DCM) (79%), (vii) Mg, HgCl2, BOM-Cl, THF, −78°C (50%), and (viii) lithium diisopropylamide (LDA), ClCH2I, THF (54%).
T55 11027-11132 Sentence denotes Saponification of amino ester 5(33) afforded the corresponding amino acid 6 in nearly quantitative yield.
T56 11133-11301 Sentence denotes Acid 6 was treated with isobutylchloroformate and triethylamine, and the resulting mixed anhydride was reacted with diazomethane34 to provide high isolated yields of 7.
T57 11302-11453 Sentence denotes Diazoketone 7 was treated with hydrochloric acid for simultaneous nitrogen deprotection and conversion to the chloromethylketone (CMK) intermediate 10.
T58 11454-11613 Sentence denotes Alternatively, the N-Boc-protected bromomethylketone was prepared by treatment of 7 with stoichiometric quantities of 48% HBr in dichloromethane to provide 11.
T59 11614-11798 Sentence denotes Another preparation of CMK intermediates that avoids the use of diazomethane was accomplished by the reaction of 5 with excess LDA and chloroiodomethane to afford 8 in moderate yields.
T60 11799-12006 Sentence denotes A direct approach to oxymethylketone intermediate 9 was achieved by conversion of acid 6 to the corresponding Weinreb amide followed by treatment with the Grignard generated from benzyl chloromethyl ether.35
T61 12007-12139 Sentence denotes A key element for rapid access to substituted methylketone derivatives was the generation of the fully elaborated CMK 12 (Scheme 2).
T62 12140-12248 Sentence denotes The utility of the CMK moiety to prepare acyloxy- and hydroxy-substituted methylketones is well established.
T63 12249-12501 Sentence denotes Elaboration of 10 in a sequence of deprotection/1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU)-mediated peptide couplings provided CMK derivative 12 in moderate yield with no epimerization observed.
T64 12502-12627 Sentence denotes Reaction of 12 with various carboxylic acids in the presence of cesium fluoride at 60 °C provided acyloxymethylketones 13–28.
T65 12628-12752 Sentence denotes Using this synthetic approach with substitution of P2 and amine capping structural elements provided inhibitors 3 and 29–31.
T66 12753-12833 Sentence denotes Scheme 2 Preparation of Substituted Acyloxymethylketones and Aminomethylketones
T67 12834-13040 Sentence denotes (i) Boc-Leu-OH, HATU, NMM, N,N-dimethylformamide (DMF), 0 °C (64%), (ii) 4 M HCl/dioxane, (iii) HATU, 4-MeO-2-indolecarboxylic acid, NMM, DMF, 0 °C (61%), and (iv) CsF, DMF, carboxylic acid, 60 °C (43–91%).
T68 13041-13149 Sentence denotes Hydroxymethylketone (HMK) derivatives were accessed by two complimentary approaches illustrated in Scheme 3.
T69 13150-13369 Sentence denotes Elaboration of the P1′-protected oxygen intermediate 9 by sequential amide bond coupling reactions provided benzylether derivatives such as 34 in moderate yields with a low propensity for epimerization at the P1 center.
T70 13370-13459 Sentence denotes Hydrogenolytic debenzylation readily afforded the final HMK inhibitors exemplified by 36.
T71 13460-13809 Sentence denotes Alternatively, fully elaborated CMK derivatives such as 35 were reacted with benzoylformic acid followed by methanolysis to generate HMK final products such as 36.36 Alkylation of the terminal hydroxyl was achieved under microwave-assisted conditions in the presence of silver (I) oxide to afford alkoxymethylketone inhibitors, as illustrated by 37.
T72 13810-13941 Sentence denotes Using these two synthetic approaches with substitution of P2 and amine capping structural elements provided inhibitors 4 and 38–50.
T73 13942-13998 Sentence denotes Scheme 3 Preparation of Hydroxymethylketone Derivatives
T74 13999-14200 Sentence denotes (i) 4 M HCl/dioxane, (ii) Boc-Leu-OH, HATU, NMM, DMF, 0 °C, (iii) HATU, 4-MeO-2-indolecarboxylic acid, NMM, 0 °C, (iv) Pd/C, H2, EtOH (77%), (v) CsF, DMF, benzoylformic acid, 60 °C, and then MeOH, cat.
T75 14201-14244 Sentence denotes K2CO3 (53%), and (vi) CH3I, Ag2O, DCE (9%).
T76 14246-14267 Sentence denotes Biological Evaluation
T77 14269-14313 Sentence denotes Irreversible Inhibitors of SARS CoV-1 3CLpro
T78 14314-14455 Sentence denotes The warhead reactivity and binding affinity to P1′ are both important design considerations to ensure specificity of irreversible inhibitors.
T79 14456-14826 Sentence denotes Krantz has demonstrated that the inherent chemical reactivity of acyloxymethylketones can be tuned to inhibit cysteine proteases through the modulation of substituent effects on the carboxylate leaving group.37 The importance of leaving group “strength” was confirmed by the strong dependence between the pKa of the leaving carboxylate and cathepsin B enzyme inhibition.
T80 14827-15004 Sentence denotes These otherwise weak electrophiles are elegant “quiescent” inhibitors that harness the very same interactions with catalytic residues that lead to proteolysis rate acceleration.
T81 15005-15242 Sentence denotes Molecular modeling of a 2,6-dichlorobenzoate design with SARS CoV-1 3CLpro indicated that a low strain conformation of the ketone carbonyl was aligned in the oxyanion hole and the substituted benzoate is accommodated within the P1′ site.
T82 15243-15325 Sentence denotes A series of acyloxymethylketone derivatives were prepared, as depicted in Table 1.
T83 15326-15403 Sentence denotes Table 1 SARS CoV-1 3CLpro Inhibition Data for Acyloxymethylketone Inhibitors
T84 15404-15433 Sentence denotes     SARS CoV-1 3CLpro FRETa
T85 15434-15471 Sentence denotes entry R kobs/I (M–1 s–1) IC50 (nM)
T86 15472-15498 Sentence denotes 12   283,039 ± 22,586  
T87 15499-15519 Sentence denotes 13 Me   220 ± 0.5
T88 15520-15546 Sentence denotes 14 cyc-propyl   182 ± 6
T89 15547-15573 Sentence denotes 15 tert-butyl   230 ± 5
T90 15574-15591 Sentence denotes 16 Ph   86 ± 3
T91 15592-15615 Sentence denotes 17 4-OMe-Ph   79 ± 3
T92 15616-15638 Sentence denotes 18 4-Me-Ph   87 ± 2
T93 15639-15661 Sentence denotes 19 4-CN-Ph   53 ± 1
T94 15662-15683 Sentence denotes 20 4-F-Ph   82 ± 3
T95 15684-15706 Sentence denotes 21 4-Cl-Ph   97 ± 3
T96 15707-15742 Sentence denotes 22 2,6-(Cl)2-Ph 62,993 ± 2,501  
T97 15743-15775 Sentence denotes 23 2,6-(F)2-Ph 12,776 ± 594  
T98 15776-15808 Sentence denotes 24 2-OH-4-Cl-Ph 11,525 ± 40  
T99 15809-15844 Sentence denotes 25 2-F, 4-CN-Ph 13,321 ± 2,309  
T100 15845-15872 Sentence denotes 26 2,6-(Me)2-Ph   74 ± 4
T101 15873-15902 Sentence denotes 27 2,6-(MeO)2-Ph   205 ± 2
T102 15903-15925 Sentence denotes 28 2-CN-Ph   17 ± 2
T103 15926-16092 Sentence denotes a See the Experimental Section for details on assay methods; the values were calculated from at least eight data points with at least two independent determinations.
T104 16093-16184 Sentence denotes As expected, chloromethylketone 12 is a potent irreversible inhibitor of SARS CoV-1 3CLpro.
T105 16185-16322 Sentence denotes Compounds 22–25 possess the most electron-deficient benzoate leaving groups and display kinetics consistent with irreversible inhibition.
T106 16323-16452 Sentence denotes The remaining entries appear to be reversible inhibitors in the time scale of the assay, with 28 possessing the most potent IC50.
T107 16453-16647 Sentence denotes A crystal structure (PDB code 6XHN)38 of 28 in complex with SARS CoV-1 3CLpro at 2.25 Å shows a covalent adduct, which demonstrates the bimodal activity of certain acyloxy inhibitors (Figure 4).
T108 16648-16851 Sentence denotes In this structure, the electron density for the 2-cyanobenzoate moiety is absent and the 3CLpro active-site cysteine (Cys145) sulfur forms a covalent bond to the methylene carbon (1.8 Å C–S bond length).
T109 16852-16995 Sentence denotes The ketone carbonyl is positioned within the oxyanion hole and as such engaging in hydrogen bonds with backbone NH groups of Gly143 and Cys145.
T110 16996-17176 Sentence denotes A detailed analysis of an extended hydrogen bond network from catalytic His41 reveals that the side-chain imidazole serves as a hydrogen bond donor to the interior of the protease.
T111 17177-17287 Sentence denotes Specifically, the imidazole hydrogen is directed toward a lone pair electron acceptor from a structural water.
T112 17288-17622 Sentence denotes We can conclude that this water must be an acceptor to His41 as one of the water hydrogens is engaged with acceptor electrons on the side chain of Asp187, and the second hydrogen engages a terminating acceptor backbone carbonyl on Asp176 through a short network that includes the side chains of an internal, neutral His164 and Thr175.
T113 17623-17725 Sentence denotes Figure 4 Cocrystal structure of the covalent adduct of 28 bound to SARS CoV-1 3CLpro (PDB code 6XHN).
T114 17726-17797 Sentence denotes The Connolly surface for the inhibitor binding pocket is shown in gray.
T115 17798-17891 Sentence denotes The bonds are represented as dashed lines, with the bond length between heavy atoms depicted.
T116 17892-18333 Sentence denotes The 2,6-dichlorobenzoate derivative 22 displays the highest levels of potency in the SARS CoV-1 3CLpro and in antiviral cytopathic effect assays in Vero 76 cells (EC50 = 0.29 ± 0.19 μM).39 We note here that the assay in Vero 76 cells provided data establishing antiviral activity, but the translation of potency measured in Vero cells, which have high efflux potential, to the potency achievable in human lung cells was unknown (vide infra).
T117 18334-18715 Sentence denotes As expected, 22 possesses low levels of reactivity toward endogenous nucleophiles such as glutathione (t1/2 > 60 min)40 and exhibits high levels of stability in human plasma (t1/2 > 240 min).41 Although 22 displays a promising activity profile, it possesses very poor solubility in clinically relevant IV vehicle formulations, thus limiting its development as an IV clinical agent.
T118 18716-18932 Sentence denotes To improve the solubility characteristics of inhibitors incorporating the lipophilic 2,6-dichlorobenzoate, a limited set of inhibitors containing smaller or more polar amine capping fragments were prepared (Table 2).
T119 18933-19020 Sentence denotes Replacement of the 4-methoxy indole cap present in 22 with a benzimidazole provided 31.
T120 19021-19132 Sentence denotes This inhibitor displayed potent irreversible inhibition kinetics but did not improve solubility compared to 22.
T121 19133-19290 Sentence denotes Reduction in the size of the P2 capping element as represented by 29 and 30 provided derivatives that possessed weak reversible SARS CoV-1 3CLpro inhibition.
T122 19291-19380 Sentence denotes Table 2 SARS CoV-1 3CLpro Inhibition Data for P3-Modified Acyloxymethylketone Inhibitors
T123 19381-19547 Sentence denotes a See the Experimental Section for details on assay methods; the values were calculated from at least eight data points with at least two independent determinations.
T124 19548-19784 Sentence denotes Another design to replace the 4-methoxy indole was the (2R)-tetrahydrofuran-2-carboxylate, which molecular modeling suggested could make additional favorable protein interactions with a Gln189 side chain and led to the preparation of 3.
T125 19785-19860 Sentence denotes Initially, this derivative appeared to display reversible binding kinetics.
T126 19861-20042 Sentence denotes However, further kinetic studies of compound 3 with the SARS CoV-1 3CLpro protein demonstrated irreversible time-dependent inactivation of this enzyme (kobs/I = 5834 ± 151 M–1 s–1).
T127 20043-20194 Sentence denotes Additionally, 3 possessed potent antiviral activity in Vero cells (EC50 = 2.4 μM) and solubility in vehicle formulations almost 20-fold higher than 22.
T128 20195-20371 Sentence denotes Evaluation of the pharmacokinetic profile of 3 in rat suggested that this inhibitor possessed properties potentially sufficient for an IV continuous infusion dosing paradigm.42
T129 20372-20592 Sentence denotes Although irreversible inhibition can provide an extended pharmacodynamic effect when protein resynthesis rate is slow compared to drug clearance, such extended effects for 3CLpro inhibition were not necessarily expected.
T130 20593-20819 Sentence denotes The 3CLpro-mediated proteolysis of newly expressed viral polyproteins is essential to virus replication; however, this activity only occurs during a single step in the virus life cycle that closely follows each cell infection.
T131 20820-20933 Sentence denotes Viral particles themselves are not reliant on 3CLpro activity nor are the remaining coronavirus life cycle steps.
T132 20934-20998 Sentence denotes Each event of cell infection initiates newly synthesized 3CLpro.
T133 20999-21126 Sentence denotes Because detailed kinetics of this process are not understood, reversible and irreversible inhibitors were investigated equally.
T134 21128-21170 Sentence denotes Reversible Inhibitors of SARS CoV-1 3CLpro
T135 21171-21620 Sentence denotes Peptidyl HMK inhibitors and their corresponding ethers have been designed as potent reversible cysteine protease inhibitors of cathepsin K34 and cruzain.43 High-resolution crystal structures of two such inhibitors complexed with cruzain highlighted the presence of a strong hydrogen bond between the catalytic His and the α-hydroxyl moiety of the inhibitor but interestingly no covalent bond between the active-site Cys and the ketone pharmacophore.
T136 21621-21964 Sentence denotes Utilizing the crystal structure of 28 in complex with SARS CoV-1 3CLpro, molecular modeling of an HMK-based design indicated the potential for establishing a covalent bond between the sulfur of the active-site cysteine (Cys145) and the HMK carbonyl as well as hydrogen bond interactions between catalytic His41 and the terminal hydroxy moiety.
T137 21965-22137 Sentence denotes Additionally, the structure of 28 suggested the possibility to increase the lipophilic filling of the deep hydrophobic S2 pocket as a strategy to increase binding affinity.
T138 22138-22285 Sentence denotes To evaluate these structure-based observations, a series of reversible HMK inhibitors containing P2 diversity were prepared as depicted in Table 3.
T139 22286-22353 Sentence denotes Table 3 SARS 3CLpro Inhibition Data for P2-Modified HMK Inhibitors
T140 22354-22522 Sentence denotes a&b See the Experimental Section for details on assay methods; the values were calculated from at least eight data points with at least two independent determinations.
T141 22523-22557 Sentence denotes c This value is a Ki measurement.
T142 22558-22606 Sentence denotes d These values are from a single determination.
T143 22607-22758 Sentence denotes As suggested by molecular modeling, the S2 site appears to accommodate a variety of linear, branched, and cyclic alkyl moieties (entries 36 and 39–41).
T144 22759-22902 Sentence denotes Interestingly, the P2 Phe derivative 42 displayed less potent inhibition of the SARS CoV-1 3CLpro than the corresponding saturated analogue 41.
T145 22903-23048 Sentence denotes Also noteworthy is the large attenuation in enzyme inhibition seen with P2-N-methyl-Leu inhibitor 38 (IC50 = 83 nM) as compared to 4 (Ki = 4 nM).
T146 23049-23229 Sentence denotes This loss of potency is consistent with the inhibitor ligand interactions observed with 2 and 4 that show the P2 NH involved in a hydrogen bond with the side-chain amide of Gln189.
T147 23230-23426 Sentence denotes Additionally, the methyl substitution in 38 would be expected to alter the conformation of the 4-methoxy indole cap and perturb the observed ligand–enzyme hydrogen bond network present in 2 and 4.
T148 23427-23571 Sentence denotes The results for 4 and the other examples in Table 3 reveal a high antiviral EC50/enzyme IC50 ratio, which may arise from poor cell permeability.
T149 23572-23709 Sentence denotes Indeed, these HMK inhibitors exhibit very low permeability and high levels of efflux beyond the sensitivity of the Caco-2 in vitro assay.
T150 23710-23879 Sentence denotes However, the impact of high efflux on antiviral potencies from Vero 76 cells (derived from monkey kidney) versus disease-relevant human lung epithelial cells is unknown.
T151 23880-24076 Sentence denotes To better understand the observed high antiviral EC50/enzyme IC50 ratio for 4, we evaluated the role of efflux in the Vero 76 cell line by the in vitro experimental design discussed further below.
T152 24077-24249 Sentence denotes Concurrently, a strategy to design molecules reducing efflux by active transporters, such as P-glycoprotein, was pursued to decrease high antiviral EC50/enzyme IC50 ratios.
T153 24250-24519 Sentence denotes An analysis of the physicochemical properties of 4 suggested that increasing logP, reducing polar surface area (PSA), and reducing the number of hydrogen bond donors/acceptors were design strategies with the potential to improve cellular permeability and reduce efflux.
T154 24520-24696 Sentence denotes An examination of the crystal structure of 2 in complex with SARS CoV-1 3CLpro suggested a limited functional role for the 4-methoxy substituent contained in the P3 indole cap.
T155 24697-24833 Sentence denotes Additionally, the terminal α-hydroxyl moiety located at P1′ appeared to provide a potential opportunity to remove a hydrogen bond donor.
T156 24834-24993 Sentence denotes Although it was anticipated that the α-hydroxyl moiety would form a hydrogen bond to the catalytic His41, the directionality of this interaction was uncertain.
T157 24994-25226 Sentence denotes As noted earlier, His41 presents a hydrogen bond donor to the interior of the protease, leaving an acceptor to participate in the proton transfer cycling from neutral to cationic in the putative catalytic mechanism44 of proteolysis.
T158 25227-25399 Sentence denotes If His41 is protonated in the inhibitor-bound complex, a lone pair from the α-hydroxyl moiety would function as a hydrogen bond acceptor from the proton on the His residue.
T159 25400-25563 Sentence denotes On the other hand, if His41 is deprotonated, the hydrogen of the α-hydroxyl moiety would act as a hydrogen bond donor to the nitrogen lone pair of the His residue.
T160 25564-25754 Sentence denotes Consistent with the strategy to decrease PSA and hydrogen bond donors, a series of inhibitors were prepared that contained alterations to the P3 cap and substitution of the α-hydroxyl group.
T161 25755-25865 Sentence denotes Table 4 summarizes this effort where two of the optimal P2 residues (Leu and β-tert-butyl-Ala) were conserved.
T162 25866-26123 Sentence denotes Removal of the methoxy group from the indole generally led to slightly weaker potency in both the enzymatic and antiviral assays across pairs (43 vs 36, 44 vs 37, 50 vs 48 and 49 vs 4) and therefore no improvement in the antiviral/protease inhibition ratio.
T163 26124-26235 Sentence denotes The impact of more significant changes to the P3 cap is illustrated by tetrahydrofuranyl derivatives 46 and 47.
T164 26236-26410 Sentence denotes These derivatives lack the lipophilic aryl ring and NH hydrogen bond donor present in the indole P3 cap and exhibit a pronounced reduction in enzymatic and antiviral potency.
T165 26411-26574 Sentence denotes A noteworthy reduction in biochemical and antiviral potency was observed in comparing each hydroxymethylketone derivative with its corresponding ether counterpart.
T166 26575-26748 Sentence denotes These results suggest that modest structural and physicochemical alterations of 4 fail to significantly decrease the high EC50/IC50 ratios for this class of peptidomimetics.
T167 26749-27056 Sentence denotes However, in vitro analysis of 4 revealed this derivative to possess high levels of metabolic stability in human liver microsomes (t1/2 = 107 min).45 Further evaluation of this breakthrough derivative in several aqueous-based formulations suitable for IV administration indicated high levels of solubility.46
T168 27057-27171 Sentence denotes Table 4 SARS CoV-1 3CLpro Inhibition Data for P3- and P2-Modified Hydroxymethyl and Alkoxymethylketone Inhibitors
T169 27172-27340 Sentence denotes a&b See the Experimental Section for details on assay methods; the values were calculated from at least eight data points with at least two independent determinations.
T170 27341-27375 Sentence denotes c This value is a Ki measurement.
T171 27376-27424 Sentence denotes d These values are from a single determination.
T172 27425-27740 Sentence denotes Cocrystal structures of 4 bound to the 3CLpro of both SARS CoV-1 and CoV-2 were solved at 1.47 and 1.26 Å resolutions, respectively (PDB codes 6XHL and 6XHM).47 As expected, the ligand binding sites of the main protease from SARS CoV-1 and SARS CoV-2 are conserved in sequence and are nearly identical structurally.
T173 27741-27867 Sentence denotes The schematic diagram in Figure 5 is representative of the covalent adduct between 4 and the 3CLpro from both CoV-1 and CoV-2.
T174 27868-28044 Sentence denotes The warhead HMK carbonyl carbon of 4 forms a covalent bond to the 3CLpro active-site cysteine (Cys145) sulfur generating a tetrahedral carbinol complex (1.8 Å C–S bond length).
T175 28045-28182 Sentence denotes This carbinol hydroxyl forms hydrogen bonds with the backbone NH of Cys145 and with the amide NH of Gly143 via a bridging water molecule.
T176 28183-28304 Sentence denotes Another key active-site interaction is the hydrogen bond between the primary alcohol moiety of 4 and the catalytic His41.
T177 28305-28441 Sentence denotes Similar interactions between catalytic His residues and the OH moiety of HMK in other protease–inhibitor complexes have been reported.43
T178 28442-28534 Sentence denotes Figure 5 Cocrystal structure of the covalent adduct of 4 bound to SARS CoV-2 3CLpro (6XHM).
T179 28535-28606 Sentence denotes The Connolly surface for the inhibitor binding pocket is shown in gray.
T180 28607-28700 Sentence denotes The bonds are represented as dashed lines, with the bond length between heavy atoms depicted.
T181 28701-28873 Sentence denotes The schematic rendering of the active site with dashed lines represented as hydrogen bonds with key residues and curved lines to show S1 and S2 binding pockets is depicted.
T182 28874-29116 Sentence denotes In S1, the lactam carbonyl of 4 forms a strong hydrogen bond with the side chain of His163, while the lactam NH is within the hydrogen-bonding distance but poorly aligned with the side-chain oxygen of Glu166 and the backbone oxygen of Phe140.
T183 29117-29192 Sentence denotes These three residues partially define the bottom and edge of the S1 pocket.
T184 29193-29350 Sentence denotes Additionally, the backbone carbonyl and NH of Glu166 form β-sheet-like hydrogen-bonding interactions with the NH and C2-carbonyl of the indole fragment of 4.
T185 29351-29493 Sentence denotes The NH of the P2 Leu of inhibitor 4 and the side chain of Gln189 form a hydrogen bond, while the carbonyl of P2 Leu is exposed to the solvent.
T186 29494-29580 Sentence denotes The inhibitor P1 NH forms a strong hydrogen bond with the backbone carbonyl of His164.
T187 29581-29741 Sentence denotes The inhibitor’s lipophilic leucine residue is bound to the SARS 3CLpro in the hydrophobic S2 pocket formed by residues Asp187, Arg188, Gln189, Met49, and His41.
T188 29742-29938 Sentence denotes The indole portion of 4 does not protrude into the S3 pocket but rather rests across a partially collapsed S3, making extended van der Waals interactions across the 189–191 residue backbone atoms.
T189 29939-30356 Sentence denotes The closed S3 is the only significant conformational difference compared to a recently reported structure of SARS CoV-2 3CLpro inhibited by α-ketoamides.8 The energetics of this extended interaction, the associated protein conformation stabilities, or warhead difference may contribute to the 3-order-of-magnitude increased SARS CoV-2 3CLpro potency of HMK 4 (see below) compared to that of the referenced ketoamides.
T190 30357-30454 Sentence denotes Hydroxymethylketone 4 was evaluated against a panel of other viral and human proteases (Table 5).
T191 30455-30692 Sentence denotes In general, 4 is highly selective for 3CLpro inhibition, displaying IC50 values of >10 μM against many of the other proteases and possessing modest levels of inhibition of cathepsin B (IC50 = 1.3 μM) and rhinovirus 3Cpro (IC50 = 1.7 μM).
T192 30693-30825 Sentence denotes High levels of similarity between the catalytic sites of 3CLpro proteases suggest the potential of 4 as a pan-coronavirus inhibitor.
T193 30826-31047 Sentence denotes Testing revealed that 4 demonstrates potent inhibition of the related hCoV 229E protease (IC50 = 0.004 μM) but more importantly, given the current global pandemic, potently inhibits SARS CoV-2 3CLpro with a Ki of 0.27 nM.
T194 31048-31081 Sentence denotes Table 5 Protease Inhibition by 4
T195 31082-31133 Sentence denotes protease source % inhibition @ 10 μMa IC50 (μM)a
T196 31134-31172 Sentence denotes 3CLpro SARS CoV-1   0.004 ± 0.0003b
T197 31173-31210 Sentence denotes 3CLpro SARS CoV-2 0.00027 ± 0.0001b
T198 31211-31244 Sentence denotes cathepsin B human 93 1.3 ± 0.1
T199 31245-31271 Sentence denotes cathepsin D human 3 >10
T200 31272-31307 Sentence denotes leukocyte elastase human –31 >10
T201 31308-31335 Sentence denotes chymotrypsin human 8 >10
T202 31336-31361 Sentence denotes thrombin human –28 >10
T203 31362-31384 Sentence denotes pepsin human –2 >10
T204 31385-31411 Sentence denotes caspase 2 human –20 >10
T205 31412-31432 Sentence denotes HIV-1 HIV-1 0 >10
T206 31433-31450 Sentence denotes HCV HCV 16 >10
T207 31451-31471 Sentence denotes HRV HRV   1.7 ± 1
T208 31472-31507 Sentence denotes hCoV 229E human   0.004 ± 0.0004
T209 31508-31674 Sentence denotes a See the Experimental Section for details on assay methods; the values were calculated from at least eight data points with at least two independent determinations.
T210 31675-31739 Sentence denotes b For SARS CoV-1 and CoV-2 3CLpro, Ki values are reported here.
T211 31740-31822 Sentence denotes The antiviral specificity of 4 was evaluated against a panel of viruses (Table 6).
T212 31823-32022 Sentence denotes No antiviral activity was observed when 4 was tested against two human rhinovirus strains (HRV-14 and HRV-16), human immunodeficiency virus-1 (HIV-1), or human cytomegalovirus (HCMV) in cell culture.
T213 32023-32076 Sentence denotes This compound also does not inhibit the HCV replicon.
T214 32077-32255 Sentence denotes As anticipated by the potent hCoV 229E protease activity, 4 is a potent inhibitor of the human coronavirus hCoV 229E in MRC-5 cells (human lung-derived) with an EC50 of 0.090 μM.
T215 32256-32286 Sentence denotes Table 6 Viral Inhibition by 4
T216 32287-32316 Sentence denotes virus EC50 (μM)a CC50 (μM)a
T217 32317-32343 Sentence denotes SARS CoV-1 4.8 ± 2.2 452
T218 32344-32371 Sentence denotes hCoV 229E 0.09 ± 0.04 >40
T219 32372-32392 Sentence denotes HRV-14 >100 >1,260
T220 32393-32413 Sentence denotes HRV-16 >100 >1,260
T221 32414-32432 Sentence denotes HIV-1 RF >32 >32
T222 32433-32457 Sentence denotes HCV replicon >320 >320
T223 32458-32480 Sentence denotes HCMV RC256 >100 >100
T224 32481-32647 Sentence denotes a See the Experimental Section for details on assay methods; the values were calculated from at least eight data points with at least two independent determinations.
T225 32648-32860 Sentence denotes The hCoV 229E antiviral potency is more than 50-fold greater than that for SARS CoV-1 in the Vero 76 line, even though 4 possesses nearly equivalent 3CLpro biochemical potency for the hCoV 229E and CoV-1 viruses.
T226 32861-33120 Sentence denotes While undefined differences between hCoV 229E and SARS CoV-1 could account for these large differences in antiviral EC50/enzyme IC50 ratios, different active transporter expression levels between MRC-5 and Vero 76 cell lines may also be a contributing factor.
T227 33121-33396 Sentence denotes Consistent with the previously stated goal to characterize the impact of efflux on potency measured in the SARS CoV-1 antiviral assay, we co-dosed a known P-glycoprotein transport inhibitor at a fixed concentration (0.5 μM CP-100356)48 in a full dose–response of inhibitor 4.
T228 33397-33562 Sentence denotes This resulted in a pronounced potency shift of SARS CoV-1 antiviral activity (EC50 = 0.11 μM) that now more closely matched the antiviral potency seen for hCoV 229E.
T229 33563-33806 Sentence denotes As a control, the same co-dosing of efflux inhibitor led to no such shift in the hCoV 229E antiviral potency of 4, demonstrating that the human lung-derived MRC-5 cells show less P-glycoprotein-based transporter under similar assay conditions.
T230 33807-34077 Sentence denotes These results suggest that the high antiviral EC50/enzyme IC50 ratio observed in Vero 76 cells is an artifact of the high efflux potential of that assay cell line and may underestimate the antiviral potency in human lung cells, the relevant tissue for SARS and COVID-19.
T231 34078-34225 Sentence denotes Assays to directly measure the antiviral potency of 4 against SARS CoV-2 in clinically relevant human lung cells are currently under investigation.
T232 34227-34238 Sentence denotes Conclusions
T233 34239-34442 Sentence denotes This report details the efforts to identify irreversible and reversible peptidomimetic inhibitors of the SARS CoV-1 3CLpro as potential IV agents for the treatment of SARS and other coronavirus diseases.
T234 34443-34559 Sentence denotes Two classes, acyloxymethylketones and hydroxymethylketones, were discovered as potent inhibitors of the SARS 3CLpro.
T235 34560-34670 Sentence denotes The hydroxymethylketone derivative 4 demonstrated potent SARS CoV-1 inhibition in 3CLpro and antiviral assays.
T236 34671-35017 Sentence denotes Additionally, 4 possesses acceptable solubility, stability in plasma, and low in vitro and in vivo clearances suitable for further development as a coronavirus treatment.49 Importantly, the potent inhibition of SARS CoV-2 3CLpro has prompted further preclinical investigations of 4 as a potential therapeutic treatment for patients with COVID-19.
T237 35019-35039 Sentence denotes Experimental Section
T238 35041-35059 Sentence denotes General Procedures
T239 35060-35172 Sentence denotes Unless otherwise noted, materials were obtained from commercial suppliers and used without further purification.
T240 35173-35326 Sentence denotes The removal of solvent under reduced pressure or concentration refers to distillation using a Büchi rotary evaporator attached to a vacuum pump (3 mmHg).
T241 35327-35409 Sentence denotes Products obtained as solids or high-boiling oils were dried under vacuum (1 mmHg).
T242 35410-35536 Sentence denotes Silica gel chromatography was performed on either a CombiFlash (Teledyne ISCO), SP4, or Isolera (Biotage) purification system.
T243 35537-35737 Sentence denotes All reactions were performed under a positive pressure of nitrogen or argon or with a drying tube at an ambient temperature (unless otherwise stated) in anhydrous solvents, unless otherwise indicated.
T244 35738-35907 Sentence denotes Analytical thin-layer chromatography (TLC) was performed on glass-backed silica gel 60 F254 plates (Analtech, 0.25 mm), eluting with the appropriate solvent ratio (v/v).
T245 35908-36078 Sentence denotes The reactions were assayed by high-performance liquid chromatography–mass spectrometry (LCMS) or TLC and terminated as judged by the consumption of the starting material.
T246 36079-36249 Sentence denotes LCMS utilized wavelengths of 254 and 220 nm and either electrospray ionization (ESI) in positive mode or atmospheric-pressure chemical ionization (APCI) in positive mode.
T247 36250-36354 Sentence denotes The TLC plates were visualized using UV light, p-anisaldehyde, phosphomolybdic acid, or iodine staining.
T248 36355-36416 Sentence denotes Microwave-assisted reactions were run in a Biotage Initiator.
T249 36417-36490 Sentence denotes 1H NMR spectra were recorded on a Bruker XWIN-NMR (400 MHz) spectrometer.
T250 36491-36587 Sentence denotes Proton chemical shifts are reported in parts per million downfield from tetramethylsilane (TMS).
T251 36588-36678 Sentence denotes 1H NMR data are reported as chemical shift (multiplicity, coupling constant, integration).
T252 36679-36839 Sentence denotes Multiplicities are denoted as follows: s, singlet; d, doublet; t, triplet; q, quartet; dd, doublet of doublets; dt, doublet of triplets; and brs, broad singlet.
T253 36840-36990 Sentence denotes For spectra obtained in CDCl3, DMSO-d6, and CD3OD, the residual protons (7.27, 2.50, and 3.31 ppm, respectively) were used as the internal references.
T254 36991-37077 Sentence denotes The purity of the final products is >95% as determined by HPLC and/or 1H NMR analyses.
T255 37079-37146 Sentence denotes N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (6)
T256 37147-37435 Sentence denotes A 3 L multineck flask equipped with an overhead stirrer and internal thermometer was charged with methyl N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alaninate (compound 5)33 (205 g, 716 mmol) followed by methanol (1 L), and the solution was cooled to 0 °C using ice/NaCl bath.
T257 37436-37638 Sentence denotes NaOH (115 g in 950 mL water, 2.9 mol) solution was precooled to 0 °C and then added to the flask via a pressure-equalizing dropping funnel at such a rate to maintain the internal temperature below 5 °C.
T258 37639-37826 Sentence denotes The resulting solution was stirred at 0 °C for 1 h before neutralizing with conc. hydrochloric acid (keeping the internal temperature below 10 °C) and then removing the methanol in vacuo.
T259 37827-38012 Sentence denotes The residue was diluted with ethyl acetate (400 mL), acidified to pH 3 with conc. hydrochloric acid, and then the mixture was transferred to a sep funnel, and the organics were removed.
T260 38013-38216 Sentence denotes The aqueous was extracted with ethyl acetate (2 × 400 mL), and the combined organics were washed with brine, dried over MgSO4, filtered, and concentrated to yield the title compound as a white foam, 95%.
T261 38217-38414 Sentence denotes 1H NMR (400 MHz, MeOD) δ 3.98–4.28 (m, 1H), 3.25–3.41 (m, 2H), 2.44–2.57 (m, 1H), 2.29–2.41 (m, 1H), 2.03–2.14 (m, 1H), 1.73–1.90 (m, 2H), 1.44 (s, 9H); MS (APCI−) for C12H20N2O5m/z 272.3 (M – H)−.
T262 38416-38504 Sentence denotes tert-Butyl ((1S)-3-Diazo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (7)
T263 38505-38677 Sentence denotes A solution of N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (2.72 g, 10.0 mmol) in THF (100 mL) was placed under an atmosphere of N2 and cooled to −23 °C.
T264 38678-38835 Sentence denotes The resulting clear colorless solution was successively treated with triethylamine (2.1 mL, 15.0 mmol) followed by isobutylchloroformate (1.6 mL, 12.0 mmol).
T265 38836-38938 Sentence denotes The reaction mixture gradually became opaque with a fine white precipitate and after 1 h was filtered.
T266 38939-39111 Sentence denotes The colorless filtrate was transferred to a nonground joint flask, cooled to 0 °C, and slowly treated with a solution of diazomethane (∼35 mL, ∼16.6 mmol) in diethyl ether.
T267 39112-39117 Sentence denotes Note:
T268 39118-39251 Sentence denotes The diazomethane was generated employing a Diazald kit according to the procedure described in the Aldrich Technical Bulletin AL-180.
T269 39252-39344 Sentence denotes The resulting yellow clear solution was gradually warmed to room temperature (RT) over 16 h.
T270 39345-39460 Sentence denotes At this time, N2 was bubbled through the reaction to remove excess diazomethane followed by in vacuo concentration.
T271 39461-39545 Sentence denotes The resulting residue was diluted with ethyl acetate (100 mL), washed once with sat.
T272 39546-39660 Sentence denotes NaHCO3 (50 mL), once with brine (50 mL), dried over MgSO4, filtered, and concentrated to give a crude yellow foam.
T273 39661-39809 Sentence denotes This material was purified by LC (150 g 230–400 SiO2, 3–4% methanol/chloroform) to afford 2.72 g (92%) of the title compound as a light yellow foam.
T274 39810-40030 Sentence denotes 1H NMR (DMSO-d6) δ 7.63 (bs, 1H), 7.42 (d, J = 8 Hz, 1H), 6.06 (bs, 1H), 3.96 (m, 1H), 3.13 (m, 2H), 2.21 (m, 1H), 2.01 (m, 1H), 1.86 (m, 1H), 1.63–1.52 (m, 2H), 1.38 (s, 9H); MS (ESI+) for C13H20N4O4m/z 319.0 (M + Na)+.
T275 40032-40121 Sentence denotes tert-Butyl ((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (8)
T276 40122-40411 Sentence denotes A three-neck flame-dried flask equipped with a nitrogen inlet and internal thermometer was charged with methyl N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alaninate (10 g, 35 mmol), THF (200 mL), and chloroiodomethane (10.2 mL, 140 mmol), and the solution was cooled to −77 °C.
T277 40412-40587 Sentence denotes LDA (140 mL, 210 mmol, 1.5 M mono-THF complex in cyclohexane) was added via a pressure-equalizing dropping funnel at such a rate to keep the internal temperature below −70 °C.
T278 40588-40806 Sentence denotes After complete addition, the reaction was stirred for an additional hour and quenched with a mixture of AcOH (33 mL) and THF (200 mL) with a rate of addition regulated to maintain the internal temperature below −65 °C.
T279 40807-40917 Sentence denotes After complete addition, the dark suspension was stirred for 10 min and then warmed to an ambient temperature.
T280 40918-41027 Sentence denotes The reaction was diluted with ethyl acetate (500 mL), and the organics were washed with water (250 mL), satd.
T281 41028-41244 Sentence denotes NaHCO3 (250 mL), and brine (250 mL), dried over MgSO4, filtered, and the solvents were removed in vacuo to yield the crude product as a dark oil, which was purified by flash chromatography eluting with ethyl acetate.
T282 41245-41363 Sentence denotes The resulting solid was triturated with diethyl ether to afford the title compound as a pale yellow solid, 5.7 g, 54%.
T283 41364-41677 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 7.88 (s, 1H), 7.75 (d, J = 7.6 Hz, 1H), 4.73–4.94 (m, 2H), 4.37 (m, 1H), 3.28–3.43 (m, 2H), 2.46 (m, 1H), 2.30–2.40 (m, 1H), 2.02–2.14 (m, 1H), 1.77–1.95 (m, 2H), 1.60 (s, 9H); MS (API-ES+) for C13H21N2O4Cl m/z 327.1 (M + Na)+; anal. calcd for C13H21ClN2O4: C, 51.23; H, 6.95; N, 9.19.
T284 41678-41712 Sentence denotes Found: C, 51.03; H, 6.93; N, 9.03.
T285 41714-41807 Sentence denotes tert-Butyl((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (9)
T286 41808-42106 Sentence denotes To a 3 L multinecked flask equipped with an overhead stirrer, nitrogen inlet, and internal thermometer was charged N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (190 g, 698 mmol) followed by dichloromethane (1100 mL) and the solution was cooled to 0 °C employing an ice/NaCl bath.
T287 42107-42390 Sentence denotes N,O-Dimethylhydroxylamine hydrochloric acid salt (68 g, 698 mmol) was added followed by N-methylmorpholine (230 mL, 2.09 mol), HOBt.hydrate (106 g, 698 mmol), and EDCI (147 g, 768 mmol), and the mixture was stirred at 0 °C under nitrogen for 6 h before quenching with water (500 mL).
T288 42391-42546 Sentence denotes The biphasic mixture was transferred to a sep funnel, and the organics were isolated, washed with 1 M hydrochloric acid (2 × 500 mL), water (400 mL), satd.
T289 42547-42811 Sentence denotes NaHCO3 (2 × 700 mL), and brine (300 mL) and then dried over MgSO4, filtered, and the solvents were evaporated in vacuo to yield tert-butyl ((1S)-2-[methoxy(methyl)amino]-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}ethyl)carbamate as a pale yellow solid, 173 g, 79%.
T290 42812-43054 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 5.92 (s, 1H), 5.39 (d, J = 8.8 Hz, 1H), 4.66 (td, J = 9.6, 2.8 Hz, 1H), 3.77 (s, 3H), 3.33 (dd, J = 9.3, 4.0 Hz, 2H), 3.19 (s, 2H), 2.41–2.62 (m, 2H), 2.05–2.16 (m, 1H), 1.75–1.95 (m, 1H), 1.67 (m, 1H), 1.41 (s, 9H).
T291 43055-43321 Sentence denotes To a 100 mL multinecked flask equipped with a stirrer bar, nitrogen inlet, and internal thermometer were charged magnesium turnings (dried in oven at 100 °C overnight, 1.04 g, 43 mmol) and HgCl2 (774 mg, 2.85 mmol), and the flask was purged with nitrogen for 10 min.
T292 43322-43510 Sentence denotes THF (50 mL) was added, and the suspension was cooled to −45 °C before adding BOM-Cl (5.94 mL, 43 mmol), and the resulting suspension was stirred for 5 h, the temperature returning to 5 °C.
T293 43511-43796 Sentence denotes The suspension was recooled to −50 °C, and tert-butyl ((1S)-2-[methoxy(methyl)amino]-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}ethyl)carbamate (1.5 g, 4.76 mmol) was added, and the thick suspension was stirred for 48 h under nitrogen and was allowed to come to an ambient temperature.
T294 43797-43855 Sentence denotes The reaction was quenched by the careful addition of satd.
T295 43856-43986 Sentence denotes NH4Cl solution (25 mL), and the mixture was stirred until effervescence ceased and then extracted with ethyl acetate (3 × 120 mL).
T296 43987-44259 Sentence denotes The combined organics were dried over MgSO4, filtered, and the solvents were evaporated in vacuo to yield a crude orange gum, which was purified by flash chromatography, eluting with 1–3% methanol/dichloromethane to afford the title compound as a clear glass, 900 mg, 50%.
T297 44260-44480 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 7.21–7.33 (m, 5H), 5.63–5.73 (m, 2H), 4.52 (m, 3H), 4.19 (q, J = 17.4 Hz, 2H), 3.19–3.25 (m, 2H), 2.29–2.42 (m, 2H), 1.68–1.93 (m, 3H), 1.35 (s, 9H); MS (APCI+) for C20H28N2O5m/z 378.1 (M + H)+.
T298 44482-44564 Sentence denotes (3S)-3-[(2S)-2-Amino-4-chloro-3-oxobutyl]pyrrolidin-2-one, Hydrochloride Salt (10)
T299 44565-44762 Sentence denotes A solution of tert-butyl ((1S)-3-diazo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl) carbamate (592 mg, 2.0 mmol) in 1,4-dioxane (7 mL) was placed under an atmosphere of N2 and cooled to 0 °C.
T300 44763-44924 Sentence denotes This clear pale yellow solution was dropwise treated with a solution of 4 M hydrochloric acid in 1,4-dioxane (5 mL, 20 mmol) with copious gas evolution observed.
T301 44925-45030 Sentence denotes Upon complete addition, the reaction was warmed to RT over 1 h with the formation of a white precipitate.
T302 45031-45168 Sentence denotes The solid was collected by filtration, washed with diethyl ether, and dried to give 401 mg (83%) of the title compound as a white powder.
T303 45169-45395 Sentence denotes 1H NMR (DMSO-d6) δ 8.76 (bs, 3H), 7.96 (s, 1H), 4.93 (d, J = 16 Hz, 1H), 4.80 (d, J = 16 Hz, 1H), 4.28 (m, 1H), 3.18 (m, 2H), 2.61 (m, 1H), 2.30 (m, 1H), 1.93 (m, 2H), 1.70 (m, 1H); MS (ESI+) for C8H13ClN2O2m/z 205.0 (M + H)+.
T304 45397-45486 Sentence denotes tert-Butyl ((1S)-3-Bromo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (11)
T305 45487-45743 Sentence denotes A solution of tert-butyl ((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (1.26 g, 4.3 mmol) in dichloromethane (107 mL) at 0 °C under nitrogen was treated with 48% hydrobromic acid (0.48 mL, 4.3 mmol) with effervescence observed.
T306 45744-45925 Sentence denotes The reaction was stirred at 0 °C for 1 h, washed once with water (30 mL), dried over MgSO4, filtered, and concentrated to afford 1.23 g (83%) of the title compound as a white solid.
T307 45926-46185 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.51 (d, J = 8 Hz, 1H), 4.46 (d, J = 16 Hz, 1H), 4.41 (d, J = 16 Hz, 1H), 4.19 (m, 1H), 3.13 (m, 2H), 2.26 (m, 1H), 2.13 (m, 1H), 1.87 (m, 1H), 1.63 (m, 2H), 1.38 (s, 9H); MS (ESI+) for C13H21BrN2O4m/z 371.0 (M + H)+.
T308 46187-46333 Sentence denotes N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (12)
T309 46334-46541 Sentence denotes A solution of 29, N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide (244 mg, 0.59 mmol) in 1,4-dioxane (1.0 mL) was placed under an atmosphere of N2.
T310 46542-46666 Sentence denotes This clear colorless solution was treated with a solution of 4 M hydrochloric acid in 1,4-dioxane with no observable change.
T311 46667-46746 Sentence denotes The reaction gradually became opaque with the formation of a gummy precipitate.
T312 46747-46996 Sentence denotes After 2 h, the volatiles were removed in vacuo, diluted with 1:1 ethanol/1,4-dioxane, concentrated, and high-vacuum-dried to give N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide hydrochloride as an off-white solid.
T313 46997-47288 Sentence denotes 1H NMR (DMSO-d6) δ 9.18 (d, J = 8 Hz, 1H), 8.40 (bs, 3H), 7.69 (s, 1H), 4.68 (s, 2H), 4.49 (m, 1H), 3.81 (m, 1H), 3.15 (m, 2H), 2.37 (m, 1H), 2.17 (m, 1H), 1.92 (m, 1H), 1.67 (m, 3H), 1.55 (m, 2H), 0.92 (d, J = 4 Hz, 3H), 0.88 (d, J = 4 Hz, 3H); MS (ESI+) for C14H24ClN3O3m/z 318.1 (M + H)+.
T314 47289-47466 Sentence denotes A solution of the crude hydrochloride salt and 4-methoxy-1H-indole-2-carboxylic acid (123 mg, 0.64 mmol) in DMF (2.5 mL) was placed under an atmosphere of N2 and cooled to 0 °C.
T315 47467-47617 Sentence denotes This pale yellow solution was successively treated with HATU (245 mg, 0.64 mmol) and N-methylmorpholine (0.14 mL, 1.29 mmol) turning a brighter color.
T316 47618-47743 Sentence denotes After 30 min, the reaction was quenched with 1:1 ice/sat NaHCO3 (25 mL) and extracted three times with ethyl acetate (20 mL).
T317 47744-47871 Sentence denotes The combined organics were washed once with brine (30 mL), dried over MgSO4, filtered, and concentrated to give a yellow syrup.
T318 47872-48016 Sentence denotes This material was purified by LC (30 g 230–400 SiO2, 4% methanol/chloroform) to afford 167 mg (58%) of the title compound as an off-white solid.
T319 48017-48508 Sentence denotes 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.62 (d, J = 8 Hz, 1H), 8.44 (d, J = 4 Hz, 1H), 7.65 (s, 1H), 7.38 (s, 1H), 7.10 (t, J = 8 Hz, 1H), 7.02 (d, J = 8 Hz, 1H), 6.51 (d, J = 8 Hz, 1H), 4.60 (d, J = 16 Hz, 1H), 4.58 (d, J = 16 Hz, 1H), 4.46 (m, 2H), 3.89 (s, 3H), 3.11 (m, 2H), 2.29 (m, 1H), 2.11 (m, 1H), 1.99 (m, 1H), 1.76–1.54 (m, 5H), 0.95 (d, J = 8 Hz, 3H), 0.9 (d, J = 8 Hz, 3H); MS (ESI+) for C24H31ClN4O5m/z 491.1 (M + H)+; HRMS (ESI+) calcd for C24H31ClN4O5+H1 491.2056, found 491.2058.
T320 48510-48626 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13)
T321 48627-48952 Sentence denotes An oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2.
T322 48953-49126 Sentence denotes This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring.
T323 49127-49243 Sentence denotes After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL).
T324 49244-49349 Sentence denotes The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo.
T325 49350-49496 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid.
T326 49497-50011 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+.
T327 50012-50077 Sentence denotes Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65.
T328 50078-50113 Sentence denotes Found: C, 59.41; H, 6.63; N, 10.68.
T329 50115-50247 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Cyclopropanecarboxylate (14)
T330 50248-50521 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting cyclopropanecarboxylic acid and making noncritical variations provided a crude product.
T331 50522-50651 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 82 mg (43%) of the title compound.
T332 50652-51114 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.57 (d, J = 2.0 Hz, 1H), 8.56 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.63 (s, 1H), 7.36 (d, J = 1.5 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.97–7.02 (m, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.85 (d, 1H), 4.78–4.96 (m, 1H), 4.33–4.51 (m, 2H), 3.87 (s, 3H), 3.02–3.16 (m, 2H), 2.22–2.35 (m, 1H), 2.01–2.11 (m, 1H), 1.89–2.00 (m, 1H), 1.65–1.77 (m, 3H), 1.46–1.65 (m, 3H), 0.81–0.98 (m, 10 H); MS (ESI+) for C28H36N4O7m/z 541.2 (M + H)+.
T333 51115-51180 Sentence denotes Anal. calcd for C28H36N4O7·0.59 H2O: C, 61.01; H, 6.80; N, 10.16.
T334 51181-51216 Sentence denotes Found: C, 61.04; H, 6.72; N, 10.00.
T335 51218-51335 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Pivalate (15)
T336 51336-51594 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting pivalic acid and making noncritical variations provided a crude product.
T337 51595-51725 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 152 mg (78%) of the title compound.
T338 51726-52147 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.56 (d, J = 7.8 Hz, 1H), 8.44 (d, J = 7.8 Hz, 1H), 7.64 (s, 1H), 7.36 (s, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.84 (s, 1H), 4.77–4.94 (m, 1H), 4.34–4.51 (m, 2H), 3.87 (s, 3H), 3.02–3.16 (m, 2H), 1.91–2.36 (m, 3H), 1.48–1.78 (m, 5H), 1.16 (s, 9H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C29H40N4O7m/z 557.2 (M + H)+.
T339 52148-52212 Sentence denotes Anal. calcd for C29H40N4O7·0.76 H2O: C, 61.07; H, 7.34; N, 9.82.
T340 52213-52247 Sentence denotes Found: C, 61.14; H, 7.63; N, 9.59.
T341 52249-52366 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Benzoate (16)
T342 52367-52625 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting benzoic acid and making noncritical variations provided a crude product.
T343 52626-52756 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 183 mg (91%) of the title compound.
T344 52757-53297 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.59 (s, 1H), 8.64 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.1 Hz, 2H), 7.91–7.95 (m, 1H), 7.66–7.71 (m, 1H), 7.66 (s, 1H), 7.52–7.57 (m, 1H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.96–7.02 (m, 1H), 6.49 (d, J = 7.6 Hz, 1H), 5.13 (s, 1H), 5.06–5.24 (m, 1H), 4.44–4.53 (m, 2H), 3.87 (s, 3H), 3.04–3.15 (m, 2H), 2.34 (m, 1H), 2.07–2.27 (m, 1H), 1.98–2.07 (m, 1H), 1.52–1.79 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H36N4O7m/z 577.2 (M + H)+.
T345 53298-53362 Sentence denotes Anal. calcd for C31H36N4O7·1.04 H2O: C, 62.54; H, 6.45; N, 9.41.
T346 53363-53397 Sentence denotes Found: C, 62.49; H, 6.54; N, 9.31.
T347 53399-53525 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Methoxybenzoate (17)
T348 53526-53793 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-methoxybenzoic acid and making noncritical variations provided a crude product.
T349 53794-53924 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 145 mg (68%) of the title compound.
T350 53925-54445 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.59 (d, J = 1.8 Hz, 1H), 8.62 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.93 (d, J = 9.1 Hz, 2H), 7.65 (s, 1H), 7.37 (d, J = 2.0 Hz, 1H), 7.04–7.11 (m, 2H), 7.00 (dd, J = 8.6, 3.0 Hz, 2H), 6.50 (d, J = 7.6 Hz, 1H), 5.07 (s, 1H), 5.01–5.18 (m, 1H), 4.44–4.51 (m, 2H), 3.87 (s, 3H), 3.83 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.25 (m, 1H), 1.97–2.06 (m, 1H), 1.50–1.79 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H38N4O8m/z 607.2 (M + H)+.
T351 54446-54519 Sentence denotes Anal. calcd for C32H38N4O8·0.80 H2O·0.05 DCM: C, 61.56; H, 6.40; N, 8.96.
T352 54520-54554 Sentence denotes Found: C, 61.84; H, 6.36; N, 8.58.
T353 54556-54681 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Methylbenzoate (18)
T354 54682-54948 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-methylbenzoic acid and making noncritical variations provided a crude product.
T355 54949-55078 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 92 mg (44%) of the title compound.
T356 55079-55619 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.59 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.87 (d, J = 8.1 Hz, 2H), 7.65 (s, 1H), 7.37 (d, J = 1.8 Hz, 1H), 7.34 (d, J = 8.3 Hz, 2H), 7.08 (t, J = 8.0 Hz, 1H), 6.97–7.01 (m, 1H), 6.50 (d, J = 7.8 Hz, 1H), 5.09 (s, 1H), 5.03–5.20 (m, 1H), 4.43–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.38 (s, 3H), 2.28–2.34 (m, 1H), 2.06–2.14 (m, 1H), 1.96–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H38N4O7m/z 591.2 (M + H)+.
T357 55620-55693 Sentence denotes Anal. calcd for C32H38N4O7·0.10 H2O·0.11 DCM: C, 64.08; H, 6.43; N, 9.31.
T358 55694-55728 Sentence denotes Found: C, 64.36; H, 6.41; N, 8.92.
T359 55730-55854 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Cyanobenzoate (19)
T360 55855-56120 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-cyanobenzoic acid and making noncritical variations provided a crude product.
T361 56121-56251 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 159 mg (75%) of the title compound.
T362 56252-56783 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 2.0 Hz, 1H), 8.64 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 8.09–8.14 (m, 2H), 7.99–8.05 (m, 2H), 7.66 (s, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.17 (d, J = 2.8 Hz, 1H), 5.11–5.27 (m, 1H), 4.44–4.53 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+.
T363 56784-56849 Sentence denotes Anal. calcd for C32H35N5O7·0.90 H2O: C, 62.21; H, 6.00; N, 11.33.
T364 56850-56885 Sentence denotes Found: C, 62.23; H, 6.06; N, 11.58.
T365 56887-57012 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Fluorobenzoate (20)
T366 57013-57279 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-fluorobenzoic acid and making noncritical variations provided a crude product.
T367 57280-57410 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 136 mg (65%) of the title compound.
T368 57411-57930 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 2.0 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 8.04 (dd, J = 8.6, 5.6 Hz, 2H), 7.65 (s, 1H), 7.35–7.41 (m, 3H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.12 (d, J = 1.3 Hz, 1H), 5.06–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.26 (m, 1H), 1.98–2.06 (m, 1H), 1.52–1.79 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35FN4O7m/z 595.2 (M + H)+.
T369 57931-58005 Sentence denotes Anal. calcd for C31H35FN4O7·0.59 H2O·0.06 DCM: C, 61.28; H, 5.98; N, 9.20.
T370 58006-58040 Sentence denotes Found: C, 61.27; H, 5.98; N, 9.11.
T371 58042-58167 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Chlorobenzoate (21)
T372 58168-58434 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product.
T373 58435-58565 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound.
T374 58566-59113 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+.
T375 59114-59189 Sentence denotes Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92.
T376 59190-59224 Sentence denotes Found: C, 59.31; H, 5.99; N, 9.23.
T377 59226-59355 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (22)
T378 59356-59626 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 2,6-dichlorobenzoic acid and making noncritical variations provided a crude product.
T379 59627-59766 Sentence denotes This material was purified by LC (20 g 230–400 SiO2, 3% methanol/chloroform) to afford 114 mg (65%) of the title compound as a white solid.
T380 59767-60203 Sentence denotes 1H NMR (DMSO-d6) δ 11.57 (d, J = 2 Hz, 1H), 8.62 (d, J = 8 Hz, 1H), 8.46 (d, J = 4 Hz, 1H), 7.65–7.53 (m, 4H), 7.36 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (d, J = 20 Hz, 1H), 5.15 (d, J = 20 Hz, 1H), 4.51 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.30 (m, 1H), 2.06 (m, 2H), 1.76–1.51 (m, 5H), 0.94 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C31H34Cl2N4O7m/z 645.1 (M + H)+; Anal.
T381 60204-60264 Sentence denotes Calcd for C31H34Cl2N4O7·0.2 H2O: C, 57.36; H, 5.34; N, 8.63.
T382 60265-60299 Sentence denotes Found: C, 57.23; H, 5.55; N, 8.46.
T383 60300-60364 Sentence denotes HRMS (ESI+) calcd for C31H34Cl2N4O7+H1 645.1877, found 645.1871.
T384 60366-60495 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Difluorobenzoate (23)
T385 60496-60775 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 2,6-difluorobenzoic acid and making noncritical variations provided a crude brown oily solid.
T386 60776-60897 Sentence denotes This material was triturated with chloroform/ethyl acetate to afford 180 mg (75%) of the title compound as a white solid.
T387 60898-61420 Sentence denotes 1H NMR (DMSO-d6) δ 11.65 (d, J = 2 Hz, 1H), 8.68 (d, J = 8 Hz, 1H), 8.54 (d, J = 8 Hz, 1H), 7.73–7.65 (m, 2H), 7.36 (s, 1H), 7.27 (t, J = 8 Hz, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (d, J = 16 Hz, 1H), 5.14 (d, J = 16 Hz, 1H), 4.48 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.11–1.91 (m, 2H), 1.81–1.56 (m, 5H), 0.94 (d, J = 4 Hz, 3H), 0.89 (d, J = 4 Hz, 3H); MS (ESI+) for C31H34F2N4O7m/z 613.2 (M + H)+; HRMS (ESI+) calcd for C31H34F2N4O7+H1 613.2469, found 613.2476.
T388 61422-61557 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Chloro-2-hydroxybenzoate (24)
T389 61558-61830 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorosalicylic acid and making noncritical variations provided a crude brown syrup.
T390 61831-61971 Sentence denotes This material was purified by Biotage MPLC (25 M, 2–3% methanol/dichloromethane) to afford 64 mg (25%) of the title compound as a tan solid.
T391 61972-62488 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 10.50 (bs, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 7.81 (d, J = 8 Hz, 1H), 7.63 (m, 1H), 7.37 (s, 1H), 7.08 (m, 2H), 7.00 (m, 2H), 6.50 (d, J = 8 Hz, 1H), 5.16 (d, J = 16 Hz, 2H), 5.11 (d, J = 16 Hz, 2H), 4.49 (m, 2H), 3.87 (s, 3H), 3.13 (m, 2H), 2.32 (m, 1H), 2.11–1.98 (m, 2H), 1.76–1.55 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI-) for C31H35ClN4O8m/z 625.1 (M – H)−; anal. calcd for C31H35ClN4O8·0.1 H2O·0.14 CHCl3: C, 57.93; H, 5.52; N, 8.68.
T392 62489-62587 Sentence denotes Found: C, 58.04; H, 5.78; N, 8.74; HRMS (ESI+) calcd for C31H35ClN4O8+H1 627.2216, found 627.2219.
T393 62589-62722 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Cyano-2-fluorobenzoate (25)
T394 62723-63006 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-cyano-2-fluorobenzoic acid and making noncritical variations provided a crude oily brown solid.
T395 63007-63160 Sentence denotes This material was purified by Biotage MPLC (25 M, 2.5–3.5% methanol/dichloromethane) to afford 119 mg (48%) of the title compound as an off-white powder.
T396 63161-63703 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (d, J = 2 Hz, 1H), 8.63 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 8.06 (m, 2H), 7.83 (d, J = 8 Hz, 1H), 7.65 (s, 1H), 7.36 (d, J = 2 Hz, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.50 (d, J = 8 Hz, 1H), 5.16 (d, J = 16 Hz, 1H), 5.11 (d, J = 16 Hz, 1H), 4.49 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.10–1.98 (m, 2H), 1.77–1.53 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI+) for C32H34FN5O7m/z 620.1 (M + H)+; anal. calcd for C32H34FN5O7·0.3 H2O: C, 61.49; H, 5.58; N, 11.20.
T397 63704-63802 Sentence denotes Found: C, 61.47; H, 5.61; N, 10.98; HRMS (ESI+) calcd for C32H34FN5O7+H1 620.2515, found 620.2532.
T398 63804-63933 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dimethylbenzoate (26)
T399 63934-64207 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 2,6-dimethylbenzoic acid and making noncritical variations provided a crude brown foam.
T400 64208-64356 Sentence denotes This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 177 mg (73%) of the title compound as an off-white glass.
T401 64357-64836 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (d, J = 2 Hz, 1H), 8.63 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 7.65 (s, 1H), 7.36 (s, 1H), 7.25 (t, J = 8 Hz, 1H), 7.08 (m, 3H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.11 (s, 2H), 4.51 (m, 2H), 3.87 (s, 3H), 3.10 (m, 2H), 2.32–2.21 (m, 7H), 2.07 (m, 2H), 1.78–1.53 (m, 5H), 0.94 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C33H40N4O7m/z 605.2 (M + H)+; anal. calcd for C33H40N4O7·0.3 H2O·0.2 CHCl3: C, 62.90; H, 6.49; N, 8.84.
T402 64837-64871 Sentence denotes Found: C, 62.95; H, 6.42; N, 8.72.
T403 64872-64933 Sentence denotes HRMS (ESI+) calcd for C33H40N4O7+H1 605.2970, found 605.2985.
T404 64935-65065 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dimethoxybenzoate (27)
T405 65066-65340 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 2,6-dimethoxybenzoic acid and making noncritical variations provided a crude brown foam.
T406 65341-65489 Sentence denotes This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 169 mg (66%) of the title compound as an off-white solid.
T407 65490-66041 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (d, J = 2 Hz, 1H), 8.55 (d, J = 8 Hz, 1H), 8.45 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.40–7.35 (m, 2H), 7.08 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.71 (d, J = 8 Hz, 1H), 6.50 (d, J = 8 Hz, 1H), 5.01 (d, J = 16 Hz, 1H), 4.95 (d, J = 16 Hz, 1H), 4.53–4.48 (m, 2H), 3.87 (s, 3H), 3.75 (s, 6H), 3.08 (m, 2H), 2.31 (m, 1H), 2.11–1.90 (m, 2H), 1.75–1.55 (m, 5H), 0.94 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C33H40N4O9m/z 637.2 (M + H)+; anal. calcd for C33H40N4O9·0.25 H2O·0.25 CHCl3: C, 59.51; H, 6.12; N, 8.35.
T408 66042-66076 Sentence denotes Found: C, 59.49; H, 6.08; N, 8.42.
T409 66078-66202 Sentence denotes (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2-Cyanobenzoate (28)
T410 66203-66477 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 2-cyanobenzoic acid and making noncritical variations provided a crude brown oily solid.
T411 66478-66598 Sentence denotes This material was triturated with chloroform/ethyl acetate to afford 91 mg (38%) of the title compound as a white solid.
T412 66599-67087 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 8.17 (m, 1H), 8.04 (m, 1H), 7.88 (m, 1H), 7.65 (s, 1H), 7.37 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (m, 2H), 4.50 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.07–1.97 (m, 2H), 1.76–1.56 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+; anal. calcd for C32H35N5O7·0.4 H2O: C, 63.12, H, 5.93; N, 11.50.
T413 67088-67185 Sentence denotes Found: C, 63.16; H, 5.96; N, 11.43; HRMS (ESI+) calcd for C32H35N5O7+H1 602.2609, found 602.2610.
T414 67187-67284 Sentence denotes (3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate
T415 67285-67526 Sentence denotes A solution of tert-butyl ((1S)-3-bromo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (1.17 g, 3.2 mmol) in DMF (16 mL) was treated with 2,6-dichlorobenzoic acid (794 mg, 4.2 mmol) followed by cesium fluoride (1.18 g, 7.4 mmol).
T416 67527-67604 Sentence denotes The resulting suspension was placed in a preheated oil bath at 65 °C for 2 h.
T417 67605-67822 Sentence denotes The reaction was cooled to an ambient temperature, diluted with ethyl acetate (100 mL), washed once with water (40 mL) and with brine (40 mL), dried over MgSO4, filtered, and concentrated to give a crude yellow syrup.
T418 67823-67972 Sentence denotes This material was purified by Biotage MPLC (25 M, 4.5% methanol/dichloromethane) to afford 1.19 mg (80%) of the title compound as an off-white glass.
T419 67973-68238 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 7.60 (m, 5H), 5.35 (s, 2H), 4.32 (m, 1H), 3.23 (m, 2H), 2.24 (m, 1H), 2.11 (m, 1H), 1.86 (m, 1H), 1.67 (m, 2H), 1.35 (s, 9H); MS (ESI+) for C20H24Cl2N2O6m/z 481.0 (M + Na)+; HRMS (ESI+) calcd for C20H24Cl2N2O6+H 481.0903, found 481.0890.
T420 68240-68347 Sentence denotes N2-(tert-Butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide
T421 68348-68557 Sentence denotes A solution of (3S)-3-[(2S)-2-amino-4-chloro-3-oxobutyl]pyrrolidin-2-one hydrochloride (391 mg, 1.6 mmol) and Boc-Leu-OH (412 mg, 1.8 mmol) in DMF (9 mL) was placed under an atmosphere of N2 and cooled to 0 °C.
T422 68558-68695 Sentence denotes This clear pale yellow solution was successively treated with HATU (678 mg, 1.8 mmol) followed by N-methylmorpholine (0.41 mL, 3.7 mmol).
T423 68696-68861 Sentence denotes The reaction mixture gradually became opaque and after 1 h was quenched with 1:1 ice/sat aqueous NaHCO3 (40 mL) and extracted three times with ethyl acetate (40 mL).
T424 68862-68989 Sentence denotes The combined organics were washed once with brine (30 mL), dried over MgSO4, filtered, and concentrated to give a yellow syrup.
T425 68990-69219 Sentence denotes This material was purified by LC (50 g 230–400 SiO2, 3–5% methanol/chloroform) to afford 636 mg (40%) of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide as a white foam.
T426 69220-69577 Sentence denotes 1H NMR (DMSO-d6) δ 8.47 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.04 (d, J = 8 Hz, 1H), 4.60 (d, J = 16 Hz, 1H), 4.53 (d, J = 16 Hz, 1H), 4.40 (m, 1H), 3.90 (m, 1H), 3.16 (m, 1H), 3.08 (m, 1H), 2.24 (m, 1H), 2.10 (m, 1H), 1.98 (m, 1H), 1.63 (m, 2H), 1.45–1.37 (m, 11 H), 0.89 (d, J = 4 Hz, 3H), 0.85 (d, J = 4 Hz, 3H); MS (ESI+) for C19H32ClN3O5m/z 418.1 (M + H)+.
T427 69578-69643 Sentence denotes Anal. calcd for C19H32ClN3O5·0.6 H2O: C, 53.22; H, 7.81; N, 9.80.
T428 69644-69678 Sentence denotes Found: C, 53.00; H, 7.65; N, 9.54.
T429 69679-69742 Sentence denotes HRMS (ESI+) calcd for C19H32ClN3O5+H1 418.2103, found 418.2091.
T430 69744-69859 Sentence denotes (3S)-3-{[N-(tert-Butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (29)
T431 69860-70196 Sentence denotes Following the procedure described for the preparation of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide but substituting (3S)-3-[(tert-butoxycarbonyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and making noncritical variations provided a brown foam.
T432 70197-70348 Sentence denotes This material was purified by LC (50 g 230–400 SiO2, 2.5–3.5% methanol/chloroform) to afford 413 mg (61%) of the title compound as a light yellow foam.
T433 70349-70707 Sentence denotes 1H NMR (DMSO-d6) δ 8.47 (d, J = 8 Hz, 1H), 7.60 (m, 4H), 7.05 (d, J = 8 Hz, 1H), 5.19 (d, J = 16 Hz, 1H), 5.13 (d, J = 16 Hz, 1H), 4.47 (m, 1H), 3.95 (m, 1H), 3.16 (m, 1H), 3.08 (m, 1H), 2.27 (m, 1H), 2.10 (m, 1H), 2.03 (m, 1H), 1.65 (m, 2H), 1.47–1.37 (m, 11 H), 0.89 (d, J = 4 Hz, 3H), 0.85 (d, J = 4 Hz, 3H); MS (ESI+) for C26H35Cl2N3O7m/z 572.1 (M + H)+.
T434 70708-70774 Sentence denotes Anal. calcd for C26H35Cl2N3O7·0.5 H2O: C, 53.70; H, 6.24; N, 7.23.
T435 70775-70874 Sentence denotes Found: C, 53.74; H, 6.31; N, 7.31; HRMS (ESI+) calcd for C26H35Cl2N3O7+Na 594.1744, found 594.1729.
T436 70876-70976 Sentence denotes (3S)-3-[(N-Acetyl-l-leucyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (30)
T437 70977-71313 Sentence denotes Following the procedure described for the preparation of N2-acetyl-N1-[(1S)-1-(chloroacetyl)-4-(dimethylamino)-4-oxobutyl]-N2-methyl-l-leucinamide but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and making noncritical variations provided a pale yellow oil.
T438 71314-71460 Sentence denotes This material was purified by Biotage MPLC (25 M, 3.5–4.5% methanol/dichloromethane) to afford 161 mg (78%) of the title compound as a white foam.
T439 71461-71895 Sentence denotes 1H NMR (DMSO-d6) δ 8.56 (d, J = 8 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.65–7.53 (m, 4H), 5.17 (d, J = 16 Hz, 1H), 5.10 (d, J = 16 Hz, 1H), 4.44 (m, 1H), 4.25 (m, 1H), 3.12 (m, 2H), 2.25 (m, 1H), 2.06 (m, 1H), 1.97 (m, 1H), 1.84 (s, 3H), 1.63 (m, 3H), 1.45 (m, 2H), 0.90 (d, J = 8 Hz, 3H), 0.85 (d, J = 8 Hz, 3H); MS (ESI+) for C23H29Cl2N3O6m/z 514.0 (M + H)+; anal. calcd for C23H29Cl2N3O6·0.25 H2O·0.1 EtOAc: C, 53.26; H, 5.79; N, 7.96.
T440 71896-71930 Sentence denotes Found: C, 53.27; H, 5.82; N, 7.84.
T441 71931-71995 Sentence denotes HRMS (ESI+) calcd for C23H29Cl2N3O6+H1 514.1506, found 514.1508.
T442 71997-72121 Sentence denotes (3S)-3-{[N-(1H-Benzimidazol-2-ylcarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (31)
T443 72122-72550 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and 1H-benzimidazole-2-carboxylic acid and making noncritical variations provided a crude yellow oil.
T444 72551-72697 Sentence denotes This material was purified by Biotage MPLC (25 M, 3–4% methanol/dichloromethane) to afford 95 mg (72%) of the title compound as an off-white foam.
T445 72698-73060 Sentence denotes 1H NMR (DMSO-d6) δ 13.32 (s, 1H), 8.89 (d, J = 8 Hz, 1H), 8.60 (d, J = 8 Hz, 1H), 7.74 (d, J = 8 Hz, 1H), 7.59 (m, 5H), 7.29 (m, 2H), 5.20 (d, J = 20 Hz, 1H), 5.15 (d, J = 20 Hz, 1H), 4.56 (m, 2H), 3.12 (m, 2H), 2.30 (m, 1H), 2.01 (m, 2H), 1.83 (m, 1H), 1.65 (m, 4H), 0.92 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C29H31Cl2N5O6m/z 616.0 (M + H)+.
T446 73061-73120 Sentence denotes Anal. calcd for C29H31Cl2N5O6: C, 56.50; H, 5.07; N, 11.36.
T447 73121-73156 Sentence denotes Found: C, 57.28; H, 5.32; N, 11.35.
T448 73157-73221 Sentence denotes HRMS (ESI+) calcd for C29H31Cl2N5O6+H1 616.1724, found 616.1729.
T449 73223-73360 Sentence denotes (3S)-3-({4-Methyl-N-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (3)
T450 73361-73772 Sentence denotes Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-N2-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucinamide and 2,6-dichlorobenzoic acid and making noncritical variations provided a light amber residue.
T451 73773-73985 Sentence denotes The residue was purified by preparative HPLC (Luna 10μ C18) eluting with a gradient of MeCN containing 0.1% AcOH in water containing 0.1% AcOH to give 0.155 g (54%) of the title compound as a cream colored solid.
T452 73986-74351 Sentence denotes 1H NMR (300 MHz, DMSO-d6) δ 8.52 (d, J = 8 Hz, 1H), 7.79 (d, J = 8 Hz, 1H), 7.71 (s, 1H), 7.66–7.55 (m, 3H), 5.18 (s, 2H), 4.54–4.40 (m, 1H), 4.37–4.35 (m, 1H), 4.25 (m, 1H), 3.98–3.91 (m, 1H), 3.84–3.72 (m, 1H), 3.23–3.07 (m, 2H), 2.33–2.23 (m, 1H), 2.16–2.05 (m, 2H), 1.86–1.74 (m, 3H), 1.72–1.62 (m, 5H), 0.89 (s, 9H); MS (ESI+) for C27H35Cl2N3O7m/z 584 (M + H).
T453 74352-74418 Sentence denotes Anal. calcd for C27H35Cl2N3O7·0.5 H2O: C, 54.64; H, 6.11; N, 7.08.
T454 74419-74453 Sentence denotes Found: C, 54.26; H, 6.00; N, 6.87.
T455 74454-74518 Sentence denotes HRMS (ESI+) calcd for C27H35Cl2N3O7+H1 584.1925, found 584.1921.
T456 74520-74641 Sentence denotes N2-(tert-Butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide (32)
T457 74642-74905 Sentence denotes Following the procedure described for the preparation of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide but substituting Boc-(β t-butyl)-Ala-OH and making noncritical variations provided a golden syrup.
T458 74906-75053 Sentence denotes This material was purified by Biotage MPLC (65i column, 2.5–3.5% methanol/chloroform) to afford 3.41 g (40%) of the title compound as a white foam.
T459 75054-75404 Sentence denotes 1H NMR (DMSO-d6) δ 8.39 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.00 (d, J = 8 Hz, 1H), 4.58 (d, J = 16 Hz, 1H), 4.52 (d, J = 16 Hz, 1H), 4.38 (m, 1H), 3.92 (m, 1H), 3.15 (t, J = 8 Hz, 1H), 3.07 (q, J = 8 Hz, 1H), 2.22 (m, 1H), 2.09 (m, 1H), 1.97 (m, 1H), 1.62 (m, 2H), 1.50 (m, 2H), 1.36 (s, 9H), 0.88 (s, 9H); MS (ESI+) for C20H34ClN3O6m/z 432.1 (M + H)+.
T460 75406-75532 Sentence denotes N1-((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-4-methyl-l-leucinamide (33)
T461 75533-75826 Sentence denotes Following the procedure described for the preparation of tert-butyl [(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]carbamate but substituting Boc-(β t-butyl)-Ala-OH and making noncritical variations provided a brown syrup.
T462 75827-75976 Sentence denotes This material was purified by LC (33 g 230–400 SiO2, 1–2.5% methanol/chloroform) to afford 258 mg (55%) of the title compound as a light yellow foam.
T463 75977-76299 Sentence denotes 1H NMR (DMSO-d6) δ 8.23 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.32 (m, 5H), 6.96 (d, J = 8 Hz, 1H), 4.46 (s, 2H), 4.35–4.33 (m, 2H), 4.21 (d, J = 16 Hz, 1H), 3.95 (m, 1H), 3.09 (m, 2H), 2.24 (m, 1H), 2.07 (m, 1H), 1.92 (m, 1H), 1.58 (m, 2H), 1.46 (m, 2H), 1.35 (s, 9H), 0.87 (m, 9H); MS (ESI+) for C27H41N3O6m/z 504.2 (M + H)+.
T464 76301-76456 Sentence denotes N-((1S)-1-{[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide (34)
T465 76457-76866 Sentence denotes Following the procedure described for the preparation of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-4-methyl-l-leucinamide and making noncritical variations provided a golden syrup.
T466 76867-77014 Sentence denotes This material was purified by Biotage MPLC (25 M column, 3% methanol/chloroform) to afford 173 mg (60%) of the title compound as an off-white foam.
T467 77015-77469 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.43 (app t, J = 8 Hz, 2H), 7.62 (s, 1H), 7.32 (m, 6H), 7.08 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.52 (m, 1H), 4.47–4.35 (m, 4H), 4.22 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.05 (m, 2H), 2.28 (m, 1H), 2.06 (m, 1H), 1.93 (m, 1H), 1.64–1.57 (m, 3H), 0.92 (s, 9H); MS (ESI+) for C32H40N4O6m/z 577.2 (M + H)+; anal. calcd for C32H40N4O6·0.33 methanol·0.25 H2O: C, 65.62; H, 7.13; N, 9.47.
T468 77470-77563 Sentence denotes Found: C, 65.65; H, 6.90; N, 9.58; HRMS (ESI+) calcd for C32H40N4O6 577.3021, found 577.3001.
T469 77565-77715 Sentence denotes N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide (35)
T470 77716-78112 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and making noncritical variations provided a pale yellow solid.
T471 78113-78264 Sentence denotes This material was purified by Biotage MPLC (40 M column, 2–4.5% methanol/chloroform) to afford 920 g (60%) of the title compound as an off-white solid.
T472 78265-78786 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.59 (d, J = 1.8 Hz, 1H), 8.54 (d, J = 7.8 Hz, 1H), 8.45 (d, J = 8.1 Hz, 1H), 7.64 (s, 1H), 7.32 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 7.00 (d, J = 8.3 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.52–4.62 (m, 1H), 4.40–4.51 (m, 2H), 3.87 (s, 3H), 3.01–3.16 (m, 2H), 2.19–2.31 (m, 1H), 2.03–2.12 (m, 1H), 1.91–2.01 (m, 1H), 1.81 (dd, J = 14.1, 9.9 Hz, 1H), 1.54–1.72 (m, 3H), 0.93 (s, 9H); MS (ESI+) for C25H33ClN4O5m/z 505.1 (M + H)+; HRMS (ESI+) calcd for (M + H)+ 505.2212, found 505.2204.
T473 78788-78939 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide (36)
T474 78940-79366 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide and making noncritical variations provided a crude brown glass.
T475 79367-79513 Sentence denotes This material was purified by Biotage MPLC (40 M column, 2–10% methanol/chloroform) to afford 415 mg (53%) of the title compound as a white solid.
T476 79514-79557 Sentence denotes MS (ESI+) for C25H34N4O6m/z 487.2 (M + H)+.
T477 79558-80004 Sentence denotes Alternatively, following the procedure described for the preparation of N-{(1S)-1-(cyclohexylmethyl)-2-[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-2-oxoethyl}-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide and making noncritical variations provided a tan solid.
T478 80005-80150 Sentence denotes This material was purified by Biotage MPLC (25 M column, 6–7% methanol/chloroform) to afford 100 mg (77%) of the title compound as a white solid.
T479 80151-80664 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.42 (d, J = 8 Hz, 1H), 8.37 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.32 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.04 (t, J = 8 Hz, 1H), 4.52 (m, 1H), 4.42 (m, 1H), 4.24 (dd, J = 8, 20 Hz, 1H), 4.12 (dd, J = 8, 20 Hz, 1H), 3.87 (s, 3H), 3.09 (m, 2H), 2.25 (m, 1H), 2.06 (m, 1H), 1.93 (m, 1H), 1.80 (dd, J = 8, 16 Hz, 1H), 0.93 (s, 9H); MS (ESI+) for C25H34N4O6m/z 487.2 (M + H)+; anal. calcd for C25H34N4O6·0.3 H2O: C, 61.03; H, 7.09; N, 11.39.
T480 80665-80759 Sentence denotes Found: C, 61.07; H, 7.09; N, 11.22; HRMS (ESI+) calcd for C25H34N4O6 487.2551, found 487.2541.
T481 80761-80912 Sentence denotes 4-Methoxy-N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide (37)
T482 80913-81337 Sentence denotes Following the procedure described for the preparation of 4-methoxy-N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide and making noncritical variations provided a crude product.
T483 81338-81483 Sentence denotes This material was purified by Biotage MPLC (40S column, 2–5% methanol/chloroform) to afford 21 mg (9%) of the title compound as a pale tan solid.
T484 81484-81999 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.42 (d, J = 6.8 Hz, 1H), 7.62 (s, 1H), 7.32 (s, 1H), 7.08 (t, J = 7.7 Hz, 1H), 7.00 (d, J = 7.8 Hz, 1H), 6.49 (d, J = 7.3 Hz, 1H), 4.49–4.55 (m, 1H), 4.32–4.41 (m, 1H), 4.21–4.30 (m, 1H), 4.12 (t, J = 16.9 Hz, 1H), 3.87 (s, 3H), 3.23 (s, 3H), 3.01–3.16 (m, 2H), 2.20–2.32 (m, 1H), 2.03–2.15 (m, 1H), 1.87–1.98 (m, 1H), 1.73–1.85 (m, 1H), 1.54–1.70 (m, 3H), 0.93 (s, 9H); MS (ESI+) for C26H36N4O6m/z 501.2 (M + H)+; HRMS (ESI+) calcd for (M + H)+ 501.2708, found 501.2701.
T485 82001-82147 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (4)
T486 82148-82419 Sentence denotes A solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (488 mg, 0.99 mmol) and benzoylformic acid (195 mg, 1.3 mmol) in DMF (6.5 mL) was placed under an atmosphere of N2.
T487 82420-82533 Sentence denotes This clear pale yellow solution was treated with cesium fluoride (350 mg, 2.3 mmol) followed by heating to 65 °C.
T488 82534-82891 Sentence denotes After 4 h, the now yellow suspension was cooled to RT, diluted with ethyl acetate (60 mL), washed three times with water (30 mL) and once with brine (30 mL), dried over MgSO4, filtered, and concentrated to give (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl oxo(phenyl)acetate as a crude yellow foam.
T489 82892-82935 Sentence denotes MS (ESI+) for C32H36N4O8m/z 605.2 (M + H)+.
T490 82936-83218 Sentence denotes A solution of the crude (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl oxo(phenyl)acetate in methanol (40 mL) was placed under an atmosphere of N2 and treated with potassium carbonate (7 mg, 0.05 mmol) with vigorous stirring.
T491 83219-83310 Sentence denotes After 1 h, the volatiles were removed in vacuo (bath < 30 °C) to give a crude yellow glass.
T492 83311-83459 Sentence denotes This material was purified by Biotage MPLC (25 M column, 6% methanol/chloroform) to afford 346 mg (73%) of the title compound as an off-white solid.
T493 83460-83918 Sentence denotes 1H NMR (DMSO-d6) δ 11.56 (s, 1H), 8.44 (d, J = 8 Hz, 1H), 8.39 (d, J = 8 Hz, 1H), 7.61 (s, 1H), 7.35 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.04 (t, J = 8 Hz, 1H), 4.46 (m, 2H), 4.25 (dd, J = 8, 20 Hz, 1H), 4.13 (dd, J = 8, 20 Hz, 1H), 3.87 (s, 3H), 3.10 (m, 2H), 2.28 (m, 1H), 2.08 (m, 1H), 1.92 (m, 1H), 1.70–1.53 (m, 5H), 0.93 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C24H32N4O6m/z 473.2 (M + H)+.
T494 83920-84042 Sentence denotes N1-((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-N2-methyl-l-leucinamide
T495 84043-84334 Sentence denotes Following the procedure described for the preparation of tert-butyl [(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]carbamate but substituting Boc-N-methyl-Leu and making noncritical variations provided a crude brown oil.
T496 84335-84492 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound (123 mg, 47%) as a yellow gum.
T497 84493-84756 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 7.22–7.33 (m, 5H), 5.76 (bd, 1H), 4.73 (s, 1H), 4.46–4.59 (m, 2H), 4.08–4.27 (m, 2H), 3.14–3.28 (m, 2H), 2.68 (s, 3H), 2.16–2.38 (m, 2H), 1.88–2.00 (m, 1H), 1.56–1.86 (m, 5H), 1.41 (s, 9H), 0.94 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H).
T498 84758-84913 Sentence denotes N-((1S)-1-{[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-N-methyl-1H-indole-2-carboxamide
T499 84914-85327 Sentence denotes Following the procedure described for the preparation of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-N2-methyl-l-leucinamide and making noncritical variations provided a crude brown oil.
T500 85328-85482 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a clear oil, 67 mg, 48%.
T501 85483-85937 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 9.83 (s, 1H), 7.95 (s, 1H), 7.26–7.36 (m, 5H), 7.18 (t, J = 8.0 Hz, 1H), 7.04 (d, J = 8.3 Hz, 1H), 7.00 (s, 1H), 6.48 (d, J = 7.8 Hz, 1H), 5.87 (s, 1H), 5.18–5.27 (m, 1H), 4.70 (s, 1H), 4.50–4.63 (m, 2H), 4.16–4.36 (m, 2H), 3.93 (s, 3H), 3.32 (s, 3H), 3.03–3.18 (m, 2H), 2.22 (s, 2H), 1.91–2.02 (m, 1H), 1.81 (t, J = 7.3 Hz, 3H), 1.66–1.72 (m, 1H), 1.55 (s, 1H), 0.87–1.01 (m, 6H); MS (API-ES−) for C32H40N4O6m/z 576.7 (M – H)−.
T502 85939-86095 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-N-methyl-1H-indole-2-carboxamide (38)
T503 86096-86540 Sentence denotes Following the procedure described for the preparation of N-{(1S)-1-(cyclohexylmethyl)-2-[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-2-oxoethyl}-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-N-methyl-1H-indole-2-carboxamide and making noncritical variations provided a crude clear glass.
T504 86541-86696 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white foam, 42 mg, 82%.
T505 86697-87083 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 10.16 (s, 1H), 8.26 (s, 1H), 7.18 (t, J = 8.0 Hz, 1H), 7.05 (d, J = 8.1 Hz, 1H), 6.99 (d, J = 2.3 Hz, 1H), 6.48 (d, J = 7.6 Hz, 1H), 6.09 (s, 1H), 5.14–5.27 (m, 1H), 4.51–4.65 (m, 1H), 4.25–4.50 (m, 2H), 3.94 (s, 3H), 3.26–3.46 (m, 3H), 3.11–3.24 (m, 1H), 3.01–3.11 (m, 1H), 1.48–2.39 (m, 9H), 0.88–1.02 (m, 6H); MS (API-ES–-) for C25H34N4O6m/z 485.3 (M – H)−.
T506 87085-87195 Sentence denotes N2-(tert-Butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-norleucinamide
T507 87196-87450 Sentence denotes Following the procedure described for the preparation of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide but substituting Boc-NorLeu-OH and making noncritical variations provided a golden syrup.
T508 87451-87603 Sentence denotes This material was purified by LC (100 g 230–400 SiO2, 2.5–3.5% methanol/chloroform) to afford 727 mg (42%) of the title compound as a light yellow foam.
T509 87604-87755 Sentence denotes 1H NMR (DMSO-d6) δ 8.45 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.00 (d, J = 8 Hz, 1H), 4.59 (d, J = 16 Hz, 1H), 4.53 (d, J = 16 foam in a 42% isolated yield.
T510 87756-87982 Sentence denotes 1H Hz, 1H), 4.38 (m, 1H), 3.80 (m, 1H), 3.15 (m, 1H), 3.06 (m, 1H), 2.22 (m, 1H), 2.07 (m, 1H), 1.98 (m, 1H), 1.63–1.51 (m, 4H), 1.36 (m, 9H), 1.24 (m, 4H), 0.83 (t, J = 8 Hz, 3H); MS (ESI+) for C19H32ClN3O5m/z 418.1 (M + H)+.
T511 87984-88117 Sentence denotes N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}pentyl)-4-methoxy-1H-indole-2-carboxamide
T512 88118-88514 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-norleucinamide and making no other critical variations provided a crude yellow foam.
T513 88515-88663 Sentence denotes This material was purified by Biotage MPLC (25 M column, 3% methanol/chloroform) to afford 254 mg (63%) of the title compound as an off-white solid.
T514 88664-89156 Sentence denotes 1H NMR (DMSO-d6) δ 11.56 (s, 1H), 8.57 (d, J = 8 Hz, 1H), 8.39 (d, J = 4 Hz, 1H), 7.62 (s, 1H), 7.36 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.58 (d, J = 16 Hz, 1H), 4.56 (d, J = 16 Hz, 1H), 4.43 (m, 1H), 4.35 (m, 1H), 3.87 (s, 3H), 3.09 (m, 2H), 2.27 (m, 1H), 2.08 (m, 1H), 1.97 (m, 1H), 1.74–1.54 (m, 4H), 1.30 (m, 4H), 0.86 (t, J = 8 Hz, 3H); MS (ESI+) for C24H31N4O5Cl m/z 491.1 (M + H)+; anal. calcd for C24H31ClN4O5: C, 58.71; H, 6.36; N, 11.41.
T515 89157-89192 Sentence denotes Found: C, 58.66; H, 6.45; N, 11.22.
T516 89194-89333 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}pentyl)-4-methoxy-1H-indole-2-carboxamide (39)
T517 89334-89751 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}pentyl)-4-methoxy-1H-indole-2-carboxamide and making noncritical variations provided a crude yellow foam.
T518 89752-89895 Sentence denotes This material was purified by Biotage MPLC (25 M column, 5–6% methanol/chloroform) to afford 82 mg (35%) of the title compound as a white foam.
T519 89896-90427 Sentence denotes 1H NMR (DMSO-d6) δ 11.57 (s, 1H), 8.42 (d, J = 8 Hz, 1H), 8.38 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.35 (s, 1H), 7.09 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.06 (t, J = 8 Hz, 1H), 4.44 (m, 2H), 4.25 (dd, J = 8, 20 Hz, 1H), 4.14 (dd, J = 8, 20 Hz, 1H), 3.87 (s, 3H), 3.08 (m, 2H), 2.28 (m, 1H), 2.10 (m, 1H), 1.91 (m, 1H), 1.74–1.54 (m, 4H), 1.32 (m, 4H), 0.87 (t, J = 8 Hz, 3H); MS (ESI+) for C24H32N4O6m/z 473.2 (M + H)+; anal. calcd for C24H32N4O6·0.6 H2O·0.2 ethyl acetate: C, 59.46; H, 7.01; N, 11.18.
T520 90428-90525 Sentence denotes Found: C, 53.37; H, 6.94; N, 11.23; HRMS (ESI+) calcd for C24H32N4O6+H1 473.2395, found 473.2382.
T521 90527-90594 Sentence denotes Methyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucinate
T522 90595-90823 Sentence denotes To a solution of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucine (2.14 g, 5.8 mmol) in methanol (15 mL) is added toluene (30 mL) followed by the dropwise addition of TMS-diazomethane (2.9 mL, 2 M in hexane, 5.8 mmol).
T523 90824-90939 Sentence denotes TLC analysis indicated incomplete reaction, and TMS-diazomethane was added dropwise until a yellow color persisted.
T524 90940-91046 Sentence denotes At this time, the reaction was quenched by the addition of AcOH (1 mL) followed by concentration in vacuo.
T525 91047-91198 Sentence denotes The residue was purified by Biotage flash chromatography, eluting with ethyl acetate/hexane to afford the title compound as a white solid, 2.18 g, 98%.
T526 91199-91590 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J = 7.6 Hz, 2H), 7.60 (dd, J = 7.2, 3.9 Hz, 2H), 7.40 (t, J = 7.2 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 5.26 (d, J = 8.6 Hz, 1H), 4.31–4.51 (m, 3H), 4.23 (t, J = 7.1 Hz, 1H), 3.75 (s, 3H), 1.78–1.93 (m, 1H), 1.60–1.76 (m, 1H), 1.45–1.60 (m, 1H), 1.05–1.34 (m, 2H), 0.88 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (APCI+) for C23H27NO4m/z 160.1 (M-Fmoc+H)+.
T527 91592-91646 Sentence denotes Methyl N-(tert-Butoxycarbonyl)-5-methyl-l-norleucinate
T528 91647-91946 Sentence denotes To a solution of methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucinate (2.18 g, 5.72 mmol) in DMF (50 mL) was added KF (2.33 g, 40.04 mmol) followed by triethylamine (1.70 mL, 12.24 mmol) and di-tert-butyl dicarbonate (7.39 mmol), and the mixture was stirred at an ambient temperature.
T529 91947-92116 Sentence denotes After 4 h, TLC analysis indicated incomplete reaction and the reaction mixture was treated with a second portion of KF (2.7 g, 46.55 mmol) and BOC2O (800 mg, 3.67 mmol).
T530 92117-92199 Sentence denotes After 16 h, the mixture was diluted with diethyl ether (300 mL), washed with satd.
T531 92200-92532 Sentence denotes NaHCO3 (2 × 50 mL), 1 M hydrochloric acid (2 × 50 mL), NaHCO3 (50 mL), and brine (50 mL), dried over MgSO4, filtered, and the solvents were evaporated in vacuo to yield the crude product, which was purified by Biotage flash chromatography eluting with dichloromethane/hexane to afford the title compound as a clear oil, 980 mg, 66%.
T532 92533-92783 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 4.96 (d, J = 6.8 Hz, 1H), 4.21–4.32 (m, 1H), 3.72 (s, 3H), 1.72–1.85 (m, 1H), 1.46–1.66 (m, 2H), 1.43 (s, 9H), 1.11–1.29 (m, 2H), 0.88 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (API-ES+) for C13H25NO4m/z 282.2 (M + Na)+.
T533 92785-92830 Sentence denotes N-(tert-Butoxycarbonyl)-5-methyl-l-norleucine
T534 92831-93128 Sentence denotes To a solution of methyl N-(tert-butoxycarbonyl)-5-methyl-l-norleucinate (980 mg, 3.78 mmol) in THF (30 mL) at 0 °C was added a solution (precooled to 5 °C) of LiOH (1 M, 11.3 mL, 11.33 mmol), and the resulting mixture was stirred at 0 °C for 1 h and then allowed to warm to an ambient temperature.
T535 93129-93236 Sentence denotes The reaction was acidified to pH 2 with 1 M hydrochloric acid and extracted with ethyl acetate (3 × 60 mL).
T536 93237-93413 Sentence denotes The combined organics were washed with brine (100 mL), dried over MgSO4, filtered, and the solvent was removed in vacuo to yield the title compound as a clear oil, 990 mg, 99%.
T537 93414-93669 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 4.96 (d, J = 7.8 Hz, 1H), 4.23–4.34 (m, 1H), 1.75–1.93 (m, 2H), 1.60–1.72 (m, 1H), 1.50–1.59 (m, 1H), 1.44 (s, 9H), 1.19–1.30 (m, 1H), 0.88 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (API-ES+) for C12H23NO4m/z 268.1 (M + Na)+.
T538 93671-93790 Sentence denotes N2-(tert-Butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-5-methyl-l-norleucinamide
T539 93791-94081 Sentence denotes Following the procedure described for the preparation of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide but substituting N-(tert-butoxycarbonyl)-5-methyl-l-norleucine and making noncritical variations provided a crude golden oil.
T540 94082-94244 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as an off-white solid, 360 mg, 41%.
T541 94245-94661 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 8.45 (d, J = 8.1 Hz, 1H), 7.62 (s, 1H), 7.02 (d, J = 7.1 Hz, 1H), 4.49–4.62 (m, 2H), 4.33–4.44 (m, 1H), 3.78 (m, 1H), 3.15 (t, J = 8.7 Hz, 1H), 3.00–3.10 (m, 1H), 2.18–2.30 (m, 1H), 2.04–2.14 (m, 1H), 1.92–2.02 (m, 1H), 1.40–1.68 (m, 5H), 1.36 (s, 9H), 1.05–1.25 (m, J = 7.3 Hz, 2H), 0.83 (d, J = 1.52 Hz, 3H), 0.82 (d, J = 1.52 Hz, 3H); MS (API-ES+) for C20H34N3O5Cl m/z 454.2 (M + Na)+.
T542 94663-94805 Sentence denotes N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-4-methoxy-1H-indole-2-carboxamide
T543 94806-95211 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-5-methyl-l-norleucinamide and making no other critical variations provided a crude yellow foam.
T544 95212-95361 Sentence denotes This material was purified by Biotage MPLC (25 M column, 2.5–3.5% methanol/chloroform) to afford 307 mg (73%) of the title compound as a white solid.
T545 95362-95846 Sentence denotes 1H NMR (DMSO-d6) δ 11.57 (s, 1H), 8.59 (d, J = 8 Hz, 1H), 8.41 (d, J = 4 Hz, 1H), 7.64 (s, 1H), 7.37 (s, 1H), 7.09 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.59 (s, 2H), 4.44 (m, 1H), 4.35 (m, 1H), 3.87 (s, 3H), 3.08 (m, 2H), 2.26 (m, 1H), 2.07 (m, 1H), 1.98 (m, 1H), 1.70–1.51 (m, 5H), 1.25 (m, 2H), 0.88 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (ESI+) for C25H33ClN4O5m/z 505.2 (M + H)+; HRMS (ESI+) calcd for C25H33ClN4O5+H1 505.2212, found 505.2204.
T546 95848-95996 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-4-methoxy-1H-indole-2-carboxamide (40)
T547 95997-96420 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-4-methoxy-1H-indole-2-carboxamide and making noncritical variations provided a crude yellow foam.
T548 96421-96567 Sentence denotes This material was purified by Biotage MPLC (25 M column, 5–5.5% methanol/chloroform) to afford 135 mg (50%) of the title compound as a white foam.
T549 96568-97104 Sentence denotes 1H NMR (DMSO-d6) δ 11.57 (s, 1H), 8.42 (d, J = 8 Hz, 1H), 8.38 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.35 (s, 1H), 7.09 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.06 (t, J = 8 Hz, 1H), 4.47–4.30 (m, 2H), 4.25 (dd, J = 8, 20 Hz, 1H), 4.14 (dd, J = 8, 20 Hz, 1H), 3.87 (s, 3H), 3.09 (m, 2H), 2.30 (m, 1H), 2.08 (m, 1H), 1.92 (m, 1H), 1.72–1.51 (m, 5H), 1.25 (m, 2H), 0.87 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (ESI+) for C25H34N4O6m/z 487.1 (M + H)+; HRMS (ESI+) calcd for C25H34N4O6 487.2551, found 487.2541.
T550 97106-97244 Sentence denotes tert-Butyl [(1S)-2-[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]carbamate
T551 97245-97619 Sentence denotes To a solution of tert-butyl ((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (200 mg, 0.53 mmol) in dioxane (5 mL) was added 4 M hydrochloric acid/dioxane (5 mL), and the solution was stirred at an ambient temperature for 4 h before removing the solvents in vacuo, azeotroping the residue with toluene (2 × 10 mL), and drying in vacuo for 1 h.
T552 97620-97901 Sentence denotes The crude hydrochloride salt was taken into DMF (3 mL), and the solution was cooled to 0 °C before adding N-Boc-cyclohexylalanine-OH (139 mg, 0.53 mmol), collidine (156 μL, 1.22 mmol), and HATU (194 mg, 0.53 mmol) in order, and the resulting suspension was stirred at 0 °C for 5 h.
T553 97902-98023 Sentence denotes The reaction was quenched by the addition of water (30 mL), and the mixture was extracted with diethyl ether (3 × 75 mL).
T554 98024-98295 Sentence denotes The combined organics were dried over MgSO4, filtered, and the solvents were removed in vacuo to yield the crude product, which was purified by flash chromatography, eluting with 1–3% methanol/dichloromethane to afford the title compound as a pale brown gum, 205 mg, 76%.
T555 98296-98362 Sentence denotes The product was contaminated with ∼20% of another diastereoisomer.
T556 98363-98669 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J = 5.6 Hz, 1H), 7.26–7.42 (m, 5H), 5.93 (s, 1H), 4.94 (d, J = 7.6 Hz, 1H), 4.72 (m, 1H), 4.60 (d, J = 11.6 Hz, 1H), 4.55 (d, J = 11.6 Hz, 1H), 4.14–4.34 (m, 3H), 3.27 (m, 2H), 2.23–2.51 (m, 3H), 1.56–2.05 (m, 9H), 1.33–1.48 (m, 9H), 1.05–1.29 (m, 4H), 0.80–1.03 (m, 2H).
T557 98671-98825 Sentence denotes N-[(1S)-2-[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide
T558 98826-99248 Sentence denotes To a solution of tert-butyl [(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]carbamate (200 mg, 0.38 mmol) in dioxane (4 mL) was added 4 M hydrochloric acid/dioxane (4 mL), and the solution was stirred at an ambient temperature for 2 h before removing the solvents in vacuo, azeotroping the residue with toluene (2 × 10 mL), and drying in vacuo for 1 h.
T559 99249-99537 Sentence denotes The crude hydrochloride salt was taken into DMF (3 mL), and the solution was cooled to 0 °C before adding 4-methoxy-indole-2-carboxylic acid (73 mg, 0.38 mmol), collidine (125 μL, 0.95 mmol), and HATU (144 mg, 0.38 mmol) in order, and the resulting suspension was stirred at 0 °C for 6 h.
T560 99538-99659 Sentence denotes The reaction was quenched by the addition of water (20 mL), and the mixture was extracted with diethyl ether (3 × 50 mL).
T561 99660-99983 Sentence denotes The combined organics were washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered, and the solvents were removed in vacuo to yield the crude product, which was purified by Biotage flash chromatography, eluting with 1–3% methanol/dichloromethane to afford the title compound as a pale brown gum, 90 mg, 39%.
T562 99984-100070 Sentence denotes The product was contaminated with ∼20% of another diastereomer from the previous step.
T563 100071-100615 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 9.59 (s, 1H), 8.13 (d, J = 6.6 Hz, 1H), 7.21–7.32 (m, 5H), 7.11 (t, J = 8.0 Hz, 1H), 7.02 (d, J = 1.5 Hz, 1H), 6.94 (d, J = 8.3 Hz, 1H), 6.72–6.78 (m, 1H), 6.42 (d, J = 7.8 Hz, 1H), 5.97 (s, 1H), 4.73 (m, 1H), 4.64 (m, 1H), 4.53 (d, J = 11.6 Hz, 1H), 4.46 (d, J = 11.6 Hz, 1H), 4.26 (d, J = 17.2 Hz, 1H), 4.15 (d, J = 17.4 Hz, 1H), 3.87 (s, 3H), 3.08–3.16 (m, 2H), 2.27–2.38 (m, 1H), 1.92 (m, 1H), 1.49–1.84 (m, 9H), 1.26–1.42 (m, 1H), 0.98–1.23 (m, 4H), 0.78–0.98 (m, 2H); MS (APCI+) for C34H42N4O6m/z 603.2 (M + H)+.
T564 100617-100772 Sentence denotes N-{(1S)-1-(Cyclohexylmethyl)-2-[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-2-oxoethyl}-4-methoxy-1H-indole-2-carboxamide (41)
T565 100773-101102 Sentence denotes To a solution of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide (80 mg, 0.13 mmol) in EtOH (3 mL) was added 10% Pd/C (50 mg), and the suspension was hydrogenated at an ambient temperature under H2 (1 atm balloon) for 5 h.
T566 101103-101367 Sentence denotes The catalyst was removed by filtration, and the solvents were evaporated in vacuo to yield the crude product, which was purified by Biotage flash chromatography, eluting with 2–10% methanol/dichloromethane to afford the title compound, 37 mg, 55% as a white solid.
T567 101368-101790 Sentence denotes 1H NMR (400 MHz, MeOD) δ 7.19 (s, 1H), 7.05 (t, J = 8.0 Hz, 1H), 6.93 (d, J = 8.1 Hz, 1H), 6.41 (d, J = 7.8 Hz, 1H), 4.52–4.59 (m, 2H), 4.27 (m, 2H), 3.83 (s, 3H), 3.08–3.21 (m, 2H), 2.47 (m, 1H), 2.13–2.24 (m, 1H), 1.92–2.03 (m, 1H), 1.53–1.79 (m, 9H), 1.31–1.45 (m, 1H), 1.04–1.29 (m, 3H), 0.81–1.02 (m, 2H); MS (APCI+) for C27H36N4O6m/z 513.2. (M + H)+; anal. calcd for C27H36N4O6· 0.8 H2O: C, 61.53; H, 7.19; N, 10.63.
T568 101791-101826 Sentence denotes Found: C, 61.83; H, 7.12; N, 10.27.
T569 101828-101939 Sentence denotes N-(tert-Butoxycarbonyl)-N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-phenylalaninamide
T570 101940-102194 Sentence denotes Following the procedure described for the preparation of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide but substituting Boc-Phe-OH and making noncritical variations provided a crude brown oil.
T571 102195-102352 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white solid, 351 mg, 36%.
T572 102353-102681 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.19–7.31 (m, 5H), 5.77 (s, 1H), 5.10 (d, J = 6.1 Hz, 1H), 4.52–4.57 (m, 1H), 4.44 (m, 1H), 4.01–4.12 (m, 2H), 3.26–3.37 (m, 2H), 3.01–3.08 (m, 2H), 2.29–2.37 (m, 1H), 2.15–2.25 (m, 1H), 1.98–2.06 (m, 1H), 1.75–1.91 (m, 2H), 1.40 (s, 9H); MS (API-ES−) for C22H30N3O5Cl m/z 450.2 (M – H)−.
T573 102683-102808 Sentence denotes N-((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-phenylalaninamide
T574 102809-103200 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-(tert-butoxycarbonyl)-N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-phenylalaninamide and making noncritical variations provided a crude green solid.
T575 103201-103358 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white solid, 300 mg, 91%.
T576 103359-103839 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.52 (d, J = 2.0 Hz, 1H), 8.68 (d, J = 7.8 Hz, 1H), 8.61 (d, J = 7.8 Hz, 1H), 7.61 (s, 1H), 7.37 (d, J = 7.1 Hz, 2H), 7.31 (d, J = 1.8 Hz, 1H), 7.26 (t, J = 7.6 Hz, 2H), 7.16 (t, J = 7.2 Hz, 1H), 7.07 (t, 1H), 6.97 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.68 (m, 1H), 4.38–4.49 (m, 3H), 3.88 (s, 3H), 2.97–3.17 (m, 4H), 2.20–2.32 (m, 1H), 2.02–2.14 (m, 1H), 1.93–2.02 (m, 1H), 1.52–1.69 (m, 2H); MS (APCI±) for C27H29N4O5Cl m/z 526.0 (M + H)−.
T577 103841-103972 Sentence denotes N-((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-phenylalaninamide (42)
T578 103973-104380 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-phenylalaninamide and making noncritical variations provided a crude greenish gum.
T579 104381-104543 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as an off-white solid, 123 mg, 44%.
T580 104544-105108 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.50 (d, J = 2.0 Hz, 1H), 8.58 (dd, J = 8.2, 3.9 Hz, 2H), 7.63 (s, 1H), 7.35–7.43 (m, 2H), 7.31 (d, J = 1.8 Hz, 1H), 7.27 (t, J = 7.6 Hz, 2H), 7.17 (t, J = 7.3 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.98 (d, J = 8.1 Hz, 1H), 6.48 (d, J = 7.8 Hz, 1H), 5.06 (t, J = 6.1 Hz, 1H), 4.72 (m, 1H), 4.48 (m, 1H), 4.16 (m, 2H), 3.89 (s, 3H), 2.97–3.18 (m, 4H), 2.24–2.36 (m, 1H), 2.04–2.18 (m, 1H), 1.88–2.01 (m, 1H), 1.55–1.76 (m, 2H); MS (APCI+) for C27H30N4O6m/z 507.1 (M + H)+; anal. calcd for C27H30N4O6· 1.25 H2O: C, 61.29; H, 6.19; N, 10.59.
T581 105109-105144 Sentence denotes Found: C, 61.37; H, 6.06; N, 10.49.
T582 105146-105281 Sentence denotes N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide
T583 105282-105713 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and indole-2-carboxylic acid and making no other critical variations provided a crude yellow foam.
T584 105714-105869 Sentence denotes This material was purified by Biotage MPLC (40 M column, 2.5–3.5% methanol/chloroform) to afford 1.06 g (62%) of the title compound as a light yellow foam.
T585 105870-106327 Sentence denotes 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.58 (d, J = 8 Hz, 1H), 8.50 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.61 (d, J = 8 Hz, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.62–4.50 (m, 3H), 4.45 (m, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.08 (m, 1H), 1.96 (m, 1H), 1.80 (m, 1H), 1.72–1.58 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H31ClN4O4m/z 475.1 (M + H)+; anal. calcd for C24H31ClN4O4·0.35 CHCl3: C, 56.59; H, 6.12; N, 10.84.
T586 106328-106424 Sentence denotes Found: C, 56.38; H, 6.18; N, 10.75; HRMS (ESI+) calcd for C24H31ClN4O4 475.2107, found 475.2122.
T587 106426-106567 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide (43)
T588 106568-106984 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide and making noncritical variations provided a crude yellow foam.
T589 106985-107134 Sentence denotes This material was purified by Biotage MPLC (40 M column, 4.5–5.5% methanol/chloroform) to afford 730 mg (72%) of the title compound as a white solid.
T590 107135-107676 Sentence denotes 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.49 (d, J = 8 Hz, 1H), 8.43 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.60 (s, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 5.05 (t, J = 8 Hz, 1H), 4.56 (m, 1H), 4.43 (m, 1H), 4.25 (dd, J = 8, 20 Hz, 1H), 4.13 (dd, J = 8, 20 Hz, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.80 (m, 1H), 1.64 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H32N4O5m/z 457.1 (M + H)+; anal. calcd for C24H32N4O5·0.2 CHCl3·0.2 ethyl acetate·0.25 H2O: C, 59.75; H, 6.88; N, 11.15.
T591 107677-107771 Sentence denotes Found: C, 59.67; H, 6.72; N, 11.03; HRMS (ESI+) calcd for C24H32N4O5 457.2446, found 457.2439.
T592 107773-107914 Sentence denotes N-((1S)-1-{[((1S)-3-Methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide (44)
T593 107915-108330 Sentence denotes Following the procedure described for the preparation of 4-methoxy-N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide and making noncritical variations provided a crude tan foam.
T594 108331-108479 Sentence denotes This material was purified by Biotage MPLC (25 M column, 3.5–4.5% methanol/chloroform) to afford 43 mg (15%) of the title compound as a white solid.
T595 108480-108975 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.48 (apar t, J = 8 Hz, 2H), 7.61 (apar d, J = 8 Hz, 2H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.55 (m, 1H), 4.37 (m, 1H), 4.25 (d, J = 20 Hz, 1H), 4.10 (d, J = 20 Hz, 1H), 3.23 (s, 3H), 3.06 (m, 2H), 2.27 (m, 1H), 2.07 (m, 1H), 1.91 (m, 1H), 1.79 (m, 1H), 1.69 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C25H34N4O5m/z 471.2 (M + H)+; anal. calcd for C25H34N4O5·0.2 ethyl acetate·0.75 H2O: C, 61.76; H, 7.46; N, 11.17.
T596 108976-109070 Sentence denotes Found: C, 61.85; H, 7.15; N, 11.02; HRMS (ESI+) calcd for C25H34N4O5 471.2602, found 471.2595.
T597 109072-109212 Sentence denotes N-((1S)-1-{[((1S)-3-Ethoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide (45)
T598 109213-109495 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide but substituting iodoethane and making noncritical variations provided a crude tan foam.
T599 109496-109644 Sentence denotes This material was purified by Biotage MPLC (25 M column, 3–5% methanol/chloroform) to afford 19 mg (6%) of the title compound as an off-white solid.
T600 109645-110158 Sentence denotes 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.48 (d, J = 8 Hz, 1H), 8.45 (d, J = 8 Hz, 1H), 7.61 (apar d, J = 8 Hz, 2H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 4.56 (m, 1H), 4.40 (m, 1H), 4.28 (d, J = 16 Hz, 1H), 4.13 (d, J = 16 Hz, 1H), 3.41 (m, 2H), 3.06 (m, 2H), 2.26 (m, 1H), 2.09 (m, 1H), 1.91 (m, 1H), 1.82 (m, 1H), 1.63 (m, 3H), 1.08 (t, J = 8 Hz, 3H), 0.94 (s, 9H); MS (ESI+) for C26H36N4O5m/z 485.2 (M + H)+; HRMS (ESI+) calcd for C26H36N4O5 485.2759, found 485.2756.
T601 110160-110290 Sentence denotes N1-((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-N2-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucinamide
T602 110291-110726 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-l-leucinamide and (2R)-tetrahydrofuran-2-carboxylic acid and making noncritical variations provided a crude product.
T603 110727-110976 Sentence denotes This crude material was purified by Biotage MPLC (40 M cartridge, chloroform mobile phase with 2% methanol followed by 3% methanol, sample loaded in chloroform) resulting in the isolation of 1.13 g (61%) of the title compound as a light yellow foam.
T604 110977-111407 Sentence denotes Rf = 0.27 (95:5 dichloromethane/methanol); 1H NMR (400 MHz, DMSO-d6) δ 8.47 (d, J = 8 Hz, 1H), 7.72 (d, J = 8 Hz, 1H), 7.68 (s, 1H), 4.55 (s, 2H), 4.44–4.36 (m, 1H), 4.35–4.27 (m, 1H), 4.21 (dd, J = 8, 5 Hz, 1H), 3.95–3.86 (m, 1H), 3.79–3.71 (m, 1H), 3.18–3.07 (m, 2H), 2.21 (td, J = 9, 4 Hz, 1H), 2.13–2.03 (m, 2H), 1.97–1.88 (m, 1H), 1.85–1.74 (m, 3H), 1.68–1.56 (m, 4H), 0.88 (s, 9H); MS (ESI+) for C20H32ClN3O5m/z 430 (M + H).
T605 111409-111545 Sentence denotes N1-((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-N2-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucinamide (46)
T606 111546-111953 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-N2-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucinamide and making noncritical variations provided a crude product.
T607 111954-112275 Sentence denotes This material was purified by a series of two radial chromatographies (first −2 mm plate, 90:10 dichloromethane/methanol to 90:20, sample loaded in 90:10) (second −1 mm plates, 90:10 dichloromethane/methanol to 95:5, sample loaded in dichloromethane) to provide 0.402 g (46%) of the title compound as a light yellow foam.
T608 112276-112697 Sentence denotes Rf = 0.44 (90:10 dichloromethane/methanol); 1H NMR (400 MHz, DMSO-d6) δ 8.27 (d, J = 8 Hz, 1H), 7.71 (d, J = 9 Hz, 1H), 7.65 (s, 1H), 5.11 (t, J = 6 Hz, 1H), 4.46–4.38 (m, 1H), 4.37–4.30 (m, 1H), 4.24–4.15 (m, 2H), 4.14–4.08 (m, 1H), 3.96–3.87 (m, 1H), 3.79–3.70 (m, 1H), 3.18–3.06 (m, 2H), 2.25–2.16 (m, 1H), 2.13–2.02 (m, 2H), 1.87–1.75 (m, 4H), 1.66–1.54 (m, 4H), 0.88 (s, 9H); MS (ESI+) for C20H33N3O6m/z 412 (M + H).
T609 112698-112760 Sentence denotes Anal. calcd for C20H33N3O6·0.5H2O: C, 57.12; H, 8.16; N, 9.99.
T610 112761-112795 Sentence denotes Found: C, 57.25; H, 7.93; N, 9.68.
T611 112796-112856 Sentence denotes HRMS (ESI+) calcd for C20H33N3O6+H 412.2442, found 412.2447.
T612 112858-112994 Sentence denotes N1-((1S)-3-Methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-N2-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucinamide (47)
T613 112995-113404 Sentence denotes Following the procedure described for the preparation of 4-methoxy-N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-1H-indole-2-carboxamide but substituting N1-((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-4-methyl-N2-[(2R)-tetrahydrofuran-2-ylcarbonyl]-l-leucinamide and making noncritical variations provided a crude product.
T614 113405-113657 Sentence denotes This material was purified by radial chromatography (1 mm plate, 95:5 dichloromethane/methanol, sample loaded in dichloromethane) resulting in the isolation of 45.6 mg (22%) of the title compound as a light orange gum and as a mixture of diastereomers.
T615 113658-114055 Sentence denotes Rf = 0.30 (95:5 dichloromethane/methanol); 1H NMR (400 MHz, DMSO-d6, major diastereomer) δ 8.33 (d, J = 8 Hz, 1H), 7.70 (d, J = 9 Hz, 1H), 7.66 (s, 1H), 4.39–4.28 (m, 2H), 4.24–4.07 (m, 3H), 3.94–3.86 (m, 1H), 3.75 (q, J = 7 Hz, 1H), 3.24 (s, 3H), 3.18–3.06 (m, 2H), 2.27–2.15 (m, 1H), 2.14–2.03 (m, 2H), 1.92–1.73 (m, 4H), 1.67–1.53 (m, 4H), 0.88 (s, 9H); MS (ESI+) for C21H35N3O6m/z 426 (M + H).
T616 114056-114117 Sentence denotes HRMS (ESI+) calcd for C21H35N3O6+H1 426.2599, found 426.2604.
T617 114119-114266 Sentence denotes 4-Methoxy-N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-1H-indole-2-carboxamide (48)
T618 114267-114582 Sentence denotes A solution of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (185 mg, 0.39 mmol), iodomethane (0.12 mL, 2.0 mmol), and silver(I) oxide (182 mg, 0.79 mmol) in dichloromethane (12 mL) was placed under an atmosphere of N2.
T619 114583-114763 Sentence denotes The resulting black thick suspension was heated to reflux for 18 h, treated with a second portion of iodomethane (0.12 mL, 2.0 mmol), and returned to reflux for an additional 24 h.
T620 114764-114961 Sentence denotes The reaction was cooled to RT, diluted with dichloromethane (20 mL), washed once with water (20 mL), once with brine (20 mL), dried over MgSO4, filtered, and concentrated to give a crude tan solid.
T621 114962-115115 Sentence denotes This material was purified by Biotage MPLC (25 M column, 3.5–4.5% methanol/chloroform) to afford 19 mg (10%) of the title compound as an off-white solid.
T622 115116-115632 Sentence denotes 1H NMR (DMSO-d6) δ 11.57 (s, 1H), 8.48 (d, J = 8 Hz, 1H), 8.40 (d, J = 8 Hz, 1H), 7.63 (s, 1H), 7.35 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.47 (m, 1H), 4.38 (m, 1H), 4.25 (d, J = 16 Hz, 1H), 4.11 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.23 (s, 3H), 3.08 (m, 2H), 2.31 (m, 1H), 2.08 (m, 1H), 1.92 (m, 1H), 1.72–1.51 (m, 5H), 0.93 (d, J = 8 Hz, 3H), 0.88 (d, J = 8 Hz, 3H); MS (ESI+) for C25H34N4O6m/z 487.2 (M + H)+; HRMS (ESI+) calcd for C25H34N4O6+H1 487.2551, found 487.2563.
T623 115634-115765 Sentence denotes N-((1S)-1-{[((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-1H-indole-2-carboxamide
T624 115766-116070 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting indole-2-carboxylic acid and making noncritical variations provided a crude orange foam.
T625 116071-116233 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as an off-white solid, 1.75 g, 82%.
T626 116234-116672 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.64 (d, J = 7.8 Hz, 1H), 8.50 (d, J = 7.8 Hz, 1H), 7.55–7.69 (m, 2H), 7.42 (d, J = 8.3 Hz, 1H), 7.26 (d, J = 1.5 Hz, 1H), 7.16 (m, 1H), 7.02 (t, J = 7.5 Hz, 1H), 4.53–4.66 (m, 2H), 4.39–4.52 (m, 2H), 2.94–3.18 (m, 2H), 2.22–2.35 (m, 1H), 2.03–2.16 (m, 1H), 1.89–2.02 (m, 1H), 1.45–1.82 (m, 5H), 0.93 (d, J = 6.3 Hz, 3H), 0.88 (d, J = 6.3 Hz, 3H); MS (APCI−) for C23H29N4O4Cl m/z 459.1 (M – H)−.
T627 116674-116811 Sentence denotes N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-1H-indole-2-carboxamide (49)
T628 116812-117222 Sentence denotes Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-1H-indole-2-carboxamide and making noncritical variations provided a crude black gum.
T629 117223-117385 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as an off-white solid, 218 mg, 18%.
T630 117386-117846 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.42–8.61 (m, 2H), 7.61 (d, J = 8.6 Hz, 2H), 7.41 (d, J = 8.1 Hz, 1H), 7.26 (s, 1H), 7.17 (t, J = 7.6 Hz, 1H), 7.02 (t, J = 7.5 Hz, 1H), 5.02 (t, 1H), 4.38–4.58 (m, 2H), 4.09–4.32 (m, 2H), 3.01–3.17 (m, 2H), 2.24–2.38 (m, 1H), 2.03–2.22 (m, 2H), 1.92 (m, 1H), 1.46–1.77 (m, 4H), 0.85–0.99 (m, 6H); MS (APCI+) for C23H30N4O5m/z 443.1 (M + H)+; anal. calcd for C23H30N4O5·0.55 H2O·0.05 DCM: C, 60.62; H, 6.89; N, 12.27.
T631 117847-117881 Sentence denotes Found: C, 60.83; H, 6.90; N,11.93.
T632 117883-118020 Sentence denotes N-((1S)-1-{[((1S)-3-Methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-1H-indole-2-carboxamide (50)
T633 118021-118438 Sentence denotes Following the procedure described for the preparation of 4-methoxy-N-((1S)-1-{[((1S)-3-methoxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-4-methylpentyl)-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-1H-indole-2-carboxamide and making noncritical variations provided a crude pale brown oil.
T634 118439-118593 Sentence denotes This material was purified by Biotage flash chromatography, eluting with methanol/dichloromethane to afford the title compound as a white foam, 15 mg, 7%.
T635 118594-119050 Sentence denotes 1H NMR (CDCl3) δ 9.52 (s, 1H), 8.38 (d, J = 6.1 Hz, 1H), 7.62 (d, J = 8.1 Hz, 1H), 7.40 (dd, J = 8.1, 3.8 Hz, 1H), 7.20–7.29 (m, 1H), 7.11 (t, J = 7.5 Hz, 1H), 6.98 (dd, J = 11.4, 1.5 Hz, 1H), 6.87 (d, J = 8.3 Hz, 1H), 5.98 (d, J = 13.1 Hz, 1H), 4.71–4.88 (m, 1H), 4.63 (m, 1H), 4.08–4.33 (m, 2H), 3.38–3.44 (s, 3H), 3.08–3.33 (m, 2H), 2.28–2.63 (m, 2H), 2.13–2.25 (m, 1H), 1.55–2.10 (m, 4H), 0.85–1.03 (m, 6H); MS (APCI−) for C24H32N4O5m/z 455.2 (M – H)−.
T636 119052-119095 Sentence denotes SARS CoV-1 Protease FRET Assay and Analysis
T637 119096-119221 Sentence denotes Proteolytic activity of coronavirus 3CL protease is measured using a continuous fluorescence resonance energy-transfer assay.
T638 119222-119368 Sentence denotes The SARS 3CLpro FRET assay measures the protease-catalyzed cleavage of TAMRA-SITSAVLQSGFRKMK-(DABCYL)-OH to TAMRA-SITSAVLQ and SGFRKMK(DABCYL)-OH.
T639 119369-119411 Sentence denotes The fluorescence of the cleaved TAMRA (ex.
T640 119412-119422 Sentence denotes 558 nm/em.
T641 119423-119525 Sentence denotes 581 nm) peptide was measured using a TECAN SAFIRE fluorescence plate reader over the course of 10 min.
T642 119526-119645 Sentence denotes Typical reaction solutions contained 20 mM HEPES (pH 7.0), 1 mM EDTA, 4.0 FRET substrate, 4% DMSO, and 0.005% Tween-20.
T643 119646-119843 Sentence denotes Assays were initiated with the addition of 25 nM SARS CoV-1 3CLpro nucleotide sequence 9985–10902 of the Urbani strain of SARS coronavirus complete genome sequence (NCBI accession number AY278741).
T644 119844-119924 Sentence denotes Percent inhibition was determined in duplicate at a 0.001 mM level of inhibitor.
T645 119925-120174 Sentence denotes Data was analyzed with the nonlinear regression analysis program KaleidaGraph using the equationwhere offset equals the fluorescence signal of the uncleaved peptide substrate, and limit equals the fluorescence of the fully cleaved peptide substrate.
T646 120175-120315 Sentence denotes The kobs is the first-order rate constant for this reaction and, in the absence of any inhibitor, represents the utilization of a substrate.
T647 120316-120553 Sentence denotes In an enzyme start reaction, which contains an irreversible inhibitor, and where the calculated limit is less than 20% of the theoretical maximum limit, the calculated kobs represents the rate of inactivation of coronavirus 3CL protease.
T648 120554-120657 Sentence denotes The slope (kobs/I) of a plot of kobs vs [I] is a measure of the avidity of the inhibitor for an enzyme.
T649 120658-120782 Sentence denotes For very fast irreversible inhibitors, kobs/I is calculated from observations at only one or two [I] rather than as a slope.
T650 120783-121008 Sentence denotes For the determination of IC50 values for reversible inhibitors, the data was analyzed with the nonlinear regression analysis programs Xlfit3.05 (IDBS, Guildford, U.K.) or GraphPad Prism 8.02 (GraphPad Software San Diego, CA).
T651 121010-121053 Sentence denotes SARS CoV-2 Protease FRET Assay and Analysis
T652 121054-121208 Sentence denotes The proteolytic activity of the main protease, 3CLpro, of SARS CoV-2 was monitored using a continuous fluorescence resonance energy-transfer (FRET) assay.
T653 121209-121619 Sentence denotes The SARS CoV-2 3CLpro assay measures the activity of full-length SARS CoV-2 3CL protease to cleave a synthetic fluorogenic substrate peptide with the following sequence DABCYL-KTSAVLQ-SGFRKME-EDANS modeled on a consensus peptide.50 The fluorescence of the cleaved EDANS peptide (excitation 340 nm/emission 490 nm) is measured using a fluorescence intensity protocol on a Flexstation reader (Molecular Devices).
T654 121620-121726 Sentence denotes The fluorescent signal is reduced in the presence of PF-00835231, a potent inhibitor of SARS CoV-2 3CLpro.
T655 121727-121851 Sentence denotes The assay reaction buffer contained 20 mM Tris–HCl (pH 7.3), 100 nM NaCl, 1 mM EDTA, 5 mM TCEP, and 25 μM peptide substrate.
T656 121852-121978 Sentence denotes Enzyme reactions were initiated with the addition of 15 nM SARS CoV-2 3CL protease and allowed to proceed for 60 min at 23 °C.
T657 121979-122154 Sentence denotes Percent inhibition or activity was calculated based on control wells containing no compound (0% inhibition/100% activity) and a control compound (100% inhibition/0% activity).
T658 122155-122243 Sentence denotes IC50 values were generated using a four-parameter fit model using ABASE software (IDBS).
T659 122244-122470 Sentence denotes Ki values were fit to the Morrison equation with the enzyme concentration parameter fixed to 15 nM, the Km parameter fixed to 14 μM, and the substrate concentration parameter fixed to 25 μM using Activity Base software (IDBS).
T660 122472-122499 Sentence denotes SARS CoV-1 Antiviral Assays
T661 122500-122546 Sentence denotes All assays were performed in BSL3 containment.
T662 122547-122641 Sentence denotes Vero 76 cells were plated at 10 000 cells per well using phenol red-free DMEM or IMEM (Gibco).
T663 122642-122941 Sentence denotes After adhering for 2 h at 37 °C, various concentrations of compound (320, 100, 33, 10, 3.3, 1.0, 0.3, or 0.1 μM) were added and the cells were infected with 2.6 × 103 PFU/well SARS CoV Toronto-2 (provided as a gift from Dr. Heinz Feldman (NIAID, Hamilton, MT)) or mock-infected with the medium only.
T664 122942-123097 Sentence denotes After 66 h, cell viability was determined using either the neutral red method or the CellTiter-Glo Luminescent Cell Viability Assay (Promega, Madison, WI).
T665 123098-123260 Sentence denotes For the neutral red method, the cells were washed twice with PBS, and 100 μL of DMEM pH 4.5 containing 0.066% neutral red was added to the cells for 2 h at 37 °C.
T666 123261-123447 Sentence denotes The cells were again washed twice with PBS, 100 μL of buffer solution (50% EtOH, 1% acetic acid) was added, and the OD was read at 540 nM after a 10 min incubation at 37 °C with shaking.
T667 123448-123621 Sentence denotes Data are expressed as the percent of neutral red or luminescent signal in wells of compound-treated cells compared to the signal in wells of uninfected, compound-free cells.
T668 123622-123875 Sentence denotes The 50% effective concentration (EC50) is calculated as the concentration of the compound that increases the percent of the neutral red or luminescent signal in infected, compound-treated cells to 50% of that produced by uninfected, compound-free cells.
T669 123876-124139 Sentence denotes The 50% cytotoxicity concentration (CC50) is calculated as the concentration of the compound that decreases the percent of the neutral red or luminescent signal in uninfected, compound-treated cells to 50% of that produced in uninfected, compound-free cells.51,52
T670 124141-124167 Sentence denotes hCOV 229E Antiviral assays
T671 124168-124251 Sentence denotes MRC-5 cells were plated at 10 000 cells per well using phenol red-free MEM (Gibco).
T672 124252-124477 Sentence denotes Various concentrations of compound (320, 100, 33, 10, 3.3, 1.0, 0.3, or 0.1 μM) were added, and the cells were infected with an amount of hCoV 229E, which caused 80% cell death in 4 days or mock-infected with the medium only.
T673 124478-124733 Sentence denotes After 4 days, cell viability was determined using the XTT dye reduction method.53 Data are expressed as the percent of neutral red or luminescent signal in wells of compound-treated cells compared to the signal in wells of uninfected, compound-free cells.
T674 124734-124987 Sentence denotes The 50% effective concentration (EC50) is calculated as the concentration of the compound that increases the percent of the neutral red or luminescent signal in infected, compound-treated cells to 50% of that produced by uninfected, compound-free cells.
T675 124988-125246 Sentence denotes The 50% cytotoxicity concentration (CC50) is calculated as the concentration of the compound that decreases the percent of the neutral red or luminescent signal in uninfected, compound-treated cells to 50% of that produced in uninfected, compound-free cells.
T676 125248-125270 Sentence denotes Other Antiviral Assays
T677 125271-125432 Sentence denotes The following antiviral assays for HCMV,54 HIV-RF,55 HRV-14, and HRV-16,54 as well as the HCV replicon,56,57 were performed as described in the above references.
T678 125434-125483 Sentence denotes Expression and Purification of CoV-2 3CL Protease
T679 125484-125735 Sentence denotes The expression and purification strategy followed previous studies on SARS CoV-1 3CLpro.58 Genes encoding SARS CoV-1 3CLpro and SARS CoV-2 Mpro MN908947.3 were synthesized with codon usage optimized for Escherichia coli expression (Genscript and IDT).
T680 125736-125862 Sentence denotes Genes were cloned into a modified pET24a vector to produce a TEV-cleavable N-terminal 6xHis tag under the T7 promoter control.
T681 125863-126008 Sentence denotes BL21(DE3) cells (LifeTech) were grown in Terrific Broth (Teknova) at 37 °C until an OD600 = 0.6–0.8 and induced with 0.4 M IPTG for 5 h at 30 °C.
T682 126009-126063 Sentence denotes Cell pellets were stored at −80 °C until purification.
T683 126064-126171 Sentence denotes Cell pellets were resuspended and lysed by microfluidization in Buffer A (20 mM Tris pH 8.0 + 150 mM NaCl).
T684 126172-126225 Sentence denotes Lysates were clarified at 25,000 × g for 1 h at 4 °C.
T685 126226-126361 Sentence denotes The soluble lysate was loaded onto a nickel affinity column (Probond) and washed sequentially with Buffer A + 5 mM and 20 mM imidazole.
T686 126362-126421 Sentence denotes The proteases were eluted with Buffer A + 300 mM imidazole.
T687 126422-126526 Sentence denotes The His-tag was removed by TEV protease (1:40) during an overnight dialysis step in Buffer A + 1 mM DTT.
T688 126527-126812 Sentence denotes The CoV Mpro proteins were further purified on a HiTrap Q hp (GE Healthcare), and the Q-flow-through material was concentrated and loaded onto a 26/60 Superdex-75 (GE Healthcare) gel filtration column equilibrated with Buffer B (20 mM Tris pH 7.8 + 150 mM NaCl + 1 mM EDTA + 1 mM DTT).
T689 126813-126966 Sentence denotes Final proteins were concentrated from 5 to 25 mg/mL and were directly moved to crystallization experiments or snap-frozen in liquid nitrogen for storage.
T690 126968-127015 Sentence denotes Crystallization/Soak Protocols for SARS1 with 2
T691 127016-127109 Sentence denotes Crystals of compound 2 bound to SARS1/CoV-1 DC2 protease were produced via cocrystallization.
T692 127110-127222 Sentence denotes SARS1/CoV-1 DC2 protease at 10.00 mg/mL was incubated with a 3-fold molar excess of compound 2 for 18 h at 4 °C.
T693 127223-127380 Sentence denotes The complex was then passed through a 0.45 μM cellulose acetate spin filter and set up for crystallization using an NT-8 crystallization robot (Formulatrix).
T694 127381-127602 Sentence denotes Using MRC-2 crystallization plates, wells containing 40 μL of 4% w/v PEG 6000, 0.1 M MES pH 6.0, and 2.5 mM DTT were dispensed, and then sitting drops consisting of 0.3 μL protein were set up against a 0.3 μL well buffer.
T695 127603-127725 Sentence denotes Crystallization plates were incubated at 21 °C, and rectangular crystals measuring 0.1 × 0.25 × 0.25 mm3 grew within 24 h.
T696 127726-127860 Sentence denotes Cocrystals were flash-frozen in liquid nitrogen after being passed through a cryo consisting of a well buffer containing 20% glycerol.
T697 127862-127910 Sentence denotes Crystallization/Soak Protocols for SARS1 with 28
T698 127911-128005 Sentence denotes Crystals of compound 28 bound to SARS1/CoV-1 DC2 protease were produced via cocrystallization.
T699 128006-128119 Sentence denotes SARS1/CoV-1 DC2 protease at 10.00 mg/mL was incubated with a 3-fold molar excess of compound 28 for 18 h at 4 °C.
T700 128120-128277 Sentence denotes The complex was then passed through a 0.45 μM cellulose acetate spin filter and set up for crystallization using an NT-8 crystallization robot (Formulatrix).
T701 128278-128546 Sentence denotes Using MRC-2 crystallization plates, wells containing 40 μL of 10% w/v PEG 8000, 0.2 M sodium chloride, 0.1 M sodium potassium phosphate pH 6.2, and 10 mM TCEP were dispensed, and then sitting drops consisting of 0.3 μL protein were set up against a 0.3 μL well buffer.
T702 128547-128669 Sentence denotes Crystallization plates were incubated at 21 °C, and rectangular crystals measuring 0.1 × 0.25 × 0.25 mm3 grew within 24 h.
T703 128670-128804 Sentence denotes Cocrystals were flash-frozen in liquid nitrogen after being passed through a cryo consisting of a well buffer containing 20% glycerol.
T704 128806-128877 Sentence denotes Crystallization/Soak Protocols for SARS1 and SARS2 with 4 (PF-00835231)
T705 128879-128901 Sentence denotes LJEC2520 + PF-00835231
T706 128902-128982 Sentence denotes Crystals of PF-00835231 bound to SARS1/CoV-1 DC2 protease via cocrystallization:
T707 128983-129113 Sentence denotes Freshly prepared SARS1/CoV-1 DC2 protease at 10.00 mg/mL was incubated with a 3-fold molar excess of PF-00835231 for 18 h at 4 °C.
T708 129114-129271 Sentence denotes The complex was then passed through a 0.45 μM cellulose acetate spin filter and set up for crystallization using an NT-8 crystallization robot (Formulatrix).
T709 129272-129498 Sentence denotes Using MRC-2 crystallization plates, wells containing 40 μL of 10% w/v PEG 6000, 0.1 M MES pH 6.0, and 10% glycerol were dispensed, and then sitting drops consisting of 0.15 μL protein were set up against a 0.15 μL well buffer.
T710 129499-129619 Sentence denotes Crystallization plates were incubated at 21 °C, and rectangular crystals measuring 0.2 × 0.25 × 0.15 mm3 grew overnight.
T711 129620-129752 Sentence denotes Crystals were flash-frozen in liquid nitrogen after being passed through a cryo consisting of a well buffer containing 20% glycerol.
T712 129754-129776 Sentence denotes LJEC2521 + PF-00835231
T713 129777-129860 Sentence denotes Crystals of PF-00835231 bound to SARS2/CoV-2 mature protease via cocrystallization:
T714 129861-129993 Sentence denotes Freshly prepared SARS2/CoV-2 mature protease at 11.3 mg/mL was incubated with a 3-fold molar excess of PF-00835231 for 18 h at 4 °C.
T715 129994-130151 Sentence denotes The complex was then passed through a 0.45 μM cellulose acetate spin filter and set up for crystallization using an NT-8 crystallization robot (Formulatrix).
T716 130152-130388 Sentence denotes Using MRC-2 crystallization plates, wells containing 40 μL of 15% v/v 2-propanol, 0.1 M citric acid pH 5.0, and 10% w/v PEG 10 000 were dispensed, and then sitting drops consisting of 0.3 μL protein and a 0.3 μL well buffer were set up.
T717 130389-130524 Sentence denotes Crystallization plates were incubated at 13 °C, and crystals shaped as rectangular blocks measuring 0.1 × 0.2 × 0.2 mm3 grew overnight.
T718 130525-130657 Sentence denotes Crystals were flash-frozen in liquid nitrogen after being passed through a cryo consisting of a well buffer containing 20% glycerol.
T719 130659-130681 Sentence denotes LJEC2522 + PF-00835231
T720 130682-130752 Sentence denotes Crystals of PF-00835231 bound to SARS2/CoV-2 DC2 protease via soaking:
T721 130753-130949 Sentence denotes Freshly prepared SARS2/CoV-2 DC2 protease at 25.8 mg/mL was passed through a 0.45 mM cellulose acetate spin filter and set up for crystallization using an NT-8 crystallization robot (Formulatrix).
T722 130950-131192 Sentence denotes Using MRC-2 crystallization plates, wells containing 40 mL of 0.2 M potassium sodium tartrate tetrahydrate and 20% w/v PEG 3350 were dispensed, and then sitting drops consisting of 0.3 μL protein were set up in a 1:1 ratio with a well buffer.
T723 131193-131334 Sentence denotes Crystallization plates were incubated at 13 °C, and large crystals shaped as beveled plates measuring 0.35 × 0.2 × 0.025 mm3 grew after 48 h.
T724 131335-131480 Sentence denotes PF-00835231 (in 100% DMSO solution) was introduced to the drop (in situ), at a final concentration of 1 mM, and then incubated at 13 °C for 24 h.
T725 131481-131620 Sentence denotes Soaked crystals were flash-frozen in liquid nitrogen after being passed through a cryo consisting of a well buffer containing 20% glycerol.
T726 131621-131645 Sentence denotes Structure determination.
T727 131646-131795 Sentence denotes X-ray diffraction data were collected at the IMCA-CAT 17-ID beamline of Advanced Photon Source at Argonne National Labs and processed using autoPROC.
T728 131796-132069 Sentence denotes Structure of the SARS CoV main protease in complex with PF-835231 was determined by molecular replacement using the published protein structure (PDBID 1Q2W) as the starting model in program Phaser and refined iteratively using autoBUSTER followed by model building in Coot.
T729 132070-132285 Sentence denotes Structure of the SARS CoV-2 main protease in complex with PF-835231 was determined similarly by rigid body refinement using the SARS CoV main protease structure in complex with the same ligand as the starting model.
T730 132287-132319 Sentence denotes Supporting Information Available
T731 132320-132502 Sentence denotes The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c01063.Molecular formula strings for all compounds with biological data (CSV)
T732 132503-132535 Sentence denotes HPLC purity for compound 4 (PDF)
T733 132537-132559 Sentence denotes Supplementary Material
T734 132560-132580 Sentence denotes jm0c01063_si_001.csv
T735 132581-132601 Sentence denotes jm0c01063_si_002.pdf
T736 132603-132623 Sentence denotes Author Contributions
T737 132624-132692 Sentence denotes The manuscript was written through the contributions of all authors.
T738 132693-132764 Sentence denotes All authors have given approval to the final version of the manuscript.
T739 132766-132877 Sentence denotes Funding for the antiviral testing was provided by NIAID under a cooperative agreement between NIAID and Pfizer.
T740 132879-132931 Sentence denotes The authors declare no competing financial interest.
T741 132933-132948 Sentence denotes Acknowledgments
T742 132949-133101 Sentence denotes The authors would like to thank the Pfizer La Jolla Discovery Technology group who were responsible for all HRMS, preparative HPLC, and SFC separations.
T743 133102-133186 Sentence denotes Antiviral testing was performed at the Southern Research Institute (Birmingham, AL).
T744 133187-133329 Sentence denotes The authors wish to thank Dr. Heinz Feldman (NIAID, Hamilton, MT) for the kind gift of the SARS CoV Toronto-2 cell line enabling this testing.
T745 133330-133446 Sentence denotes The authors wish to thank Cathy Laughlin, Christopher Tseng, and Jack Secrist for their roles in this collaboration.
T746 133447-133535 Sentence denotes The authors would also like to thank Kevin Freeman-Cook, Charlotte Allerton, and Gina M.
T747 133536-133631 Sentence denotes Yanochko-Hoffman for critically reading the manuscript and offering valued editing suggestions.

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T1 1189-1216 Phenotype denotes respiratory tract infection http://purl.obolibrary.org/obo/HP_0011947
T2 1618-1623 Phenotype denotes fever http://purl.obolibrary.org/obo/HP_0001945
T3 1625-1633 Phenotype denotes coughing http://purl.obolibrary.org/obo/HP_0012735
T4 1639-1659 Phenotype denotes difficulty breathing http://purl.obolibrary.org/obo/HP_0002098
T5 10910-10913 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T6 31940-31956 Phenotype denotes immunodeficiency http://purl.obolibrary.org/obo/HP_0002721
T7 54487-54490 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T8 55661-55664 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T9 57973-57976 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T10 59157-59160 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T11 117813-117816 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
3 49-60 Species denotes Coronavirus Tax:11118
4 13-19 Chemical denotes Ketone MESH:D007659
5 118-126 Disease denotes COVID-19 MESH:C000657245
19 220-230 Species denotes SARS CoV-2 Tax:2697049
20 277-285 Species denotes SARS CoV Tax:694009
21 355-371 Species denotes SARS coronavirus Tax:694009
22 560-571 Species denotes coronavirus Tax:11118
23 610-613 Species denotes CoV Tax:11118
24 620-625 Species denotes CoV-2 Tax:2697049
25 818-826 Species denotes SARS CoV Tax:694009
26 1015-1020 Species denotes CoV-2 Tax:2697049
27 791-797 Chemical denotes ketone MESH:D007659
28 141-166 Disease denotes novel coronavirus disease MESH:C000657245
29 167-175 Disease denotes COVID-19 MESH:C000657245
30 307-333 Disease denotes acute respiratory syndrome MESH:D012120
31 1131-1139 Disease denotes COVID-19 MESH:C000657245
59 1971-1975 Gene denotes pp1a Gene:5499
60 1276-1293 Species denotes novel coronavirus Tax:2697049
61 1294-1304 Species denotes SARS CoV-2 Tax:2697049
62 1420-1428 Species denotes SARS CoV Tax:694009
63 1436-1447 Species denotes coronavirus Tax:11118
64 1523-1531 Species denotes SARS CoV Tax:694009
65 1596-1606 Species denotes SARS CoV-2 Tax:2697049
66 1723-1733 Species denotes SARS CoV-2 Tax:2697049
67 1771-1779 Species denotes SARS CoV Tax:694009
68 1918-1926 Species denotes SARS CoV Tax:694009
69 2229-2237 Species denotes SARS CoV Tax:694009
70 2334-2345 Species denotes coronavirus Tax:11118
71 2376-2385 Species denotes hCoV 229E Tax:11137
72 2390-2394 Species denotes TGEV Tax:11149
73 2423-2433 Species denotes SARS CoV-2 Tax:2697049
74 2460-2468 Species denotes SARS CoV Tax:694009
75 2475-2485 Species denotes SARS CoV-2 Tax:2697049
76 2718-2726 Species denotes SARS CoV Tax:694009
77 2774-2784 Species denotes SARS CoV-2 Tax:2697049
78 1189-1216 Disease denotes respiratory tract infection MESH:D012141
79 1347-1355 Disease denotes COVID-19 MESH:C000657245
80 1467-1493 Disease denotes acute respiratory syndrome MESH:D012120
81 1557-1563 Disease denotes deaths MESH:D003643
82 1618-1623 Disease denotes fever MESH:D005334
83 1625-1633 Disease denotes coughing MESH:D003371
84 1846-1856 Disease denotes infections MESH:D007239
85 1886-1892 Disease denotes deaths MESH:D003643
102 3575-3579 Gene denotes Mpro Gene:8673700
103 2869-2886 Gene denotes cysteine protease Gene:1508
104 3592-3605 Species denotes coronaviruses Tax:11118
105 3746-3754 Species denotes SARS CoV Tax:694009
106 3814-3824 Species denotes SARS CoV-2 Tax:2697049
107 2913-2922 Chemical denotes aldehydes MESH:D000447
108 2925-2954 Chemical denotes −13 thio- or oxymethylketones
109 2958-2972 Chemical denotes cyclic ketones
110 2976-2994 Chemical denotes amidomethylketones
111 2998-3006 Chemical denotes nitriles MESH:D009570
112 3024-3038 Chemical denotes 1,2-dicarbonyl
113 3070-3076 Chemical denotes carbon MESH:D002244
114 3124-3130 Chemical denotes sulfur MESH:D013455
115 3154-3162 Chemical denotes cysteine MESH:D003545
116 3501-3512 Chemical denotes α-ketoamide
117 3513-3520 Chemical denotes warhead
126 4286-4297 Gene denotes cathepsin B Gene:1508
127 4454-4471 Gene denotes cysteine protease Gene:1508
128 4472-4481 Gene denotes caspase-1 Gene:834
129 4695-4698 Gene denotes SN2 Gene:92745
130 3979-3998 Chemical denotes chloromethylketones
131 4205-4225 Chemical denotes acyloxymethylketones
132 4244-4250 Chemical denotes Krantz
133 4716-4722 Chemical denotes sulfur MESH:D013455
135 4964-4969 Chemical denotes amide MESH:D000577
144 5315-5318 Species denotes CoV Tax:11118
145 5394-5410 Species denotes human rhinovirus Tax:169066
146 5715-5719 Species denotes TGEV Tax:11149
147 5909-5917 Species denotes SARS CoV Tax:694009
148 5412-5415 Species denotes HRV Tax:169066
149 5582-5585 Species denotes HRV Tax:169066
150 5537-5540 Chemical denotes Gln MESH:D005973
151 5618-5629 Chemical denotes rupintrivir MESH:C118874
158 6092-6116 Gene denotes CLpro inhibitors 3 and 4
159 5987-5995 Species denotes SARS CoV Tax:694009
160 6080-6088 Species denotes SARS CoV Tax:694009
161 5948-5951 Species denotes HRV Tax:169066
162 5971-5982 Chemical denotes rupintrivir MESH:C118874
163 6176-6184 Chemical denotes cysteine MESH:D003545
192 6314-6322 Species denotes SARS CoV Tax:694009
193 6489-6497 Species denotes SARS CoV Tax:694009
194 6641-6645 Species denotes kobs Tax:59530
195 6715-6723 Species denotes SARS CoV Tax:694009
196 6930-6938 Species denotes SARS CoV Tax:694009
197 7283-7291 Species denotes SARS CoV Tax:694009
198 7610-7618 Species denotes SARS CoV Tax:694009
199 6252-6255 Species denotes HRV Tax:169066
200 6806-6809 Species denotes HRV Tax:169066
201 6904-6907 Species denotes HRV Tax:169066
202 7422-7425 Species denotes HRV Tax:169066
203 7005-7020 Chemical denotes sp3 α,β-carbons
204 7085-7095 Chemical denotes oxygen sp2
205 7156-7164 Chemical denotes hydrogen MESH:D006859
206 7216-7224 Chemical denotes hydrogen MESH:D006859
207 7251-7257 Chemical denotes oxygen MESH:D010100
208 7266-7272 Chemical denotes Gly143
209 7343-7351 Chemical denotes hydrogen MESH:D006859
210 7496-7502 Chemical denotes lactam MESH:D007769
211 7585-7594 Chemical denotes glutamine MESH:D005973
212 7686-7694 Chemical denotes hydrogen MESH:D006859
213 7703-7709 Chemical denotes His163
214 7725-7731 Chemical denotes lactam MESH:D007769
215 7746-7754 Chemical denotes hydrogen MESH:D006859
216 7772-7778 Chemical denotes Glu166
217 7796-7802 Chemical denotes oxygen MESH:D010100
218 7806-7812 Chemical denotes Phe140
219 7889-7897 Chemical denotes hydrogen MESH:D006859
221 8072-8080 Species denotes SARS CoV Tax:694009
238 8442-8450 Species denotes SARS CoV Tax:694009
239 9143-9151 Species denotes SARS CoV Tax:694009
240 9244-9252 Species denotes SARS CoV Tax:694009
241 9471-9481 Species denotes SARS CoV-2 Tax:2697049
242 9669-9682 Species denotes coronaviruses Tax:11118
243 9961-9969 Species denotes SARS CoV Tax:694009
244 10157-10170 Species denotes coronaviruses Tax:11118
245 8687-8693 Chemical denotes lactam MESH:D007769
246 8712-8726 Chemical denotes methoxy indole
247 8878-8883 Chemical denotes amide MESH:D000577
248 9046-9051 Chemical denotes amide MESH:D000577
249 9079-9085 Chemical denotes ketone MESH:D007659
250 9934-9940 Chemical denotes ketone MESH:D007659
251 9391-9399 Disease denotes COVID-19 MESH:C000657245
252 9845-9853 Disease denotes COVID-19 MESH:C000657245
253 10182-10190 Disease denotes COVID-19 MESH:C000657245
258 10264-10270 Chemical denotes ketone MESH:D007659
259 10356-10368 Chemical denotes methylketone MESH:D000096
260 10420-10436 Chemical denotes halomethylketone
261 10515-10526 Chemical denotes diazoketone
279 11475-11478 Gene denotes Boc Gene:91653
280 11045-11056 Chemical denotes amino ester
281 11157-11178 Chemical denotes isobutylchloroformate MESH:C039311
282 11183-11196 Chemical denotes triethylamine MESH:C016162
283 11249-11261 Chemical denotes diazomethane MESH:D003978
284 11302-11313 Chemical denotes Diazoketone
285 11333-11350 Chemical denotes hydrochloric acid MESH:D006851
286 11368-11376 Chemical denotes nitrogen MESH:D009584
287 11412-11430 Chemical denotes chloromethylketone
288 11432-11435 Chemical denotes CMK
289 11583-11598 Chemical denotes dichloromethane MESH:D008752
290 11678-11690 Chemical denotes diazomethane MESH:D003978
291 11741-11744 Chemical denotes LDA MESH:C007442
292 11749-11766 Chemical denotes chloroiodomethane
293 11820-11835 Chemical denotes oxymethylketone
294 11909-11922 Chemical denotes Weinreb amide
295 11978-12003 Chemical denotes benzyl chloromethyl ether
305 12053-12065 Chemical denotes methylketone MESH:D000096
306 12181-12227 Chemical denotes acyloxy- and hydroxy-substituted methylketones
307 12297-12390 Chemical denotes 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate
308 12392-12396 Chemical denotes HATU MESH:C472082
309 12530-12546 Chemical denotes carboxylic acids MESH:D002264
310 12566-12581 Chemical denotes cesium fluoride MESH:C027754
311 12600-12620 Chemical denotes acyloxymethylketones
312 12679-12681 Chemical denotes P2 MESH:C020845
313 12686-12691 Chemical denotes amine MESH:D000588
316 12790-12810 Chemical denotes Acyloxymethylketones
317 12815-12833 Chemical denotes Aminomethylketones
331 12838-12841 Gene denotes Boc Gene:91653
332 12850-12854 Chemical denotes HATU MESH:C472082
333 12856-12859 Chemical denotes NMM MESH:C035596
334 12861-12882 Chemical denotes N,N-dimethylformamide MESH:D004126
335 12884-12887 Chemical denotes DMF MESH:D004126
336 12911-12914 Chemical denotes HCl MESH:D006851
337 12915-12922 Chemical denotes dioxane MESH:C025223
338 12930-12934 Chemical denotes HATU MESH:C472082
339 12936-12965 Chemical denotes 4-MeO-2-indolecarboxylic acid
340 12967-12970 Chemical denotes NMM MESH:C035596
341 12972-12975 Chemical denotes DMF MESH:D004126
342 13003-13006 Chemical denotes DMF MESH:D004126
343 13008-13023 Chemical denotes carboxylic acid MESH:D002264
354 13041-13060 Chemical denotes Hydroxymethylketone
355 13062-13065 Chemical denotes HMK
356 13183-13189 Chemical denotes oxygen MESH:D010100
357 13219-13224 Chemical denotes amide MESH:D000577
358 13537-13555 Chemical denotes benzoylformic acid MESH:C012482
359 13653-13661 Chemical denotes hydroxyl MESH:D017665
360 13730-13746 Chemical denotes silver (I) oxide MESH:C040225
361 13757-13775 Chemical denotes alkoxymethylketone
362 13868-13870 Chemical denotes P2 MESH:C020845
363 13875-13880 Chemical denotes amine MESH:D000588
365 13967-13986 Chemical denotes Hydroxymethylketone
384 14025-14028 Gene denotes Boc Gene:91653
385 14007-14010 Chemical denotes HCl MESH:D006851
386 14011-14018 Chemical denotes dioxane MESH:C025223
387 14037-14041 Chemical denotes HATU MESH:C472082
388 14043-14046 Chemical denotes NMM MESH:C035596
389 14048-14051 Chemical denotes DMF MESH:D004126
390 14065-14069 Chemical denotes HATU MESH:C472082
391 14071-14100 Chemical denotes 4-MeO-2-indolecarboxylic acid
392 14102-14105 Chemical denotes NMM MESH:C035596
393 14124-14126 Chemical denotes H2 MESH:D003903
394 14128-14132 Chemical denotes EtOH MESH:D000431
395 14149-14152 Chemical denotes DMF MESH:D004126
396 14154-14172 Chemical denotes benzoylformic acid MESH:C012482
397 14190-14194 Chemical denotes MeOH
398 14201-14206 Chemical denotes K2CO3 MESH:C037593
399 14223-14227 Chemical denotes CH3I
400 14229-14233 Chemical denotes Ag2O MESH:C040225
401 14235-14238 Chemical denotes DCE
403 14296-14304 Species denotes SARS CoV Tax:694009
414 14796-14807 Gene denotes cathepsin B Gene:1508
415 15062-15070 Species denotes SARS CoV Tax:694009
416 14456-14462 Chemical denotes Krantz
417 14521-14541 Chemical denotes acyloxymethylketones
418 14638-14649 Chemical denotes carboxylate
419 14780-14791 Chemical denotes carboxylate
420 15029-15049 Chemical denotes 2,6-dichlorobenzoate
421 15128-15134 Chemical denotes ketone MESH:D007659
422 15197-15205 Chemical denotes benzoate MESH:D001565
423 15255-15274 Chemical denotes acyloxymethylketone
426 15410-15418 Species denotes SARS CoV Tax:694009
427 15444-15448 Species denotes kobs Tax:59530
430 15335-15343 Species denotes SARS CoV Tax:694009
431 15373-15392 Chemical denotes Acyloxymethylketone
461 16166-16174 Species denotes SARS CoV Tax:694009
462 16513-16521 Species denotes SARS CoV Tax:694009
463 16106-16124 Chemical denotes chloromethylketone
464 16237-16245 Chemical denotes benzoate MESH:D001565
465 16696-16711 Chemical denotes 2-cyanobenzoate
466 16756-16764 Chemical denotes cysteine MESH:D003545
467 16766-16772 Chemical denotes Cys145
468 16774-16780 Chemical denotes sulfur MESH:D013455
469 16820-16826 Chemical denotes carbon MESH:D002244
470 16856-16862 Chemical denotes ketone MESH:D007659
471 16935-16943 Chemical denotes hydrogen MESH:D006859
472 16977-16983 Chemical denotes Gly143
473 16988-16994 Chemical denotes Cys145
474 17031-17039 Chemical denotes hydrogen MESH:D006859
475 17068-17073 Chemical denotes His41
476 17102-17111 Chemical denotes imidazole MESH:C029899
477 17124-17132 Chemical denotes hydrogen MESH:D006859
478 17195-17204 Chemical denotes imidazole MESH:C029899
479 17205-17213 Chemical denotes hydrogen MESH:D006859
480 17281-17286 Chemical denotes water MESH:D014867
481 17314-17319 Chemical denotes water MESH:D014867
482 17343-17348 Chemical denotes His41
483 17363-17368 Chemical denotes water MESH:D014867
484 17369-17378 Chemical denotes hydrogens MESH:D006859
485 17435-17441 Chemical denotes Asp187
486 17458-17466 Chemical denotes hydrogen MESH:D006859
487 17519-17525 Chemical denotes Asp176
488 17604-17610 Chemical denotes His164
489 17615-17621 Chemical denotes Thr175
491 17691-17699 Species denotes SARS CoV Tax:694009
497 17977-17985 Species denotes SARS CoV Tax:694009
498 18291-18296 Species denotes human Tax:9606
499 18495-18500 Species denotes human Tax:9606
500 17896-17916 Chemical denotes 2,6-dichlorobenzoate
501 18424-18435 Chemical denotes glutathione MESH:D005978
509 19273-19278 Gene denotes CLpro
510 19261-19269 Species denotes SARS CoV Tax:694009
511 18801-18821 Chemical denotes 2,6-dichlorobenzoate
512 18884-18889 Chemical denotes amine MESH:D000588
513 18952-18968 Chemical denotes 4-methoxy indole
514 18994-19007 Chemical denotes benzimidazole MESH:C031000
515 19162-19164 Chemical denotes P2 MESH:C020845
518 19300-19308 Species denotes SARS CoV Tax:694009
519 19350-19369 Chemical denotes Acyloxymethylketone
526 19917-19925 Species denotes SARS CoV Tax:694009
527 20013-20017 Species denotes kobs Tax:59530
528 20245-20248 Species denotes rat Tax:10116
529 19578-19594 Chemical denotes 4-methoxy indole
530 19603-19637 Chemical denotes (2R)-tetrahydrofuran-2-carboxylate
531 19734-19740 Chemical denotes Gln189
536 20904-20915 Species denotes coronavirus Tax:11118
537 20544-20550 Chemical denotes 3CLpro
538 20809-20818 Disease denotes infection MESH:D007239
539 20953-20962 Disease denotes infection MESH:D007239
541 21153-21161 Species denotes SARS CoV Tax:694009
555 21298-21309 Gene denotes cathepsin K Gene:1513
556 21266-21283 Gene denotes cysteine protease Gene:1508
557 21675-21683 Species denotes SARS CoV Tax:694009
558 21445-21453 Chemical denotes hydrogen MESH:D006859
559 21481-21484 Chemical denotes His MESH:D006639
560 21587-21590 Chemical denotes Cys MESH:D003545
561 21599-21605 Chemical denotes ketone MESH:D007659
562 21805-21811 Chemical denotes sulfur MESH:D013455
563 21831-21839 Chemical denotes cysteine MESH:D003545
564 21841-21847 Chemical denotes Cys145
565 21881-21889 Chemical denotes hydrogen MESH:D006859
566 21926-21931 Chemical denotes His41
567 22235-22237 Chemical denotes P2 MESH:C020845
577 22839-22847 Species denotes SARS CoV Tax:694009
578 22778-22780 Chemical denotes P2 MESH:C020845
579 22781-22784 Chemical denotes Phe MESH:D010649
580 22975-22990 Chemical denotes P2-N-methyl-Leu
581 23179-23187 Chemical denotes hydrogen MESH:D006859
582 23213-23218 Chemical denotes amide MESH:D000577
583 23222-23228 Chemical denotes Gln189
584 23325-23341 Chemical denotes 4-methoxy indole
585 23385-23393 Chemical denotes hydrogen MESH:D006859
590 24170-24184 Gene denotes P-glycoprotein Gene:5243
591 23840-23845 Species denotes human Tax:9606
592 23687-23693 Chemical denotes Caco-2
593 24395-24403 Chemical denotes hydrogen MESH:D006859
608 24581-24589 Species denotes SARS CoV Tax:694009
609 24813-24821 Chemical denotes hydrogen MESH:D006859
610 24902-24910 Chemical denotes hydrogen MESH:D006859
611 24933-24938 Chemical denotes His41
612 25029-25037 Chemical denotes hydrogen MESH:D006859
613 25230-25235 Chemical denotes His41
614 25341-25349 Chemical denotes hydrogen MESH:D006859
615 25387-25390 Chemical denotes His MESH:D006639
616 25422-25427 Chemical denotes His41
617 25449-25457 Chemical denotes hydrogen MESH:D006859
618 25498-25506 Chemical denotes hydrogen MESH:D006859
619 25525-25533 Chemical denotes nitrogen MESH:D009584
620 25551-25554 Chemical denotes His MESH:D006639
621 25613-25621 Chemical denotes hydrogen MESH:D006859
632 26855-26860 Species denotes human Tax:9606
633 25811-25813 Chemical denotes P2 MESH:C020845
634 25824-25827 Chemical denotes Leu MESH:D007930
635 25832-25848 Chemical denotes β-tert-butyl-Ala
636 26170-26172 Chemical denotes P3
637 26195-26212 Chemical denotes tetrahydrofuranyl
638 26291-26299 Chemical denotes hydrogen MESH:D006859
639 26326-26335 Chemical denotes indole P3
640 26502-26521 Chemical denotes hydroxymethylketone
641 26556-26561 Chemical denotes ether MESH:D004986
643 27066-27074 Species denotes SARS CoV Tax:694009
665 27479-27487 Species denotes SARS CoV Tax:694009
666 27494-27499 Species denotes CoV-2 Tax:2697049
667 27650-27658 Species denotes SARS CoV Tax:694009
668 27665-27675 Species denotes SARS CoV-2 Tax:2697049
669 27851-27854 Species denotes CoV Tax:11118
670 27861-27866 Species denotes CoV-2 Tax:2697049
671 27893-27899 Chemical denotes carbon MESH:D002244
672 27953-27961 Chemical denotes cysteine MESH:D003545
673 27963-27969 Chemical denotes Cys145
674 27971-27977 Chemical denotes sulfur MESH:D013455
675 28003-28011 Chemical denotes carbinol MESH:D000432
676 28050-28067 Chemical denotes carbinol hydroxyl
677 28074-28082 Chemical denotes hydrogen MESH:D006859
678 28113-28119 Chemical denotes Cys145
679 28133-28138 Chemical denotes amide MESH:D000577
680 28145-28151 Chemical denotes Gly143
681 28167-28172 Chemical denotes water MESH:D014867
682 28226-28234 Chemical denotes hydrogen MESH:D006859
683 28260-28267 Chemical denotes alcohol MESH:D000438
684 28298-28303 Chemical denotes His41
685 28344-28347 Chemical denotes His MESH:D006639
688 28509-28519 Species denotes SARS CoV-2 Tax:2697049
689 28777-28785 Chemical denotes hydrogen MESH:D006859
719 30048-30058 Species denotes SARS CoV-2 Tax:2697049
720 30263-30273 Species denotes SARS CoV-2 Tax:2697049
721 28885-28891 Chemical denotes lactam MESH:D007769
722 28921-28929 Chemical denotes hydrogen MESH:D006859
723 28958-28964 Chemical denotes His163
724 28976-28982 Chemical denotes lactam MESH:D007769
725 29000-29008 Chemical denotes hydrogen MESH:D006859
726 29065-29071 Chemical denotes oxygen MESH:D010100
727 29075-29081 Chemical denotes Glu166
728 29099-29105 Chemical denotes oxygen MESH:D010100
729 29109-29115 Chemical denotes Phe140
730 29239-29245 Chemical denotes Glu166
731 29264-29272 Chemical denotes hydrogen MESH:D006859
732 29365-29367 Chemical denotes P2 MESH:C020845
733 29368-29371 Chemical denotes Leu MESH:D007930
734 29409-29415 Chemical denotes Gln189
735 29423-29431 Chemical denotes hydrogen MESH:D006859
736 29460-29462 Chemical denotes P2 MESH:C020845
737 29463-29466 Chemical denotes Leu MESH:D007930
738 29529-29537 Chemical denotes hydrogen MESH:D006859
739 29573-29579 Chemical denotes His164
740 29608-29615 Chemical denotes leucine MESH:D007930
741 29700-29706 Chemical denotes Asp187
742 29708-29714 Chemical denotes Arg188
743 29716-29722 Chemical denotes Gln189
744 29724-29729 Chemical denotes Met49
745 29735-29740 Chemical denotes His41
746 30079-30091 Chemical denotes α-ketoamides
747 30345-30355 Chemical denotes ketoamides
755 30627-30638 Gene denotes cathepsin B Gene:1508
756 30428-30433 Species denotes human Tax:9606
757 30659-30669 Species denotes rhinovirus Tax:12059
758 30803-30814 Species denotes coronavirus Tax:11118
759 30896-30905 Species denotes hCoV 229E Tax:11137
760 31008-31018 Species denotes SARS CoV-2 Tax:2697049
761 30357-30376 Chemical denotes Hydroxymethylketone
778 31211-31222 Gene denotes cathepsin B Gene:1508
779 31385-31392 Gene denotes caspase Gene:834
780 31142-31150 Species denotes SARS CoV Tax:694009
781 31181-31191 Species denotes SARS CoV-2 Tax:2697049
782 31224-31229 Species denotes human Tax:9606
783 31292-31297 Species denotes human Tax:9606
784 31322-31327 Species denotes human Tax:9606
785 31346-31351 Species denotes human Tax:9606
786 31370-31375 Species denotes human Tax:9606
787 31396-31401 Species denotes human Tax:9606
788 31412-31417 Species denotes HIV-1 Tax:11676
789 31419-31424 Species denotes HIV-1 Tax:11676
790 31456-31465 Species denotes HRV   1 Tax:573824
791 31472-31481 Species denotes hCoV 229E Tax:11137
792 31483-31488 Species denotes human Tax:9606
793 31451-31454 Species denotes HRV Tax:169066
796 31682-31690 Species denotes SARS CoV Tax:694009
797 31697-31702 Species denotes CoV-2 Tax:2697049
808 31888-31904 Species denotes human rhinovirus Tax:169066
809 31914-31920 Species denotes HRV-14 Tax:12131
810 31977-31998 Species denotes human cytomegalovirus Tax:10359
811 32106-32115 Species denotes hCoV 229E Tax:11137
812 32166-32183 Species denotes human coronavirus Tax:694448
813 32184-32193 Species denotes hCoV 229E Tax:11137
814 32210-32215 Species denotes human Tax:9606
815 32000-32004 Species denotes HCMV Tax:10359
816 31940-31972 Disease denotes immunodeficiency virus-1 (HIV-1) MESH:D015658
817 32197-32202 CellLine denotes MRC-5 CVCL:0440
823 32317-32325 Species denotes SARS CoV Tax:694009
824 32344-32353 Species denotes hCoV 229E Tax:11137
825 32372-32378 Species denotes HRV-14 Tax:12131
826 32414-32419 Species denotes HIV-1 Tax:11676
827 32458-32462 Species denotes HCMV Tax:10359
848 33276-33290 Gene denotes P-glycoprotein Gene:5243
849 33742-33756 Gene denotes P-glycoprotein Gene:5243
850 32723-32731 Species denotes SARS CoV Tax:694009
851 32832-32841 Species denotes hCoV 229E Tax:11137
852 32846-32849 Species denotes CoV Tax:11118
853 32897-32906 Species denotes hCoV 229E Tax:11137
854 32911-32919 Species denotes SARS CoV Tax:694009
855 33552-33561 Species denotes hCoV 229E Tax:11137
856 33701-33706 Species denotes human Tax:9606
857 34017-34022 Species denotes human Tax:9606
858 34140-34150 Species denotes SARS CoV-2 Tax:2697049
859 34174-34179 Species denotes human Tax:9606
860 32652-32661 Species denotes hCoV 229E Tax:11137
861 33228-33236 Species denotes SARS CoV Tax:694009
862 33444-33452 Species denotes SARS CoV Tax:694009
863 33644-33653 Species denotes hCoV 229E Tax:11137
864 33344-33353 Chemical denotes CP-100356 MESH:C087168
865 34068-34076 Disease denotes COVID-19 MESH:C000657245
866 33057-33062 CellLine denotes MRC-5 CVCL:0440
867 33720-33725 CellLine denotes MRC-5 CVCL:0440
879 34344-34352 Species denotes SARS CoV Tax:694009
880 34617-34625 Species denotes SARS CoV Tax:694009
881 34819-34830 Species denotes coronavirus Tax:11118
882 34882-34892 Species denotes SARS CoV-2 Tax:2697049
883 34994-35002 Species denotes patients Tax:9606
884 34456-34476 Chemical denotes acyloxymethylketones
885 34481-34501 Chemical denotes hydroxymethylketones
886 34547-34558 Chemical denotes SARS 3CLpro
887 34564-34583 Chemical denotes hydroxymethylketone
888 34421-34441 Disease denotes coronavirus diseases MESH:D018352
889 35008-35016 Disease denotes COVID-19 MESH:C000657245
906 35490-35493 Gene denotes SP4 Gene:6671
907 35595-35603 Chemical denotes nitrogen MESH:D009584
908 35607-35612 Chemical denotes argon MESH:D001128
909 35811-35821 Chemical denotes silica gel MESH:D058428
910 36297-36311 Chemical denotes p-anisaldehyde MESH:C024896
911 36313-36333 Chemical denotes phosphomolybdic acid MESH:C003125
912 36338-36344 Chemical denotes iodine MESH:D007455
913 36417-36419 Chemical denotes 1H
914 36563-36580 Chemical denotes tetramethylsilane MESH:C073196
915 36582-36585 Chemical denotes TMS MESH:C073196
916 36588-36590 Chemical denotes 1H
917 36864-36869 Chemical denotes CDCl3
918 36871-36878 Chemical denotes DMSO-d6
919 36884-36889 Chemical denotes CD3OD
920 37061-37063 Chemical denotes 1H
921 35462-35472 Disease denotes CombiFlash
923 37079-37142 Chemical denotes N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine
937 37245-37317 Chemical denotes methyl N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alaninate
938 37363-37371 Chemical denotes methanol MESH:D000432
939 37421-37424 Chemical denotes ice MESH:D007053
940 37425-37429 Chemical denotes NaCl MESH:D012965
941 37436-37440 Chemical denotes NaOH
942 37458-37463 Chemical denotes water MESH:D014867
943 37721-37738 Chemical denotes hydrochloric acid MESH:D006851
944 37808-37816 Chemical denotes methanol MESH:D000432
945 37856-37869 Chemical denotes ethyl acetate MESH:C007650
946 37909-37926 Chemical denotes hydrochloric acid MESH:D006851
947 38044-38057 Chemical denotes ethyl acetate MESH:C007650
948 38115-38120 Chemical denotes brine MESH:C017082
949 38133-38138 Chemical denotes MgSO4 MESH:D008278
951 38416-38500 Chemical denotes tert-Butyl ((1S)-3-Diazo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
970 38519-38582 Chemical denotes N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine
971 38606-38609 Chemical denotes THF MESH:C018674
972 38653-38655 Chemical denotes N2
973 38747-38760 Chemical denotes triethylamine MESH:C016162
974 38793-38814 Chemical denotes isobutylchloroformate MESH:C039311
975 39060-39072 Chemical denotes diazomethane MESH:D003978
976 39097-39110 Chemical denotes diethyl ether MESH:D004986
977 39122-39134 Chemical denotes diazomethane MESH:D003978
978 39359-39361 Chemical denotes N2
979 39412-39424 Chemical denotes diazomethane MESH:D003978
980 39500-39513 Chemical denotes ethyl acetate MESH:C007650
981 39546-39552 Chemical denotes NaHCO3 MESH:D017693
982 39572-39577 Chemical denotes brine MESH:C017082
983 39598-39603 Chemical denotes MgSO4 MESH:D008278
984 39709-39713 Chemical denotes SiO2
985 39720-39728 Chemical denotes methanol MESH:D000432
986 39729-39739 Chemical denotes chloroform MESH:D002725
987 39217-39224 Disease denotes Aldrich MESH:D014923
989 40032-40117 Chemical denotes tert-Butyl ((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1003 40169-40177 Chemical denotes nitrogen MESH:D009584
1004 40948-40961 Chemical denotes ethyl acetate MESH:C007650
1005 41006-41011 Chemical denotes water MESH:D014867
1006 41028-41034 Chemical denotes NaHCO3 MESH:D017693
1007 41049-41054 Chemical denotes brine MESH:C017082
1008 41076-41081 Chemical denotes MgSO4 MESH:D008278
1009 41230-41243 Chemical denotes ethyl acetate MESH:C007650
1010 41285-41298 Chemical denotes diethyl ether MESH:D004986
1011 41636-41648 Chemical denotes C13H21ClN2O4
1012 41650-41651 Chemical denotes C MESH:D002244
1013 41669-41670 Chemical denotes N MESH:D009584
1014 41685-41686 Chemical denotes C MESH:D002244
1015 41704-41705 Chemical denotes N MESH:D009584
1017 41714-41803 Chemical denotes tert-Butyl((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1034 41870-41878 Chemical denotes nitrogen MESH:D009584
1035 41923-41986 Chemical denotes N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine
1036 42017-42032 Chemical denotes dichloromethane MESH:D008752
1037 42096-42100 Chemical denotes NaCl MESH:D012965
1038 42107-42155 Chemical denotes N,O-Dimethylhydroxylamine hydrochloric acid salt
1039 42195-42213 Chemical denotes N-methylmorpholine MESH:C038816
1040 42234-42238 Chemical denotes HOBt MESH:C011852
1041 42270-42274 Chemical denotes EDCI MESH:D005022
1042 42336-42344 Chemical denotes nitrogen MESH:D009584
1043 42375-42380 Chemical denotes water MESH:D014867
1044 42493-42510 Chemical denotes hydrochloric acid MESH:D006851
1045 42525-42530 Chemical denotes water MESH:D014867
1046 42541-42545 Chemical denotes satd
1047 42547-42553 Chemical denotes NaHCO3 MESH:D017693
1048 42572-42577 Chemical denotes brine MESH:C017082
1049 42607-42612 Chemical denotes MgSO4 MESH:D008278
1058 43114-43122 Chemical denotes nitrogen MESH:D009584
1059 43301-43309 Chemical denotes nitrogen MESH:D009584
1060 43737-43745 Chemical denotes nitrogen MESH:D009584
1061 43856-43861 Chemical denotes NH4Cl
1062 43959-43972 Chemical denotes ethyl acetate MESH:C007650
1063 44025-44030 Chemical denotes MgSO4 MESH:D008278
1064 44175-44183 Chemical denotes methanol MESH:D000432
1065 44184-44199 Chemical denotes dichloromethane MESH:D008752
1067 44482-44559 Chemical denotes (3S)-3-[(2S)-2-Amino-4-chloro-3-oxobutyl]pyrrolidin-2-one, Hydrochloride Salt
1069 45082-45095 Chemical denotes diethyl ether MESH:D004986
1071 45397-45481 Chemical denotes tert-Butyl ((1S)-3-Bromo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1078 45501-45586 Chemical denotes tert-butyl ((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1079 45609-45624 Chemical denotes dichloromethane MESH:D008752
1080 45648-45656 Chemical denotes nitrogen MESH:D009584
1081 45678-45694 Chemical denotes hydrobromic acid MESH:D018054
1082 45803-45808 Chemical denotes water MESH:D014867
1083 45829-45834 Chemical denotes MgSO4 MESH:D008278
1092 46483-46494 Chemical denotes 1,4-dioxane MESH:C025223
1093 46538-46540 Chemical denotes N2
1094 46607-46624 Chemical denotes hydrochloric acid MESH:D006851
1095 46628-46639 Chemical denotes 1,4-dioxane MESH:C025223
1096 46728-46733 Chemical denotes gummy
1097 46812-46819 Chemical denotes ethanol MESH:D000431
1098 46820-46831 Chemical denotes 1,4-dioxane MESH:C025223
1099 46877-46973 Chemical denotes N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide hydrochloride
1115 48477-48482 Species denotes O5+H1 Tax:2491878
1116 47313-47331 Chemical denotes hydrochloride salt
1117 47336-47373 Chemical denotes 4-methoxy-1H-indole-2-carboxylic acid
1118 47397-47400 Chemical denotes DMF MESH:D004126
1119 47444-47446 Chemical denotes N2
1120 47523-47527 Chemical denotes HATU MESH:C472082
1121 47552-47570 Chemical denotes N-methylmorpholine MESH:C038816
1122 47675-47681 Chemical denotes NaHCO3 MESH:D017693
1123 47721-47734 Chemical denotes ethyl acetate MESH:C007650
1124 47788-47793 Chemical denotes brine MESH:C017082
1125 47814-47819 Chemical denotes MgSO4 MESH:D008278
1126 47919-47923 Chemical denotes SiO2
1127 47928-47936 Chemical denotes methanol MESH:D000432
1128 47937-47947 Chemical denotes chloroform MESH:D002725
1129 48445-48449 Disease denotes HRMS
1142 49182-49187 Chemical denotes water MESH:D014867
1143 49216-49231 Chemical denotes dichloromethane MESH:D008752
1144 49289-49294 Chemical denotes water MESH:D014867
1145 49308-49313 Chemical denotes brine MESH:C017082
1146 49409-49417 Chemical denotes methanol MESH:D000432
1147 49418-49433 Chemical denotes dichloromethane MESH:D008752
1148 50028-50038 Chemical denotes C26H34N4O7
1149 50044-50047 Chemical denotes H2O
1150 50049-50050 Chemical denotes C MESH:D002244
1151 50068-50069 Chemical denotes N MESH:D009584
1152 50085-50086 Chemical denotes C MESH:D002244
1153 50104-50105 Chemical denotes N MESH:D009584
1163 50434-50461 Chemical denotes cyclopropanecarboxylic acid MESH:C015766
1164 50581-50589 Chemical denotes methanol MESH:D000432
1165 50590-50605 Chemical denotes dichloromethane MESH:D008752
1166 51131-51141 Chemical denotes C28H36N4O7
1167 51147-51150 Chemical denotes H2O
1168 51152-51153 Chemical denotes C MESH:D002244
1169 51171-51172 Chemical denotes N MESH:D009584
1170 51188-51189 Chemical denotes C MESH:D002244
1171 51207-51208 Chemical denotes N MESH:D009584
1181 51522-51534 Chemical denotes pivalic acid MESH:C005566
1182 51654-51662 Chemical denotes methanol MESH:D000432
1183 51663-51678 Chemical denotes dichloromethane MESH:D008752
1184 52164-52174 Chemical denotes C29H40N4O7
1185 52180-52183 Chemical denotes H2O
1186 52185-52186 Chemical denotes C MESH:D002244
1187 52204-52205 Chemical denotes N MESH:D009584
1188 52220-52221 Chemical denotes C MESH:D002244
1189 52239-52240 Chemical denotes N MESH:D009584
1199 52553-52565 Chemical denotes benzoic acid MESH:D019817
1200 52685-52693 Chemical denotes methanol MESH:D000432
1201 52694-52709 Chemical denotes dichloromethane MESH:D008752
1202 53314-53324 Chemical denotes C31H36N4O7
1203 53330-53333 Chemical denotes H2O
1204 53335-53336 Chemical denotes C MESH:D002244
1205 53354-53355 Chemical denotes N MESH:D009584
1206 53370-53371 Chemical denotes C MESH:D002244
1207 53389-53390 Chemical denotes N MESH:D009584
1218 53712-53733 Chemical denotes 4-methoxybenzoic acid MESH:C000626346
1219 53853-53861 Chemical denotes methanol MESH:D000432
1220 53862-53877 Chemical denotes dichloromethane MESH:D008752
1221 54462-54472 Chemical denotes C32H38N4O8
1222 54478-54481 Chemical denotes H2O
1223 54487-54490 Chemical denotes DCM MESH:D008752
1224 54492-54493 Chemical denotes C MESH:D002244
1225 54511-54512 Chemical denotes N MESH:D009584
1226 54527-54528 Chemical denotes C MESH:D002244
1227 54546-54547 Chemical denotes N MESH:D009584
1238 54868-54888 Chemical denotes 4-methylbenzoic acid MESH:C009504
1239 55008-55016 Chemical denotes methanol MESH:D000432
1240 55017-55032 Chemical denotes dichloromethane MESH:D008752
1241 55636-55646 Chemical denotes C32H38N4O7
1242 55652-55655 Chemical denotes H2O
1243 55661-55664 Chemical denotes DCM MESH:D008752
1244 55666-55667 Chemical denotes C MESH:D002244
1245 55685-55686 Chemical denotes N MESH:D009584
1246 55701-55702 Chemical denotes C MESH:D002244
1247 55720-55721 Chemical denotes N MESH:D009584
1257 56041-56060 Chemical denotes 4-cyanobenzoic acid MESH:C097383
1258 56180-56188 Chemical denotes methanol MESH:D000432
1259 56189-56204 Chemical denotes dichloromethane MESH:D008752
1260 56800-56810 Chemical denotes C32H35N5O7
1261 56816-56819 Chemical denotes H2O
1262 56821-56822 Chemical denotes C MESH:D002244
1263 56840-56841 Chemical denotes N MESH:D009584
1264 56857-56858 Chemical denotes C MESH:D002244
1265 56876-56877 Chemical denotes N MESH:D009584
1276 57199-57219 Chemical denotes 4-fluorobenzoic acid MESH:C022893
1277 57339-57347 Chemical denotes methanol MESH:D000432
1278 57348-57363 Chemical denotes dichloromethane MESH:D008752
1279 57947-57958 Chemical denotes C31H35FN4O7
1280 57964-57967 Chemical denotes H2O
1281 57973-57976 Chemical denotes DCM MESH:D008752
1282 57978-57979 Chemical denotes C MESH:D002244
1283 57997-57998 Chemical denotes N MESH:D009584
1284 58013-58014 Chemical denotes C MESH:D002244
1285 58032-58033 Chemical denotes N MESH:D009584
1296 58354-58374 Chemical denotes 4-chlorobenzoic acid MESH:C040768
1297 58494-58502 Chemical denotes methanol MESH:D000432
1298 58503-58518 Chemical denotes dichloromethane MESH:D008752
1299 59130-59142 Chemical denotes C31H35ClN4O7
1300 59148-59151 Chemical denotes H2O
1301 59157-59160 Chemical denotes DCM MESH:D008752
1302 59162-59163 Chemical denotes C MESH:D002244
1303 59181-59182 Chemical denotes N MESH:D009584
1304 59197-59198 Chemical denotes C MESH:D002244
1305 59216-59217 Chemical denotes N MESH:D009584
1318 59542-59566 Chemical denotes 2,6-dichlorobenzoic acid
1319 59674-59678 Chemical denotes SiO2
1320 59683-59691 Chemical denotes methanol MESH:D000432
1321 59692-59702 Chemical denotes chloroform MESH:D002725
1322 60214-60227 Chemical denotes C31H34Cl2N4O7
1323 60232-60235 Chemical denotes H2O
1324 60237-60238 Chemical denotes C MESH:D002244
1325 60256-60257 Chemical denotes N MESH:D009584
1326 60272-60273 Chemical denotes C MESH:D002244
1327 60291-60292 Chemical denotes N MESH:D009584
1328 60322-60335 Chemical denotes C31H34Cl2N4O7
1329 60300-60304 Disease denotes HRMS
1334 60682-60706 Chemical denotes 2,6-difluorobenzoic acid MESH:C077004
1335 60810-60820 Chemical denotes chloroform MESH:D002725
1336 60821-60834 Chemical denotes ethyl acetate MESH:C007650
1337 61357-61361 Disease denotes HRMS
1350 61744-61766 Chemical denotes 4-chlorosalicylic acid MESH:C479918
1351 61886-61894 Chemical denotes methanol MESH:D000432
1352 61895-61910 Chemical denotes dichloromethane MESH:D008752
1353 62428-62440 Chemical denotes C31H35ClN4O8
1354 62445-62448 Chemical denotes H2O
1355 62454-62459 Chemical denotes CHCl3
1356 62461-62462 Chemical denotes C MESH:D002244
1357 62480-62481 Chemical denotes N MESH:D009584
1358 62496-62497 Chemical denotes C MESH:D002244
1359 62515-62516 Chemical denotes N MESH:D009584
1360 62546-62558 Chemical denotes C31H35ClN4O8
1361 62524-62528 Disease denotes HRMS
1373 62909-62937 Chemical denotes 4-cyano-2-fluorobenzoic acid
1374 63066-63074 Chemical denotes methanol MESH:D000432
1375 63075-63090 Chemical denotes dichloromethane MESH:D008752
1376 63654-63665 Chemical denotes C32H34FN5O7
1377 63670-63673 Chemical denotes H2O
1378 63675-63676 Chemical denotes C MESH:D002244
1379 63694-63695 Chemical denotes N MESH:D009584
1380 63711-63712 Chemical denotes C MESH:D002244
1381 63730-63731 Chemical denotes N MESH:D009584
1382 63762-63773 Chemical denotes C32H34FN5O7
1383 63740-63744 Disease denotes HRMS
1396 64120-64144 Chemical denotes 2,6-dimethylbenzoic acid
1397 64263-64271 Chemical denotes methanol MESH:D000432
1398 64272-64287 Chemical denotes dichloromethane MESH:D008752
1399 64779-64789 Chemical denotes C33H40N4O7
1400 64794-64797 Chemical denotes H2O
1401 64802-64807 Chemical denotes CHCl3
1402 64809-64810 Chemical denotes C MESH:D002244
1403 64828-64829 Chemical denotes N MESH:D009584
1404 64844-64845 Chemical denotes C MESH:D002244
1405 64863-64864 Chemical denotes N MESH:D009584
1406 64894-64904 Chemical denotes C33H40N4O7
1407 64872-64876 Disease denotes HRMS
1418 65252-65277 Chemical denotes 2,6-dimethoxybenzoic acid MESH:C472445
1419 65396-65404 Chemical denotes methanol MESH:D000432
1420 65405-65420 Chemical denotes dichloromethane MESH:D008752
1421 65982-65992 Chemical denotes C33H40N4O9
1422 65998-66001 Chemical denotes H2O
1423 66007-66012 Chemical denotes CHCl3
1424 66014-66015 Chemical denotes C MESH:D002244
1425 66033-66034 Chemical denotes N MESH:D009584
1426 66049-66050 Chemical denotes C MESH:D002244
1427 66068-66069 Chemical denotes N MESH:D009584
1439 66389-66408 Chemical denotes 2-cyanobenzoic acid
1440 66512-66522 Chemical denotes chloroform MESH:D002725
1441 66523-66536 Chemical denotes ethyl acetate MESH:C007650
1442 67039-67049 Chemical denotes C32H35N5O7
1443 67054-67057 Chemical denotes H2O
1444 67059-67060 Chemical denotes C MESH:D002244
1445 67078-67079 Chemical denotes N MESH:D009584
1446 67095-67096 Chemical denotes C MESH:D002244
1447 67114-67115 Chemical denotes N MESH:D009584
1448 67146-67156 Chemical denotes C32H35N5O7
1449 67124-67128 Disease denotes HRMS
1451 67187-67284 Chemical denotes (3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate
1464 67299-67383 Chemical denotes tert-butyl ((1S)-3-bromo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1465 67406-67409 Chemical denotes DMF MESH:D004126
1466 67435-67459 Chemical denotes 2,6-dichlorobenzoic acid
1467 67491-67506 Chemical denotes cesium fluoride MESH:C027754
1468 67578-67581 Chemical denotes oil MESH:D009821
1469 67669-67682 Chemical denotes ethyl acetate MESH:C007650
1470 67710-67715 Chemical denotes water MESH:D014867
1471 67733-67738 Chemical denotes brine MESH:C017082
1472 67759-67764 Chemical denotes MgSO4 MESH:D008278
1473 67878-67886 Chemical denotes methanol MESH:D000432
1474 67887-67902 Chemical denotes dichloromethane MESH:D008752
1475 68175-68179 Disease denotes HRMS
1492 68457-68460 Gene denotes Boc Gene:91653
1493 69711-69716 Species denotes O5+H1 Tax:2491878
1494 68793-68799 Chemical denotes NaHCO3 MESH:D017693
1495 68839-68852 Chemical denotes ethyl acetate MESH:C007650
1496 68906-68911 Chemical denotes brine MESH:C017082
1497 68932-68937 Chemical denotes MgSO4 MESH:D008278
1498 69037-69041 Chemical denotes SiO2
1499 69048-69056 Chemical denotes methanol MESH:D000432
1500 69057-69067 Chemical denotes chloroform MESH:D002725
1501 69594-69606 Chemical denotes C19H32ClN3O5
1502 69611-69614 Chemical denotes H2O
1503 69616-69617 Chemical denotes C MESH:D002244
1504 69635-69636 Chemical denotes N MESH:D009584
1505 69651-69652 Chemical denotes C MESH:D002244
1506 69670-69671 Chemical denotes N MESH:D009584
1507 69679-69683 Disease denotes HRMS
1519 70244-70248 Chemical denotes SiO2
1520 70259-70267 Chemical denotes methanol MESH:D000432
1521 70268-70278 Chemical denotes chloroform MESH:D002725
1522 70724-70737 Chemical denotes C26H35Cl2N3O7
1523 70742-70745 Chemical denotes H2O
1524 70747-70748 Chemical denotes C MESH:D002244
1525 70766-70767 Chemical denotes N MESH:D009584
1526 70782-70783 Chemical denotes C MESH:D002244
1527 70801-70802 Chemical denotes N MESH:D009584
1528 70832-70845 Chemical denotes C26H35Cl2N3O7
1529 70810-70814 Disease denotes HRMS
1531 70876-70971 Chemical denotes (3S)-3-[(N-Acetyl-l-leucyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate
1543 71373-71381 Chemical denotes methanol MESH:D000432
1544 71382-71397 Chemical denotes dichloromethane MESH:D008752
1545 71834-71847 Chemical denotes C23H29Cl2N3O6
1546 71853-71856 Chemical denotes H2O
1547 71861-71866 Chemical denotes EtOAc
1548 71868-71869 Chemical denotes C MESH:D002244
1549 71887-71888 Chemical denotes N MESH:D009584
1550 71903-71904 Chemical denotes C MESH:D002244
1551 71922-71923 Chemical denotes N MESH:D009584
1552 71953-71966 Chemical denotes C23H29Cl2N3O6
1553 71931-71935 Disease denotes HRMS
1563 72606-72614 Chemical denotes methanol MESH:D000432
1564 72615-72630 Chemical denotes dichloromethane MESH:D008752
1565 73077-73090 Chemical denotes C29H31Cl2N5O6
1566 73092-73093 Chemical denotes C MESH:D002244
1567 73111-73112 Chemical denotes N MESH:D009584
1568 73128-73129 Chemical denotes C MESH:D002244
1569 73147-73148 Chemical denotes N MESH:D009584
1570 73179-73192 Chemical denotes C29H31Cl2N5O6
1571 73157-73161 Disease denotes HRMS
1585 73819-73831 Gene denotes Luna 10μ C18 Gene:27241
1586 73860-73864 Chemical denotes MeCN
1587 73881-73885 Chemical denotes AcOH
1588 73889-73894 Chemical denotes water MESH:D014867
1589 73911-73915 Chemical denotes AcOH
1590 74368-74381 Chemical denotes C27H35Cl2N3O7
1591 74386-74389 Chemical denotes H2O
1592 74391-74392 Chemical denotes C MESH:D002244
1593 74410-74411 Chemical denotes N MESH:D009584
1594 74426-74427 Chemical denotes C MESH:D002244
1595 74445-74446 Chemical denotes N MESH:D009584
1596 74476-74489 Chemical denotes C27H35Cl2N3O7
1597 74454-74458 Disease denotes HRMS
1601 74824-74827 Gene denotes Boc Gene:91653
1602 74971-74979 Chemical denotes methanol MESH:D000432
1603 74980-74990 Chemical denotes chloroform MESH:D002725
1608 75746-75749 Gene denotes Boc Gene:91653
1609 75874-75878 Chemical denotes SiO2
1610 75887-75895 Chemical denotes methanol MESH:D000432
1611 75896-75906 Chemical denotes chloroform MESH:D002725
1623 76927-76935 Chemical denotes methanol MESH:D000432
1624 76936-76946 Chemical denotes chloroform MESH:D002725
1625 77407-77417 Chemical denotes C32H40N4O6
1626 77423-77431 Chemical denotes methanol MESH:D000432
1627 77437-77440 Chemical denotes H2O
1628 77442-77443 Chemical denotes C MESH:D002244
1629 77461-77462 Chemical denotes N MESH:D009584
1630 77477-77478 Chemical denotes C MESH:D002244
1631 77496-77497 Chemical denotes N MESH:D009584
1632 77527-77537 Chemical denotes C32H40N4O6
1633 77505-77509 Disease denotes HRMS
1638 78177-78185 Chemical denotes methanol MESH:D000432
1639 78186-78196 Chemical denotes chloroform MESH:D002725
1640 78730-78734 Disease denotes HRMS
1641 78638-78644 CellLine denotes 9.9 Hz CVCL:Z676
1655 79430-79438 Chemical denotes methanol MESH:D000432
1656 79439-79449 Chemical denotes chloroform MESH:D002725
1657 79528-79539 Chemical denotes C25H34N4O6m
1658 80067-80075 Chemical denotes methanol MESH:D000432
1659 80076-80086 Chemical denotes chloroform MESH:D002725
1660 80616-80626 Chemical denotes C25H34N4O6
1661 80631-80634 Chemical denotes H2O
1662 80636-80637 Chemical denotes C MESH:D002244
1663 80655-80656 Chemical denotes N MESH:D009584
1664 80672-80673 Chemical denotes C MESH:D002244
1665 80691-80692 Chemical denotes N MESH:D009584
1666 80723-80733 Chemical denotes C25H34N4O6
1667 80701-80705 Disease denotes HRMS
1671 81399-81407 Chemical denotes methanol MESH:D000432
1672 81408-81418 Chemical denotes chloroform MESH:D002725
1673 81943-81947 Disease denotes HRMS
1681 82649-82654 Chemical denotes water MESH:D014867
1682 82906-82917 Chemical denotes C32H36N4O8m
1683 83086-83094 Chemical denotes methanol MESH:D000432
1684 83137-83139 Chemical denotes N2
1685 83157-83176 Chemical denotes potassium carbonate MESH:C037593
1686 83371-83379 Chemical denotes methanol MESH:D000432
1687 83380-83390 Chemical denotes chloroform MESH:D002725
1691 84256-84259 Gene denotes Boc Gene:91653
1692 84408-84416 Chemical denotes methanol MESH:D000432
1693 84417-84432 Chemical denotes dichloromethane MESH:D008752
1696 85401-85409 Chemical denotes methanol MESH:D000432
1697 85410-85425 Chemical denotes dichloromethane MESH:D008752
1700 86614-86622 Chemical denotes methanol MESH:D000432
1701 86623-86638 Chemical denotes dichloromethane MESH:D008752
1712 87378-87381 Gene denotes Boc Gene:91653
1713 87499-87503 Chemical denotes SiO2
1714 87514-87522 Chemical denotes methanol MESH:D000432
1715 87523-87533 Chemical denotes chloroform MESH:D002725
1716 87604-87606 Chemical denotes 1H
1717 87612-87619 Chemical denotes DMSO-d6
1718 87642-87644 Chemical denotes 1H
1719 87656-87658 Chemical denotes 1H
1720 87680-87682 Chemical denotes 1H
1721 87705-87707 Chemical denotes 1H
1729 88575-88583 Chemical denotes methanol MESH:D000432
1730 88584-88594 Chemical denotes chloroform MESH:D002725
1731 89114-89126 Chemical denotes C24H31ClN4O5
1732 89128-89129 Chemical denotes C MESH:D002244
1733 89147-89148 Chemical denotes N MESH:D009584
1734 89164-89165 Chemical denotes C MESH:D002244
1735 89183-89184 Chemical denotes N MESH:D009584
1747 89814-89822 Chemical denotes methanol MESH:D000432
1748 89823-89833 Chemical denotes chloroform MESH:D002725
1749 90361-90371 Chemical denotes C24H32N4O6
1750 90376-90379 Chemical denotes H2O
1751 90384-90397 Chemical denotes ethyl acetate MESH:C007650
1752 90399-90400 Chemical denotes C MESH:D002244
1753 90418-90419 Chemical denotes N MESH:D009584
1754 90435-90436 Chemical denotes C MESH:D002244
1755 90454-90455 Chemical denotes N MESH:D009584
1756 90486-90496 Chemical denotes C24H32N4O6
1757 90464-90468 Disease denotes HRMS
1759 90527-90594 Chemical denotes Methyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucinate
1770 90612-90670 Chemical denotes N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucine
1771 90693-90701 Chemical denotes methanol MESH:D000432
1772 90719-90726 Chemical denotes toluene MESH:D014050
1773 90772-90788 Chemical denotes TMS-diazomethane
1774 90805-90811 Chemical denotes hexane MESH:D006586
1775 90872-90875 Chemical denotes TMS MESH:C073196
1776 90876-90888 Chemical denotes diazomethane MESH:D003978
1777 90999-91003 Chemical denotes AcOH
1778 91118-91131 Chemical denotes ethyl acetate MESH:C007650
1779 91132-91138 Chemical denotes hexane MESH:D006586
1781 91592-91646 Chemical denotes Methyl N-(tert-Butoxycarbonyl)-5-methyl-l-norleucinate
1796 91664-91731 Chemical denotes methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucinate
1797 91755-91758 Chemical denotes DMF MESH:D004126
1798 91813-91826 Chemical denotes triethylamine MESH:C016162
1799 91853-91878 Chemical denotes di-tert-butyl dicarbonate MESH:C027600
1800 92090-92095 Chemical denotes BOC2O MESH:C027600
1801 92158-92171 Chemical denotes diethyl ether MESH:D004986
1802 92194-92198 Chemical denotes satd
1803 92200-92206 Chemical denotes NaHCO3 MESH:D017693
1804 92224-92241 Chemical denotes hydrochloric acid MESH:D006851
1805 92255-92261 Chemical denotes NaHCO3 MESH:D017693
1806 92275-92280 Chemical denotes brine MESH:C017082
1807 92301-92306 Chemical denotes MgSO4 MESH:D008278
1808 92452-92467 Chemical denotes dichloromethane MESH:D008752
1809 92468-92474 Chemical denotes hexane MESH:D006586
1811 92785-92830 Chemical denotes N-(tert-Butoxycarbonyl)-5-methyl-l-norleucine
1819 92848-92902 Chemical denotes methyl N-(tert-butoxycarbonyl)-5-methyl-l-norleucinate
1820 92926-92929 Chemical denotes THF MESH:C018674
1821 92990-92994 Chemical denotes LiOH
1822 93173-93190 Chemical denotes hydrochloric acid MESH:D006851
1823 93210-93223 Chemical denotes ethyl acetate MESH:C007650
1824 93276-93281 Chemical denotes brine MESH:C017082
1825 93303-93308 Chemical denotes MgSO4 MESH:D008278
1830 93973-94018 Chemical denotes N-(tert-butoxycarbonyl)-5-methyl-l-norleucine
1831 94070-94080 Chemical denotes golden oil
1832 94155-94163 Chemical denotes methanol MESH:D000432
1833 94164-94179 Chemical denotes dichloromethane MESH:D008752
1838 95815-95820 Species denotes O5+H1 Tax:2491878
1839 95278-95286 Chemical denotes methanol MESH:D000432
1840 95287-95297 Chemical denotes chloroform MESH:D002725
1841 95783-95787 Disease denotes HRMS
1845 96485-96493 Chemical denotes methanol MESH:D000432
1846 96494-96504 Chemical denotes chloroform MESH:D002725
1847 97046-97050 Disease denotes HRMS
1854 97728-97731 Gene denotes Boc Gene:91653
1855 98272-98281 Species denotes brown gum Tax:338536
1856 97947-97952 Chemical denotes water MESH:D014867
1857 98062-98067 Chemical denotes MgSO4 MESH:D008278
1858 98208-98216 Chemical denotes methanol MESH:D000432
1859 98217-98232 Chemical denotes dichloromethane MESH:D008752
1867 99961-99970 Species denotes brown gum Tax:338536
1868 99583-99588 Chemical denotes water MESH:D014867
1869 99699-99704 Chemical denotes water MESH:D014867
1870 99717-99722 Chemical denotes brine MESH:C017082
1871 99743-99748 Chemical denotes MgSO4 MESH:D008278
1872 99897-99905 Chemical denotes methanol MESH:D000432
1873 99906-99921 Chemical denotes dichloromethane MESH:D008752
1881 101741-101751 Chemical denotes C27H36N4O6
1882 101757-101760 Chemical denotes H2O
1883 101762-101763 Chemical denotes C MESH:D002244
1884 101781-101782 Chemical denotes N MESH:D009584
1885 101798-101799 Chemical denotes C MESH:D002244
1886 101817-101818 Chemical denotes N MESH:D009584
1887 101085-101092 Disease denotes balloon MESH:D054549
1891 102122-102125 Gene denotes Boc Gene:91653
1892 102268-102276 Chemical denotes methanol MESH:D000432
1893 102277-102292 Chemical denotes dichloromethane MESH:D008752
1896 103274-103282 Chemical denotes methanol MESH:D000432
1897 103283-103298 Chemical denotes dichloromethane MESH:D008752
1906 104454-104462 Chemical denotes methanol MESH:D000432
1907 104463-104478 Chemical denotes dichloromethane MESH:D008752
1908 105058-105068 Chemical denotes C27H30N4O6
1909 105075-105078 Chemical denotes H2O
1910 105080-105081 Chemical denotes C MESH:D002244
1911 105099-105100 Chemical denotes N MESH:D009584
1912 105116-105117 Chemical denotes C MESH:D002244
1913 105135-105136 Chemical denotes N MESH:D009584
1924 105780-105788 Chemical denotes methanol MESH:D000432
1925 105789-105799 Chemical denotes chloroform MESH:D002725
1926 106274-106286 Chemical denotes C24H31ClN4O4
1927 106292-106297 Chemical denotes CHCl3
1928 106299-106300 Chemical denotes C MESH:D002244
1929 106318-106319 Chemical denotes N MESH:D009584
1930 106335-106336 Chemical denotes C MESH:D002244
1931 106354-106355 Chemical denotes N MESH:D009584
1932 106386-106398 Chemical denotes C24H31ClN4O4
1933 106364-106368 Disease denotes HRMS
1946 107051-107059 Chemical denotes methanol MESH:D000432
1947 107060-107070 Chemical denotes chloroform MESH:D002725
1948 107599-107609 Chemical denotes C24H32N4O5
1949 107614-107619 Chemical denotes CHCl3
1950 107624-107637 Chemical denotes ethyl acetate MESH:C007650
1951 107643-107646 Chemical denotes H2O
1952 107648-107649 Chemical denotes C MESH:D002244
1953 107667-107668 Chemical denotes N MESH:D009584
1954 107684-107685 Chemical denotes C MESH:D002244
1955 107703-107704 Chemical denotes N MESH:D009584
1956 107735-107745 Chemical denotes C24H32N4O5
1957 107713-107717 Disease denotes HRMS
1969 108397-108405 Chemical denotes methanol MESH:D000432
1970 108406-108416 Chemical denotes chloroform MESH:D002725
1971 108908-108918 Chemical denotes C25H34N4O5
1972 108923-108936 Chemical denotes ethyl acetate MESH:C007650
1973 108942-108945 Chemical denotes H2O
1974 108947-108948 Chemical denotes C MESH:D002244
1975 108966-108967 Chemical denotes N MESH:D009584
1976 108983-108984 Chemical denotes C MESH:D002244
1977 109002-109003 Chemical denotes N MESH:D009584
1978 109034-109044 Chemical denotes C25H34N4O5
1979 109012-109016 Disease denotes HRMS
1984 109424-109434 Chemical denotes iodoethane MESH:C521551
1985 109558-109566 Chemical denotes methanol MESH:D000432
1986 109567-109577 Chemical denotes chloroform MESH:D002725
1987 110100-110104 Disease denotes HRMS
1992 110793-110803 Chemical denotes chloroform MESH:D002725
1993 110825-110833 Chemical denotes methanol MESH:D000432
1994 110849-110857 Chemical denotes methanol MESH:D000432
1995 110876-110886 Chemical denotes chloroform MESH:D002725
2008 112050-112065 Chemical denotes dichloromethane MESH:D008752
2009 112066-112074 Chemical denotes methanol MESH:D000432
2010 112137-112152 Chemical denotes dichloromethane MESH:D008752
2011 112153-112161 Chemical denotes methanol MESH:D000432
2012 112188-112203 Chemical denotes dichloromethane MESH:D008752
2013 112714-112731 Chemical denotes C20H33N3O6·0.5H2O
2014 112733-112734 Chemical denotes C MESH:D002244
2015 112752-112753 Chemical denotes N MESH:D009584
2016 112768-112769 Chemical denotes C MESH:D002244
2017 112787-112788 Chemical denotes N MESH:D009584
2018 112818-112828 Chemical denotes C20H33N3O6
2019 112796-112800 Disease denotes HRMS
2025 113475-113490 Chemical denotes dichloromethane MESH:D008752
2026 113491-113499 Chemical denotes methanol MESH:D000432
2027 113518-113533 Chemical denotes dichloromethane MESH:D008752
2028 114078-114088 Chemical denotes C21H35N3O6
2029 114056-114060 Disease denotes HRMS
2038 114684-114695 Chemical denotes iodomethane MESH:C014055
2039 114808-114823 Chemical denotes dichloromethane MESH:D008752
2040 114850-114855 Chemical denotes water MESH:D014867
2041 114875-114880 Chemical denotes brine MESH:C017082
2042 114901-114906 Chemical denotes MgSO4 MESH:D008278
2043 115028-115036 Chemical denotes methanol MESH:D000432
2044 115037-115047 Chemical denotes chloroform MESH:D002725
2045 115571-115575 Disease denotes HRMS
2049 115982-116006 Chemical denotes indole-2-carboxylic acid MESH:C058980
2050 116144-116152 Chemical denotes methanol MESH:D000432
2051 116153-116168 Chemical denotes dichloromethane MESH:D008752
2061 117296-117304 Chemical denotes methanol MESH:D000432
2062 117305-117320 Chemical denotes dichloromethane MESH:D008752
2063 117788-117798 Chemical denotes C23H30N4O5
2064 117804-117807 Chemical denotes H2O
2065 117813-117816 Chemical denotes DCM MESH:D008752
2066 117818-117819 Chemical denotes C MESH:D002244
2067 117837-117838 Chemical denotes N MESH:D009584
2068 117854-117855 Chemical denotes C MESH:D002244
2069 117873-117874 Chemical denotes N MESH:D009584
2072 118512-118520 Chemical denotes methanol MESH:D000432
2073 118521-118536 Chemical denotes dichloromethane MESH:D008752
2075 119052-119060 Species denotes SARS CoV Tax:694009
2092 119120-119131 Species denotes coronavirus Tax:11118
2093 119768-119784 Species denotes SARS coronavirus Tax:694009
2094 120179-120183 Species denotes kobs Tax:59530
2095 120484-120488 Species denotes kobs Tax:59530
2096 120528-120539 Species denotes coronavirus Tax:11118
2097 120565-120569 Species denotes kobs Tax:59530
2098 120586-120590 Species denotes kobs Tax:59530
2099 120697-120701 Species denotes kobs Tax:59530
2100 119293-119298 Chemical denotes TAMRA
2101 119330-119335 Chemical denotes TAMRA
2102 119401-119406 Chemical denotes TAMRA
2103 119569-119574 Chemical denotes HEPES MESH:D006531
2104 119590-119594 Chemical denotes EDTA MESH:D004492
2105 119619-119623 Chemical denotes DMSO MESH:D004121
2106 119636-119644 Chemical denotes Tween-20 MESH:D011136
2107 119700-119723 Chemical denotes CoV-1 3CLpro nucleotide
2109 121010-121020 Species denotes SARS CoV-2 Tax:2697049
2119 121112-121122 Species denotes SARS CoV-2 Tax:2697049
2120 121213-121223 Species denotes SARS CoV-2 Tax:2697049
2121 121274-121284 Species denotes SARS CoV-2 Tax:2697049
2122 121708-121718 Species denotes SARS CoV-2 Tax:2697049
2123 121911-121921 Species denotes SARS CoV-2 Tax:2697049
2124 121769-121777 Chemical denotes Tris–HCl
2125 121795-121799 Chemical denotes NaCl MESH:D012965
2126 121806-121810 Chemical denotes EDTA MESH:D004492
2127 121817-121821 Chemical denotes TCEP MESH:C080938
2129 122472-122480 Species denotes SARS CoV Tax:694009
2142 122818-122826 Species denotes SARS CoV Tax:694009
2143 122604-122614 Chemical denotes phenol red MESH:D010637
2144 122620-122624 Chemical denotes DMEM
2145 123159-123162 Chemical denotes PBS MESH:D007854
2146 123178-123182 Chemical denotes DMEM
2147 123300-123303 Chemical denotes PBS MESH:D007854
2148 123336-123340 Chemical denotes EtOH MESH:D000431
2149 123345-123356 Chemical denotes acetic acid MESH:D019342
2150 122785-122793 Disease denotes infected MESH:D007239
2151 122911-122919 Disease denotes infected MESH:D007239
2152 123783-123791 Disease denotes infected MESH:D007239
2153 123884-123896 Disease denotes cytotoxicity MESH:D064420
2155 124141-124150 Species denotes hCOV 229E Tax:11137
2163 124390-124399 Species denotes hCoV 229E Tax:11137
2164 124223-124233 Chemical denotes phenol red MESH:D010637
2165 124363-124371 Disease denotes infected MESH:D007239
2166 124442-124455 Disease denotes mock-infected MESH:D007239
2167 124895-124903 Disease denotes infected MESH:D007239
2168 124996-125008 Disease denotes cytotoxicity MESH:D064420
2169 124168-124173 CellLine denotes MRC-5 CVCL:0440
2172 125306-125310 Species denotes HCMV Tax:10359
2173 125314-125330 Disease denotes HIV-RF,55 HRV-14 MESH:C538347
2175 125465-125470 Species denotes CoV-2 Tax:2697049
2197 126535-126539 Gene denotes Mpro Gene:8673700
2198 125623-125627 Gene denotes Mpro Gene:8673700
2199 125554-125562 Species denotes SARS CoV Tax:694009
2200 125590-125598 Species denotes SARS CoV Tax:694009
2201 125612-125622 Species denotes SARS CoV-2 Tax:2697049
2202 125687-125703 Species denotes Escherichia coli Tax:562
2203 126531-126534 Species denotes CoV Tax:11118
2204 125986-125990 Chemical denotes IPTG MESH:D007544
2205 126144-126148 Chemical denotes Tris
2206 126165-126169 Chemical denotes NaCl MESH:D012965
2207 126263-126269 Chemical denotes nickel MESH:D009532
2208 126351-126360 Chemical denotes imidazole MESH:C029899
2209 126411-126420 Chemical denotes imidazole MESH:C029899
2210 126522-126525 Chemical denotes DTT MESH:D004229
2211 126762-126766 Chemical denotes Tris
2212 126783-126787 Chemical denotes NaCl MESH:D012965
2213 126795-126799 Chemical denotes EDTA MESH:D004492
2214 126807-126810 Chemical denotes DTT MESH:D004229
2215 126945-126953 Chemical denotes nitrogen MESH:D009584
2216 125628-125638 CellLine denotes MN908947.3 CVCL:U508
2217 125863-125867 CellLine denotes BL21 CVCL:M639
2229 127122-127125 Gene denotes DC2 Gene:58505
2230 127054-127057 Species denotes CoV Tax:11118
2231 127116-127119 Species denotes CoV Tax:11118
2232 127060-127063 Gene denotes DC2 Gene:58505
2233 127269-127286 Chemical denotes cellulose acetate MESH:C005062
2234 127450-127458 Chemical denotes PEG 6000 MESH:C000595215
2235 127466-127469 Chemical denotes MES MESH:C004550
2236 127489-127492 Chemical denotes DTT MESH:D004229
2237 127765-127773 Chemical denotes nitrogen MESH:D009584
2238 127851-127859 Chemical denotes glycerol MESH:D005990
2239 127387-127392 CellLine denotes MRC-2 CVCL:0440
2252 128018-128021 Gene denotes DC2 Gene:58505
2253 127950-127953 Species denotes CoV Tax:11118
2254 128012-128015 Species denotes CoV Tax:11118
2255 127956-127959 Gene denotes DC2 Gene:58505
2256 128166-128183 Chemical denotes cellulose acetate MESH:C005062
2257 128348-128356 Chemical denotes PEG 8000 MESH:C000595216
2258 128364-128379 Chemical denotes sodium chloride MESH:D012965
2259 128387-128413 Chemical denotes sodium potassium phosphate
2260 128432-128436 Chemical denotes TCEP MESH:C080938
2261 128709-128717 Chemical denotes nitrogen MESH:D009584
2262 128795-128803 Chemical denotes glycerol MESH:D005990
2263 128284-128289 CellLine denotes MRC-2 CVCL:0440
2265 128851-128856 Species denotes SARS2 Tax:2697049
2277 128947-128950 Gene denotes DC2 Gene:58505
2278 129012-129015 Gene denotes DC2 Gene:58505
2279 128941-128944 Species denotes CoV Tax:11118
2280 129006-129009 Species denotes CoV Tax:11118
2281 129160-129177 Chemical denotes cellulose acetate MESH:C005062
2282 129342-129350 Chemical denotes PEG 6000 MESH:C000595215
2283 129358-129361 Chemical denotes MES MESH:C004550
2284 129378-129386 Chemical denotes glycerol MESH:D005990
2285 129657-129665 Chemical denotes nitrogen MESH:D009584
2286 129743-129751 Chemical denotes glycerol MESH:D005990
2287 129278-129283 CellLine denotes MRC-2 CVCL:0440
2299 129810-129815 Species denotes SARS2 Tax:2697049
2300 129816-129821 Species denotes CoV-2 Tax:2697049
2301 129878-129883 Species denotes SARS2 Tax:2697049
2302 129884-129889 Species denotes CoV-2 Tax:2697049
2303 130040-130057 Chemical denotes cellulose acetate MESH:C005062
2304 130222-130232 Chemical denotes 2-propanol MESH:D019840
2305 130240-130251 Chemical denotes citric acid MESH:D019343
2306 130272-130275 Chemical denotes PEG
2307 130562-130570 Chemical denotes nitrogen MESH:D009584
2308 130648-130656 Chemical denotes glycerol MESH:D005990
2309 130158-130163 CellLine denotes MRC-2 CVCL:0440
2323 130782-130785 Gene denotes DC2 Gene:58505
2324 130727-130730 Gene denotes DC2 Gene:58505
2325 130715-130720 Species denotes SARS2 Tax:2697049
2326 130721-130726 Species denotes CoV-2 Tax:2697049
2327 130770-130775 Species denotes SARS2 Tax:2697049
2328 130776-130781 Species denotes CoV-2 Tax:2697049
2329 130838-130855 Chemical denotes cellulose acetate MESH:C005062
2330 131018-131056 Chemical denotes potassium sodium tartrate tetrahydrate MESH:C029768
2331 131069-131072 Chemical denotes PEG
2332 131356-131360 Chemical denotes DMSO MESH:D004121
2333 131525-131533 Chemical denotes nitrogen MESH:D009584
2334 131611-131619 Chemical denotes glycerol MESH:D005990
2335 130956-130961 CellLine denotes MRC-2 CVCL:0440
2337 131813-131821 Species denotes SARS CoV Tax:694009
2341 132087-132097 Species denotes SARS CoV-2 Tax:2697049
2342 132198-132206 Species denotes SARS CoV Tax:694009
2343 132128-132137 Chemical denotes PF-835231

2_test

Id Subject Object Predicate Lexical cue
33054210-32015508-61913438 1356-1357 32015508 denotes 1
33054210-32015507-61913439 1358-1359 32015507 denotes 2
33054210-32015507-61913440 1514-1515 32015507 denotes 2
33054210-12730500-61913441 1516-1517 12730500 denotes 4
33054210-12917450-61913442 2223-2224 12917450 denotes 7
33054210-32321856-61913443 2826-2827 32321856 denotes 9
33054210-9667969-61913444 2923-2925 9667969 denotes 10
33054210-7794931-61913445 2926-2928 7794931 denotes 13
33054210-12270191-61913446 2973-2975 12270191 denotes 15
33054210-8230139-61913447 3046-3048 8230139 denotes 19
33054210-11848867-61913448 3404-3406 11848867 denotes 21
33054210-32045235-61913449 3841-3843 32045235 denotes 23
33054210-12475205-61913450 4193-4195 12475205 denotes 24
33054210-8126694-61913451 4394-4396 8126694 denotes 26
33054210-10353641-61913452 4836-4838 10353641 denotes 27
33054210-12746549-61913453 5423-5425 12746549 denotes 28
33054210-10197965-61913454 7502-7504 10197965 denotes 30
33054210-1433192-61913455 10539-10541 1433192 denotes 31
33054210-10746010-61913456 10592-10594 10746010 denotes 32
33054210-2029515-61913457 14664-14666 2029515 denotes 37
33054210-15450003-61913458 25208-25210 15450003 denotes 44
33054210-10534321-61913459 26895-26897 10534321 denotes 45
33054210-10463589-61913460 33354-33356 10463589 denotes 48
33054210-17397958-61913461 121438-121440 17397958 denotes 50
33054210-3983963-61913462 124134-124136 3983963 denotes 51
33054210-28359770-61913463 124137-124139 28359770 denotes 52
33054210-3409223-61913464 124557-124559 3409223 denotes 53
33054210-2495366-61913465 125311-125313 2495366 denotes 54
33054210-8863994-61913466 125321-125323 8863994 denotes 55
33054210-2495366-61913467 125343-125345 2495366 denotes 54
33054210-10508022-61913468 125374-125376 10508022 denotes 56
33054210-11110665-61913469 125377-125379 11110665 denotes 57
33054210-18237196-61913470 125572-125574 18237196 denotes 58