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PMC:7571312 / 10193-34225 JSONTXT

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LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T53161 897-907 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T58451 2805-2808 Body_part denotes CsF http://purl.org/sig/ont/fma/fma20935
T56425 3951-3954 Body_part denotes CsF http://purl.org/sig/ont/fma/fma20935
T49380 4373-4381 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T87686 6563-6571 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T47943 6641-6644 Body_part denotes C–S http://purl.org/sig/ont/fma/fma284995
T89780 6762-6770 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T71020 7305-7313 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T29395 7855-7860 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T77718 7927-7932 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T39660 8028-8033 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T54465 8104-8108 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T44584 8109-8114 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T80152 8308-8314 Body_part denotes plasma http://purl.org/sig/ont/fma/fma62970
T12289 9513-9520 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T15026 9742-9749 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T44316 9910-9915 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T16632 10264-10271 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T93878 10611-10615 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T88519 10755-10759 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T52556 11073-11081 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T92468 11638-11646 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T63397 13360-13364 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T53789 13588-13593 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T46 13615-13621 Body_part denotes kidney http://purl.org/sig/ont/fma/fma7203
T40778 13653-13657 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T47080 13658-13674 Body_part denotes epithelial cells http://purl.org/sig/ont/fma/fma66768
T52254 13669-13674 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T65361 13813-13817 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T97321 13979-13991 Body_part denotes glycoprotein http://purl.org/sig/ont/fma/fma62925
T89000 15220-15224 Body_part denotes hand http://purl.org/sig/ont/fma/fma9712
T53 16668-16673 Body_part denotes liver http://purl.org/sig/ont/fma/fma7197
T54 16674-16684 Body_part denotes microsomes http://purl.org/sig/ont/fma/fma67438
T55 17760-17768 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T56 17834-17837 Body_part denotes C–S http://purl.org/sig/ont/fma/fma284995
T57 17905-17913 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T58 18897-18905 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T59 19018-19026 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T60 19359-19367 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T61 19415-19422 Body_part denotes leucine http://purl.org/sig/ont/fma/fma82757
T62 19730-19738 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T63 19961-19968 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T64 21079-21088 Body_part denotes leukocyte http://purl.org/sig/ont/fma/fma62852
T65 21219-21222 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T66 21226-21229 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T67 21773-21776 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T68 21816-21820 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T69 22010-22015 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T70 22023-22027 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T71 22221-22224 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T72 22882-22886 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T73 23085-23097 Body_part denotes glycoprotein http://purl.org/sig/ont/fma/fma62925
T74 23514-23518 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T75 23533-23538 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T76 23551-23563 Body_part denotes glycoprotein http://purl.org/sig/ont/fma/fma62925
T77 23703-23708 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T78 23767-23771 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T79 23830-23834 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T80 23835-23840 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T81 23855-23861 Body_part denotes tissue http://purl.org/sig/ont/fma/fma9637
T82 23987-23991 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T83 23992-23997 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646

LitCovid-PD-UBERON

Id Subject Object Predicate Lexical cue uberon_id
T2 6199-6204 Body_part denotes scale http://purl.obolibrary.org/obo/UBERON_0002542
T3 8104-8108 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T4 13615-13621 Body_part denotes kidney http://purl.obolibrary.org/obo/UBERON_0002113
T5 13653-13657 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T6 15220-15224 Body_part denotes hand http://purl.obolibrary.org/obo/UBERON_0002398
T7 16668-16673 Body_part denotes liver http://purl.obolibrary.org/obo/UBERON_0002107
T8 22023-22027 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T9 23514-23518 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T10 23830-23834 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T11 23855-23861 Body_part denotes tissue http://purl.obolibrary.org/obo/UBERON_0000479
T12 23987-23991 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048

LitCovid-PD-MONDO

Id Subject Object Predicate Lexical cue mondo_id
T49 4103-4107 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T50 4869-4873 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T51 5142-5146 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T52 5217-5221 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T53 5973-5977 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T54 6320-6324 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T55 7498-7502 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T56 7784-7788 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T57 9068-9072 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T58 9107-9111 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T59 9724-9728 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T60 10616-10625 Disease denotes infection http://purl.obolibrary.org/obo/MONDO_0005550
T61 10760-10769 Disease denotes infection http://purl.obolibrary.org/obo/MONDO_0005550
T62 10960-10964 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T63 11482-11486 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T64 12102-12106 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T65 12646-12650 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T66 14388-14392 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T67 16873-16877 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T68 17286-17290 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T69 17457-17461 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T70 17472-17476 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T71 18316-18320 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T72 19447-19451 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T73 19855-19859 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T74 20070-20074 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T75 20815-20819 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T76 20949-20953 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T77 20988-20992 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T78 21489-21493 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T79 21747-21763 Disease denotes immunodeficiency http://purl.obolibrary.org/obo/MONDO_0021094
T80 22124-22128 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T81 22530-22534 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T82 22718-22722 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T83 23035-23039 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T84 23251-23255 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T85 23866-23870 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091
T86 23875-23883 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T87 23947-23951 Disease denotes SARS http://purl.obolibrary.org/obo/MONDO_0005091

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T8217 278-279 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T52201 320-321 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T96491 364-365 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T72259 452-454 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T79057 651-653 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T4510 750-752 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T19787 1239-1242 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T8586 1379-1381 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T41909 1417-1419 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T84353 1444-1447 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T64722 1606-1607 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T21026 1811-1813 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T93676 1814-1815 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T62552 1928-1931 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T38138 1966-1969 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T5895 2077-2078 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T91690 2158-2159 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T7075 2214-2221 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T97610 2241-2244 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T35533 2285-2298 http://purl.obolibrary.org/obo/UBERON_0002329 denotes epimerization
T32370 2486-2488 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T64601 2976-2978 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T24049 3097-3099 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T15952 3124-3125 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T58065 3145-3158 http://purl.obolibrary.org/obo/UBERON_0002329 denotes epimerization
T75772 3166-3168 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T70942 3263-3265 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T27962 3299-3302 http://purl.obolibrary.org/obo/CLO_0002526 denotes CMK
T47002 3323-3325 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T84592 3675-3677 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T16252 3925-3929 http://purl.obolibrary.org/obo/CL_0000784 denotes Pd/C
T28229 4168-4170 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T30736 4270-4273 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T42783 4613-4614 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T59953 4834-4835 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T67520 4902-4903 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69080 5040-5042 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T29047 5050-5051 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T27082 5259-5262 http://purl.obolibrary.org/obo/CLO_0007437 denotes M–1
T89112 5259-5262 http://purl.obolibrary.org/obo/CLO_0007448 denotes M–1
T44311 5259-5262 http://purl.obolibrary.org/obo/CLO_0007449 denotes M–1
T11842 5259-5262 http://purl.obolibrary.org/obo/CLO_0050175 denotes M–1
T68824 5259-5262 http://purl.obolibrary.org/obo/CLO_0052399 denotes M–1
T53118 5263-5266 http://purl.obolibrary.org/obo/CLO_0050050 denotes s–1
T18679 5310-5312 http://purl.obolibrary.org/obo/CLO_0007653 denotes Me
T64538 5423-5425 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T67844 5429-5431 http://purl.obolibrary.org/obo/CLO_0007653 denotes Me
T54087 5497-5499 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T91151 5514-5516 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T73065 5522-5527 http://purl.obolibrary.org/obo/CLO_0002488 denotes (Cl)2
T12274 5558-5562 http://purl.obolibrary.org/obo/CLO_0002972 denotes (F)2
T81297 5594-5596 http://purl.obolibrary.org/obo/CLO_0052906 denotes Cl
T26335 5661-5663 http://purl.obolibrary.org/obo/CLO_0007653 denotes Me
T57513 5680-5682 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T77214 5733-5734 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T43067 5938-5939 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T17773 6002-6004 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T88669 6260-6261 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T51542 6346-6347 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T17790 6354-6355 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T86458 6404-6412 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T80470 6551-6557 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T34478 6594-6595 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T81268 6639-6640 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T15335 6803-6804 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T62436 6929-6930 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T40750 7040-7041 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T8354 7075-7076 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75567 7282-7283 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T94234 7341-7342 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T35747 7735-7737 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T36376 7847-7854 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T60100 7855-7860 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T41307 7919-7926 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T44344 7927-7932 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T95747 7970-7978 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T41737 8023-8027 http://purl.obolibrary.org/obo/CLO_0009524 denotes Vero
T58120 8023-8027 http://purl.obolibrary.org/obo/CLO_0050515 denotes Vero
T23029 8028-8033 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T96607 8098-8103 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T31340 8104-8108 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T79444 8104-8108 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T79987 8109-8114 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T84247 8154-8156 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T92769 8302-8307 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T56673 8308-8314 http://purl.obolibrary.org/obo/UBERON_0001969 denotes plasma
T32052 8332-8334 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T59638 8344-8346 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T18074 8356-8357 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T19548 8368-8376 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T94580 8630-8631 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T9015 8791-8793 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T67341 8799-8800 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T16805 8936-8938 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T11594 8969-8971 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T58796 9188-9189 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T39597 9539-9540 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T24511 9840-9843 http://purl.obolibrary.org/obo/CLO_0007437 denotes M–1
T12434 9840-9843 http://purl.obolibrary.org/obo/CLO_0007448 denotes M–1
T28200 9840-9843 http://purl.obolibrary.org/obo/CLO_0007449 denotes M–1
T54715 9840-9843 http://purl.obolibrary.org/obo/CLO_0050175 denotes M–1
T71311 9840-9843 http://purl.obolibrary.org/obo/CLO_0052399 denotes M–1
T97946 9844-9847 http://purl.obolibrary.org/obo/CLO_0050050 denotes s–1
T96800 9893-9901 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T32450 9905-9909 http://purl.obolibrary.org/obo/CLO_0009524 denotes Vero
T14088 9905-9909 http://purl.obolibrary.org/obo/CLO_0050515 denotes Vero
T54297 9910-9915 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T91837 9998-10000 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T99824 10486-10491 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T45488 10519-10527 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T66631 10547-10548 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T29691 10568-10573 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T82549 10611-10615 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T68545 10680-10688 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T85347 10755-10759 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T59256 11243-11244 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T19419 11382-11388 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T18919 11584-11585 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T36051 11626-11632 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T23602 11891-11893 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T57314 11891-11893 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T18914 11904-11905 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T63101 11993-11994 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T52927 12042-12044 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T52376 12134-12136 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T57943 12161-12162 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T83388 12163-12164 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T97788 12347-12348 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T22715 12390-12391 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T17416 12454-12456 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T390 12454-12456 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T74194 12485-12486 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T29295 12551-12553 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T38768 12561-12563 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T2687 12585-12587 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T76472 12706-12708 http://purl.obolibrary.org/obo/CLO_0053794 denotes 41
T47677 12782-12784 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T57536 12966-12968 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T68663 12984-12985 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75668 13293-13294 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75637 13360-13364 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T94133 13494-13500 http://purl.obolibrary.org/obo/CLO_0002172 denotes Caco-2
T56692 13494-13500 http://purl.obolibrary.org/obo/CLO_0051943 denotes Caco-2
T24243 13494-13500 http://purl.obolibrary.org/obo/CLO_0051958 denotes Caco-2
T87690 13494-13500 http://purl.obolibrary.org/obo/CLO_0051960 denotes Caco-2
T229 13580-13587 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T230 13588-13593 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T231 13608-13614 http://purl.obolibrary.org/obo/NCBITaxon_9479 denotes monkey
T232 13615-13621 http://purl.obolibrary.org/obo/UBERON_0002113 denotes kidney
T233 13615-13621 http://www.ebi.ac.uk/efo/EFO_0000927 denotes kidney
T234 13615-13621 http://www.ebi.ac.uk/efo/EFO_0000929 denotes kidney
T235 13647-13652 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T236 13653-13674 http://purl.obolibrary.org/obo/CL_0000082 denotes lung epithelial cells
T237 13805-13812 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T238 13813-13822 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell line
T239 13898-13899 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T240 13948-13954 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T241 14416-14417 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T242 14560-14562 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T243 14584-14585 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T244 14618-14619 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T245 14707-14708 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T246 14834-14835 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T247 15089-15090 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T248 15146-15147 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T249 15303-15304 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T250 15442-15443 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T251 15618-15620 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T252 15822-15824 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T253 15842-15844 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T254 16159-16160 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T255 16218-16219 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T256 16662-16667 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T257 16668-16673 http://purl.obolibrary.org/obo/UBERON_0002107 denotes liver
T258 16668-16673 http://www.ebi.ac.uk/efo/EFO_0000887 denotes liver
T259 16702-16704 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T260 16919-16921 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T261 16979-16980 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T262 16981-16982 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T263 17165-17166 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T264 17208-17209 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T265 17336-17337 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T266 17718-17719 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T267 17748-17754 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T268 17796-17797 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T269 17832-17833 http://purl.obolibrary.org/obo/CLO_0001020 denotes Å
T270 17963-17964 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T271 18002-18008 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T272 18539-18545 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T273 18642-18644 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T274 18649-18651 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T275 18649-18651 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T276 18684-18686 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T277 18719-18720 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T278 18989-18991 http://purl.obolibrary.org/obo/CLO_0050050 denotes S1
T279 19117-19119 http://purl.obolibrary.org/obo/CLO_0002105 denotes C2
T280 19117-19119 http://purl.obolibrary.org/obo/CLO_0051742 denotes C2
T281 19172-19174 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T282 19228-19229 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T283 19267-19269 http://purl.obolibrary.org/obo/CLO_0008307 denotes P2
T284 19315-19317 http://purl.obolibrary.org/obo/CLO_0008285 denotes P1
T285 19327-19328 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T286 19478-19480 http://purl.obolibrary.org/obo/CLO_0008922 denotes S2
T287 19478-19480 http://purl.obolibrary.org/obo/CLO_0050052 denotes S2
T288 19634-19635 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T289 19822-19823 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T290 20208-20209 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T291 20235-20240 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T292 20444-20445 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T293 20604-20605 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T294 20606-20609 http://purl.obolibrary.org/obo/NCBITaxon_9596 denotes pan
T295 20633-20640 http://purl.obolibrary.org/obo/UBERON_0000473 denotes Testing
T296 20838-20839 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T297 20939-20940 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T298 21028-21029 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T299 21031-21036 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T300 21065-21070 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T301 21099-21104 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T302 21129-21134 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T303 21153-21158 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T304 21177-21182 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T305 21203-21208 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T306 21290-21295 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T307 21315-21316 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T308 21482-21483 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T309 21600-21601 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T310 21611-21618 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T311 21643-21651 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T312 21676-21682 http://purl.obolibrary.org/obo/UBERON_0000473 denotes tested
T313 21695-21700 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T314 21741-21746 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T315 21764-21769 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T316 21784-21789 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T317 21816-21820 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T318 21932-21940 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T319 21947-21948 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T320 21973-21978 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T321 22004-22015 http://purl.obolibrary.org/obo/CLO_0052043 denotes MRC-5 cells
T322 22004-22015 http://purl.obolibrary.org/obo/CLO_0052044 denotes MRC-5 cells
T323 22004-22015 http://purl.obolibrary.org/obo/CLO_0052045 denotes MRC-5 cells
T324 22017-22022 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T325 22023-22027 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T326 22023-22027 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T327 22094-22099 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T328 22110-22111 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T329 22122-22123 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T330 22288-22289 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T331 22548-22555 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T332 22659-22666 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T333 22819-22825 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T334 22864-22869 http://purl.obolibrary.org/obo/CLO_0007865 denotes MRC-5
T335 22864-22869 http://purl.obolibrary.org/obo/CLO_0050055 denotes MRC-5
T336 22874-22886 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76 cell
T337 22905-22906 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T338 23075-23076 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T339 23121-23122 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T340 23151-23153 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T341 23161-23163 http://purl.obolibrary.org/obo/CLO_0001382 denotes 48
T342 23167-23168 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T343 23221-23222 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T344 23272-23280 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T345 23373-23374 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T346 23508-23513 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T347 23514-23518 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T348 23514-23518 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T349 23527-23538 http://purl.obolibrary.org/obo/CLO_0052043 denotes MRC-5 cells
T350 23527-23538 http://purl.obolibrary.org/obo/CLO_0052044 denotes MRC-5 cells
T351 23527-23538 http://purl.obolibrary.org/obo/CLO_0052045 denotes MRC-5 cells
T352 23695-23702 http://purl.obolibrary.org/obo/CLO_0009526 denotes Vero 76
T353 23703-23708 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T354 23767-23776 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell line
T355 23824-23829 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T356 23830-23834 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T357 23830-23834 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T358 23835-23840 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T359 23981-23986 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T360 23987-23991 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T361 23987-23991 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T362 23992-23997 http://purl.obolibrary.org/obo/GO_0005623 denotes cells

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T123 71-77 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T124 452-454 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T125 487-491 Chemical denotes NaOH http://purl.obolibrary.org/obo/CHEBI_32145
T126 493-497 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T127 540-553 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T128 555-558 Chemical denotes TEA http://purl.obolibrary.org/obo/CHEBI_28621|http://purl.obolibrary.org/obo/CHEBI_35026
T130 561-576 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T131 578-581 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 596-601 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T135 618-621 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T136 622-629 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T137 655-658 Chemical denotes HBr http://purl.obolibrary.org/obo/CHEBI_47266
T138 684-687 Chemical denotes EDC http://purl.obolibrary.org/obo/CHEBI_27789
T139 700-715 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T140 717-720 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T141 735-737 Chemical denotes Mg http://purl.obolibrary.org/obo/CHEBI_25107
T142 739-744 Chemical denotes HgCl2 http://purl.obolibrary.org/obo/CHEBI_31823
T143 750-752 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T144 754-757 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 783-790 Chemical denotes lithium http://purl.obolibrary.org/obo/CHEBI_30145
T148 823-826 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 852-857 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T152 858-863 Chemical denotes ester http://purl.obolibrary.org/obo/CHEBI_35701
T153 897-907 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T154 897-902 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T155 903-907 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T156 940-944 Chemical denotes Acid http://purl.obolibrary.org/obo/CHEBI_37527
T157 990-1003 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T158 1140-1157 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T159 1153-1157 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T160 1175-1183 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T161 1282-1285 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T162 1383-1386 Chemical denotes HBr http://purl.obolibrary.org/obo/CHEBI_47266
T163 1390-1405 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T164 1485-1497 Chemical denotes diazomethane http://purl.obolibrary.org/obo/CHEBI_73716
T165 1688-1692 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T166 1716-1729 Chemical denotes Weinreb amide http://purl.obolibrary.org/obo/CHEBI_59741
T167 1724-1729 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T169 1785-1791 Chemical denotes benzyl http://purl.obolibrary.org/obo/CHEBI_22744
T170 1805-1810 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T171 2001-2008 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T172 2125-2134 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 2136-2138 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T176 2214-2221 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T177 2337-2353 Chemical denotes carboxylic acids http://purl.obolibrary.org/obo/CHEBI_33575
T178 2348-2353 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T179 2373-2379 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T180 2380-2388 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T181 2486-2488 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T182 2493-2498 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T183 2536-2546 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T184 2645-2648 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T185 2649-2652 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 2668-2689 Chemical denotes N,N-dimethylformamide http://purl.obolibrary.org/obo/CHEBI_17741
T189 2691-2694 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T190 2718-2721 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T191 2722-2729 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T192 2751-2772 Chemical denotes indolecarboxylic acid http://purl.obolibrary.org/obo/CHEBI_38610
T193 2768-2772 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T194 2779-2782 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T195 2810-2813 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T196 2815-2830 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T197 2826-2830 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T198 2976-2978 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T199 2990-2996 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T200 3026-3031 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T202 3166-3168 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T203 3237-3247 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T204 3358-3362 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T205 3460-3468 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T207 3537-3543 Chemical denotes silver http://purl.obolibrary.org/obo/CHEBI_30512|http://purl.obolibrary.org/obo/CHEBI_9141
T209 3548-3553 Chemical denotes oxide http://purl.obolibrary.org/obo/CHEBI_25741|http://purl.obolibrary.org/obo/CHEBI_29356
T211 3583-3593 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T212 3675-3677 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T213 3682-3687 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T214 3725-3735 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T215 3814-3817 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T216 3818-3825 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T217 3832-3835 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T218 3836-3839 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 3855-3858 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T222 3886-3907 Chemical denotes indolecarboxylic acid http://purl.obolibrary.org/obo/CHEBI_38610
T223 3903-3907 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T224 3925-3927 Chemical denotes Pd http://purl.obolibrary.org/obo/CHEBI_33363
T225 3931-3933 Chemical denotes H2 http://purl.obolibrary.org/obo/CHEBI_18276
T226 3935-3939 Chemical denotes EtOH http://purl.obolibrary.org/obo/CHEBI_16236
T227 3956-3959 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T228 3975-3979 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T229 3997-4001 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T230 4003-4006 Chemical denotes cat http://purl.obolibrary.org/obo/CHEBI_32402
T231 4008-4013 Chemical denotes K2CO3 http://purl.obolibrary.org/obo/CHEBI_131526
T232 4030-4034 Chemical denotes CH3I http://purl.obolibrary.org/obo/CHEBI_39282
T233 4042-4045 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T234 4168-4170 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T235 4251-4261 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T236 4373-4381 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T237 4465-4470 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T238 4500-4505 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T239 4655-4668 Chemical denotes electrophiles http://purl.obolibrary.org/obo/CHEBI_59739
T240 4693-4703 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T241 4836-4856 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T242 4935-4941 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T243 4942-4950 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T244 5004-5012 Chemical denotes benzoate http://purl.obolibrary.org/obo/CHEBI_16150
T245 5040-5042 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T246 5335-5341 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T247 5358-5368 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T248 5363-5368 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T249 5385-5387 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T250 5409-5411 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T251 5432-5434 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T252 5455-5457 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T253 5477-5479 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T254 5497-5499 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T255 5500-5502 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T256 5523-5525 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T257 5528-5530 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T258 5563-5565 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T259 5594-5596 Chemical denotes Cl http://purl.obolibrary.org/obo/CHEBI_23116
T260 5597-5599 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T261 5630-5632 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T262 5666-5668 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T263 5695-5697 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T264 5719-5721 Chemical denotes Ph http://purl.obolibrary.org/obo/CHEBI_30396
T265 5960-5969 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T266 6025-6033 Chemical denotes electron http://purl.obolibrary.org/obo/CHEBI_10545
T267 6044-6052 Chemical denotes benzoate http://purl.obolibrary.org/obo/CHEBI_16150
T268 6176-6186 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T269 6432-6442 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T270 6478-6486 Chemical denotes electron http://purl.obolibrary.org/obo/CHEBI_10545
T271 6563-6571 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T272 6581-6587 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T273 6617-6626 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 6627-6633 Chemical denotes carbon http://purl.obolibrary.org/obo/CHEBI_27594|http://purl.obolibrary.org/obo/CHEBI_33415
T278 6663-6669 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T279 6670-6678 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T280 6742-6750 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T281 6771-6773 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T283 6838-6846 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T284 6909-6918 Chemical denotes imidazole http://purl.obolibrary.org/obo/CHEBI_14434|http://purl.obolibrary.org/obo/CHEBI_16069
T286 6931-6939 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T287 6945-6950 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T288 7002-7011 Chemical denotes imidazole http://purl.obolibrary.org/obo/CHEBI_14434|http://purl.obolibrary.org/obo/CHEBI_16069
T290 7012-7020 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T291 7052-7069 Chemical denotes electron acceptor http://purl.obolibrary.org/obo/CHEBI_17654|http://purl.obolibrary.org/obo/CHEBI_39143
T293 7052-7060 Chemical denotes electron http://purl.obolibrary.org/obo/CHEBI_10545
T294 7061-7069 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T295 7088-7093 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T296 7121-7126 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T297 7138-7146 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T298 7170-7175 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T299 7202-7210 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T300 7265-7273 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T301 7296-7304 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T302 7314-7322 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T303 7562-7571 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T304 7683-7688 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T305 7703-7723 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T306 7809-7818 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T307 7960-7969 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T308 8210-8222 Chemical denotes nucleophiles http://purl.obolibrary.org/obo/CHEBI_59740
T309 8231-8242 Chemical denotes glutathione http://purl.obolibrary.org/obo/CHEBI_16856|http://purl.obolibrary.org/obo/CHEBI_57925
T311 8443-8445 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T312 8504-8506 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T313 8568-8578 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T314 8608-8628 Chemical denotes 2,6-dichlorobenzoate http://purl.obolibrary.org/obo/CHEBI_48624
T315 8647-8657 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T316 8691-8696 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T317 8761-8768 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T319 8769-8775 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T321 8801-8814 Chemical denotes benzimidazole http://purl.obolibrary.org/obo/CHEBI_36622|http://purl.obolibrary.org/obo/CHEBI_41275
T323 8833-8842 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T324 8969-8971 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T325 9387-9394 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T327 9395-9401 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T329 9415-9430 Chemical denotes tetrahydrofuran http://purl.obolibrary.org/obo/CHEBI_26911
T330 9513-9520 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T331 9742-9749 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T332 9883-9892 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T333 10076-10085 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T334 10137-10139 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T335 10264-10271 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T336 10309-10313 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T337 10896-10906 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T338 10991-11001 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T339 11026-11032 Chemical denotes ethers http://purl.obolibrary.org/obo/CHEBI_25698
T340 11073-11101 Chemical denotes cysteine protease inhibitors http://purl.obolibrary.org/obo/CHEBI_64152
T341 11073-11081 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T342 11082-11101 Chemical denotes protease inhibitors http://purl.obolibrary.org/obo/CHEBI_37670|http://purl.obolibrary.org/obo/CHEBI_60258
T344 11091-11101 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T345 11181-11191 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T346 11252-11260 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T347 11302-11310 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T349 11325-11334 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T350 11394-11397 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 11406-11412 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T354 11612-11618 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T355 11638-11646 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T356 11668-11676 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T357 11688-11696 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T358 11756-11763 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T359 11891-11893 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T360 12020-12030 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T361 12042-12044 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T362 12134-12136 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T363 12454-12456 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T364 12585-12587 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T365 12588-12591 Chemical denotes Phe http://purl.obolibrary.org/obo/CHEBI_17295|http://purl.obolibrary.org/obo/CHEBI_29997
T367 12782-12784 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T368 12787-12793 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T370 12794-12797 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 12798-12807 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T374 12900-12909 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T375 12910-12916 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T376 12966-12968 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T377 12969-12971 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T379 12986-12994 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T380 13020-13025 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T382 13055-13061 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T384 13134-13141 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T386 13142-13148 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T388 13178-13184 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T389 13192-13200 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T390 13300-13309 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T391 13397-13407 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T392 13555-13564 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T393 13726-13735 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T394 13919-13928 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T395 13979-13991 Chemical denotes glycoprotein http://purl.obolibrary.org/obo/CHEBI_17089
T396 14022-14031 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T397 14169-14172 Chemical denotes PSA http://purl.obolibrary.org/obo/CHEBI_61599
T398 14202-14210 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T399 14452-14459 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T401 14492-14498 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T403 14533-14541 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T405 14560-14562 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T406 14620-14628 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T407 14634-14639 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T408 14680-14688 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T410 14709-14717 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T411 14836-14844 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T412 14850-14855 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T413 14900-14908 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T414 14931-14937 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T415 15064-15073 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T416 15112-15120 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T418 15148-15156 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T419 15162-15170 Chemical denotes acceptor http://purl.obolibrary.org/obo/CHEBI_15339
T420 15180-15186 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T421 15256-15264 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T422 15274-15282 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T424 15305-15313 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T425 15319-15324 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T426 15332-15340 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T427 15412-15415 Chemical denotes PSA http://purl.obolibrary.org/obo/CHEBI_61599
T428 15420-15428 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T429 15454-15464 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T430 15546-15560 Chemical denotes hydroxyl group http://purl.obolibrary.org/obo/CHEBI_43176
T431 15546-15554 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191
T432 15555-15560 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T433 15618-15620 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T434 15631-15634 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 15641-15651 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T438 15646-15651 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T439 15652-15655 Chemical denotes Ala http://purl.obolibrary.org/obo/CHEBI_16977|http://purl.obolibrary.org/obo/CHEBI_46217
T441 15688-15701 Chemical denotes methoxy group http://purl.obolibrary.org/obo/CHEBI_44520
T442 15688-15695 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772
T443 15696-15701 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T444 15711-15717 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T446 15785-15794 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T447 15894-15903 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T448 16095-16097 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T450 16098-16106 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T451 16112-16117 Chemical denotes donor http://purl.obolibrary.org/obo/CHEBI_17891
T452 16133-16139 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T454 16199-16208 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T455 16260-16269 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T456 16363-16368 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T457 16539-16554 Chemical denotes peptidomimetics http://purl.obolibrary.org/obo/CHEBI_63175
T458 16807-16809 Chemical denotes IV http://purl.obolibrary.org/obo/CHEBI_74327
T459 16919-16921 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T460 17410-17416 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T461 17691-17699 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T462 17700-17706 Chemical denotes carbon http://purl.obolibrary.org/obo/CHEBI_27594|http://purl.obolibrary.org/obo/CHEBI_33415
T464 17760-17768 Chemical denotes cysteine http://purl.obolibrary.org/obo/CHEBI_15356
T465 17778-17784 Chemical denotes sulfur http://purl.obolibrary.org/obo/CHEBI_26833
T466 17810-17818 Chemical denotes carbinol http://purl.obolibrary.org/obo/CHEBI_17790
T467 17857-17865 Chemical denotes carbinol http://purl.obolibrary.org/obo/CHEBI_17790
T468 17866-17874 Chemical denotes hydroxyl http://purl.obolibrary.org/obo/CHEBI_29191|http://purl.obolibrary.org/obo/CHEBI_43176
T470 17881-17889 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T471 17914-17916 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T473 17940-17945 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T475 17946-17948 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T477 17974-17979 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T478 17980-17988 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T479 18033-18041 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T480 18059-18074 Chemical denotes primary alcohol http://purl.obolibrary.org/obo/CHEBI_15734
T481 18067-18074 Chemical denotes alcohol http://purl.obolibrary.org/obo/CHEBI_16236|http://purl.obolibrary.org/obo/CHEBI_30879
T483 18207-18216 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T484 18371-18380 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T485 18492-18497 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T486 18584-18592 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T487 18649-18651 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T488 18692-18698 Chemical denotes lactam http://purl.obolibrary.org/obo/CHEBI_24995
T489 18699-18707 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T490 18728-18736 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T491 18783-18789 Chemical denotes lactam http://purl.obolibrary.org/obo/CHEBI_24995
T492 18790-18792 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T494 18807-18815 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T495 18872-18878 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T496 18906-18912 Chemical denotes oxygen http://purl.obolibrary.org/obo/CHEBI_25805
T497 19027-19035 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T498 19040-19042 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T500 19071-19079 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T501 19110-19112 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T503 19117-19119 Chemical denotes C2 http://purl.obolibrary.org/obo/CHEBI_30083
T504 19120-19128 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T505 19136-19142 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T507 19162-19164 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T509 19172-19174 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T510 19175-19178 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 19182-19191 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T514 19230-19238 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T515 19255-19263 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T516 19267-19269 Chemical denotes P2 http://purl.obolibrary.org/obo/CHEBI_33472
T517 19270-19273 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 19292-19299 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T521 19305-19314 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T522 19315-19317 Chemical denotes P1 http://purl.obolibrary.org/obo/CHEBI_60949
T523 19318-19320 Chemical denotes NH http://purl.obolibrary.org/obo/CHEBI_29339|http://purl.obolibrary.org/obo/CHEBI_73424
T525 19336-19344 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
T526 19368-19376 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T527 19415-19430 Chemical denotes leucine residue http://purl.obolibrary.org/obo/CHEBI_32630
T528 19415-19422 Chemical denotes leucine http://purl.obolibrary.org/obo/CHEBI_25017
T529 19478-19480 Chemical denotes S2 http://purl.obolibrary.org/obo/CHEBI_29387
T530 19553-19559 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T532 19600-19602 Chemical denotes S3 http://purl.obolibrary.org/obo/CHEBI_29388
T533 19656-19658 Chemical denotes S3 http://purl.obolibrary.org/obo/CHEBI_29388
T534 19739-19744 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T535 19757-19759 Chemical denotes S3 http://purl.obolibrary.org/obo/CHEBI_29388
T536 19961-19968 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T537 20622-20631 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T538 21551-21560 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T539 21633-21642 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T540 21956-21965 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T541 22227-22229 Chemical denotes RF http://purl.obolibrary.org/obo/CHEBI_73818
T542 22469-22478 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T543 22774-22783 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T544 23046-23055 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T545 23085-23097 Chemical denotes glycoprotein http://purl.obolibrary.org/obo/CHEBI_17089
T546 23108-23117 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T547 23151-23153 Chemical denotes CP http://purl.obolibrary.org/obo/CHEBI_3380|http://purl.obolibrary.org/obo/CHEBI_73461
T549 23191-23200 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T550 23262-23271 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T551 23332-23341 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T552 23413-23422 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T553 23461-23470 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T554 23551-23563 Chemical denotes glycoprotein http://purl.obolibrary.org/obo/CHEBI_17089
T555 23650-23659 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T556 23803-23812 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587
T557 23916-23925 Chemical denotes antiviral http://purl.obolibrary.org/obo/CHEBI_22587

LitCovid-PD-GO-BP

Id Subject Object Predicate Lexical cue
T8 4781-4792 http://purl.obolibrary.org/obo/GO_0006508 denotes proteolysis
T9 7988-7999 http://purl.obolibrary.org/obo/GO_0006412 denotes translation
T10 8051-8057 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T11 8051-8057 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T12 10420-10431 http://purl.obolibrary.org/obo/GO_0006508 denotes proteolysis
T13 13457-13463 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T14 13457-13463 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T15 13545-13551 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T16 13545-13551 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T17 13791-13797 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T18 13791-13797 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T19 13938-13944 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T20 13938-13944 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T21 13948-13967 http://purl.obolibrary.org/obo/GO_0015291 denotes active transporters
T22 13977-13991 http://purl.obolibrary.org/obo/GO_0008559 denotes P-glycoprotein
T23 14319-14325 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T24 14319-14325 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T25 15021-15032 http://purl.obolibrary.org/obo/GO_0006508 denotes proteolysis
T26 21923-21940 http://purl.obolibrary.org/obo/GO_0008233 denotes protease activity
T27 22819-22837 http://purl.obolibrary.org/obo/GO_0015291 denotes active transporter
T28 23001-23007 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T29 23001-23007 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T30 23083-23097 http://purl.obolibrary.org/obo/GO_0008559 denotes P-glycoprotein
T31 23098-23107 http://purl.obolibrary.org/obo/GO_0006810 denotes transport
T32 23406-23412 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T33 23406-23412 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux
T34 23549-23563 http://purl.obolibrary.org/obo/GO_0008559 denotes P-glycoprotein
T35 23570-23581 http://purl.obolibrary.org/obo/GO_0006810 denotes transporter
T36 23736-23742 http://purl.obolibrary.org/obo/GO_0140352 denotes efflux
T37 23736-23742 http://purl.obolibrary.org/obo/GO_0140115 denotes efflux

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T49 0-22 Sentence denotes Results and Discussion
T50 24-33 Sentence denotes Chemistry
T51 34-207 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 208-426 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 427-478 Sentence denotes Scheme 1 Preparation of P1 Synthetic Intermediates
T54 479-833 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 834-939 Sentence denotes Saponification of amino ester 5(33) afforded the corresponding amino acid 6 in nearly quantitative yield.
T56 940-1108 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 1109-1260 Sentence denotes Diazoketone 7 was treated with hydrochloric acid for simultaneous nitrogen deprotection and conversion to the chloromethylketone (CMK) intermediate 10.
T58 1261-1420 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 1421-1605 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 1606-1813 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 1814-1946 Sentence denotes A key element for rapid access to substituted methylketone derivatives was the generation of the fully elaborated CMK 12 (Scheme 2).
T62 1947-2055 Sentence denotes The utility of the CMK moiety to prepare acyloxy- and hydroxy-substituted methylketones is well established.
T63 2056-2308 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 2309-2434 Sentence denotes Reaction of 12 with various carboxylic acids in the presence of cesium fluoride at 60 °C provided acyloxymethylketones 13–28.
T65 2435-2559 Sentence denotes Using this synthetic approach with substitution of P2 and amine capping structural elements provided inhibitors 3 and 29–31.
T66 2560-2640 Sentence denotes Scheme 2 Preparation of Substituted Acyloxymethylketones and Aminomethylketones
T67 2641-2847 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 2848-2956 Sentence denotes Hydroxymethylketone (HMK) derivatives were accessed by two complimentary approaches illustrated in Scheme 3.
T69 2957-3176 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 3177-3266 Sentence denotes Hydrogenolytic debenzylation readily afforded the final HMK inhibitors exemplified by 36.
T71 3267-3616 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 3617-3748 Sentence denotes Using these two synthetic approaches with substitution of P2 and amine capping structural elements provided inhibitors 4 and 38–50.
T73 3749-3805 Sentence denotes Scheme 3 Preparation of Hydroxymethylketone Derivatives
T74 3806-4007 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 4008-4051 Sentence denotes K2CO3 (53%), and (vi) CH3I, Ag2O, DCE (9%).
T76 4053-4074 Sentence denotes Biological Evaluation
T77 4076-4120 Sentence denotes Irreversible Inhibitors of SARS CoV-1 3CLpro
T78 4121-4262 Sentence denotes The warhead reactivity and binding affinity to P1′ are both important design considerations to ensure specificity of irreversible inhibitors.
T79 4263-4633 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 4634-4811 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 4812-5049 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 5050-5132 Sentence denotes A series of acyloxymethylketone derivatives were prepared, as depicted in Table 1.
T83 5133-5210 Sentence denotes Table 1 SARS CoV-1 3CLpro Inhibition Data for Acyloxymethylketone Inhibitors
T84 5211-5240 Sentence denotes     SARS CoV-1 3CLpro FRETa
T85 5241-5278 Sentence denotes entry R kobs/I (M–1 s–1) IC50 (nM)
T86 5279-5305 Sentence denotes 12   283,039 ± 22,586  
T87 5306-5326 Sentence denotes 13 Me   220 ± 0.5
T88 5327-5353 Sentence denotes 14 cyc-propyl   182 ± 6
T89 5354-5380 Sentence denotes 15 tert-butyl   230 ± 5
T90 5381-5398 Sentence denotes 16 Ph   86 ± 3
T91 5399-5422 Sentence denotes 17 4-OMe-Ph   79 ± 3
T92 5423-5445 Sentence denotes 18 4-Me-Ph   87 ± 2
T93 5446-5468 Sentence denotes 19 4-CN-Ph   53 ± 1
T94 5469-5490 Sentence denotes 20 4-F-Ph   82 ± 3
T95 5491-5513 Sentence denotes 21 4-Cl-Ph   97 ± 3
T96 5514-5549 Sentence denotes 22 2,6-(Cl)2-Ph 62,993 ± 2,501  
T97 5550-5582 Sentence denotes 23 2,6-(F)2-Ph 12,776 ± 594  
T98 5583-5615 Sentence denotes 24 2-OH-4-Cl-Ph 11,525 ± 40  
T99 5616-5651 Sentence denotes 25 2-F, 4-CN-Ph 13,321 ± 2,309  
T100 5652-5679 Sentence denotes 26 2,6-(Me)2-Ph   74 ± 4
T101 5680-5709 Sentence denotes 27 2,6-(MeO)2-Ph   205 ± 2
T102 5710-5732 Sentence denotes 28 2-CN-Ph   17 ± 2
T103 5733-5899 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 5900-5991 Sentence denotes As expected, chloromethylketone 12 is a potent irreversible inhibitor of SARS CoV-1 3CLpro.
T105 5992-6129 Sentence denotes Compounds 22–25 possess the most electron-deficient benzoate leaving groups and display kinetics consistent with irreversible inhibition.
T106 6130-6259 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 6260-6454 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 6455-6658 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 6659-6802 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 6803-6983 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 6984-7094 Sentence denotes Specifically, the imidazole hydrogen is directed toward a lone pair electron acceptor from a structural water.
T112 7095-7429 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 7430-7532 Sentence denotes Figure 4 Cocrystal structure of the covalent adduct of 28 bound to SARS CoV-1 3CLpro (PDB code 6XHN).
T114 7533-7604 Sentence denotes The Connolly surface for the inhibitor binding pocket is shown in gray.
T115 7605-7698 Sentence denotes The bonds are represented as dashed lines, with the bond length between heavy atoms depicted.
T116 7699-8140 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 8141-8522 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 8523-8739 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 8740-8827 Sentence denotes Replacement of the 4-methoxy indole cap present in 22 with a benzimidazole provided 31.
T120 8828-8939 Sentence denotes This inhibitor displayed potent irreversible inhibition kinetics but did not improve solubility compared to 22.
T121 8940-9097 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 9098-9187 Sentence denotes Table 2 SARS CoV-1 3CLpro Inhibition Data for P3-Modified Acyloxymethylketone Inhibitors
T123 9188-9354 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 9355-9591 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 9592-9667 Sentence denotes Initially, this derivative appeared to display reversible binding kinetics.
T126 9668-9849 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 9850-10001 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 10002-10178 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 10179-10399 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 10400-10626 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 10627-10740 Sentence denotes Viral particles themselves are not reliant on 3CLpro activity nor are the remaining coronavirus life cycle steps.
T132 10741-10805 Sentence denotes Each event of cell infection initiates newly synthesized 3CLpro.
T133 10806-10933 Sentence denotes Because detailed kinetics of this process are not understood, reversible and irreversible inhibitors were investigated equally.
T134 10935-10977 Sentence denotes Reversible Inhibitors of SARS CoV-1 3CLpro
T135 10978-11427 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 11428-11771 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 11772-11944 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 11945-12092 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 12093-12160 Sentence denotes Table 3 SARS 3CLpro Inhibition Data for P2-Modified HMK Inhibitors
T140 12161-12329 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 12330-12364 Sentence denotes c This value is a Ki measurement.
T142 12365-12413 Sentence denotes d These values are from a single determination.
T143 12414-12565 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 12566-12709 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 12710-12855 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 12856-13036 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 13037-13233 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 13234-13378 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 13379-13516 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 13517-13686 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 13687-13883 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 13884-14056 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 14057-14326 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 14327-14503 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 14504-14640 Sentence denotes Additionally, the terminal α-hydroxyl moiety located at P1′ appeared to provide a potential opportunity to remove a hydrogen bond donor.
T156 14641-14800 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 14801-15033 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 15034-15206 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 15207-15370 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 15371-15561 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 15562-15672 Sentence denotes Table 4 summarizes this effort where two of the optimal P2 residues (Leu and β-tert-butyl-Ala) were conserved.
T162 15673-15930 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 15931-16042 Sentence denotes The impact of more significant changes to the P3 cap is illustrated by tetrahydrofuranyl derivatives 46 and 47.
T164 16043-16217 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 16218-16381 Sentence denotes A noteworthy reduction in biochemical and antiviral potency was observed in comparing each hydroxymethylketone derivative with its corresponding ether counterpart.
T166 16382-16555 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 16556-16863 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 16864-16978 Sentence denotes Table 4 SARS CoV-1 3CLpro Inhibition Data for P3- and P2-Modified Hydroxymethyl and Alkoxymethylketone Inhibitors
T169 16979-17147 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 17148-17182 Sentence denotes c This value is a Ki measurement.
T171 17183-17231 Sentence denotes d These values are from a single determination.
T172 17232-17547 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 17548-17674 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 17675-17851 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 17852-17989 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 17990-18111 Sentence denotes Another key active-site interaction is the hydrogen bond between the primary alcohol moiety of 4 and the catalytic His41.
T177 18112-18248 Sentence denotes Similar interactions between catalytic His residues and the OH moiety of HMK in other protease–inhibitor complexes have been reported.43
T178 18249-18341 Sentence denotes Figure 5 Cocrystal structure of the covalent adduct of 4 bound to SARS CoV-2 3CLpro (6XHM).
T179 18342-18413 Sentence denotes The Connolly surface for the inhibitor binding pocket is shown in gray.
T180 18414-18507 Sentence denotes The bonds are represented as dashed lines, with the bond length between heavy atoms depicted.
T181 18508-18680 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 18681-18923 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 18924-18999 Sentence denotes These three residues partially define the bottom and edge of the S1 pocket.
T184 19000-19157 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 19158-19300 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 19301-19387 Sentence denotes The inhibitor P1 NH forms a strong hydrogen bond with the backbone carbonyl of His164.
T187 19388-19548 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 19549-19745 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 19746-20163 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 20164-20261 Sentence denotes Hydroxymethylketone 4 was evaluated against a panel of other viral and human proteases (Table 5).
T191 20262-20499 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 20500-20632 Sentence denotes High levels of similarity between the catalytic sites of 3CLpro proteases suggest the potential of 4 as a pan-coronavirus inhibitor.
T193 20633-20854 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 20855-20888 Sentence denotes Table 5 Protease Inhibition by 4
T195 20889-20940 Sentence denotes protease source % inhibition @ 10 μMa IC50 (μM)a
T196 20941-20979 Sentence denotes 3CLpro SARS CoV-1   0.004 ± 0.0003b
T197 20980-21017 Sentence denotes 3CLpro SARS CoV-2 0.00027 ± 0.0001b
T198 21018-21051 Sentence denotes cathepsin B human 93 1.3 ± 0.1
T199 21052-21078 Sentence denotes cathepsin D human 3 >10
T200 21079-21114 Sentence denotes leukocyte elastase human –31 >10
T201 21115-21142 Sentence denotes chymotrypsin human 8 >10
T202 21143-21168 Sentence denotes thrombin human –28 >10
T203 21169-21191 Sentence denotes pepsin human –2 >10
T204 21192-21218 Sentence denotes caspase 2 human –20 >10
T205 21219-21239 Sentence denotes HIV-1 HIV-1 0 >10
T206 21240-21257 Sentence denotes HCV HCV 16 >10
T207 21258-21278 Sentence denotes HRV HRV   1.7 ± 1
T208 21279-21314 Sentence denotes hCoV 229E human   0.004 ± 0.0004
T209 21315-21481 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 21482-21546 Sentence denotes b For SARS CoV-1 and CoV-2 3CLpro, Ki values are reported here.
T211 21547-21629 Sentence denotes The antiviral specificity of 4 was evaluated against a panel of viruses (Table 6).
T212 21630-21829 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 21830-21883 Sentence denotes This compound also does not inhibit the HCV replicon.
T214 21884-22062 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 22063-22093 Sentence denotes Table 6 Viral Inhibition by 4
T216 22094-22123 Sentence denotes virus EC50 (μM)a CC50 (μM)a
T217 22124-22150 Sentence denotes SARS CoV-1 4.8 ± 2.2 452
T218 22151-22178 Sentence denotes hCoV 229E 0.09 ± 0.04 >40
T219 22179-22199 Sentence denotes HRV-14 >100 >1,260
T220 22200-22220 Sentence denotes HRV-16 >100 >1,260
T221 22221-22239 Sentence denotes HIV-1 RF >32 >32
T222 22240-22264 Sentence denotes HCV replicon >320 >320
T223 22265-22287 Sentence denotes HCMV RC256 >100 >100
T224 22288-22454 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 22455-22667 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 22668-22927 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 22928-23203 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 23204-23369 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 23370-23613 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 23614-23884 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 23885-24032 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.

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T5 717-720 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T6 21747-21763 Phenotype denotes immunodeficiency http://purl.obolibrary.org/obo/HP_0002721

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
258 71-77 Chemical denotes ketone MESH:D007659
259 163-175 Chemical denotes methylketone MESH:D000096
260 227-243 Chemical denotes halomethylketone
261 322-333 Chemical denotes diazoketone
279 1282-1285 Gene denotes Boc Gene:91653
280 852-863 Chemical denotes amino ester
281 964-985 Chemical denotes isobutylchloroformate MESH:C039311
282 990-1003 Chemical denotes triethylamine MESH:C016162
283 1056-1068 Chemical denotes diazomethane MESH:D003978
284 1109-1120 Chemical denotes Diazoketone
285 1140-1157 Chemical denotes hydrochloric acid MESH:D006851
286 1175-1183 Chemical denotes nitrogen MESH:D009584
287 1219-1237 Chemical denotes chloromethylketone
288 1239-1242 Chemical denotes CMK
289 1390-1405 Chemical denotes dichloromethane MESH:D008752
290 1485-1497 Chemical denotes diazomethane MESH:D003978
291 1548-1551 Chemical denotes LDA MESH:C007442
292 1556-1573 Chemical denotes chloroiodomethane
293 1627-1642 Chemical denotes oxymethylketone
294 1716-1729 Chemical denotes Weinreb amide
295 1785-1810 Chemical denotes benzyl chloromethyl ether
305 1860-1872 Chemical denotes methylketone MESH:D000096
306 1988-2034 Chemical denotes acyloxy- and hydroxy-substituted methylketones
307 2104-2197 Chemical denotes 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate
308 2199-2203 Chemical denotes HATU MESH:C472082
309 2337-2353 Chemical denotes carboxylic acids MESH:D002264
310 2373-2388 Chemical denotes cesium fluoride MESH:C027754
311 2407-2427 Chemical denotes acyloxymethylketones
312 2486-2488 Chemical denotes P2 MESH:C020845
313 2493-2498 Chemical denotes amine MESH:D000588
316 2597-2617 Chemical denotes Acyloxymethylketones
317 2622-2640 Chemical denotes Aminomethylketones
331 2645-2648 Gene denotes Boc Gene:91653
332 2657-2661 Chemical denotes HATU MESH:C472082
333 2663-2666 Chemical denotes NMM MESH:C035596
334 2668-2689 Chemical denotes N,N-dimethylformamide MESH:D004126
335 2691-2694 Chemical denotes DMF MESH:D004126
336 2718-2721 Chemical denotes HCl MESH:D006851
337 2722-2729 Chemical denotes dioxane MESH:C025223
338 2737-2741 Chemical denotes HATU MESH:C472082
339 2743-2772 Chemical denotes 4-MeO-2-indolecarboxylic acid
340 2774-2777 Chemical denotes NMM MESH:C035596
341 2779-2782 Chemical denotes DMF MESH:D004126
342 2810-2813 Chemical denotes DMF MESH:D004126
343 2815-2830 Chemical denotes carboxylic acid MESH:D002264
354 2848-2867 Chemical denotes Hydroxymethylketone
355 2869-2872 Chemical denotes HMK
356 2990-2996 Chemical denotes oxygen MESH:D010100
357 3026-3031 Chemical denotes amide MESH:D000577
358 3344-3362 Chemical denotes benzoylformic acid MESH:C012482
359 3460-3468 Chemical denotes hydroxyl MESH:D017665
360 3537-3553 Chemical denotes silver (I) oxide MESH:C040225
361 3564-3582 Chemical denotes alkoxymethylketone
362 3675-3677 Chemical denotes P2 MESH:C020845
363 3682-3687 Chemical denotes amine MESH:D000588
365 3774-3793 Chemical denotes Hydroxymethylketone
384 3832-3835 Gene denotes Boc Gene:91653
385 3814-3817 Chemical denotes HCl MESH:D006851
386 3818-3825 Chemical denotes dioxane MESH:C025223
387 3844-3848 Chemical denotes HATU MESH:C472082
388 3850-3853 Chemical denotes NMM MESH:C035596
389 3855-3858 Chemical denotes DMF MESH:D004126
390 3872-3876 Chemical denotes HATU MESH:C472082
391 3878-3907 Chemical denotes 4-MeO-2-indolecarboxylic acid
392 3909-3912 Chemical denotes NMM MESH:C035596
393 3931-3933 Chemical denotes H2 MESH:D003903
394 3935-3939 Chemical denotes EtOH MESH:D000431
395 3956-3959 Chemical denotes DMF MESH:D004126
396 3961-3979 Chemical denotes benzoylformic acid MESH:C012482
397 3997-4001 Chemical denotes MeOH
398 4008-4013 Chemical denotes K2CO3 MESH:C037593
399 4030-4034 Chemical denotes CH3I
400 4036-4040 Chemical denotes Ag2O MESH:C040225
401 4042-4045 Chemical denotes DCE
403 4103-4111 Species denotes SARS CoV Tax:694009
414 4603-4614 Gene denotes cathepsin B Gene:1508
415 4869-4877 Species denotes SARS CoV Tax:694009
416 4263-4269 Chemical denotes Krantz
417 4328-4348 Chemical denotes acyloxymethylketones
418 4445-4456 Chemical denotes carboxylate
419 4587-4598 Chemical denotes carboxylate
420 4836-4856 Chemical denotes 2,6-dichlorobenzoate
421 4935-4941 Chemical denotes ketone MESH:D007659
422 5004-5012 Chemical denotes benzoate MESH:D001565
423 5062-5081 Chemical denotes acyloxymethylketone
426 5217-5225 Species denotes SARS CoV Tax:694009
427 5251-5255 Species denotes kobs Tax:59530
430 5142-5150 Species denotes SARS CoV Tax:694009
431 5180-5199 Chemical denotes Acyloxymethylketone
461 5973-5981 Species denotes SARS CoV Tax:694009
462 6320-6328 Species denotes SARS CoV Tax:694009
463 5913-5931 Chemical denotes chloromethylketone
464 6044-6052 Chemical denotes benzoate MESH:D001565
465 6503-6518 Chemical denotes 2-cyanobenzoate
466 6563-6571 Chemical denotes cysteine MESH:D003545
467 6573-6579 Chemical denotes Cys145
468 6581-6587 Chemical denotes sulfur MESH:D013455
469 6627-6633 Chemical denotes carbon MESH:D002244
470 6663-6669 Chemical denotes ketone MESH:D007659
471 6742-6750 Chemical denotes hydrogen MESH:D006859
472 6784-6790 Chemical denotes Gly143
473 6795-6801 Chemical denotes Cys145
474 6838-6846 Chemical denotes hydrogen MESH:D006859
475 6875-6880 Chemical denotes His41
476 6909-6918 Chemical denotes imidazole MESH:C029899
477 6931-6939 Chemical denotes hydrogen MESH:D006859
478 7002-7011 Chemical denotes imidazole MESH:C029899
479 7012-7020 Chemical denotes hydrogen MESH:D006859
480 7088-7093 Chemical denotes water MESH:D014867
481 7121-7126 Chemical denotes water MESH:D014867
482 7150-7155 Chemical denotes His41
483 7170-7175 Chemical denotes water MESH:D014867
484 7176-7185 Chemical denotes hydrogens MESH:D006859
485 7242-7248 Chemical denotes Asp187
486 7265-7273 Chemical denotes hydrogen MESH:D006859
487 7326-7332 Chemical denotes Asp176
488 7411-7417 Chemical denotes His164
489 7422-7428 Chemical denotes Thr175
491 7498-7506 Species denotes SARS CoV Tax:694009
497 7784-7792 Species denotes SARS CoV Tax:694009
498 8098-8103 Species denotes human Tax:9606
499 8302-8307 Species denotes human Tax:9606
500 7703-7723 Chemical denotes 2,6-dichlorobenzoate
501 8231-8242 Chemical denotes glutathione MESH:D005978
509 9080-9085 Gene denotes CLpro
510 9068-9076 Species denotes SARS CoV Tax:694009
511 8608-8628 Chemical denotes 2,6-dichlorobenzoate
512 8691-8696 Chemical denotes amine MESH:D000588
513 8759-8775 Chemical denotes 4-methoxy indole
514 8801-8814 Chemical denotes benzimidazole MESH:C031000
515 8969-8971 Chemical denotes P2 MESH:C020845
518 9107-9115 Species denotes SARS CoV Tax:694009
519 9157-9176 Chemical denotes Acyloxymethylketone
526 9724-9732 Species denotes SARS CoV Tax:694009
527 9820-9824 Species denotes kobs Tax:59530
528 10052-10055 Species denotes rat Tax:10116
529 9385-9401 Chemical denotes 4-methoxy indole
530 9410-9444 Chemical denotes (2R)-tetrahydrofuran-2-carboxylate
531 9541-9547 Chemical denotes Gln189
536 10711-10722 Species denotes coronavirus Tax:11118
537 10351-10357 Chemical denotes 3CLpro
538 10616-10625 Disease denotes infection MESH:D007239
539 10760-10769 Disease denotes infection MESH:D007239
541 10960-10968 Species denotes SARS CoV Tax:694009
555 11105-11116 Gene denotes cathepsin K Gene:1513
556 11073-11090 Gene denotes cysteine protease Gene:1508
557 11482-11490 Species denotes SARS CoV Tax:694009
558 11252-11260 Chemical denotes hydrogen MESH:D006859
559 11288-11291 Chemical denotes His MESH:D006639
560 11394-11397 Chemical denotes Cys MESH:D003545
561 11406-11412 Chemical denotes ketone MESH:D007659
562 11612-11618 Chemical denotes sulfur MESH:D013455
563 11638-11646 Chemical denotes cysteine MESH:D003545
564 11648-11654 Chemical denotes Cys145
565 11688-11696 Chemical denotes hydrogen MESH:D006859
566 11733-11738 Chemical denotes His41
567 12042-12044 Chemical denotes P2 MESH:C020845
577 12646-12654 Species denotes SARS CoV Tax:694009
578 12585-12587 Chemical denotes P2 MESH:C020845
579 12588-12591 Chemical denotes Phe MESH:D010649
580 12782-12797 Chemical denotes P2-N-methyl-Leu
581 12986-12994 Chemical denotes hydrogen MESH:D006859
582 13020-13025 Chemical denotes amide MESH:D000577
583 13029-13035 Chemical denotes Gln189
584 13132-13148 Chemical denotes 4-methoxy indole
585 13192-13200 Chemical denotes hydrogen MESH:D006859
590 13977-13991 Gene denotes P-glycoprotein Gene:5243
591 13647-13652 Species denotes human Tax:9606
592 13494-13500 Chemical denotes Caco-2
593 14202-14210 Chemical denotes hydrogen MESH:D006859
608 14388-14396 Species denotes SARS CoV Tax:694009
609 14620-14628 Chemical denotes hydrogen MESH:D006859
610 14709-14717 Chemical denotes hydrogen MESH:D006859
611 14740-14745 Chemical denotes His41
612 14836-14844 Chemical denotes hydrogen MESH:D006859
613 15037-15042 Chemical denotes His41
614 15148-15156 Chemical denotes hydrogen MESH:D006859
615 15194-15197 Chemical denotes His MESH:D006639
616 15229-15234 Chemical denotes His41
617 15256-15264 Chemical denotes hydrogen MESH:D006859
618 15305-15313 Chemical denotes hydrogen MESH:D006859
619 15332-15340 Chemical denotes nitrogen MESH:D009584
620 15358-15361 Chemical denotes His MESH:D006639
621 15420-15428 Chemical denotes hydrogen MESH:D006859
632 16662-16667 Species denotes human Tax:9606
633 15618-15620 Chemical denotes P2 MESH:C020845
634 15631-15634 Chemical denotes Leu MESH:D007930
635 15639-15655 Chemical denotes β-tert-butyl-Ala
636 15977-15979 Chemical denotes P3
637 16002-16019 Chemical denotes tetrahydrofuranyl
638 16098-16106 Chemical denotes hydrogen MESH:D006859
639 16133-16142 Chemical denotes indole P3
640 16309-16328 Chemical denotes hydroxymethylketone
641 16363-16368 Chemical denotes ether MESH:D004986
643 16873-16881 Species denotes SARS CoV Tax:694009
665 17286-17294 Species denotes SARS CoV Tax:694009
666 17301-17306 Species denotes CoV-2 Tax:2697049
667 17457-17465 Species denotes SARS CoV Tax:694009
668 17472-17482 Species denotes SARS CoV-2 Tax:2697049
669 17658-17661 Species denotes CoV Tax:11118
670 17668-17673 Species denotes CoV-2 Tax:2697049
671 17700-17706 Chemical denotes carbon MESH:D002244
672 17760-17768 Chemical denotes cysteine MESH:D003545
673 17770-17776 Chemical denotes Cys145
674 17778-17784 Chemical denotes sulfur MESH:D013455
675 17810-17818 Chemical denotes carbinol MESH:D000432
676 17857-17874 Chemical denotes carbinol hydroxyl
677 17881-17889 Chemical denotes hydrogen MESH:D006859
678 17920-17926 Chemical denotes Cys145
679 17940-17945 Chemical denotes amide MESH:D000577
680 17952-17958 Chemical denotes Gly143
681 17974-17979 Chemical denotes water MESH:D014867
682 18033-18041 Chemical denotes hydrogen MESH:D006859
683 18067-18074 Chemical denotes alcohol MESH:D000438
684 18105-18110 Chemical denotes His41
685 18151-18154 Chemical denotes His MESH:D006639
688 18316-18326 Species denotes SARS CoV-2 Tax:2697049
689 18584-18592 Chemical denotes hydrogen MESH:D006859
719 19855-19865 Species denotes SARS CoV-2 Tax:2697049
720 20070-20080 Species denotes SARS CoV-2 Tax:2697049
721 18692-18698 Chemical denotes lactam MESH:D007769
722 18728-18736 Chemical denotes hydrogen MESH:D006859
723 18765-18771 Chemical denotes His163
724 18783-18789 Chemical denotes lactam MESH:D007769
725 18807-18815 Chemical denotes hydrogen MESH:D006859
726 18872-18878 Chemical denotes oxygen MESH:D010100
727 18882-18888 Chemical denotes Glu166
728 18906-18912 Chemical denotes oxygen MESH:D010100
729 18916-18922 Chemical denotes Phe140
730 19046-19052 Chemical denotes Glu166
731 19071-19079 Chemical denotes hydrogen MESH:D006859
732 19172-19174 Chemical denotes P2 MESH:C020845
733 19175-19178 Chemical denotes Leu MESH:D007930
734 19216-19222 Chemical denotes Gln189
735 19230-19238 Chemical denotes hydrogen MESH:D006859
736 19267-19269 Chemical denotes P2 MESH:C020845
737 19270-19273 Chemical denotes Leu MESH:D007930
738 19336-19344 Chemical denotes hydrogen MESH:D006859
739 19380-19386 Chemical denotes His164
740 19415-19422 Chemical denotes leucine MESH:D007930
741 19507-19513 Chemical denotes Asp187
742 19515-19521 Chemical denotes Arg188
743 19523-19529 Chemical denotes Gln189
744 19531-19536 Chemical denotes Met49
745 19542-19547 Chemical denotes His41
746 19886-19898 Chemical denotes α-ketoamides
747 20152-20162 Chemical denotes ketoamides
755 20434-20445 Gene denotes cathepsin B Gene:1508
756 20235-20240 Species denotes human Tax:9606
757 20466-20476 Species denotes rhinovirus Tax:12059
758 20610-20621 Species denotes coronavirus Tax:11118
759 20703-20712 Species denotes hCoV 229E Tax:11137
760 20815-20825 Species denotes SARS CoV-2 Tax:2697049
761 20164-20183 Chemical denotes Hydroxymethylketone
778 21018-21029 Gene denotes cathepsin B Gene:1508
779 21192-21199 Gene denotes caspase Gene:834
780 20949-20957 Species denotes SARS CoV Tax:694009
781 20988-20998 Species denotes SARS CoV-2 Tax:2697049
782 21031-21036 Species denotes human Tax:9606
783 21099-21104 Species denotes human Tax:9606
784 21129-21134 Species denotes human Tax:9606
785 21153-21158 Species denotes human Tax:9606
786 21177-21182 Species denotes human Tax:9606
787 21203-21208 Species denotes human Tax:9606
788 21219-21224 Species denotes HIV-1 Tax:11676
789 21226-21231 Species denotes HIV-1 Tax:11676
790 21263-21272 Species denotes HRV   1 Tax:573824
791 21279-21288 Species denotes hCoV 229E Tax:11137
792 21290-21295 Species denotes human Tax:9606
793 21258-21261 Species denotes HRV Tax:169066
796 21489-21497 Species denotes SARS CoV Tax:694009
797 21504-21509 Species denotes CoV-2 Tax:2697049
808 21695-21711 Species denotes human rhinovirus Tax:169066
809 21721-21727 Species denotes HRV-14 Tax:12131
810 21784-21805 Species denotes human cytomegalovirus Tax:10359
811 21913-21922 Species denotes hCoV 229E Tax:11137
812 21973-21990 Species denotes human coronavirus Tax:694448
813 21991-22000 Species denotes hCoV 229E Tax:11137
814 22017-22022 Species denotes human Tax:9606
815 21807-21811 Species denotes HCMV Tax:10359
816 21747-21779 Disease denotes immunodeficiency virus-1 (HIV-1) MESH:D015658
817 22004-22009 CellLine denotes MRC-5 CVCL:0440
823 22124-22132 Species denotes SARS CoV Tax:694009
824 22151-22160 Species denotes hCoV 229E Tax:11137
825 22179-22185 Species denotes HRV-14 Tax:12131
826 22221-22226 Species denotes HIV-1 Tax:11676
827 22265-22269 Species denotes HCMV Tax:10359
848 23083-23097 Gene denotes P-glycoprotein Gene:5243
849 23549-23563 Gene denotes P-glycoprotein Gene:5243
850 22530-22538 Species denotes SARS CoV Tax:694009
851 22639-22648 Species denotes hCoV 229E Tax:11137
852 22653-22656 Species denotes CoV Tax:11118
853 22704-22713 Species denotes hCoV 229E Tax:11137
854 22718-22726 Species denotes SARS CoV Tax:694009
855 23359-23368 Species denotes hCoV 229E Tax:11137
856 23508-23513 Species denotes human Tax:9606
857 23824-23829 Species denotes human Tax:9606
858 23947-23957 Species denotes SARS CoV-2 Tax:2697049
859 23981-23986 Species denotes human Tax:9606
860 22459-22468 Species denotes hCoV 229E Tax:11137
861 23035-23043 Species denotes SARS CoV Tax:694009
862 23251-23259 Species denotes SARS CoV Tax:694009
863 23451-23460 Species denotes hCoV 229E Tax:11137
864 23151-23160 Chemical denotes CP-100356 MESH:C087168
865 23875-23883 Disease denotes COVID-19 MESH:C000657245
866 22864-22869 CellLine denotes MRC-5 CVCL:0440
867 23527-23532 CellLine denotes MRC-5 CVCL:0440

2_test

Id Subject Object Predicate Lexical cue
33054210-1433192-61913455 346-348 1433192 denotes 31
33054210-10746010-61913456 399-401 10746010 denotes 32
33054210-2029515-61913457 4471-4473 2029515 denotes 37
33054210-15450003-61913458 15015-15017 15450003 denotes 44
33054210-10534321-61913459 16702-16704 10534321 denotes 45
33054210-10463589-61913460 23161-23163 10463589 denotes 48