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PMC:7594251 JSONTXT

Annnotations TAB JSON ListView MergeView

LitCovid_Glycan-Motif-Structure

Id Subject Object Predicate Lexical cue
T1 121294-121301 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T2 121382-121389 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T3 123795-123802 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T4 127858-127865 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T5 127961-127968 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T8612 17037-17044 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T44926 17161-17168 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T45962 65216-65236 https://glytoucan.org/Structures/Glycans/G64581RP denotes N-acetyl glucosamine
T71124 70514-70521 https://glytoucan.org/Structures/Glycans/G22418PV denotes (VIM)-2
T79079 70515-70518 https://glytoucan.org/Structures/Glycans/G00065MO denotes VIM
T6 94144-94151 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose
T7 94206-94213 https://glytoucan.org/Structures/Glycans/G15021LG denotes glucose

LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T1 100042-100049 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T2 100160-100167 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T3 100387-100394 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T4 100649-100656 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T5 100766-100773 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T6 101232-101239 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T7 101291-101298 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T8 101405-101412 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T9 101536-101543 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T10 101583-101590 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T11 101844-101854 Body_part denotes intestinal http://purl.org/sig/ont/fma/fma7199
T12 101855-101865 Body_part denotes fatty acid http://purl.org/sig/ont/fma/fma82738
T13 101874-101881 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T14 102036-102043 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T15 102196-102203 Body_part denotes Protein http://purl.org/sig/ont/fma/fma67257
T16 102284-102302 Body_part denotes proteins complexes http://purl.org/sig/ont/fma/fma67906
T17 102345-102352 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T18 102435-102442 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T19 102723-102729 Body_part denotes serine http://purl.org/sig/ont/fma/fma82764
T20 103381-103385 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T21 103435-103443 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T22 103541-103545 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T23 103651-103655 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T24 103684-103688 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T25 103723-103727 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T26 103791-103795 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T27 103857-103864 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T28 103866-103870 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T29 104018-104022 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T30 104092-104096 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T31 104291-104295 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T32 104326-104330 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T33 104406-104413 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T34 104437-104445 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T35 104481-104485 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T36 104563-104567 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T37 104636-104640 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T38 104674-104681 Body_part denotes oocytes http://purl.org/sig/ont/fma/fma18644
T39 104695-104700 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T40 104718-104723 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T41 104736-104741 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T42 104764-104769 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T43 104831-104835 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T44 104865-104869 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T45 105058-105066 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T46 105131-105138 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T47 105233-105240 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T48 105322-105344 Body_part denotes proteins and complexes http://purl.org/sig/ont/fma/fma67906
T49 105322-105330 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T50 105448-105455 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T51 105497-105501 Body_part denotes Cell http://purl.org/sig/ont/fma/fma68646
T52 105509-105513 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T53 105533-105541 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T54 105580-105583 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T55 105597-105610 Body_part denotes RNA molecules http://purl.org/sig/ont/fma/fma84126
T56 105597-105600 Body_part denotes RNA http://purl.org/sig/ont/fma/fma67095
T57 105688-105692 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T58 105729-105733 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T59 106063-106070 Body_part denotes histone http://purl.org/sig/ont/fma/fma74413
T60 106365-106373 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T61 106389-106394 Body_part denotes blood http://purl.org/sig/ont/fma/fma9670
T62 106454-106474 Body_part denotes scaffolding proteins http://purl.org/sig/ont/fma/fma62376
T63 106476-106479 Body_part denotes SPs http://purl.org/sig/ont/fma/fma62376
T64 106537-106545 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T65 106575-106583 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T66 106651-106654 Body_part denotes SPs http://purl.org/sig/ont/fma/fma62376
T67 106953-106970 Body_part denotes protein complexes http://purl.org/sig/ont/fma/fma67906
T68 106953-106960 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T69 107225-107229 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T70 107288-107296 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T71 107322-107330 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T72 107389-107394 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T73 107427-107435 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T74 112446-112448 Body_part denotes CS http://purl.org/sig/ont/fma/fma284995
T75 117168-117173 Body_part denotes Orbit http://purl.org/sig/ont/fma/fma54379
T76 117748-117764 Body_part denotes transverse plane http://purl.org/sig/ont/fma/fma71928
T77 117874-117890 Body_part denotes transverse plane http://purl.org/sig/ont/fma/fma71928
T78 117925-117929 Body_part denotes axis http://purl.org/sig/ont/fma/fma12520
T79 119876-119880 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T80 119920-119924 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T81 119955-119959 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T82 119990-119994 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T83 120366-120368 Body_part denotes CS http://purl.org/sig/ont/fma/fma284995
T84 121170-121180 Body_part denotes tryptophan http://purl.org/sig/ont/fma/fma82767
T85 121269-121274 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T86 121276-121283 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T87 121294-121301 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T88 121303-121312 Body_part denotes glutamine http://purl.org/sig/ont/fma/fma82752
T89 121327-121334 Body_part denotes leucine http://purl.org/sig/ont/fma/fma82757
T90 121355-121362 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T91 121382-121389 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T92 121391-121398 Body_part denotes glycine http://purl.org/sig/ont/fma/fma82753
T93 121637-121647 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T94 122200-122205 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T95 122242-122251 Body_part denotes glutamine http://purl.org/sig/ont/fma/fma82752
T96 122269-122275 Body_part denotes plasma http://purl.org/sig/ont/fma/fma62970
T97 122372-122376 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T98 122475-122489 Body_part denotes cell membranes http://purl.org/sig/ont/fma/fma63841
T99 122475-122479 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T100 122801-122807 Body_part denotes breast http://purl.org/sig/ont/fma/fma9601
T101 123028-123033 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T102 123107-123111 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T103 123457-123467 Body_part denotes fatty acid http://purl.org/sig/ont/fma/fma82738
T104 123618-123621 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T105 123731-123736 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T106 123795-123802 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T107 123818-123825 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T108 123833-123838 Body_part denotes liver http://purl.org/sig/ont/fma/fma7197
T109 124347-124352 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T110 124576-124581 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T111 124654-124660 Body_part denotes kidney http://purl.org/sig/ont/fma/fma7203
T112 124662-124667 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T113 124701-124705 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T114 124754-124759 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T115 124761-124766 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T116 125050-125055 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T117 125252-125263 Body_part denotes myoinositol http://purl.org/sig/ont/fma/fma82800
T118 125267-125272 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T119 125449-125463 Body_part denotes nervous system http://purl.org/sig/ont/fma/fma7157
T120 125498-125501 Body_part denotes gut http://purl.org/sig/ont/fma/fma7199
T121 125695-125705 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T122 125934-125939 Body_part denotes brain http://purl.org/sig/ont/fma/fma50801
T123 125940-125946 Body_part denotes tissue http://purl.org/sig/ont/fma/fma9637
T124 125975-125982 Body_part denotes neurons http://purl.org/sig/ont/fma/fma54527
T125 126004-126011 Body_part denotes glycine http://purl.org/sig/ont/fma/fma82753
T126 126078-126083 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T127 126358-126377 Body_part denotes cerebrospinal fluid http://purl.org/sig/ont/fma/fma20935
T128 126544-126554 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T129 127083-127088 Body_part denotes blood http://purl.org/sig/ont/fma/fma9670
T130 127307-127317 Body_part denotes fatty acid http://purl.org/sig/ont/fma/fma82738
T131 127351-127361 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T132 127612-127615 Body_part denotes gut http://purl.org/sig/ont/fma/fma7199
T133 127858-127865 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T134 127961-127968 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T135 128736-128739 Body_part denotes ITD http://purl.org/sig/ont/fma/fma58066
T136 130623-130625 Body_part denotes CS http://purl.org/sig/ont/fma/fma284995
T137 131330-131337 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T138 131568-131572 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T139 131630-131640 Body_part denotes cell parts http://purl.org/sig/ont/fma/fma78563
T140 131630-131634 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T141 131761-131768 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T142 131837-131844 Body_part denotes Protein http://purl.org/sig/ont/fma/fma67257
T143 131922-131930 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T144 132193-132200 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T7999 358-363 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T38790 5459-5466 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T60513 6467-6480 Body_part denotes aspartic acid http://purl.org/sig/ont/fma/fma82760
T80219 6556-6563 Body_part denotes neurons http://purl.org/sig/ont/fma/fma54527
T8361 7288-7296 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T10253 8695-8718 Body_part denotes transverse to the plane http://purl.org/sig/ont/fma/fma71928
T45898 8850-8866 Body_part denotes transverse plane http://purl.org/sig/ont/fma/fma71928
T76500 10321-10324 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T71803 10338-10346 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T51396 10965-10970 Body_part denotes urine http://purl.org/sig/ont/fma/fma12274
T52620 10975-10986 Body_part denotes blood serum http://purl.org/sig/ont/fma/fma63083
T43252 17037-17044 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T49086 17161-17168 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T48591 19286-19298 Body_part denotes phospholipid http://purl.org/sig/ont/fma/fma82779
T16532 19361-19364 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T27437 19518-19521 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T23683 20606-20611 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T17125 20648-20652 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T47161 23203-23208 Body_part denotes blood http://purl.org/sig/ont/fma/fma9670
T51661 23290-23295 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T25681 23300-23305 Body_part denotes urine http://purl.org/sig/ont/fma/fma12274
T23891 23831-23836 Body_part denotes blood http://purl.org/sig/ont/fma/fma9670
T12355 25908-25914 Body_part denotes breast http://purl.org/sig/ont/fma/fma9601
T33062 26039-26044 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T4462 26252-26257 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T92872 26653-26658 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T38324 26681-26687 Body_part denotes breast http://purl.org/sig/ont/fma/fma9601
T65570 28088-28093 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T64417 28197-28202 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T30907 28416-28421 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T71500 28488-28493 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T7498 28549-28554 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T49050 28632-28637 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T73203 28679-28684 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T75762 28850-28855 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T68385 29265-29273 Body_part denotes backbone http://purl.org/sig/ont/fma/fma13478
T68513 29277-29285 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T30146 30353-30358 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T11099 30360-30366 Body_part denotes kidney http://purl.org/sig/ont/fma/fma7203
T30625 30372-30377 Body_part denotes liver http://purl.org/sig/ont/fma/fma7197
T37089 30378-30384 Body_part denotes tissue http://purl.org/sig/ont/fma/fma9637
T93967 30871-30881 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T77772 30898-30903 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T43843 30957-30964 Body_part denotes kidneys http://purl.org/sig/ont/fma/fma7203
T96240 30969-30974 Body_part denotes liver http://purl.org/sig/ont/fma/fma7197
T49148 31363-31367 Body_part denotes axis http://purl.org/sig/ont/fma/fma12520
T36122 31712-31716 Body_part denotes axis http://purl.org/sig/ont/fma/fma12520
T39858 33465-33468 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T62847 33754-33761 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T88379 34038-34050 Body_part denotes blood plasma http://purl.org/sig/ont/fma/fma62970
T40091 34134-34141 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T37259 34246-34254 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T43243 36166-36174 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T42194 36370-36377 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T57538 37078-37082 Body_part denotes back http://purl.org/sig/ont/fma/fma25056
T52848 37167-37174 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T21500 38338-38345 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T80070 39073-39077 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T24520 39215-39219 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T39453 41658-41669 Body_part denotes lymphocytic http://purl.org/sig/ont/fma/fma62863
T84514 43011-43018 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T31879 43865-43873 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T80711 45401-45408 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T98872 45950-45958 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T86319 46225-46232 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T90624 47202-47209 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T33016 47324-47331 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T22016 47756-47759 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T39193 47764-47767 Body_part denotes RNA http://purl.org/sig/ont/fma/fma67095
T62167 48752-48759 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T15931 48882-48890 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T23445 49672-49679 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T55851 50972-50975 Body_part denotes RNA http://purl.org/sig/ont/fma/fma67095
T75217 51111-51118 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T89011 51245-51250 Body_part denotes blood http://purl.org/sig/ont/fma/fma9670
T17259 51367-51375 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T48151 52056-52064 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T14880 52102-52113 Body_part denotes amino acids http://purl.org/sig/ont/fma/fma82739
T73802 52917-52924 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T89652 53293-53300 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T76018 53547-53554 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T90230 53590-53598 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T69206 53723-53730 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T64359 53995-54010 Body_part denotes protein complex http://purl.org/sig/ont/fma/fma67906
T291 54489-54496 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T72984 54525-54529 Body_part denotes hand http://purl.org/sig/ont/fma/fma9712
T88588 54987-54994 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T33800 55541-55556 Body_part denotes polysaccharides http://purl.org/sig/ont/fma/fma82746
T79791 55603-55613 Body_part denotes E-selectin http://purl.org/sig/ont/fma/fma62932
T42543 55631-55638 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T16389 55653-55656 Body_part denotes IgG http://purl.org/sig/ont/fma/fma62872
T72564 56071-56078 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T83107 56668-56675 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T98493 56812-56819 Body_part denotes tubulin http://purl.org/sig/ont/fma/fma67116
T25827 56967-56982 Body_part denotes protein complex http://purl.org/sig/ont/fma/fma67906
T12583 57368-57375 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T45014 60105-60111 Body_part denotes radius http://purl.org/sig/ont/fma/fma23463
T35535 63170-63178 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T29116 64395-64402 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T42127 65216-65236 Body_part denotes N-acetyl glucosamine http://purl.org/sig/ont/fma/fma82787
T31376 65461-65466 Body_part denotes serum http://purl.org/sig/ont/fma/fma63083
T43729 66059-66066 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T41747 66067-66074 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T53232 67013-67020 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T29588 67077-67085 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T33707 67971-67974 Body_part denotes A2A http://purl.org/sig/ont/fma/fma68761
T71880 68002-68009 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T40803 69034-69041 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T15753 69172-69180 Body_part denotes cysteine http://purl.org/sig/ont/fma/fma82751
T4885 69182-69192 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T7460 69501-69506 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T32139 69822-69826 Body_part denotes palm http://purl.org/sig/ont/fma/fma24920
T25080 70155-70162 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T54465 71003-71011 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T71697 71390-71397 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T41642 71438-71445 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T462 71536-71543 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T15051 71788-71796 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T29733 72161-72169 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T89089 72171-72174 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T83508 72180-72183 Body_part denotes RNA http://purl.org/sig/ont/fma/fma67095
T508 73649-73658 Body_part denotes protein’s http://purl.org/sig/ont/fma/fma67257
T64393 73679-73682 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T14796 74034-74041 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T31078 74063-74066 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T2567 74112-74115 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T82556 74292-74295 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T5753 74537-74545 Body_part denotes oxytocin http://purl.org/sig/ont/fma/fma74647
T78175 74550-74561 Body_part denotes vasopressin http://purl.org/sig/ont/fma/fma74646
T41120 74646-74654 Body_part denotes oxytocin http://purl.org/sig/ont/fma/fma74647
T81108 74659-74670 Body_part denotes vasopressin http://purl.org/sig/ont/fma/fma74646
T14848 74858-74866 Body_part denotes oxytocin http://purl.org/sig/ont/fma/fma74647
T92268 74871-74882 Body_part denotes vasopressin http://purl.org/sig/ont/fma/fma74646
T89759 75393-75400 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T97560 75413-75420 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T64825 75548-75555 Body_part denotes G-actin http://purl.org/sig/ont/fma/fma67893
T72415 75556-75563 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T78500 75569-75577 Body_part denotes thymosin http://purl.org/sig/ont/fma/fma67128
T87872 75585-75607 Body_part denotes actin- binding protein http://purl.org/sig/ont/fma/fma67119
T55142 75742-75749 Body_part denotes G-actin http://purl.org/sig/ont/fma/fma67893
T40518 75791-75795 Body_part denotes hand http://purl.org/sig/ont/fma/fma9712
T80287 75831-75838 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T51165 75925-75933 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T82421 76105-76113 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T145 76277-76284 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T146 76368-76376 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T147 76406-76413 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T148 76940-76948 Body_part denotes collagen http://purl.org/sig/ont/fma/fma63891
T149 76952-76957 Body_part denotes lipid http://purl.org/sig/ont/fma/fma67264
T150 77180-77188 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T151 79476-79484 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T152 80164-80172 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T153 81163-81168 Body_part denotes cells http://purl.org/sig/ont/fma/fma68646
T154 81173-81177 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T155 81196-81202 Body_part denotes breast http://purl.org/sig/ont/fma/fma9601
T156 81221-81225 Body_part denotes lung http://purl.org/sig/ont/fma/fma7195
T157 81548-81553 Body_part denotes sugar http://purl.org/sig/ont/fma/fma82737
T158 81571-81575 Body_part denotes cell http://purl.org/sig/ont/fma/fma68646
T159 81856-81863 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T160 82623-82632 Body_part denotes histidine http://purl.org/sig/ont/fma/fma82755
T161 82682-82692 Body_part denotes histidines http://purl.org/sig/ont/fma/fma82755
T162 83898-83905 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T163 84202-84209 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T164 84294-84301 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T165 85287-85294 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T166 85329-85336 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T167 85603-85610 Body_part denotes histone http://purl.org/sig/ont/fma/fma74413
T168 86241-86245 Body_part denotes sole http://purl.org/sig/ont/fma/fma25000
T169 86766-86769 Body_part denotes HIV http://purl.org/sig/ont/fma/fma278683
T170 87221-87232 Body_part denotes amino acids http://purl.org/sig/ont/fma/fma82739
T171 87835-87842 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T172 87843-87850 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T173 88074-88081 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T174 88082-88089 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T175 89094-89101 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T176 89306-89313 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T177 89609-89616 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T178 89617-89624 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T179 89695-89704 Body_part denotes protein’s http://purl.org/sig/ont/fma/fma67257
T180 89764-89772 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T181 91273-91280 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T182 91281-91288 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T183 91985-91988 Body_part denotes map http://purl.org/sig/ont/fma/fma67847
T184 92198-92205 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T185 92448-92455 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T186 92559-92561 Body_part denotes H4 http://purl.org/sig/ont/fma/fma84132
T187 92665-92667 Body_part denotes H3 http://purl.org/sig/ont/fma/fma84131
T188 92863-92866 Body_part denotes map http://purl.org/sig/ont/fma/fma67847
T189 93021-93028 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T190 93175-93178 Body_part denotes map http://purl.org/sig/ont/fma/fma67847
T191 93342-93349 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T192 93849-93856 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T193 93887-93895 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T194 94109-94114 Body_part denotes heart http://purl.org/sig/ont/fma/fma7088
T195 94144-94151 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T196 94206-94213 Body_part denotes glucose http://purl.org/sig/ont/fma/fma82743
T197 94488-94495 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T198 94565-94575 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T199 94660-94670 Body_part denotes amino acid http://purl.org/sig/ont/fma/fma82739
T200 94746-94753 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T201 94796-94803 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T202 95061-95072 Body_part denotes amino acids http://purl.org/sig/ont/fma/fma82739
T203 95257-95268 Body_part denotes amino acids http://purl.org/sig/ont/fma/fma82739
T204 95831-95838 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T205 96031-96040 Body_part denotes protein’s http://purl.org/sig/ont/fma/fma67257
T206 96185-96202 Body_part denotes protein complexes http://purl.org/sig/ont/fma/fma67906
T207 96185-96192 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T208 96440-96448 Body_part denotes proteins http://purl.org/sig/ont/fma/fma67257
T209 96669-96676 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T210 96734-96741 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T211 97448-97455 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T212 98309-98316 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T213 98438-98445 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257
T214 98525-98532 Body_part denotes protein http://purl.org/sig/ont/fma/fma67257

LitCovid-PD-UBERON

Id Subject Object Predicate Lexical cue uberon_id
T1 10743-10747 Body_part denotes tube http://purl.obolibrary.org/obo/UBERON_0000025
T2 10751-10755 Body_part denotes tube http://purl.obolibrary.org/obo/UBERON_0000025
T3 10965-10970 Body_part denotes urine http://purl.obolibrary.org/obo/UBERON_0001088
T4 10975-10980 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T5 10981-10986 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T6 23203-23208 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T7 23290-23295 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T8 23300-23305 Body_part denotes urine http://purl.obolibrary.org/obo/UBERON_0001088
T9 23831-23836 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T10 24036-24045 Body_part denotes extension http://purl.obolibrary.org/obo/UBERON_2000106
T11 25908-25914 Body_part denotes breast http://purl.obolibrary.org/obo/UBERON_0000310
T12 26039-26044 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T13 26252-26257 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T14 26653-26658 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T15 26681-26687 Body_part denotes breast http://purl.obolibrary.org/obo/UBERON_0000310
T16 30353-30358 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T17 30360-30366 Body_part denotes kidney http://purl.obolibrary.org/obo/UBERON_0002113
T18 30372-30377 Body_part denotes liver http://purl.obolibrary.org/obo/UBERON_0002107
T19 30378-30384 Body_part denotes tissue http://purl.obolibrary.org/obo/UBERON_0000479
T20 30969-30974 Body_part denotes liver http://purl.obolibrary.org/obo/UBERON_0002107
T21 34038-34050 Body_part denotes blood plasma http://purl.obolibrary.org/obo/UBERON_0001969
T22 34038-34043 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T23 34332-34336 Body_part denotes Gill http://purl.obolibrary.org/obo/UBERON_0002535
T24 34988-34992 Body_part denotes Gill http://purl.obolibrary.org/obo/UBERON_0002535
T25 37230-37235 Body_part denotes scale http://purl.obolibrary.org/obo/UBERON_0002542
T26 51245-51250 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T27 54525-54529 Body_part denotes hand http://purl.obolibrary.org/obo/UBERON_0002398
T28 61100-61104 Body_part denotes tube http://purl.obolibrary.org/obo/UBERON_0000025
T29 65461-65466 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T30 75791-75795 Body_part denotes hand http://purl.obolibrary.org/obo/UBERON_0002398
T31 81196-81202 Body_part denotes breast http://purl.obolibrary.org/obo/UBERON_0000310
T32 81221-81225 Body_part denotes lung http://purl.obolibrary.org/obo/UBERON_0002048
T33 90183-90187 Body_part denotes Gill http://purl.obolibrary.org/obo/UBERON_0002535
T34 94109-94114 Body_part denotes heart http://purl.obolibrary.org/obo/UBERON_0000948
T35 106389-106394 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T36 115154-115159 Body_part denotes scale http://purl.obolibrary.org/obo/UBERON_0002542
T37 121269-121274 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T38 121530-121535 Body_part denotes Shell http://purl.obolibrary.org/obo/UBERON_0006612
T39 122801-122807 Body_part denotes breast http://purl.obolibrary.org/obo/UBERON_0000310
T40 123833-123838 Body_part denotes liver http://purl.obolibrary.org/obo/UBERON_0002107
T41 124347-124352 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T42 124654-124660 Body_part denotes kidney http://purl.obolibrary.org/obo/UBERON_0002113
T43 125267-125272 Body_part denotes serum http://purl.obolibrary.org/obo/UBERON_0001977
T44 125449-125463 Body_part denotes nervous system http://purl.obolibrary.org/obo/UBERON_0001016
T45 125934-125939 Body_part denotes brain http://purl.obolibrary.org/obo/UBERON_0000955
T46 125940-125946 Body_part denotes tissue http://purl.obolibrary.org/obo/UBERON_0000479
T47 126358-126377 Body_part denotes cerebrospinal fluid http://purl.obolibrary.org/obo/UBERON_0001359
T48 127083-127088 Body_part denotes blood http://purl.obolibrary.org/obo/UBERON_0000178
T49 131630-131640 Body_part denotes cell parts http://purl.obolibrary.org/obo/UBERON_0000470

LitCovid-PD-MONDO

Id Subject Object Predicate Lexical cue mondo_id
T1 235-245 Disease denotes infections http://purl.obolibrary.org/obo/MONDO_0005550
T2 351-357 Disease denotes Cancer http://purl.obolibrary.org/obo/MONDO_0004992
T3 496-517 Disease denotes neurological diseases http://purl.obolibrary.org/obo/MONDO_0005071
T4 613-629 Disease denotes Viral infections http://purl.obolibrary.org/obo/MONDO_0005108
T5 739-749 Disease denotes infections http://purl.obolibrary.org/obo/MONDO_0005550
T6 793-801 Disease denotes SARS-CoV http://purl.obolibrary.org/obo/MONDO_0005091
T7 1762-1770 Disease denotes SARS-CoV http://purl.obolibrary.org/obo/MONDO_0005091
T8 1773-1781 Disease denotes COVID-19 http://purl.obolibrary.org/obo/MONDO_0100096
T9 6416-6435 Disease denotes Alzheimer’s disease http://purl.obolibrary.org/obo/MONDO_0004975
T10 6531-6538 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T11 6594-6613 Disease denotes Alzheimer’s disease http://purl.obolibrary.org/obo/MONDO_0004975
T12 25908-25921 Disease denotes breast cancer http://purl.obolibrary.org/obo/MONDO_0007254
T13 25915-25921 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T14 26681-26694 Disease denotes breast cancer http://purl.obolibrary.org/obo/MONDO_0007254
T15 26688-26694 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T16 28056-28073 Disease denotes ovarian carcinoma http://purl.obolibrary.org/obo/MONDO_0005140
T17 28064-28073 Disease denotes carcinoma http://purl.obolibrary.org/obo/MONDO_0004993
T18 30197-30199 Disease denotes HD http://purl.obolibrary.org/obo/MONDO_0007739
T19 33500-33503 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T20 33647-33649 Disease denotes he http://purl.obolibrary.org/obo/MONDO_0017319
T21 35495-35497 Disease denotes R2 http://purl.obolibrary.org/obo/MONDO_0019903
T22 38684-38687 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T23 39609-39612 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T24 39672-39675 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T25 40209-40212 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T26 40494-40497 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T27 41481-41487 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T28 41569-41588 Disease denotes metastatic melanoma http://purl.obolibrary.org/obo/MONDO_0005191
T29 41580-41588 Disease denotes melanoma http://purl.obolibrary.org/obo/MONDO_0005105
T30 41650-41678 Disease denotes chronic lymphocytic leukemia http://purl.obolibrary.org/obo/MONDO_0004948
T31 41658-41678 Disease denotes lymphocytic leukemia http://purl.obolibrary.org/obo/MONDO_0005402
T32 41670-41678 Disease denotes leukemia http://purl.obolibrary.org/obo/MONDO_0005059
T33 43982-43985 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T34 44683-44686 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T35 44859-44862 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T36 44896-44899 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T37 45841-45844 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T38 46016-46019 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T39 46051-46054 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T40 46733-46736 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T41 46786-46789 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T42 46955-46958 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T43 47150-47153 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T44 47311-47314 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T45 47483-47486 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T46 48186-48189 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T47 48535-48538 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T48 48574-48577 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T49 49140-49143 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T50 49442-49445 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T51 49804-49807 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T52 50009-50012 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T53 50108-50111 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T54 50218-50221 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T55 50348-50351 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T56 51034-51049 Disease denotes gastroenteritis http://purl.obolibrary.org/obo/MONDO_0002269
T57 51308-51317 Disease denotes infection http://purl.obolibrary.org/obo/MONDO_0005550
T58 51444-51447 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T59 51697-51700 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T60 52127-52130 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T61 52352-52355 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T62 52567-52570 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T63 60701-60703 Disease denotes SE http://purl.obolibrary.org/obo/MONDO_0002125
T64 60746-60748 Disease denotes SE http://purl.obolibrary.org/obo/MONDO_0002125
T65 60791-60793 Disease denotes SE http://purl.obolibrary.org/obo/MONDO_0002125
T66 65000-65003 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T67 65124-65127 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T68 65387-65390 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T69 66750-66753 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T70 66809-66812 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T71 68046-68065 Disease denotes Parkinson’s disease http://purl.obolibrary.org/obo/MONDO_0005180
T72 69017-69022 Disease denotes tumor http://purl.obolibrary.org/obo/MONDO_0005070
T73 77193-77200 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T74 79953-79960 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T75 80024-80031 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T76 81156-81162 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T77 81196-81209 Disease denotes breast cancer http://purl.obolibrary.org/obo/MONDO_0007254
T78 81203-81209 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T79 81221-81232 Disease denotes lung cancer http://purl.obolibrary.org/obo/MONDO_0008903
T80 81226-81232 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T81 81746-81753 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T82 81903-81910 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T83 82055-82062 Disease denotes amyloid http://purl.obolibrary.org/obo/MONDO_0019065
T84 82852-82855 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T85 83809-83812 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T86 83949-83961 Disease denotes tuberculosis http://purl.obolibrary.org/obo/MONDO_0018076
T87 83999-84002 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T88 84066-84069 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T89 84088-84091 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T90 84164-84167 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T91 84331-84334 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T92 84440-84443 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T93 84582-84585 Disease denotes ADC http://purl.obolibrary.org/obo/MONDO_0020689
T94 84987-84990 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T95 85432-85435 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549
T96 85630-85633 Disease denotes HAT http://purl.obolibrary.org/obo/MONDO_0018048
T97 85745-85748 Disease denotes HAT http://purl.obolibrary.org/obo/MONDO_0018048
T98 85884-85887 Disease denotes HAT http://purl.obolibrary.org/obo/MONDO_0018048
T99 86740-86756 Disease denotes immunodeficiency http://purl.obolibrary.org/obo/MONDO_0021094
T100 88129-88135 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T101 89792-89795 Disease denotes VHL http://purl.obolibrary.org/obo/MONDO_0008667
T102 90156-90159 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T103 90441-90444 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T104 91767-91770 Disease denotes CSP http://purl.obolibrary.org/obo/MONDO_0005078
T105 92033-92036 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T106 94305-94308 Disease denotes SOS http://purl.obolibrary.org/obo/MONDO_0011604
T107 94407-94410 Disease denotes SOS http://purl.obolibrary.org/obo/MONDO_0011604
T108 94427-94430 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T109 94614-94617 Disease denotes SOS http://purl.obolibrary.org/obo/MONDO_0011604
T110 95359-95362 Disease denotes SOS http://purl.obolibrary.org/obo/MONDO_0011604
T111 95461-95464 Disease denotes SOS http://purl.obolibrary.org/obo/MONDO_0011604
T112 96775-96781 Disease denotes dengue http://purl.obolibrary.org/obo/MONDO_0005502
T113 96793-96796 Disease denotes NS3 http://purl.obolibrary.org/obo/MONDO_0012371
T114 101222-101225 Disease denotes CSP http://purl.obolibrary.org/obo/MONDO_0005078
T115 101241-101244 Disease denotes CSP http://purl.obolibrary.org/obo/MONDO_0005078
T116 101389-101392 Disease denotes CSP http://purl.obolibrary.org/obo/MONDO_0005078
T117 101754-101757 Disease denotes CSP http://purl.obolibrary.org/obo/MONDO_0005078
T118 102155-102158 Disease denotes CSP http://purl.obolibrary.org/obo/MONDO_0005078
T119 104027-104030 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T120 112187-112190 Disease denotes MDD http://purl.obolibrary.org/obo/MONDO_0012048|http://purl.obolibrary.org/obo/MONDO_0016217
T122 118817-118820 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T123 119575-119577 Disease denotes SE http://purl.obolibrary.org/obo/MONDO_0002125
T124 120330-120333 Disease denotes MDD http://purl.obolibrary.org/obo/MONDO_0012048|http://purl.obolibrary.org/obo/MONDO_0016217
T126 120446-120449 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T127 122365-122371 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T128 122801-122814 Disease denotes breast cancer http://purl.obolibrary.org/obo/MONDO_0007254
T129 122808-122814 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T130 124063-124083 Disease denotes rheumatoid arthritis http://purl.obolibrary.org/obo/MONDO_0008383
T131 124074-124083 Disease denotes arthritis http://purl.obolibrary.org/obo/MONDO_0005578
T132 124475-124483 Disease denotes epilepsy http://purl.obolibrary.org/obo/MONDO_0005027
T133 124609-124623 Disease denotes ovarian cancer http://purl.obolibrary.org/obo/MONDO_0008170
T134 124617-124623 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T135 125288-125291 Disease denotes CRC http://purl.obolibrary.org/obo/MONDO_0005575|http://purl.obolibrary.org/obo/MONDO_0024331
T137 125293-125310 Disease denotes colorectal cancer http://purl.obolibrary.org/obo/MONDO_0005575
T138 125304-125310 Disease denotes cancer http://purl.obolibrary.org/obo/MONDO_0004992
T139 126381-126403 Disease denotes tuberculous meningitis http://purl.obolibrary.org/obo/MONDO_0044684
T140 126393-126403 Disease denotes meningitis http://purl.obolibrary.org/obo/MONDO_0004796|http://purl.obolibrary.org/obo/MONDO_0021108
T142 126812-126834 Disease denotes gastric adenocarcinoma http://purl.obolibrary.org/obo/MONDO_0005036
T143 126820-126834 Disease denotes adenocarcinoma http://purl.obolibrary.org/obo/MONDO_0004970
T144 130406-130409 Disease denotes MDD http://purl.obolibrary.org/obo/MONDO_0012048|http://purl.obolibrary.org/obo/MONDO_0016217
T146 131339-131342 Disease denotes STD http://purl.obolibrary.org/obo/MONDO_0021681
T147 132138-132141 Disease denotes HTS http://purl.obolibrary.org/obo/MONDO_0011549

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T355 50976-50983 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T356 51102-51103 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T357 51146-51147 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T358 51218-51223 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T359 51245-51250 http://purl.obolibrary.org/obo/UBERON_0000178 denotes blood
T360 51245-51250 http://www.ebi.ac.uk/efo/EFO_0000296 denotes blood
T361 51587-51588 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T362 51594-51595 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T363 51622-51627 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T364 51653-51654 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T365 51725-51726 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T366 52005-52006 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T367 52162-52163 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T368 52424-52427 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T369 52523-52529 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T370 52957-52958 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T371 53022-53024 http://www.ebi.ac.uk/efo/EFO_0000265 denotes Da
T372 53291-53292 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T373 53462-53463 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T374 53522-53529 http://purl.obolibrary.org/obo/SO_0000418 denotes Signals
T375 53664-53665 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T376 53731-53738 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T377 53774-53776 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T378 53995-54010 http://purl.obolibrary.org/obo/GO_0043234 denotes protein complex
T379 54236-54237 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T380 54353-54354 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T381 54445-54446 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T382 54659-54660 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T383 54964-54965 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T384 54976-54977 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T385 55279-55281 http://purl.obolibrary.org/obo/CLO_0007874 denotes ms
T386 55427-55435 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T387 55507-55508 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T388 55629-55630 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T389 55670-55671 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T390 56123-56129 http://purl.obolibrary.org/obo/CLO_0054057 denotes 1, 8:1
T391 56131-56135 http://purl.obolibrary.org/obo/CLO_0001053 denotes 12:1
T392 56150-56155 http://purl.obolibrary.org/obo/CLO_0001757 denotes 1, at
T393 56546-56547 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T394 56791-56792 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T395 56835-56836 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T396 56958-56959 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T397 56967-56982 http://purl.obolibrary.org/obo/GO_0043234 denotes protein complex
T398 57111-57112 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T399 57464-57465 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T400 57591-57592 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T401 57620-57621 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T402 57626-57627 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T403 57717-57718 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T404 57723-57724 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T405 57756-57757 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T406 57852-57853 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T407 57858-57859 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T408 57993-57994 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T409 58076-58078 http://purl.obolibrary.org/obo/CLO_0004265 denotes HT
T410 58211-58212 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T411 58318-58320 http://purl.obolibrary.org/obo/CLO_0004265 denotes HT
T412 58367-58369 http://purl.obolibrary.org/obo/CLO_0003622 denotes HB
T413 58374-58375 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T414 58418-58420 http://purl.obolibrary.org/obo/CLO_0003622 denotes HB
T415 58471-58472 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T416 58780-58781 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T417 58888-58889 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T418 59008-59009 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T419 59145-59146 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T420 59185-59187 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T421 59323-59324 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T422 59341-59342 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T423 59375-59376 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T424 59470-59471 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T425 59631-59632 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T426 59955-59957 http://purl.obolibrary.org/obo/CLO_0008882 denotes rs
T427 59965-59967 http://purl.obolibrary.org/obo/CLO_0007074 denotes kb
T428 59965-59967 http://purl.obolibrary.org/obo/CLO_0051988 denotes kb
T429 60082-60084 http://purl.obolibrary.org/obo/CLO_0008882 denotes rs
T430 60736-60739 http://purl.obolibrary.org/obo/CLO_0001230 denotes 293
T431 60736-60739 http://purl.obolibrary.org/obo/CLO_0037237 denotes 293
T432 60736-60739 http://purl.obolibrary.org/obo/CLO_0050903 denotes 293
T433 60736-60739 http://purl.obolibrary.org/obo/CLO_0054249 denotes 293
T434 60736-60739 http://purl.obolibrary.org/obo/CLO_0054250 denotes 293
T435 60736-60739 http://purl.obolibrary.org/obo/CLO_0054251 denotes 293
T436 60736-60739 http://purl.obolibrary.org/obo/CLO_0054252 denotes 293
T1 99880-99881 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T2 99919-99920 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T3 99943-99944 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T4 99964-99965 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T5 100129-100130 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T6 100228-100235 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T7 100458-100460 http://purl.obolibrary.org/obo/CLO_0002960 denotes F1
T8 100508-100509 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T9 100632-100633 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T10 100764-100765 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T11 101230-101231 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T12 101289-101290 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T13 101396-101397 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T14 101428-101429 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T15 101465-101466 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T16 101527-101535 http://purl.obolibrary.org/obo/CLO_0007225 denotes labelled
T17 101652-101657 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T18 101838-101843 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T19 101844-101854 http://purl.obolibrary.org/obo/UBERON_0000160 denotes intestinal
T20 101844-101854 http://www.ebi.ac.uk/efo/EFO_0000834 denotes intestinal
T21 102216-102224 http://www.ebi.ac.uk/efo/EFO_0000876 denotes Extremes
T22 102284-102302 http://purl.obolibrary.org/obo/GO_0043234 denotes proteins complexes
T23 102433-102434 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T24 102483-102484 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T25 102528-102529 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T26 102579-102580 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T27 102664-102670 http://purl.obolibrary.org/obo/UBERON_0000473 denotes tested
T28 103147-103150 http://purl.obolibrary.org/obo/CLO_0001195 denotes 219
T29 103381-103385 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T30 103541-103545 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T31 103651-103655 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T32 103684-103688 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T33 103723-103727 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T34 103791-103795 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T35 103838-103845 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T36 103866-103870 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T37 103918-103919 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T38 104018-104022 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T39 104038-104039 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T40 104092-104096 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T41 104137-104146 http://purl.obolibrary.org/obo/CLO_0007225 denotes labelling
T42 104189-104198 http://purl.obolibrary.org/obo/CLO_0007225 denotes labelling
T43 104291-104295 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T44 104326-104330 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T45 104379-104386 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T46 104398-104405 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T47 104466-104473 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T48 104481-104485 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T49 104563-104572 http://purl.obolibrary.org/obo/CL_0000000 denotes cell type
T50 104581-104589 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T51 104636-104646 http://purl.obolibrary.org/obo/CL_0000000 denotes cell types
T52 104658-104666 http://purl.obolibrary.org/obo/NCBITaxon_2 denotes bacteria
T53 104683-104686 http://purl.obolibrary.org/obo/CLO_0001360 denotes 412
T54 104695-104700 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T55 104718-104723 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T56 104731-104741 http://purl.obolibrary.org/obo/CLO_0054283 denotes HeLa cells
T57 104731-104741 http://purl.obolibrary.org/obo/CLO_0054285 denotes HeLa cells
T58 104731-104741 http://purl.obolibrary.org/obo/CLO_0054286 denotes HeLa cells
T59 104731-104741 http://purl.obolibrary.org/obo/CLO_0054287 denotes HeLa cells
T60 104731-104741 http://purl.obolibrary.org/obo/CLO_0054288 denotes HeLa cells
T61 104731-104741 http://purl.obolibrary.org/obo/CLO_0054289 denotes HeLa cells
T62 104731-104735 http://purl.obolibrary.org/obo/CLO_0003684 denotes HeLa
T63 104731-104735 http://purl.obolibrary.org/obo/CLO_0050910 denotes HeLa
T64 104764-104769 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T65 104831-104835 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T66 104865-104874 http://purl.obolibrary.org/obo/CL_0000000 denotes cell type
T67 104961-104969 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T68 105082-105090 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T69 105091-105094 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T70 105112-105113 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T71 105322-105344 http://purl.obolibrary.org/obo/GO_0043234 denotes proteins and complexes
T72 105373-105381 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T73 105497-105501 http://purl.obolibrary.org/obo/GO_0005623 denotes Cell
T74 105509-105513 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T75 105547-105550 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T76 105688-105692 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T77 105729-105733 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T78 105761-105767 http://purl.obolibrary.org/obo/CLO_0007225 denotes labels
T79 105814-105815 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T80 106051-106059 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T81 106138-106145 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T82 106174-106180 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T83 106266-106267 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T84 106383-106388 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T85 106389-106394 http://purl.obolibrary.org/obo/UBERON_0000178 denotes blood
T86 106389-106394 http://www.ebi.ac.uk/efo/EFO_0000296 denotes blood
T87 106406-106411 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes Virus
T88 106434-106441 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T89 106476-106479 http://purl.obolibrary.org/obo/CLO_0009124 denotes SPs
T90 106516-106528 http://purl.obolibrary.org/obo/OBI_0000245 denotes organization
T91 106589-106590 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92 106612-106620 http://purl.obolibrary.org/obo/PR_000001898 denotes called a
T93 106651-106654 http://purl.obolibrary.org/obo/CLO_0009124 denotes SPs
T94 106770-106771 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T95 106878-106879 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T96 106953-106970 http://purl.obolibrary.org/obo/GO_0043234 denotes protein complexes
T97 107001-107002 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T98 107225-107229 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T99 107269-107276 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T100 107389-107394 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T101 107419-107426 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T102 107490-107509 http://purl.obolibrary.org/obo/GO_0005575 denotes cellular components
T103 107544-107549 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T104 107696-107701 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T105 107890-107895 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T106 108022-108025 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T107 108026-108027 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T108 108120-108121 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T109 108205-108206 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T110 108313-108319 http://purl.obolibrary.org/obo/UBERON_0007688 denotes fields
T111 108662-108669 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T112 108969-108970 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T113 109285-109286 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T114 109507-109512 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T115 109536-109537 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T116 109573-109578 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T117 109774-109779 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T118 109800-109803 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T119 109920-109931 http://purl.obolibrary.org/obo/OBI_0000968 denotes instruments
T120 110076-110082 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T121 110642-110643 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T122 110724-110725 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T123 110995-110996 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T124 111015-111016 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T125 111315-111318 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T126 111612-111618 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T127 111645-111646 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T128 111967-111973 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T129 112343-112349 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T130 112558-112563 http://purl.obolibrary.org/obo/CLO_0009985 denotes focus
T131 112646-112652 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T132 113069-113070 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T133 113621-113631 http://purl.obolibrary.org/obo/OBI_0000968 denotes instrument
T134 114852-114858 http://purl.obolibrary.org/obo/SO_0000418 denotes Signal
T135 115005-115008 http://purl.obolibrary.org/obo/CLO_0001375 denotes 455
T136 115031-115034 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T137 115042-115043 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T138 115278-115286 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T139 115321-115324 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T140 115336-115337 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T141 115660-115663 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T142 115891-115892 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T143 116105-116114 http://purl.obolibrary.org/obo/OBI_0000245 denotes organized
T144 116631-116638 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T145 117777-117779 http://purl.obolibrary.org/obo/CLO_0007874 denotes ms
T146 117799-117806 http://www.ebi.ac.uk/efo/EFO_0000876 denotes extreme
T147 117978-117979 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T148 118011-118012 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T149 118025-118027 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T150 118078-118079 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T151 118166-118167 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T152 118375-118376 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T153 118387-118393 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T154 118471-118472 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T155 118518-118519 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T156 118782-118789 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T157 118826-118827 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T158 118845-118846 http://purl.obolibrary.org/obo/CLO_0001021 denotes b
T159 119044-119045 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T160 119061-119062 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T161 119171-119173 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T162 119239-119240 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T163 119263-119264 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T164 119623-119626 http://purl.obolibrary.org/obo/CLO_0001230 denotes 293
T165 119623-119626 http://purl.obolibrary.org/obo/CLO_0037237 denotes 293
T166 119623-119626 http://purl.obolibrary.org/obo/CLO_0050903 denotes 293
T167 119623-119626 http://purl.obolibrary.org/obo/CLO_0054249 denotes 293
T168 119623-119626 http://purl.obolibrary.org/obo/CLO_0054250 denotes 293
T169 119623-119626 http://purl.obolibrary.org/obo/CLO_0054251 denotes 293
T170 119623-119626 http://purl.obolibrary.org/obo/CLO_0054252 denotes 293
T171 119699-119701 http://purl.obolibrary.org/obo/CLO_0003414 denotes G2
T172 119876-119880 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T173 119898-119899 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T174 119920-119924 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T175 119931-119932 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T176 119955-119959 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T177 119990-119994 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T178 120034-120041 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T179 120380-120389 http://purl.obolibrary.org/obo/SO_0000418 denotes Signaling
T180 120511-120512 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T181 120622-120630 http://purl.obolibrary.org/obo/CLO_0001658 denotes Activity
T182 120779-120785 http://purl.obolibrary.org/obo/UBERON_0000473 denotes Tested
T183 121095-121096 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T184 121242-121244 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T185 121578-121579 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T186 121823-121831 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T187 121902-121904 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T188 121907-121909 http://purl.obolibrary.org/obo/CLO_0001527 denotes 94
T189 122200-122205 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T190 122269-122275 http://purl.obolibrary.org/obo/UBERON_0001969 denotes plasma
T191 122372-122376 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T192 122378-122384 http://purl.obolibrary.org/obo/CLO_0009063 denotes Skov-3
T193 122378-122384 http://purl.obolibrary.org/obo/CLO_0052004 denotes Skov-3
T194 122378-122384 http://purl.obolibrary.org/obo/CLO_0052005 denotes Skov-3
T195 122378-122384 http://purl.obolibrary.org/obo/CLO_0052006 denotes Skov-3
T196 122378-122384 http://purl.obolibrary.org/obo/CLO_0052007 denotes Skov-3
T197 122475-122479 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T198 122480-122489 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membranes
T199 122493-122494 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T200 122762-122763 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T201 122801-122807 http://purl.obolibrary.org/obo/UBERON_0000310 denotes breast
T202 123028-123033 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T203 123073-123074 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T204 123107-123117 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell lines
T205 123268-123269 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T206 123275-123278 http://purl.obolibrary.org/obo/UBERON_0001013 denotes fat
T207 123542-123544 http://purl.obolibrary.org/obo/CLO_0052676 denotes FC
T208 123646-123654 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T209 123725-123736 http://purl.obolibrary.org/obo/CLO_0051862 denotes HepG2 cells
T210 123748-123751 http://purl.obolibrary.org/obo/CLO_0054057 denotes 181
T211 123833-123838 http://purl.obolibrary.org/obo/UBERON_0002107 denotes liver
T212 123833-123838 http://www.ebi.ac.uk/efo/EFO_0000887 denotes liver
T213 123893-123895 http://purl.obolibrary.org/obo/CLO_0001627 denotes AA
T214 123941-123942 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T215 124596-124601 http://purl.obolibrary.org/obo/CLO_0001571 denotes A2780
T216 124596-124601 http://purl.obolibrary.org/obo/CLO_0051994 denotes A2780
T217 124603-124608 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T218 124633-124636 http://purl.obolibrary.org/obo/CLO_0001230 denotes 293
T219 124633-124636 http://purl.obolibrary.org/obo/CLO_0037237 denotes 293
T220 124633-124636 http://purl.obolibrary.org/obo/CLO_0050903 denotes 293
T221 124633-124636 http://purl.obolibrary.org/obo/CLO_0054249 denotes 293
T222 124633-124636 http://purl.obolibrary.org/obo/CLO_0054250 denotes 293
T223 124633-124636 http://purl.obolibrary.org/obo/CLO_0054251 denotes 293
T224 124633-124636 http://purl.obolibrary.org/obo/CLO_0054252 denotes 293
T225 124638-124643 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T226 124644-124660 http://www.ebi.ac.uk/efo/EFO_0000927 denotes embryonic kidney
T227 124662-124667 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T228 124701-124711 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell lines
T229 124747-124752 http://purl.obolibrary.org/obo/CLO_0001571 denotes A2780
T230 124747-124752 http://purl.obolibrary.org/obo/CLO_0051994 denotes A2780
T231 124754-124759 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T232 125498-125501 http://purl.obolibrary.org/obo/UBERON_0001007 denotes gut
T233 125498-125501 http://purl.obolibrary.org/obo/UBERON_0001555 denotes gut
T234 125498-125501 http://www.ebi.ac.uk/efo/EFO_0000834 denotes gut
T235 125934-125939 http://purl.obolibrary.org/obo/UBERON_0000955 denotes brain
T236 125934-125939 http://www.ebi.ac.uk/efo/EFO_0000302 denotes brain
T237 126052-126060 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T238 126078-126083 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T239 126298-126299 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T240 126872-126877 http://purl.obolibrary.org/obo/NCIT_C14239 denotes nu/nu
T241 127004-127007 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T242 127008-127009 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T243 127054-127055 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T244 127083-127088 http://purl.obolibrary.org/obo/UBERON_0000178 denotes blood
T245 127083-127088 http://www.ebi.ac.uk/efo/EFO_0000296 denotes blood
T246 127130-127132 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T247 127288-127296 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T248 127406-127412 http://purl.obolibrary.org/obo/UBERON_0002107 denotes livers
T249 127406-127412 http://www.ebi.ac.uk/efo/EFO_0000887 denotes livers
T250 127487-127488 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T251 127565-127573 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T252 127612-127615 http://purl.obolibrary.org/obo/UBERON_0001007 denotes gut
T253 127612-127615 http://purl.obolibrary.org/obo/UBERON_0001555 denotes gut
T254 127612-127615 http://www.ebi.ac.uk/efo/EFO_0000834 denotes gut
T255 127952-127953 http://purl.obolibrary.org/obo/CLO_0001020 denotes ɑ
T256 128717-128720 http://purl.obolibrary.org/obo/PR_000002062 denotes FMS
T257 128731-128735 http://purl.obolibrary.org/obo/PR_000002001 denotes FLT3
T258 128802-128804 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T259 129210-129212 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T260 129299-129302 http://purl.obolibrary.org/obo/CLO_0002697 denotes Dan
T261 129779-129787 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T262 130026-130027 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T263 130923-130924 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T264 131358-131359 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T265 131568-131572 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T266 131612-131617 http://purl.obolibrary.org/obo/CLO_0009985 denotes focus
T267 131630-131634 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T268 131651-131659 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T269 132176-132181 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T270 132241-132242 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T271 132264-132265 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T272 132291-132292 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T273 132354-132355 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T77778 7-8 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T32708 190-191 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T17685 206-211 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T97528 256-257 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T35994 358-363 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T15125 963-964 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T34822 1084-1085 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T15929 1136-1137 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T88489 1210-1213 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T44029 1221-1222 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T79838 1331-1334 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T84209 1342-1343 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T11156 1802-1804 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T1321 1898-1899 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T20418 2190-2191 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T33210 2201-2204 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T56537 2269-2270 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T14710 2528-2529 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T5958 2549-2556 http://purl.obolibrary.org/obo/UBERON_0000473 denotes testing
T70818 2602-2603 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T2693 2828-2829 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T73848 3028-3029 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T46124 3878-3881 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T768 3882-3891 http://www.ebi.ac.uk/efo/EFO_0000876 denotes extremely
T84574 4976-4977 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T27515 5342-5345 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T97004 5882-5885 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T26399 6281-6283 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T10521 6447-6448 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T91269 6449-6457 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T7501 6531-6552 http://purl.obolibrary.org/obo/PR_000036193 denotes amyloid beta peptides
T15351 6797-6798 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T61451 6983-6985 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T78635 6996-6997 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T85737 7326-7329 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T68234 7475-7476 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T99227 7509-7511 http://purl.obolibrary.org/obo/CLO_0054055 denotes 71
T43341 7719-7720 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T23700 7782-7783 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T82249 8131-8132 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T85549 8174-8179 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T55590 8281-8286 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T58445 8288-8289 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T92263 8449-8454 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T68728 8592-8597 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T45061 8637-8643 http://purl.obolibrary.org/obo/UBERON_0007688 denotes fields
T88556 8742-8747 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T91683 8937-8938 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T21171 9080-9086 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T51401 9090-9091 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T56863 9144-9151 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T47125 9350-9355 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T12208 9581-9582 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T78536 9633-9639 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T91135 9696-9702 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T25038 9762-9768 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T74964 10182-10185 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T81620 10205-10206 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92233 10411-10414 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T76872 10616-10618 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T13161 10703-10705 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T45199 10743-10747 http://purl.obolibrary.org/obo/UBERON_0000025 denotes tube
T90327 10751-10755 http://purl.obolibrary.org/obo/UBERON_0000025 denotes tube
T28659 10887-10889 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T4970 10975-10980 http://purl.obolibrary.org/obo/UBERON_0000178 denotes blood
T39983 10975-10980 http://www.ebi.ac.uk/efo/EFO_0000296 denotes blood
T71596 11070-11072 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T60852 11075-11077 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T71533 11547-11550 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T11494 11734-11735 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T62411 11819-11820 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T22590 11821-11827 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T23235 12148-12157 http://www.ebi.ac.uk/efo/EFO_0000876 denotes extremely
T66345 12202-12205 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T3179 12206-12207 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T38441 12293-12302 http://www.ebi.ac.uk/efo/EFO_0000876 denotes extremely
T85356 12392-12393 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T55626 12474-12475 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T7693 12719-12722 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T74928 12789-12795 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T89386 12825-12826 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T25318 12850-12860 http://purl.obolibrary.org/obo/UBERON_0003103 denotes in organic
T33905 13401-13402 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T68532 13421-13426 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T34126 13630-13633 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T31583 13634-13635 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T16829 13669-13676 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T20933 13709-13715 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T99257 13895-13901 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T77549 14086-14092 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T61613 14121-14122 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T96943 14313-14314 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T55349 14400-14401 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T77383 14416-14421 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T73188 14461-14462 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T78366 14514-14519 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T25547 14775-14776 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T31964 14844-14845 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T20822 14954-14955 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T63367 15143-15149 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T91886 15254-15255 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T73157 15396-15399 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T7374 15549-15556 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T55495 15564-15565 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T28108 15660-15663 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T85300 15802-15805 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T32942 15806-15807 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T90006 16273-16279 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T67222 16323-16324 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T67710 16661-16662 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T9295 16790-16791 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92474 17227-17233 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T45804 17440-17443 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T42617 17444-17445 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69056 17622-17623 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T13009 17755-17756 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T53392 17888-17889 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T47108 17935-17936 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T33086 18009-18016 http://purl.obolibrary.org/obo/CLO_0009985 denotes focuses
T45570 18106-18112 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T41073 18119-18120 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T98684 18223-18231 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T86896 18254-18257 http://purl.obolibrary.org/obo/CLO_0053001 denotes 114
T1229 18598-18604 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T1088 18621-18627 http://purl.obolibrary.org/obo/SO_0000418 denotes Signal
T92599 18869-18870 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T87879 18901-18902 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T52531 19196-19197 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T49797 19543-19551 http://purl.obolibrary.org/obo/NCBITaxon_2 denotes bacteria
T79755 19553-19555 http://purl.obolibrary.org/obo/CLO_0001527 denotes 94
T36380 19654-19655 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T78941 19704-19706 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T26738 19808-19809 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T50950 19856-19864 http://purl.obolibrary.org/obo/NCBITaxon_2 denotes bacteria
T83068 19907-19915 http://purl.obolibrary.org/obo/NCBITaxon_2 denotes bacteria
T72911 19961-19967 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T66455 20007-20008 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T71611 20126-20128 http://purl.obolibrary.org/obo/CLO_0001527 denotes 94
T15967 20228-20236 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T47909 20522-20525 http://purl.obolibrary.org/obo/CLO_0001053 denotes 121
T76054 20606-20611 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T47371 20648-20652 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T39170 21047-21052 http://purl.obolibrary.org/obo/CLO_0009985 denotes focus
T60635 21155-21156 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T17528 21605-21606 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92439 21640-21641 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T83859 21672-21673 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T91246 21700-21701 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69709 21722-21724 http://purl.obolibrary.org/obo/CLO_0050160 denotes t2
T91898 21809-21811 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T92124 21904-21906 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T26137 21954-21955 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T63635 21991-21993 http://purl.obolibrary.org/obo/CLO_0003401 denotes FT
T78725 22848-22849 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T76502 22860-22863 http://purl.obolibrary.org/obo/CLO_0054061 denotes 132
T42866 23203-23208 http://purl.obolibrary.org/obo/UBERON_0000178 denotes blood
T98943 23203-23208 http://www.ebi.ac.uk/efo/EFO_0000296 denotes blood
T84919 23554-23556 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T56516 23656-23657 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T86496 23831-23836 http://purl.obolibrary.org/obo/UBERON_0000178 denotes blood
T59085 23831-23836 http://www.ebi.ac.uk/efo/EFO_0000296 denotes blood
T91276 24130-24131 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T16293 24297-24298 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T61631 24382-24383 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T75997 24407-24408 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T45961 24663-24664 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T2549 24743-24744 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T36623 24776-24777 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T51654 25060-25061 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T1722 25550-25551 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T27590 25908-25914 http://purl.obolibrary.org/obo/UBERON_0000310 denotes breast
T45515 26681-26687 http://purl.obolibrary.org/obo/UBERON_0000310 denotes breast
T6025 26763-26764 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92227 27710-27717 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T84020 27710-27717 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T7565 28045-28055 http://purl.obolibrary.org/obo/CL_0000066 denotes epithelial
T25877 28081-28087 http://purl.obolibrary.org/obo/CLO_0009063 denotes Skov-3
T65918 28081-28087 http://purl.obolibrary.org/obo/CLO_0052004 denotes Skov-3
T15262 28081-28087 http://purl.obolibrary.org/obo/CLO_0052005 denotes Skov-3
T84733 28081-28087 http://purl.obolibrary.org/obo/CLO_0052006 denotes Skov-3
T563 28081-28087 http://purl.obolibrary.org/obo/CLO_0052007 denotes Skov-3
T68261 28088-28093 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T18385 28190-28196 http://purl.obolibrary.org/obo/CLO_0009063 denotes Skov-3
T7784 28190-28196 http://purl.obolibrary.org/obo/CLO_0052004 denotes Skov-3
T18201 28190-28196 http://purl.obolibrary.org/obo/CLO_0052005 denotes Skov-3
T44166 28190-28196 http://purl.obolibrary.org/obo/CLO_0052006 denotes Skov-3
T15184 28190-28196 http://purl.obolibrary.org/obo/CLO_0052007 denotes Skov-3
T72019 28197-28202 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T67725 28353-28358 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes Human
T49059 28481-28487 http://purl.obolibrary.org/obo/CLO_0009063 denotes Skov-3
T24432 28481-28487 http://purl.obolibrary.org/obo/CLO_0052004 denotes Skov-3
T13031 28481-28487 http://purl.obolibrary.org/obo/CLO_0052005 denotes Skov-3
T58426 28481-28487 http://purl.obolibrary.org/obo/CLO_0052006 denotes Skov-3
T52203 28481-28487 http://purl.obolibrary.org/obo/CLO_0052007 denotes Skov-3
T21105 28488-28493 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T98431 28542-28548 http://purl.obolibrary.org/obo/CLO_0009063 denotes Skov-3
T53038 28542-28548 http://purl.obolibrary.org/obo/CLO_0052004 denotes Skov-3
T12991 28542-28548 http://purl.obolibrary.org/obo/CLO_0052005 denotes Skov-3
T66845 28542-28548 http://purl.obolibrary.org/obo/CLO_0052006 denotes Skov-3
T99568 28542-28548 http://purl.obolibrary.org/obo/CLO_0052007 denotes Skov-3
T50576 28549-28554 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T80995 28679-28684 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T54819 28761-28762 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69803 28843-28849 http://purl.obolibrary.org/obo/CLO_0009063 denotes Skov-3
T3282 28843-28849 http://purl.obolibrary.org/obo/CLO_0052004 denotes Skov-3
T25858 28843-28849 http://purl.obolibrary.org/obo/CLO_0052005 denotes Skov-3
T4936 28843-28849 http://purl.obolibrary.org/obo/CLO_0052006 denotes Skov-3
T20172 28843-28849 http://purl.obolibrary.org/obo/CLO_0052007 denotes Skov-3
T80018 28850-28855 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T84214 29287-29290 http://purl.obolibrary.org/obo/CLO_0001079 denotes 148
T6479 29464-29465 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T20389 29807-29808 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T21966 29962-29963 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T74078 30158-30160 http://purl.obolibrary.org/obo/CLO_0007622 denotes MD
T25528 30223-30224 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T81398 30360-30366 http://purl.obolibrary.org/obo/UBERON_0002113 denotes kidney
T40369 30360-30366 http://www.ebi.ac.uk/efo/EFO_0000927 denotes kidney
T23231 30360-30366 http://www.ebi.ac.uk/efo/EFO_0000929 denotes kidney
T2572 30372-30377 http://purl.obolibrary.org/obo/UBERON_0002107 denotes liver
T95714 30372-30377 http://www.ebi.ac.uk/efo/EFO_0000887 denotes liver
T49055 30566-30573 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T39599 30810-30811 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T14589 30957-30964 http://purl.obolibrary.org/obo/UBERON_0002113 denotes kidneys
T43132 30957-30964 http://www.ebi.ac.uk/efo/EFO_0000927 denotes kidneys
T76931 30957-30964 http://www.ebi.ac.uk/efo/EFO_0000929 denotes kidneys
T29795 30969-30974 http://purl.obolibrary.org/obo/UBERON_0002107 denotes liver
T14410 30969-30974 http://www.ebi.ac.uk/efo/EFO_0000887 denotes liver
T94198 31040-31041 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T56129 31096-31102 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T5556 31195-31196 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92788 31650-31652 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T84489 31766-31767 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T58840 31809-31811 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T62015 31922-31924 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T43160 32102-32104 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T17546 32269-32270 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T33912 32309-32310 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T82452 32565-32571 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T73705 32600-32606 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T4765 32618-32621 http://purl.obolibrary.org/obo/CLO_0001002 denotes 162
T99665 33008-33009 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T91826 33018-33021 http://purl.obolibrary.org/obo/CLO_0001003 denotes 163
T95563 33047-33048 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T10689 33122-33123 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T87448 33488-33489 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T90168 34038-34050 http://purl.obolibrary.org/obo/UBERON_0001969 denotes blood plasma
T40421 34266-34268 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T16944 34332-34336 http://purl.obolibrary.org/obo/UBERON_0002535 denotes Gill
T99850 34453-34454 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T53426 34476-34477 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T70539 34523-34524 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T40931 34736-34737 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T32172 34988-34992 http://purl.obolibrary.org/obo/UBERON_0002535 denotes Gill
T47725 35156-35158 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T26340 35402-35408 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T37945 35426-35427 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T67693 35540-35546 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T74144 35556-35557 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T61672 35570-35571 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T776 35656-35657 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T90184 35674-35680 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T29187 35704-35706 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T80855 35787-35789 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T17769 35791-35793 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T1564 35888-35893 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T88676 35973-35975 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T90343 36054-36055 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T92264 36076-36078 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T51742 36290-36292 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T65081 36557-36558 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T76730 36637-36639 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T85793 36856-36858 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T71306 37634-37635 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T274 37750-37751 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T275 37789-37790 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T276 37871-37878 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T277 37871-37878 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T278 37888-37891 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T279 38220-38223 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T280 38299-38302 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T281 38459-38460 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T282 38485-38493 http://purl.obolibrary.org/obo/CLO_0001658 denotes Activity
T283 38809-38811 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T284 39073-39077 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T285 39215-39219 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T286 39497-39498 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T287 39700-39701 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T288 39826-39827 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T289 39876-39877 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T290 40213-40216 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T291 40516-40517 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T292 40557-40558 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T293 40583-40584 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T294 40625-40626 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T295 40730-40731 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T296 41608-41609 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T297 41680-41683 http://purl.obolibrary.org/obo/CLO_0001196 denotes 225
T298 41780-41781 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T299 42314-42322 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T300 42429-42438 http://www.ebi.ac.uk/efo/EFO_0000876 denotes extremely
T301 42563-42564 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T302 43276-43277 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T303 43341-43342 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T304 44621-44624 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T305 44814-44816 http://purl.obolibrary.org/obo/CLO_0050160 denotes T2
T306 45252-45253 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T307 45345-45346 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T308 45399-45400 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T309 45510-45511 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T310 45587-45588 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T311 45636-45642 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T312 45715-45723 http://purl.obolibrary.org/obo/PR_000001898 denotes called a
T313 45812-45818 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T314 45914-45915 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T315 45966-45967 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T316 46095-46096 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T317 46120-46121 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T318 46240-46243 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T319 46244-46245 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T320 46296-46297 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T321 46308-46314 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T322 46320-46321 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T323 46377-46383 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T324 46435-46436 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T325 46437-46443 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T326 46479-46480 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T327 46716-46717 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T328 46825-46831 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T329 47322-47323 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T330 47589-47595 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T331 47704-47707 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T332 48079-48082 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T333 48314-48319 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T334 48454-48461 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T335 48467-48468 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T336 48736-48744 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T337 48770-48773 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T338 48916-48921 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T339 49018-49023 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T340 49079-49086 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T341 49187-49192 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T342 49305-49310 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T343 49384-49391 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T344 49531-49536 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T345 49630-49631 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T346 49632-49637 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T347 49767-49770 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T348 49883-49888 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T349 49948-49949 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T350 50076-50077 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T351 50436-50443 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes viruses
T352 50482-50487 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T353 50560-50561 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T354 50832-50833 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T437 60814-60815 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T438 60864-60869 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T439 60879-60884 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T440 61004-61010 http://purl.obolibrary.org/obo/CLO_0007225 denotes labels
T441 61039-61045 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T442 61100-61104 http://purl.obolibrary.org/obo/UBERON_0000025 denotes tube
T443 61234-61241 http://purl.obolibrary.org/obo/CLO_0009985 denotes focuses
T444 61281-61282 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T445 61283-61289 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T446 61316-61317 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T447 61397-61405 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T448 61413-61419 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T449 61438-61439 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T450 61662-61668 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T451 61780-61782 http://purl.obolibrary.org/obo/CLO_0003414 denotes g2
T452 61862-61868 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T453 62141-62147 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T454 62345-62346 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T455 62712-62713 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T456 62827-62830 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T457 63261-63269 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T458 63382-63389 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T459 63443-63444 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T460 63538-63545 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T461 63614-63621 http://purl.obolibrary.org/obo/SO_0000418 denotes signals
T462 63727-63728 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T463 64006-64012 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T464 64621-64622 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T465 64640-64641 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T466 64681-64682 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T467 65149-65150 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T468 65491-65492 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T469 65546-65549 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T470 65585-65586 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T471 65718-65719 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T472 65779-65782 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T473 65816-65819 http://purl.obolibrary.org/obo/CLO_0001006 denotes 311
T474 66499-66502 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T475 66721-66722 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T476 66885-66886 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T477 66914-66915 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T478 66966-66971 http://purl.obolibrary.org/obo/CLO_0001236 denotes (2) a
T479 67023-67026 http://purl.obolibrary.org/obo/CLO_0001294 denotes 322
T480 67164-67165 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T481 67200-67203 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T482 67497-67500 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T483 67805-67806 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T484 68011-68012 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T485 68169-68170 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T486 68994-68995 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T487 69054-69055 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T488 69088-69089 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T489 69133-69139 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T490 69199-69200 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T491 69431-69437 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T492 69459-69465 http://purl.obolibrary.org/obo/UBERON_0000473 denotes tested
T493 69470-69476 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T494 69495-69500 http://purl.obolibrary.org/obo/CLO_0002932 denotes EOL-1
T495 69501-69506 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T496 69612-69618 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T497 69652-69660 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T498 69694-69700 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T499 69784-69785 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T500 69893-69901 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T501 70325-70327 http://purl.obolibrary.org/obo/CLO_0001022 denotes Li
T502 70325-70327 http://purl.obolibrary.org/obo/CLO_0007314 denotes Li
T503 70515-70518 http://purl.obolibrary.org/obo/PR_000017298 denotes VIM
T504 70714-70722 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T505 71195-71196 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T506 71494-71495 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T507 71572-71573 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T508 71896-71897 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T509 72223-72224 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T510 72349-72356 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T511 72349-72356 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T512 72372-72373 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T513 72514-72515 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T514 72774-72775 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T515 72817-72818 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T516 72973-72974 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T517 73647-73648 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T518 73762-73763 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T519 73809-73810 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T520 73831-73832 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T521 73855-73856 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T522 73919-73920 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T523 74119-74120 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T524 74281-74282 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T525 74317-74318 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T526 74358-74359 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T527 74442-74443 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T528 74468-74469 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T529 74983-74989 http://purl.obolibrary.org/obo/CLO_0001658 denotes active
T530 75084-75085 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T531 75201-75204 http://purl.obolibrary.org/obo/CLO_0001310 denotes 351
T532 75513-75514 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T533 75699-75700 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T534 75916-75924 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T535 76011-76012 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T536 76096-76104 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T537 76868-76871 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T538 76940-76948 http://purl.obolibrary.org/obo/CHEBI_3815 denotes collagen
T539 77009-77012 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T540 77037-77042 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T541 77081-77082 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T542 77128-77129 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T543 77171-77179 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T544 77242-77243 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T545 77367-77368 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T546 77390-77391 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T547 77420-77421 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T548 77588-77589 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T549 77803-77804 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T550 77836-77843 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T551 77836-77843 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T552 78227-78228 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T553 78631-78632 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T554 78648-78651 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T555 78657-78658 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T556 78986-78987 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T557 79201-79203 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T558 79318-79319 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T559 79453-79462 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membranes
T560 79467-79475 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T561 79586-79594 http://purl.obolibrary.org/obo/UBERON_0000158 denotes membrane
T562 79640-79641 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T96610 79664-79666 http://purl.obolibrary.org/obo/PR_000005794 denotes CP
T564 80109-80110 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T565 80177-80185 http://purl.obolibrary.org/obo/PR_000018263 denotes peptides
T566 80255-80256 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T567 80350-80351 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T568 80386-80387 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T569 80696-80697 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T570 80768-80769 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T571 80790-80791 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T572 80823-80824 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T573 80856-80857 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T574 80975-80976 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T575 81085-81086 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T576 81163-81168 http://purl.obolibrary.org/obo/GO_0005623 denotes cells
T577 81173-81183 http://purl.obolibrary.org/obo/CLO_0000031 denotes cell lines
T578 81184-81194 http://purl.obolibrary.org/obo/CLO_0007634 denotes MDA-MB-231
T579 81184-81194 http://purl.obolibrary.org/obo/CLO_0037291 denotes MDA-MB-231
T580 81196-81202 http://purl.obolibrary.org/obo/UBERON_0000310 denotes breast
T581 81215-81219 http://purl.obolibrary.org/obo/CLO_0001601 denotes A549
T582 81215-81219 http://purl.obolibrary.org/obo/CLO_0050025 denotes A549
T583 81215-81219 http://purl.obolibrary.org/obo/CLO_0054264 denotes A549
T584 81215-81219 http://purl.obolibrary.org/obo/CLO_0054265 denotes A549
T585 81215-81219 http://purl.obolibrary.org/obo/CLO_0054266 denotes A549
T586 81215-81219 http://purl.obolibrary.org/obo/CLO_0054267 denotes A549
T587 81215-81219 http://purl.obolibrary.org/obo/CLO_0054268 denotes A549
T588 81215-81219 http://purl.obolibrary.org/obo/CLO_0054269 denotes A549
T589 81221-81225 http://purl.obolibrary.org/obo/UBERON_0002048 denotes lung
T590 81221-81225 http://www.ebi.ac.uk/efo/EFO_0000934 denotes lung
T591 81257-81258 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T592 81571-81575 http://purl.obolibrary.org/obo/GO_0005623 denotes cell
T593 81722-81723 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T594 82138-82145 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T595 82475-82476 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T596 82477-82480 http://purl.obolibrary.org/obo/CLO_0053733 denotes 1:1
T597 82491-82498 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T598 82722-82723 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T599 82791-82792 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T600 82802-82803 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T601 82829-82830 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T602 82878-82879 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T603 82955-82956 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T604 83012-83020 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T605 83163-83164 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T606 83322-83330 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T607 83424-83425 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T608 83573-83574 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T609 83637-83638 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T610 84018-84019 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T611 84054-84062 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T612 84095-84096 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T613 84454-84462 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T614 84528-84536 http://purl.obolibrary.org/obo/CLO_0001658 denotes activity
T615 84709-84710 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T616 84812-84815 http://purl.obolibrary.org/obo/CLO_0001319 denotes 372
T617 84856-84864 http://purl.obolibrary.org/obo/PR_000001898 denotes called A
T618 85029-85030 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T619 85031-85035 http://purl.obolibrary.org/obo/UBERON_0000473 denotes test
T620 85131-85136 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes human
T621 85259-85266 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeled
T622 85299-85306 http://purl.obolibrary.org/obo/UBERON_0000473 denotes testing
T623 85550-85554 http://purl.obolibrary.org/obo/UBERON_0000473 denotes test
T624 85942-85943 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T625 86039-86042 http://purl.obolibrary.org/obo/CLO_0001319 denotes 372
T626 86519-86522 http://purl.obolibrary.org/obo/CLO_0001007 denotes 380
T627 86693-86694 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T628 86734-86739 http://purl.obolibrary.org/obo/NCBITaxon_9606 denotes Human
T629 86757-86762 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T630 87665-87666 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T631 87803-87804 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T632 88072-88073 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T633 88107-88110 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T634 88296-88298 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T635 89338-89339 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T636 89530-89531 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T637 89607-89608 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T638 89693-89694 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T639 89939-89940 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T640 89969-89976 http://purl.obolibrary.org/obo/PR_000018263 denotes peptide
T641 90041-90042 http://purl.obolibrary.org/obo/CLO_0001021 denotes B
T642 90183-90187 http://purl.obolibrary.org/obo/UBERON_0002535 denotes Gill
T643 91229-91230 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T644 91271-91272 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T645 91357-91358 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T646 91568-91571 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T647 91593-91598 http://purl.obolibrary.org/obo/UBERON_0007688 denotes field
T648 92428-92429 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T649 92438-92447 http://purl.obolibrary.org/obo/CLO_0001658 denotes activated
T650 92559-92561 http://purl.obolibrary.org/obo/CLO_0003599 denotes H4
T651 92563-92565 http://purl.obolibrary.org/obo/CLO_0003607 denotes H5
T652 92727-92728 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T653 93002-93003 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T654 93139-93140 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T655 93340-93341 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T656 93477-93478 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T657 93506-93512 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T658 93844-93845 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T659 94018-94020 http://purl.obolibrary.org/obo/CLO_0007874 denotes ms
T660 94109-94114 http://purl.obolibrary.org/obo/UBERON_0000948 denotes heart
T661 94109-94114 http://purl.obolibrary.org/obo/UBERON_0007100 denotes heart
T662 94109-94114 http://purl.obolibrary.org/obo/UBERON_0015228 denotes heart
T663 94109-94114 http://www.ebi.ac.uk/efo/EFO_0000815 denotes heart
T664 94261-94264 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T665 94313-94314 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T666 94397-94405 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T667 94546-94547 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T668 94834-94837 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T669 95085-95088 http://purl.obolibrary.org/obo/CLO_0037067 denotes Val
T670 95526-95527 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T671 95588-95597 http://purl.obolibrary.org/obo/CLO_0007225 denotes Labelling
T672 95598-95599 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T673 95705-95713 http://purl.obolibrary.org/obo/CLO_0007225 denotes labeling
T674 95743-95744 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T675 96048-96054 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T676 96071-96077 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T677 96185-96202 http://purl.obolibrary.org/obo/GO_0043234 denotes protein complexes
T678 96502-96508 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T679 96681-96682 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T680 96782-96787 http://purl.obolibrary.org/obo/NCBITaxon_10239 denotes virus
T681 96879-96880 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T682 97357-97363 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T683 97404-97410 http://purl.obolibrary.org/obo/SO_0000418 denotes signal
T684 97980-97981 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T685 98214-98215 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T686 98286-98287 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T687 98986-98987 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T688 99108-99109 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T689 99239-99240 http://purl.obolibrary.org/obo/CLO_0001020 denotes a

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T1 10-14 Chemical denotes Gold http://purl.obolibrary.org/obo/CHEBI_29287
T2 131-135 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T3 334-338 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T4 894-898 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T5 945-949 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T6 1009-1013 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T7 1240-1244 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T8 1345-1349 Chemical denotes gold http://purl.obolibrary.org/obo/CHEBI_29287|http://purl.obolibrary.org/obo/CHEBI_30050
T10 1498-1502 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T11 1712-1716 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T12 2001-2005 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T13 2047-2061 Chemical denotes pharmaceutical http://purl.obolibrary.org/obo/CHEBI_52217
T14 2118-2123 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T15 2196-2200 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T16 2278-2282 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T17 2508-2512 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T18 2701-2705 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T19 2959-2964 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T20 3752-3761 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T21 4314-4323 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T22 4619-4623 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T23 4712-4718 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T24 4780-4787 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
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T137 17161-17168 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
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T142 17204-17214 Chemical denotes synephrine http://purl.obolibrary.org/obo/CHEBI_29081|http://purl.obolibrary.org/obo/CHEBI_58606
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T145 17513-17515 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
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T221 23892-23894 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
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T51558 81106-81114 Chemical denotes platinum http://purl.obolibrary.org/obo/CHEBI_33364|http://purl.obolibrary.org/obo/CHEBI_33400
T28706 81184-81187 Chemical denotes MDA http://purl.obolibrary.org/obo/CHEBI_566274
T28722 81272-81274 Chemical denotes HL http://purl.obolibrary.org/obo/CHEBI_5729
T59735 81283-81291 Chemical denotes platinum http://purl.obolibrary.org/obo/CHEBI_33364|http://purl.obolibrary.org/obo/CHEBI_33400
T76399 81391-81393 Chemical denotes LL http://purl.obolibrary.org/obo/CHEBI_73531
T77435 81422-81424 Chemical denotes HL http://purl.obolibrary.org/obo/CHEBI_5729
T363 81617-81628 Chemical denotes application http://purl.obolibrary.org/obo/CHEBI_33232
T3032 81733-81737 Chemical denotes zinc http://purl.obolibrary.org/obo/CHEBI_27363|http://purl.obolibrary.org/obo/CHEBI_30185
T26284 81746-81760 Chemical denotes amyloid fibril http://purl.obolibrary.org/obo/CHEBI_60425
T367 81776-81781 Chemical denotes ester http://purl.obolibrary.org/obo/CHEBI_35701
T45869 81801-81805 Chemical denotes ions http://purl.obolibrary.org/obo/CHEBI_24870
T22041 81814-81818 Chemical denotes zinc http://purl.obolibrary.org/obo/CHEBI_27363|http://purl.obolibrary.org/obo/CHEBI_30185
T18081 81856-81863 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T372 82045-82050 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T24146 82121-82123 Chemical denotes Ac http://purl.obolibrary.org/obo/CHEBI_33337|http://purl.obolibrary.org/obo/CHEBI_40574
T78081 82138-82145 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T62710 82159-82162 Chemical denotes HHQ http://purl.obolibrary.org/obo/CHEBI_75306
T29394 82193-82196 Chemical denotes Zn2 http://purl.obolibrary.org/obo/CHEBI_37256
T73677 82198-82201 Chemical denotes HHQ http://purl.obolibrary.org/obo/CHEBI_75306
T93881 82240-82243 Chemical denotes Zn2 http://purl.obolibrary.org/obo/CHEBI_37256
T21514 82251-82254 Chemical denotes HHQ http://purl.obolibrary.org/obo/CHEBI_75306
T81340 82364-82367 Chemical denotes Zn2 http://purl.obolibrary.org/obo/CHEBI_37256
T13193 82433-82436 Chemical denotes Zn2 http://purl.obolibrary.org/obo/CHEBI_37256
T72066 82461-82464 Chemical denotes Zn2 http://purl.obolibrary.org/obo/CHEBI_37256
T34901 82487-82490 Chemical denotes ion http://purl.obolibrary.org/obo/CHEBI_24870
T47363 82491-82498 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T21736 82589-82597 Chemical denotes zinc ion http://purl.obolibrary.org/obo/CHEBI_27365
T1487 82589-82593 Chemical denotes zinc http://purl.obolibrary.org/obo/CHEBI_27363|http://purl.obolibrary.org/obo/CHEBI_30185
T21535 82594-82597 Chemical denotes ion http://purl.obolibrary.org/obo/CHEBI_24870
T390 82623-82632 Chemical denotes histidine http://purl.obolibrary.org/obo/CHEBI_27570
T68900 82704-82707 Chemical denotes Zn2 http://purl.obolibrary.org/obo/CHEBI_37256
T5849 82709-82713 Chemical denotes ions http://purl.obolibrary.org/obo/CHEBI_24870
T62464 82804-82812 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T30980 83273-83281 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T13331 83395-83399 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T9620 83492-83497 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T33030 83523-83531 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T2096 83576-83580 Chemical denotes gold http://purl.obolibrary.org/obo/CHEBI_29287|http://purl.obolibrary.org/obo/CHEBI_30050
T91775 83604-83608 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T59537 83657-83661 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T77020 83751-83755 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T83203 83761-83771 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T23728 83809-83812 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T91597 83863-83874 Chemical denotes L-aspartate http://purl.obolibrary.org/obo/CHEBI_29991|http://purl.obolibrary.org/obo/CHEBI_29993
T69299 83865-83874 Chemical denotes aspartate http://purl.obolibrary.org/obo/CHEBI_132943|http://purl.obolibrary.org/obo/CHEBI_29995|http://purl.obolibrary.org/obo/CHEBI_72314
T96973 83898-83905 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T33547 83910-83924 Chemical denotes carbon dioxide http://purl.obolibrary.org/obo/CHEBI_16526
T30476 83910-83916 Chemical denotes carbon http://purl.obolibrary.org/obo/CHEBI_27594|http://purl.obolibrary.org/obo/CHEBI_33415
T5496 83985-83995 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T92820 83999-84002 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T41804 84066-84069 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T91787 84088-84091 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T96763 84097-84105 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T44515 84109-84120 Chemical denotes L-aspartate http://purl.obolibrary.org/obo/CHEBI_29991|http://purl.obolibrary.org/obo/CHEBI_29993
T97142 84111-84120 Chemical denotes aspartate http://purl.obolibrary.org/obo/CHEBI_132943|http://purl.obolibrary.org/obo/CHEBI_29995|http://purl.obolibrary.org/obo/CHEBI_72314
T6242 84122-84133 Chemical denotes L-aspartate http://purl.obolibrary.org/obo/CHEBI_29991|http://purl.obolibrary.org/obo/CHEBI_29993
T69446 84124-84133 Chemical denotes aspartate http://purl.obolibrary.org/obo/CHEBI_132943|http://purl.obolibrary.org/obo/CHEBI_29995|http://purl.obolibrary.org/obo/CHEBI_72314
T40549 84164-84167 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T435 84185-84196 Chemical denotes L-aspartate http://purl.obolibrary.org/obo/CHEBI_29991|http://purl.obolibrary.org/obo/CHEBI_29993
T41649 84187-84196 Chemical denotes aspartate http://purl.obolibrary.org/obo/CHEBI_132943|http://purl.obolibrary.org/obo/CHEBI_29995|http://purl.obolibrary.org/obo/CHEBI_72314
T440 84202-84209 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T69358 84243-84254 Chemical denotes L-aspartate http://purl.obolibrary.org/obo/CHEBI_29991|http://purl.obolibrary.org/obo/CHEBI_29993
T70918 84245-84254 Chemical denotes aspartate http://purl.obolibrary.org/obo/CHEBI_132943|http://purl.obolibrary.org/obo/CHEBI_29995|http://purl.obolibrary.org/obo/CHEBI_72314
T65900 84294-84301 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T65308 84331-84334 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T75103 84339-84348 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T9845 84349-84353 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T10921 84440-84443 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T60253 84568-84578 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T31433 84582-84585 Chemical denotes ADC http://purl.obolibrary.org/obo/CHEBI_18198|http://purl.obolibrary.org/obo/CHEBI_35181
T18141 84672-84677 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T21665 84690-84695 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T95003 84865-84867 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T87043 85048-85055 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T15847 85082-85085 Chemical denotes DTT http://purl.obolibrary.org/obo/CHEBI_18320
T34147 85137-85139 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T40887 85140-85147 Chemical denotes antigen http://purl.obolibrary.org/obo/CHEBI_59132
T98818 85267-85269 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T99168 85270-85277 Chemical denotes antigen http://purl.obolibrary.org/obo/CHEBI_59132
T86355 85287-85294 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T82641 85326-85328 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T56507 85329-85336 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T98917 85555-85564 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T43119 85589-85599 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T59928 85603-85610 Chemical denotes histone http://purl.obolibrary.org/obo/CHEBI_15358
T28691 85635-85645 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T34467 85745-85759 Chemical denotes HAT inhibitors http://purl.obolibrary.org/obo/CHEBI_76395
T53938 85749-85759 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T44175 86265-86269 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T21417 86298-86302 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T76860 86670-86674 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T477 86705-86719 Chemical denotes benzodiazepine http://purl.obolibrary.org/obo/CHEBI_22720
T478 86720-86730 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T479 86968-86982 Chemical denotes benzodiazepine http://purl.obolibrary.org/obo/CHEBI_22720
T480 86983-86993 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T481 87052-87062 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T482 87181-87195 Chemical denotes benzodiazepine http://purl.obolibrary.org/obo/CHEBI_22720
T483 87196-87206 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T484 87221-87232 Chemical denotes amino acids http://purl.obolibrary.org/obo/CHEBI_33709
T485 87221-87226 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T486 87227-87232 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T487 87264-87278 Chemical denotes benzodiazepine http://purl.obolibrary.org/obo/CHEBI_22720
T488 87279-87289 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T489 87346-87348 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T490 87446-87460 Chemical denotes benzodiazepine http://purl.obolibrary.org/obo/CHEBI_22720
T491 87461-87471 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T492 87562-87576 Chemical denotes benzodiazepine http://purl.obolibrary.org/obo/CHEBI_22720
T493 87577-87587 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T494 87835-87842 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T495 87843-87850 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T496 88044-88052 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T497 88074-88081 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T498 88082-88089 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T499 88250-88258 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T500 88599-88601 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T501 88749-88751 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T502 88964-88966 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T503 89072-89081 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T504 89094-89101 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T505 89306-89313 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T506 89349-89353 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T507 89593-89603 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T508 89609-89616 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T509 89617-89624 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T510 89705-89709 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T511 89764-89772 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T512 89806-89811 Chemical denotes alpha http://purl.obolibrary.org/obo/CHEBI_30216
T513 89884-89894 Chemical denotes inhibitors http://purl.obolibrary.org/obo/CHEBI_35222
T514 89969-89976 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T515 90245-90249 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T516 90273-90277 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T517 90349-90357 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T518 90600-90609 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T519 90759-90766 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T520 90801-90810 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T521 90938-90946 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T522 91255-91259 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T523 91273-91280 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T524 91281-91288 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T525 91397-91401 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T526 91679-91683 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T527 92123-92129 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T528 92198-92205 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T529 92293-92300 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T530 92430-92437 Chemical denotes mitogen http://purl.obolibrary.org/obo/CHEBI_52290
T531 92448-92455 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T532 92472-92481 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T533 92482-92490 Chemical denotes SB203580 http://purl.obolibrary.org/obo/CHEBI_90705
T534 92577-92585 Chemical denotes SB203580 http://purl.obolibrary.org/obo/CHEBI_90705
T535 92661-92663 Chemical denotes H2 http://purl.obolibrary.org/obo/CHEBI_18276
T536 92673-92679 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T538 92729-92742 Chemical denotes pyridine ring http://purl.obolibrary.org/obo/CHEBI_52884
T539 92729-92737 Chemical denotes pyridine http://purl.obolibrary.org/obo/CHEBI_16227
T540 92769-92777 Chemical denotes SB203580 http://purl.obolibrary.org/obo/CHEBI_90705
T541 92848-92854 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T542 92884-92890 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T543 92926-92934 Chemical denotes SB203580 http://purl.obolibrary.org/obo/CHEBI_90705
T544 93021-93028 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T545 93029-93035 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T546 93210-93216 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T547 93291-93298 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T548 93342-93349 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T549 93379-93386 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T550 93488-93494 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T551 93495-93501 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T552 93534-93541 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T553 93588-93595 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T554 93717-93723 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T555 93849-93856 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T556 93887-93895 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T557 94067-94076 Chemical denotes glycolate http://purl.obolibrary.org/obo/CHEBI_29805
T558 94077-94080 Chemical denotes NAD http://purl.obolibrary.org/obo/CHEBI_13389|http://purl.obolibrary.org/obo/CHEBI_15846
T560 94144-94151 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T562 94154-94163 Chemical denotes phosphate http://purl.obolibrary.org/obo/CHEBI_18367|http://purl.obolibrary.org/obo/CHEBI_26020|http://purl.obolibrary.org/obo/CHEBI_35780|http://purl.obolibrary.org/obo/CHEBI_43474
T566 94164-94169 Chemical denotes NADPH http://purl.obolibrary.org/obo/CHEBI_16474|http://purl.obolibrary.org/obo/CHEBI_57783
T17092 94206-94213 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T570 94456-94462 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T571 94488-94495 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T572 94565-94575 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T573 94565-94570 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T574 94571-94575 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T575 94645-94651 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T576 94660-94670 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T577 94660-94665 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T578 94666-94670 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T579 94746-94753 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T580 94796-94803 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T581 94804-94810 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T582 94909-94922 Chemical denotes benzimidazole http://purl.obolibrary.org/obo/CHEBI_36622|http://purl.obolibrary.org/obo/CHEBI_41275
T584 94945-94952 Chemical denotes uridine http://purl.obolibrary.org/obo/CHEBI_16704
T585 94985-94995 Chemical denotes UDP-GlcNAc http://purl.obolibrary.org/obo/CHEBI_16264
T586 94985-94988 Chemical denotes UDP http://purl.obolibrary.org/obo/CHEBI_17659|http://purl.obolibrary.org/obo/CHEBI_58223
T588 94989-94995 Chemical denotes GlcNAc http://purl.obolibrary.org/obo/CHEBI_506227|http://purl.obolibrary.org/obo/CHEBI_73685
T590 95061-95072 Chemical denotes amino acids http://purl.obolibrary.org/obo/CHEBI_33709
T591 95061-95066 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T592 95067-95072 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T593 95080-95083 Chemical denotes Ile http://purl.obolibrary.org/obo/CHEBI_17191|http://purl.obolibrary.org/obo/CHEBI_30009
T595 95085-95088 Chemical denotes Val http://purl.obolibrary.org/obo/CHEBI_16414|http://purl.obolibrary.org/obo/CHEBI_30015
T597 95090-95093 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T600 95095-95098 Chemical denotes Met http://purl.obolibrary.org/obo/CHEBI_16044|http://purl.obolibrary.org/obo/CHEBI_16643|http://purl.obolibrary.org/obo/CHEBI_16811
T603 95106-95109 Chemical denotes Trp http://purl.obolibrary.org/obo/CHEBI_16828|http://purl.obolibrary.org/obo/CHEBI_27897|http://purl.obolibrary.org/obo/CHEBI_29954
T606 95111-95114 Chemical denotes Phe http://purl.obolibrary.org/obo/CHEBI_17295|http://purl.obolibrary.org/obo/CHEBI_29997
T608 95204-95210 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T609 95257-95268 Chemical denotes amino acids http://purl.obolibrary.org/obo/CHEBI_33709
T610 95257-95262 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T611 95263-95268 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T612 95314-95320 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T613 95411-95415 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T614 95582-95587 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T615 95722-95727 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T616 95745-95761 Chemical denotes tert-butyl group http://purl.obolibrary.org/obo/CHEBI_30355
T617 95750-95755 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T618 95756-95761 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T619 95779-95785 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T620 95831-95838 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T621 95839-95845 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T622 95865-95881 Chemical denotes tert-butyl group http://purl.obolibrary.org/obo/CHEBI_30355
T623 95870-95875 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T624 95876-95881 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T625 95948-95954 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T627 95968-95974 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T629 96001-96006 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
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T23797 98227-98234 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
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T55729 98622-98629 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
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T85582 98891-98897 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T46490 98903-98909 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
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T3389 99096-99102 Chemical denotes proton http://purl.obolibrary.org/obo/CHEBI_24636
T5082 99120-99127 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T39367 99143-99161 Chemical denotes triazolopyridazine http://purl.obolibrary.org/obo/CHEBI_48384
T28009 99204-99209 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T17318 99279-99286 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T1462 99368-99375 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
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T45570 99467-99473 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T6158 99482-99494 Chemical denotes methyl group http://purl.obolibrary.org/obo/CHEBI_32875
T85158 99482-99488 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_29309
T13480 99489-99494 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
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T32483 100271-100277 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
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T60908 100621-100627 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T47768 100649-100656 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T66836 100747-100753 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
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T57200 101232-101239 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T43008 101291-101298 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T28259 101368-101374 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T70946 101405-101412 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T39339 101474-101480 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T77983 101536-101543 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T24857 101564-101566 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
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T60641 101662-101670 Chemical denotes hydrogen http://purl.obolibrary.org/obo/CHEBI_49637
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T41675 101808-101818 Chemical denotes naphthoate http://purl.obolibrary.org/obo/CHEBI_25482
T79793 101819-101824 Chemical denotes ester http://purl.obolibrary.org/obo/CHEBI_35701
T85096 101855-101865 Chemical denotes fatty acid http://purl.obolibrary.org/obo/CHEBI_35366
T48890 101861-101865 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T92250 101874-101881 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T53375 101891-101900 Chemical denotes ketorolac http://purl.obolibrary.org/obo/CHEBI_6129
T64655 101901-101904 Chemical denotes ANS http://purl.obolibrary.org/obo/CHEBI_39708
T63906 101993-101999 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T65279 102036-102043 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T23599 102044-102050 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T79552 102196-102203 Chemical denotes Protein http://purl.obolibrary.org/obo/CHEBI_16541
T41635 102284-102292 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T4092 102345-102352 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T35786 102435-102442 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T89568 102723-102729 Chemical denotes serine http://purl.obolibrary.org/obo/CHEBI_17822
T81502 102759-102768 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T93491 102769-102791 Chemical denotes chymotrypsin inhibitor http://purl.obolibrary.org/obo/CHEBI_64943
T66488 102782-102791 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T88221 102852-102874 Chemical denotes chymotrypsin inhibitor http://purl.obolibrary.org/obo/CHEBI_64943
T34199 102865-102874 Chemical denotes inhibitor http://purl.obolibrary.org/obo/CHEBI_35222
T50928 103435-103443 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T73305 103449-103456 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T694 103464-103473 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T6431 103557-103561 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T12156 103857-103864 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T904 104406-104413 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T68030 104437-104445 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T15087 104918-104929 Chemical denotes application http://purl.obolibrary.org/obo/CHEBI_33232
T28739 105058-105066 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T30354 105121-105126 Chemical denotes probe http://purl.obolibrary.org/obo/CHEBI_50406
T31171 105131-105138 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T89156 105139-105145 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T4462 105233-105240 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T53184 105241-105247 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T12716 105322-105330 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T55010 105448-105455 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T36099 105533-105541 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T27611 105580-105583 Chemical denotes DNA http://purl.obolibrary.org/obo/CHEBI_16991
T26374 105601-105610 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T78103 105780-105786 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T8816 105865-105871 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T57310 106063-106070 Chemical denotes histone http://purl.obolibrary.org/obo/CHEBI_15358
T38623 106087-106093 Chemical denotes acetyl http://purl.obolibrary.org/obo/CHEBI_40574|http://purl.obolibrary.org/obo/CHEBI_46887
T69261 106138-106145 Chemical denotes peptide http://purl.obolibrary.org/obo/CHEBI_16670
T57840 106272-106277 Chemical denotes probe http://purl.obolibrary.org/obo/CHEBI_50406
T91758 106365-106373 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T76741 106466-106474 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T32116 106537-106545 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T22144 106575-106583 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T56756 106953-106960 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T85962 107064-107078 Chemical denotes macromolecules http://purl.obolibrary.org/obo/CHEBI_33839
T98627 107288-107296 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T21932 107322-107330 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T71997 107427-107435 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T71491 107663-107677 Chemical denotes macromolecules http://purl.obolibrary.org/obo/CHEBI_33839
T9832 107729-107738 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T55558 107871-107880 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T52166 107900-107905 Chemical denotes probe http://purl.obolibrary.org/obo/CHEBI_50406
T58696 108056-108060 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T34375 108122-108130 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T83294 108513-108522 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T52890 108550-108552 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99937 108600-108611 Chemical denotes metabolites http://purl.obolibrary.org/obo/CHEBI_25212
T24129 108744-108746 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60832 108815-108824 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T95563 108842-108844 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73804 108921-108923 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85566 108924-108928 Chemical denotes atom http://purl.obolibrary.org/obo/CHEBI_33250
T17833 108993-108999 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T65490 109007-109015 Chemical denotes molecule http://purl.obolibrary.org/obo/CHEBI_25367
T31918 109353-109357 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T99336 109634-109636 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52045 109744-109750 Chemical denotes helium http://purl.obolibrary.org/obo/CHEBI_30217|http://purl.obolibrary.org/obo/CHEBI_33681
T12505 110523-110525 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35513 110533-110535 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T63952 110610-110612 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89677 110675-110681 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T99623 110889-110893 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T80025 112187-112190 Chemical denotes MDD http://purl.obolibrary.org/obo/CHEBI_566274
T23405 112446-112448 Chemical denotes CS http://purl.obolibrary.org/obo/CHEBI_73462
T45982 112816-112822 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T35824 112976-112987 Chemical denotes application http://purl.obolibrary.org/obo/CHEBI_33232
T70136 113719-113723 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T45865 114644-114650 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T41882 114706-114709 Chemical denotes DNP http://purl.obolibrary.org/obo/CHEBI_53018
T48051 114744-114749 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T81359 114997-115003 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T38349 115045-115049 Chemical denotes gold http://purl.obolibrary.org/obo/CHEBI_29287|http://purl.obolibrary.org/obo/CHEBI_30050
T25174 115070-115074 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T70916 115390-115399 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T70443 116999-117003 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T78116 117296-117309 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T92757 117296-117301 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T95349 117302-117309 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T98922 117409-117411 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T5346 117677-117679 Chemical denotes RF http://purl.obolibrary.org/obo/CHEBI_73818
T71763 118025-118027 Chemical denotes T2 http://purl.obolibrary.org/obo/CHEBI_29298|http://purl.obolibrary.org/obo/CHEBI_75710
T86713 118084-118086 Chemical denotes RF http://purl.obolibrary.org/obo/CHEBI_73818
T28891 118571-118573 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54942 118851-118855 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T28372 118991-118997 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T172 119036-119043 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T27613 119204-119213 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T74596 119225-119233 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T2914 119437-119446 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T11478 119575-119577 Chemical denotes SE http://purl.obolibrary.org/obo/CHEBI_74813
T42044 120181-120185 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T33151 120330-120333 Chemical denotes MDD http://purl.obolibrary.org/obo/CHEBI_566274
T64333 120366-120368 Chemical denotes CS http://purl.obolibrary.org/obo/CHEBI_73462
T41133 120513-120515 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T62326 120772-120777 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T8592 120855-120864 Chemical denotes Isoniazid http://purl.obolibrary.org/obo/CHEBI_6030
T59430 121027-121029 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55975 121041-121043 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38037 121068-121076 Chemical denotes Naproxen http://purl.obolibrary.org/obo/CHEBI_7476
T60702 121078-121086 Chemical denotes Naproxen http://purl.obolibrary.org/obo/CHEBI_7476
T99092 121123-121130 Chemical denotes choline http://purl.obolibrary.org/obo/CHEBI_15354
T26968 121170-121180 Chemical denotes tryptophan http://purl.obolibrary.org/obo/CHEBI_16828|http://purl.obolibrary.org/obo/CHEBI_27897|http://purl.obolibrary.org/obo/CHEBI_57719|http://purl.obolibrary.org/obo/CHEBI_57912
T46340 121206-121208 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90687 121231-121240 Chemical denotes Cisplatin http://purl.obolibrary.org/obo/CHEBI_27899
T79027 121242-121244 Chemical denotes CP http://purl.obolibrary.org/obo/CHEBI_3380|http://purl.obolibrary.org/obo/CHEBI_73461|http://purl.obolibrary.org/obo/CHEBI_27899
T26576 121276-121283 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T69453 121285-121292 Chemical denotes betaine http://purl.obolibrary.org/obo/CHEBI_17750
T64392 121294-121301 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T27569 121303-121312 Chemical denotes glutamine http://purl.obolibrary.org/obo/CHEBI_28300
T65786 121314-121321 Chemical denotes lactate http://purl.obolibrary.org/obo/CHEBI_24996
T52241 121327-121334 Chemical denotes leucine http://purl.obolibrary.org/obo/CHEBI_25017
T65782 121355-121362 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T37509 121364-121371 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T18053 121373-121380 Chemical denotes citrate http://purl.obolibrary.org/obo/CHEBI_133748|http://purl.obolibrary.org/obo/CHEBI_16947|http://purl.obolibrary.org/obo/CHEBI_50744
T69706 121382-121389 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T1785 121391-121398 Chemical denotes glycine http://purl.obolibrary.org/obo/CHEBI_15428|http://purl.obolibrary.org/obo/CHEBI_29947|http://purl.obolibrary.org/obo/CHEBI_57305
T99520 121400-121416 Chemical denotes guanidinoacetate http://purl.obolibrary.org/obo/CHEBI_131444|http://purl.obolibrary.org/obo/CHEBI_57742
T94637 121418-121427 Chemical denotes hippurate http://purl.obolibrary.org/obo/CHEBI_132966|http://purl.obolibrary.org/obo/CHEBI_606565
T75683 121433-121440 Chemical denotes lactate http://purl.obolibrary.org/obo/CHEBI_24996
T2578 121442-121453 Chemical denotes metabolites http://purl.obolibrary.org/obo/CHEBI_25212
T66433 121489-121498 Chemical denotes cisplatin http://purl.obolibrary.org/obo/CHEBI_27899
T49360 121516-121518 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T61524 121637-121647 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T86436 121637-121642 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T35392 121643-121647 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T75948 121713-121715 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T80509 121754-121764 Chemical denotes Ampicillin http://purl.obolibrary.org/obo/CHEBI_28971
T27190 121786-121797 Chemical denotes antibiotics http://purl.obolibrary.org/obo/CHEBI_33281
T26612 121868-121881 Chemical denotes nucleic acids http://purl.obolibrary.org/obo/CHEBI_33696
T19466 121876-121881 Chemical denotes acids http://purl.obolibrary.org/obo/CHEBI_37527
T46232 121895-121897 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43041 121902-121904 Chemical denotes CP http://purl.obolibrary.org/obo/CHEBI_3380|http://purl.obolibrary.org/obo/CHEBI_73461|http://purl.obolibrary.org/obo/CHEBI_27899
T17236 121911-121917 Chemical denotes Emodin http://purl.obolibrary.org/obo/CHEBI_42223
T20609 121919-121925 Chemical denotes Emodin http://purl.obolibrary.org/obo/CHEBI_42223
T95091 121990-122001 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T54970 121997-122001 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T38179 122020-122031 Chemical denotes glutathione http://purl.obolibrary.org/obo/CHEBI_16856|http://purl.obolibrary.org/obo/CHEBI_57925
T45525 122080-122082 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43887 122094-122096 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39123 122179-122190 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T21494 122186-122190 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T8911 122231-122240 Chemical denotes glutamate http://purl.obolibrary.org/obo/CHEBI_14321|http://purl.obolibrary.org/obo/CHEBI_29987
T61293 122242-122251 Chemical denotes glutamine http://purl.obolibrary.org/obo/CHEBI_28300
T32686 122293-122295 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T64355 122307-122309 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7971 122434-122445 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T48239 122441-122445 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T66521 122535-122544 Chemical denotes cisplatin http://purl.obolibrary.org/obo/CHEBI_27899
T82218 122585-122592 Chemical denotes lactate http://purl.obolibrary.org/obo/CHEBI_24996
T68362 122609-122611 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57321 122623-122625 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31260 122672-122683 Chemical denotes carboplatin http://purl.obolibrary.org/obo/CHEBI_31355
T15844 122685-122687 Chemical denotes GC http://purl.obolibrary.org/obo/CHEBI_73890
T32244 122724-122731 Chemical denotes formate http://purl.obolibrary.org/obo/CHEBI_15740|http://purl.obolibrary.org/obo/CHEBI_52343
T260 122736-122743 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T49613 122785-122788 Chemical denotes MBC http://purl.obolibrary.org/obo/CHEBI_3392
T64708 122838-122840 Chemical denotes GC http://purl.obolibrary.org/obo/CHEBI_73890
T69324 122856-122858 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79926 122877-122879 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T18850 122887-122889 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T12619 122925-122936 Chemical denotes Doxorubicin http://purl.obolibrary.org/obo/CHEBI_28748
T50537 122938-122941 Chemical denotes DOX http://purl.obolibrary.org/obo/CHEBI_28748
T30358 122943-122954 Chemical denotes dexrazoxane http://purl.obolibrary.org/obo/CHEBI_50223
T72527 122956-122959 Chemical denotes DEX http://purl.obolibrary.org/obo/CHEBI_50223
T18594 122962-122965 Chemical denotes DOX http://purl.obolibrary.org/obo/CHEBI_28748
T9192 122976-122979 Chemical denotes ATP http://purl.obolibrary.org/obo/CHEBI_15422|http://purl.obolibrary.org/obo/CHEBI_30616
T69679 123035-123038 Chemical denotes DEX http://purl.obolibrary.org/obo/CHEBI_50223
T52309 123120-123122 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9849 123144-123152 Chemical denotes Curcumin http://purl.obolibrary.org/obo/CHEBI_3962
T87092 123154-123162 Chemical denotes Curcumin http://purl.obolibrary.org/obo/CHEBI_3962
T94712 123169-123187 Chemical denotes antihyperlipidemic http://purl.obolibrary.org/obo/CHEBI_35679
T82664 123325-123336 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T62559 123332-123336 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T73970 123410-123423 Chemical denotes ketone bodies http://purl.obolibrary.org/obo/CHEBI_73693
T65208 123410-123416 Chemical denotes ketone http://purl.obolibrary.org/obo/CHEBI_17087
T51013 123428-123439 Chemical denotes cholesterol http://purl.obolibrary.org/obo/CHEBI_16113
T7747 123445-123452 Chemical denotes choline http://purl.obolibrary.org/obo/CHEBI_15354
T25997 123457-123467 Chemical denotes fatty acid http://purl.obolibrary.org/obo/CHEBI_35366
T55617 123463-123467 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T60198 123481-123483 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70494 123501-123503 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T59989 123618-123621 Chemical denotes DNA http://purl.obolibrary.org/obo/CHEBI_16991
T38162 123662-123673 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T83688 123669-123673 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T64796 123739-123741 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T93131 123753-123761 Chemical denotes Melamine http://purl.obolibrary.org/obo/CHEBI_27915
T73579 123763-123771 Chemical denotes Melamine http://purl.obolibrary.org/obo/CHEBI_27915
T32152 123795-123802 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T55214 123804-123812 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T61061 123818-123825 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T15172 123855-123857 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7652 123874-123891 Chemical denotes Aristolochic acid http://purl.obolibrary.org/obo/CHEBI_2825
T38023 123887-123891 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T26318 123893-123895 Chemical denotes AA http://purl.obolibrary.org/obo/CHEBI_15843|http://purl.obolibrary.org/obo/CHEBI_72816|http://purl.obolibrary.org/obo/CHEBI_2825
T82804 123898-123915 Chemical denotes Aristolochic acid http://purl.obolibrary.org/obo/CHEBI_2825
T18392 123911-123915 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T73694 123993-123995 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T52066 124098-124107 Chemical denotes rituximab http://purl.obolibrary.org/obo/CHEBI_64357
T80883 124127-124138 Chemical denotes metabolites http://purl.obolibrary.org/obo/CHEBI_25212
T84447 124193-124202 Chemical denotes succinate http://purl.obolibrary.org/obo/CHEBI_26806|http://purl.obolibrary.org/obo/CHEBI_30031
T47403 124204-124211 Chemical denotes taurine http://purl.obolibrary.org/obo/CHEBI_15891|http://purl.obolibrary.org/obo/CHEBI_507393
T99870 124213-124220 Chemical denotes lactate http://purl.obolibrary.org/obo/CHEBI_24996
T33646 124222-124230 Chemical denotes pyruvate http://purl.obolibrary.org/obo/CHEBI_15361
T83140 124235-124244 Chemical denotes aspartate http://purl.obolibrary.org/obo/CHEBI_132943|http://purl.obolibrary.org/obo/CHEBI_29995|http://purl.obolibrary.org/obo/CHEBI_72314
T96044 124247-124249 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T57526 124261-124274 Chemical denotes Levetiracetam http://purl.obolibrary.org/obo/CHEBI_6437
T45818 124289-124299 Chemical denotes Topiramate http://purl.obolibrary.org/obo/CHEBI_63631
T99436 124324-124334 Chemical denotes metabolite http://purl.obolibrary.org/obo/CHEBI_25212
T46025 124380-124393 Chemical denotes levetiracetam http://purl.obolibrary.org/obo/CHEBI_6437
T9419 124395-124406 Chemical denotes lamotrigine http://purl.obolibrary.org/obo/CHEBI_6367
T80482 124411-124421 Chemical denotes topiramate http://purl.obolibrary.org/obo/CHEBI_63631
T16503 124486-124488 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T78916 124524-124533 Chemical denotes Ruthenium http://purl.obolibrary.org/obo/CHEBI_30682
T9566 124576-124581 Chemical denotes lipid http://purl.obolibrary.org/obo/CHEBI_18059
T45246 124683-124686 Chemical denotes GSH http://purl.obolibrary.org/obo/CHEBI_16856
T83737 124727-124736 Chemical denotes cisplatin http://purl.obolibrary.org/obo/CHEBI_27899
T91790 124761-124766 Chemical denotes lipid http://purl.obolibrary.org/obo/CHEBI_18059
T49326 124854-124856 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T23753 124863-124865 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2183 124875-124877 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70915 124878-124880 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35672 124887-124889 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28905 124998-125009 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T11681 125005-125009 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T66251 125050-125055 Chemical denotes lipid http://purl.obolibrary.org/obo/CHEBI_18059
T84782 125097-125099 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55290 125134-125146 Chemical denotes thiadiazoles http://purl.obolibrary.org/obo/CHEBI_38099
T32356 125171-125179 Chemical denotes glycerol http://purl.obolibrary.org/obo/CHEBI_17754
T17522 125201-125208 Chemical denotes betaine http://purl.obolibrary.org/obo/CHEBI_17750
T17397 125276-125279 Chemical denotes DMH http://purl.obolibrary.org/obo/CHEBI_73755
T12199 125326-125328 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42352 125537-125539 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56462 125551-125553 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T7825 125673-125684 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T12125 125680-125684 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T74139 125695-125705 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T80871 125695-125700 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T63266 125701-125705 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T27761 125826-125828 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T88796 125995-125999 Chemical denotes GABA http://purl.obolibrary.org/obo/CHEBI_16865
T41668 126004-126011 Chemical denotes glycine http://purl.obolibrary.org/obo/CHEBI_15428|http://purl.obolibrary.org/obo/CHEBI_29947|http://purl.obolibrary.org/obo/CHEBI_57305
T66104 126138-126140 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39070 126158-126160 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14635 126169-126171 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94784 126195-126207 Chemical denotes Pyrazinamide http://purl.obolibrary.org/obo/CHEBI_45285
T61592 126209-126218 Chemical denotes Isoniazid http://purl.obolibrary.org/obo/CHEBI_6030
T72175 126220-126236 Chemical denotes Sulfamethoxazole http://purl.obolibrary.org/obo/CHEBI_9332
T8081 126300-126304 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T19963 126349-126354 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T22591 126415-126417 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T74183 126435-126437 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T99926 126450-126457 Chemical denotes Genipin http://purl.obolibrary.org/obo/CHEBI_5298
T94443 126459-126466 Chemical denotes Genipin http://purl.obolibrary.org/obo/CHEBI_5298
T41770 126528-126539 Chemical denotes methylamine http://purl.obolibrary.org/obo/CHEBI_16830|http://purl.obolibrary.org/obo/CHEBI_59338
T77247 126544-126554 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T73179 126544-126549 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T30330 126550-126554 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T64289 126601-126603 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84578 126620-126630 Chemical denotes Adriamycin http://purl.obolibrary.org/obo/CHEBI_28748
T65801 126632-126635 Chemical denotes ADR http://purl.obolibrary.org/obo/CHEBI_28748
T37265 126674-126694 Chemical denotes trimethylamine oxide http://purl.obolibrary.org/obo/CHEBI_15724
T11530 126674-126688 Chemical denotes trimethylamine http://purl.obolibrary.org/obo/CHEBI_18139|http://purl.obolibrary.org/obo/CHEBI_58389
T52545 126689-126694 Chemical denotes oxide http://purl.obolibrary.org/obo/CHEBI_25741|http://purl.obolibrary.org/obo/CHEBI_29356
T67304 126696-126700 Chemical denotes TMAO http://purl.obolibrary.org/obo/CHEBI_15724
T49996 126703-126710 Chemical denotes taurine http://purl.obolibrary.org/obo/CHEBI_15891|http://purl.obolibrary.org/obo/CHEBI_507393
T34716 126712-126726 Chemical denotes trimethylamine http://purl.obolibrary.org/obo/CHEBI_18139|http://purl.obolibrary.org/obo/CHEBI_58389
T38410 126728-126731 Chemical denotes TMA http://purl.obolibrary.org/obo/CHEBI_166055|http://purl.obolibrary.org/obo/CHEBI_18139|http://purl.obolibrary.org/obo/CHEBI_53050|http://purl.obolibrary.org/obo/CHEBI_60567|http://purl.obolibrary.org/obo/CHEBI_60610
T8083 126734-126743 Chemical denotes hippurate http://purl.obolibrary.org/obo/CHEBI_132966|http://purl.obolibrary.org/obo/CHEBI_606565
T80118 126759-126766 Chemical denotes citrate http://purl.obolibrary.org/obo/CHEBI_133748|http://purl.obolibrary.org/obo/CHEBI_16947|http://purl.obolibrary.org/obo/CHEBI_50744
T47001 126771-126785 Chemical denotes 2-oxoglutarate http://purl.obolibrary.org/obo/CHEBI_16810
T40491 126848-126851 Chemical denotes ADR http://purl.obolibrary.org/obo/CHEBI_28748
T92145 126872-126874 Chemical denotes nu http://purl.obolibrary.org/obo/CHEBI_36352
T69119 126875-126877 Chemical denotes nu http://purl.obolibrary.org/obo/CHEBI_36352
T49757 126885-126887 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T39310 127133-127144 Chemical denotes metabolites http://purl.obolibrary.org/obo/CHEBI_25212
T56491 127177-127179 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T88158 127208-127210 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T75358 127233-127245 Chemical denotes Erythromycin http://purl.obolibrary.org/obo/CHEBI_42355
T83495 127247-127259 Chemical denotes Erythromycin http://purl.obolibrary.org/obo/CHEBI_42355
T14819 127270-127281 Chemical denotes citric acid http://purl.obolibrary.org/obo/CHEBI_30769
T40585 127277-127281 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T99316 127307-127317 Chemical denotes fatty acid http://purl.obolibrary.org/obo/CHEBI_35366
T45362 127313-127317 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T44367 127351-127361 Chemical denotes amino acid http://purl.obolibrary.org/obo/CHEBI_33709
T57294 127351-127356 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T84184 127357-127361 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T23056 127430-127432 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T3864 127714-127716 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44785 127771-127773 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T11949 127833-127841 Chemical denotes naringin http://purl.obolibrary.org/obo/CHEBI_28819
T60351 127843-127850 Chemical denotes sucrose http://purl.obolibrary.org/obo/CHEBI_17992
T63953 127858-127865 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T17899 127927-127935 Chemical denotes naringin http://purl.obolibrary.org/obo/CHEBI_28819
T2659 127937-127950 Chemical denotes neohesperidin http://purl.obolibrary.org/obo/CHEBI_59016
T28294 127961-127968 Chemical denotes glucose http://purl.obolibrary.org/obo/CHEBI_17234|http://purl.obolibrary.org/obo/CHEBI_4167
T51995 127970-127977 Chemical denotes sucrose http://purl.obolibrary.org/obo/CHEBI_17992
T59274 127979-127987 Chemical denotes limonene http://purl.obolibrary.org/obo/CHEBI_15384
T38831 127989-127998 Chemical denotes narirutin http://purl.obolibrary.org/obo/CHEBI_28705
T12346 128004-128014 Chemical denotes synephrine http://purl.obolibrary.org/obo/CHEBI_29081|http://purl.obolibrary.org/obo/CHEBI_58606
T40181 128018-128020 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95431 128182-128187 Chemical denotes drugs http://purl.obolibrary.org/obo/CHEBI_23888
T61683 128682-128689 Chemical denotes PLX3397 http://purl.obolibrary.org/obo/CHEBI_145373
T54879 128802-128804 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T36558 129058-129060 Chemical denotes II http://purl.obolibrary.org/obo/CHEBI_74067
T92376 129149-129155 Chemical denotes AT7519 http://purl.obolibrary.org/obo/CHEBI_91326
T35664 129210-129212 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T49784 129699-129705 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T78546 129717-129719 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55022 129850-129859 Chemical denotes molecules http://purl.obolibrary.org/obo/CHEBI_25367
T52980 129907-129913 Chemical denotes nuclei http://purl.obolibrary.org/obo/CHEBI_33252
T56383 130406-130409 Chemical denotes MDD http://purl.obolibrary.org/obo/CHEBI_566274
T21913 130623-130625 Chemical denotes CS http://purl.obolibrary.org/obo/CHEBI_73462
T84653 130999-131006 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T60113 131179-131185 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T79064 131320-131326 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T3417 131330-131337 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T86859 131433-131439 Chemical denotes ligand http://purl.obolibrary.org/obo/CHEBI_52214
T53221 131465-131472 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214
T59728 131761-131768 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T89255 131769-131773 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T90308 131822-131826 Chemical denotes drug http://purl.obolibrary.org/obo/CHEBI_23888
T26569 131837-131844 Chemical denotes Protein http://purl.obolibrary.org/obo/CHEBI_16541
T60248 131922-131930 Chemical denotes proteins http://purl.obolibrary.org/obo/CHEBI_36080
T69582 131954-131958 Chemical denotes ions http://purl.obolibrary.org/obo/CHEBI_24870
T8333 132041-132046 Chemical denotes atoms http://purl.obolibrary.org/obo/CHEBI_33250
T65120 132182-132184 Chemical denotes La http://purl.obolibrary.org/obo/CHEBI_33336
T78430 132185-132192 Chemical denotes antigen http://purl.obolibrary.org/obo/CHEBI_59132
T1428 132193-132200 Chemical denotes protein http://purl.obolibrary.org/obo/CHEBI_36080
T14147 132243-132260 Chemical denotes chemical compound http://purl.obolibrary.org/obo/CHEBI_37577
T89705 132535-132542 Chemical denotes ligands http://purl.obolibrary.org/obo/CHEBI_52214

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id tao:has_standard_notation
7 206-211 Species denotes human Tax:9606
8 793-803 Species denotes SARS-CoV-2 Tax:2697049
9 235-245 Disease denotes infections MESH:D007239
10 351-357 Disease denotes Cancer MESH:D009369
11 496-517 Disease denotes neurological diseases MESH:D020271
12 613-629 Disease denotes Viral infections MESH:D001102
13 739-749 Disease denotes infections MESH:D007239
18 1839-1842 Gene denotes Oct Gene:5362
19 2480-2484 Gene denotes high Gene:104137
20 1762-1772 Species denotes SARS-CoV-2 Tax:2697049
21 1773-1781 Disease denotes COVID-19 MESH:C000657245
25 2975-2982 Species denotes patient Tax:9606
26 3382-3390 Species denotes patients Tax:9606
27 3221-3240 Disease denotes learning algorithms MESH:D007859
31 3892-3896 Gene denotes high Gene:104137
32 3453-3457 Gene denotes high Gene:104137
33 5525-5538 Disease denotes drug toxicity MESH:D064420
44 6406-6412 Gene denotes BACE-1 Gene:23621
45 6437-6443 Gene denotes BACE-1 Gene:23621
46 6531-6543 Gene denotes amyloid beta Gene:351
47 6708-6714 Gene denotes BACE-1 Gene:23621
48 6964-6970 Gene denotes BACE-1 Gene:23621
49 6682-6693 Chemical denotes isothiourea MESH:D013890
50 6816-6827 Chemical denotes isothiourea MESH:D013890
51 6942-6960 Chemical denotes iminopyrimidinones
52 6416-6435 Disease denotes Alzheimer’s disease MESH:D000544
53 6594-6613 Disease denotes Alzheimer’s disease MESH:D000544
56 8489-8493 Gene denotes spin Gene:10927
57 8335-8339 Gene denotes spin Gene:10927
60 10032-10036 Gene denotes spin Gene:10927
64 10831-10835 Gene denotes high Gene:104137
65 10686-10689 Chemical denotes D2O
77 12221-12225 Gene denotes high Gene:104137
78 12011-12015 Gene denotes high Gene:104137
79 11654-11658 Gene denotes high Gene:104137
80 12138-12140 Chemical denotes 1H
81 12274-12282 Chemical denotes hydrogen MESH:D006859
82 12519-12521 Chemical denotes 1D
83 12522-12524 Chemical denotes 1H
84 12544-12547 Chemical denotes 13C MESH:C000615229
85 12556-12559 Chemical denotes 15N
86 12569-12571 Chemical denotes 1D
87 12572-12575 Chemical denotes 31P
89 12669-12674 Chemical denotes 1D 1H
115 14039-14043 Gene denotes spin Gene:10927
116 12683-12685 Chemical denotes 1H
117 12686-12694 Chemical denotes hydrogen MESH:D006859
118 12766-12773 Chemical denotes tritium MESH:D014316
119 12896-12898 Chemical denotes 1D
120 12899-12901 Chemical denotes 1H
121 13033-13035 Chemical denotes 1H
122 13249-13254 Chemical denotes water MESH:D014867
123 13456-13461 Chemical denotes water MESH:D014867
124 13514-13519 Chemical denotes water MESH:D014867
125 13889-13894 Chemical denotes water MESH:D014867
126 13919-13927 Chemical denotes hydrogen MESH:D006859
127 13933-13936 Chemical denotes H2O
128 14080-14085 Chemical denotes water MESH:D014867
129 14241-14246 Chemical denotes water MESH:D014867
130 14611-14616 Chemical denotes water MESH:D014867
131 14638-14643 Chemical denotes WATER MESH:D014867
132 14827-14832 Chemical denotes water MESH:D014867
133 14936-14941 Chemical denotes water MESH:D014867
134 15111-15116 Chemical denotes water MESH:D014867
135 15256-15261 Chemical denotes water MESH:D014867
136 15485-15487 Chemical denotes 1H
137 15614-15616 Chemical denotes 1H
138 15715-15718 Chemical denotes 13C MESH:C000615229
139 15720-15723 Chemical denotes 15N
141 15769-15775 Chemical denotes 1D 13C
167 15794-15796 Chemical denotes 1H
168 15798-15801 Chemical denotes 13C MESH:C000615229
169 15891-15894 Chemical denotes 13C MESH:C000615229
170 15971-15973 Chemical denotes 1H
171 15988-15991 Chemical denotes 13C MESH:C000615229
172 16423-16429 Chemical denotes carbon MESH:D002244
173 16551-16554 Chemical denotes 13C MESH:C000615229
174 16694-16696 Chemical denotes 1H
175 16701-16704 Chemical denotes 13C MESH:C000615229
176 16913-16915 Chemical denotes 1H
177 16923-16926 Chemical denotes 13C MESH:C000615229
178 16950-16952 Chemical denotes 1H
179 17012-17020 Chemical denotes naringin MESH:C005274
180 17022-17029 Chemical denotes sucrose MESH:D013395
181 17037-17044 Chemical denotes glucose MESH:D005947
182 17053-17056 Chemical denotes 13C MESH:C000615229
183 17127-17135 Chemical denotes naringin MESH:C005274
184 17137-17150 Chemical denotes neohesperidin MESH:C546526
185 17161-17168 Chemical denotes glucose MESH:D005947
186 17170-17177 Chemical denotes sucrose MESH:D013395
187 17179-17187 Chemical denotes limonene MESH:D000077222
188 17189-17198 Chemical denotes narirutin MESH:C500601
189 17204-17214 Chemical denotes synephrine MESH:D013578
190 17250-17253 Chemical denotes 13C MESH:C000615229
191 17356-17358 Chemical denotes 1H
193 17386-17392 Chemical denotes 1D 15N
206 18119-18123 Gene denotes a 2D Gene:11273
207 17436-17439 Chemical denotes 15N
208 17484-17487 Chemical denotes 13C MESH:C000615229
209 17513-17515 Chemical denotes 1H
210 17666-17668 Chemical denotes 1H
211 17686-17689 Chemical denotes 15N
212 17748-17750 Chemical denotes 1H
213 17788-17791 Chemical denotes 15N
214 17806-17808 Chemical denotes 1H
215 17906-17909 Chemical denotes 15N
216 17930-17933 Chemical denotes 13C MESH:C000615229
217 18065-18081 Chemical denotes 15N-ethanolamine
219 18853-18859 Chemical denotes 1D 31P
232 19621-19628 Species denotes E. coli Tax:562
233 19746-19753 Species denotes E. coli Tax:562
234 18954-18956 Chemical denotes 1H
235 18977-18987 Chemical denotes phosphorus MESH:D010758
236 19104-19107 Chemical denotes 31P
237 19198-19208 Chemical denotes phosphorus MESH:D010758
238 19225-19228 Chemical denotes 31P
239 19286-19298 Chemical denotes phospholipid MESH:D010743
240 19311-19314 Chemical denotes ATP MESH:D000255
241 19316-19320 Chemical denotes NADP MESH:D009249
242 19767-19777 Chemical denotes ampicillin MESH:D000667
243 20095-20105 Chemical denotes phosphorus MESH:D010758
251 20216-20219 Chemical denotes 13C MESH:C000615229
252 20224-20227 Chemical denotes 15N
253 20336-20380 Chemical denotes 2-chloro-4,4,5,5-tetramethyldioxaphospholane MESH:C548759
254 20382-20387 Chemical denotes CTMDP MESH:C548759
255 20413-20419 Chemical denotes lipids MESH:D008055
256 20441-20449 Chemical denotes aldehyde MESH:D000447
257 20455-20463 Chemical denotes carboxyl
261 21374-21379 Gene denotes 2.2.1 Gene:54097
262 21384-21386 Chemical denotes 1H
263 21387-21389 Chemical denotes 1H
282 23220-23224 Species denotes rats Tax:10116
283 23461-23465 Species denotes rats Tax:10116
284 21524-21526 Chemical denotes 1H
285 21527-21529 Chemical denotes 1H
286 22058-22060 Chemical denotes 1H
287 22065-22071 Chemical denotes carbon MESH:D002244
288 22088-22094 Chemical denotes carbon MESH:D002244
289 23345-23347 Chemical denotes 1H
290 23358-23360 Chemical denotes 1H
291 23377-23379 Chemical denotes 1H
292 23380-23382 Chemical denotes 1H
293 23393-23395 Chemical denotes 1H
294 23396-23399 Chemical denotes 13C MESH:C000615229
295 23588-23595 Chemical denotes lactate MESH:D019344
296 23597-23609 Chemical denotes nicotinamide MESH:D009536
297 23611-23619 Chemical denotes glycerol MESH:D005990
298 23624-23631 Chemical denotes formate MESH:C030544
299 23203-23219 Disease denotes blood deficiency MESH:D007022
302 23889-23891 Chemical denotes 1H
303 23892-23894 Chemical denotes 1H
337 25368-25372 Gene denotes spin Gene:10927
338 25330-25334 Gene denotes spin Gene:10927
339 24665-24669 Gene denotes spin Gene:10927
340 24282-24286 Gene denotes spin Gene:10927
341 25883-25891 Species denotes patients Tax:9606
342 26061-26069 Species denotes patients Tax:9606
343 26331-26339 Species denotes patients Tax:9606
344 26695-26703 Species denotes patients Tax:9606
345 26870-26878 Species denotes patients Tax:9606
346 24056-24058 Chemical denotes 1H
347 24059-24061 Chemical denotes 1H
348 25838-25849 Chemical denotes gemcitabine MESH:C056507
349 25850-25861 Chemical denotes carboplatin MESH:D016190
350 25863-25865 Chemical denotes GC
351 25973-25987 Chemical denotes anthracyclines MESH:D018943
352 25992-25999 Chemical denotes taxanes MESH:D043823
353 26116-26118 Chemical denotes 1H
354 26184-26186 Chemical denotes 1H
355 26187-26189 Chemical denotes 1H
356 26198-26200 Chemical denotes 1H
357 26208-26210 Chemical denotes 1H
358 26211-26214 Chemical denotes 13C MESH:C000615229
359 26225-26227 Chemical denotes 1H
360 26228-26231 Chemical denotes 13C MESH:C000615229
361 26306-26317 Chemical denotes gemcitabine MESH:C056507
362 26318-26329 Chemical denotes carboplatin MESH:D016190
363 26670-26677 Chemical denotes acetate MESH:D000085
364 23996-24002 Disease denotes HOHAHA
365 25908-25921 Disease denotes breast cancer MESH:D001943
366 26484-26486 Disease denotes SD MESH:D029461
367 26492-26511 Disease denotes progressive disease MESH:D018450
368 26513-26515 Disease denotes PD MESH:D010300
369 26681-26694 Disease denotes breast cancer MESH:D001943
372 26954-26956 Chemical denotes 1H
373 26957-26960 Chemical denotes 13C MESH:C000615229
391 27101-27104 Chemical denotes 13C MESH:C000615229
392 27169-27172 Chemical denotes 13C MESH:C000615229
393 27276-27278 Chemical denotes 1H
394 27279-27282 Chemical denotes 13C MESH:C000615229
395 27286-27288 Chemical denotes 1H
396 27289-27292 Chemical denotes 15N
397 27450-27452 Chemical denotes 1H
398 27453-27456 Chemical denotes 13C MESH:C000615229
399 27457-27460 Chemical denotes 15N
400 27547-27549 Chemical denotes 1H
401 27584-27587 Chemical denotes 13C MESH:C000615229
402 27588-27591 Chemical denotes 15N
403 27733-27739 Chemical denotes carbon MESH:D002244
404 27778-27781 Chemical denotes 13C MESH:C000615229
405 27842-27844 Chemical denotes 1H
406 27848-27851 Chemical denotes 13C MESH:C000615229
407 27915-27918 Chemical denotes 13C MESH:C000615229
425 28353-28358 Species denotes Human Tax:9606
426 28025-28034 Chemical denotes cisplatin MESH:D002945
427 28229-28235 Chemical denotes Ptac2S
428 28262-28264 Chemical denotes 1H
429 28265-28268 Chemical denotes 13C MESH:C000615229
430 28285-28287 Chemical denotes 1H
431 28416-28421 Chemical denotes lipid MESH:D008055
432 28507-28513 Chemical denotes Ptac2S
433 28528-28536 Chemical denotes pyruvate MESH:D019289
434 28568-28577 Chemical denotes cisplatin MESH:D002945
435 28632-28637 Chemical denotes lipid MESH:D008055
436 28698-28704 Chemical denotes Ptac2S
437 28728-28737 Chemical denotes cisplatin MESH:D002945
438 28792-28798 Chemical denotes Ptac2S
439 28819-28828 Chemical denotes cisplatin MESH:D002945
440 28005-28017 Disease denotes cytotoxicity MESH:D064420
441 28045-28073 Disease denotes epithelial ovarian carcinoma MESH:D010051
444 28874-28876 Chemical denotes 1H
445 28878-28881 Chemical denotes 13C MESH:C000615229
449 28987-28989 Chemical denotes 1H
450 29023-29026 Chemical denotes 13C MESH:C000615229
451 29348-29350 Chemical denotes 1H
467 30759-30763 Gene denotes pill Gene:8319132
468 30180-30184 Gene denotes high Gene:104137
469 29896-29900 Species denotes rats Tax:10116
470 30013-30017 Species denotes rats Tax:10116
471 30302-30305 Species denotes rat Tax:10116
472 29956-29960 Gene denotes pill Gene:8319132
473 30522-30524 Chemical denotes 1H
474 30633-30635 Chemical denotes 1H
475 30636-30638 Chemical denotes 1H
476 30645-30647 Chemical denotes 1H
477 30648-30651 Chemical denotes 13C MESH:C000615229
478 30662-30664 Chemical denotes 1H
479 30665-30668 Chemical denotes 13C MESH:C000615229
480 30898-30903 Chemical denotes lipid MESH:D008055
481 30197-30199 Disease denotes HD MESH:D006816
485 31869-31873 Gene denotes spin Gene:10927
486 31864-31868 Gene denotes spin Gene:10927
487 31696-31700 Gene denotes spin Gene:10927
495 33574-33576 Chemical denotes 1D
496 33581-33583 Chemical denotes 2D
497 33666-33668 Chemical denotes 1D
498 33740-33745 Chemical denotes FK506 MESH:D016559
499 33861-33863 Chemical denotes 1H
500 34130-34133 Chemical denotes 15N
501 34189-34192 Chemical denotes 15N
503 34311-34315 Gene denotes Carr Gene:407
508 35022-35026 Gene denotes Carr Gene:407
509 34525-34529 Gene denotes spin Gene:10927
510 35228-35231 Chemical denotes 13C MESH:C000615229
511 35276-35279 Chemical denotes 13C MESH:C000615229
514 36221-36225 Gene denotes spin Gene:10927
515 36216-36220 Gene denotes spin Gene:10927
518 37804-37808 Gene denotes high Gene:104137
519 37140-37143 Chemical denotes 15N
521 38509-38512 Species denotes SAR Tax:2698737
526 39582-39586 Gene denotes High Gene:104137
527 39309-39313 Chemical denotes FBDD
528 39429-39433 Chemical denotes FBDD
529 40138-40142 Chemical denotes FBDD
542 41469-41473 Gene denotes BRAF Gene:673
543 41782-41786 Gene denotes CDK4 Gene:1019
544 41555-41563 Species denotes patients Tax:9606
545 41636-41644 Species denotes patients Tax:9606
546 41389-41400 Chemical denotes vemurafenib MESH:D000077484
547 41408-41419 Chemical denotes Vemurafenib MESH:D000077484
548 41596-41606 Chemical denotes Venetoclax MESH:C579720
549 41743-41747 Chemical denotes FBDD
550 41883-41894 Chemical denotes vemurafenib MESH:D000077484
551 41481-41487 Disease denotes cancer MESH:D009369
552 41580-41588 Disease denotes melanoma MESH:D008545
553 41650-41678 Disease denotes chronic lymphocytic leukemia MESH:D015451
559 42291-42294 Species denotes SAR Tax:2698737
560 42383-42386 Species denotes SAR Tax:2698737
561 42598-42600 Chemical denotes 1H
562 42601-42604 Chemical denotes 15N
563 42979-42996 Chemical denotes 2-phenylimidazole MESH:C059194
566 43552-43555 Species denotes SAR Tax:2698737
567 43320-43324 Chemical denotes FBDD
574 43987-43991 Gene denotes High Gene:104137
575 43643-43646 Species denotes SAR Tax:2698737
576 43934-43937 Species denotes SAR Tax:2698737
577 44021-44024 Species denotes SAR Tax:2698737
578 44220-44223 Species denotes SAR Tax:2698737
579 44508-44511 Species denotes SAR Tax:2698737
582 45033-45036 Chemical denotes 13C MESH:C000615229
583 45041-45044 Chemical denotes 15N
586 46648-46653 Chemical denotes Water MESH:D014867
587 46802-46807 Chemical denotes water MESH:D014867
591 48314-48330 Species denotes human rhinovirus Tax:169066
592 48343-48347 Species denotes HRV2 Tax:12130
593 48481-48485 Species denotes HRV2 Tax:12130
595 49681-49685 Gene denotes spin Gene:10927
597 50562-50566 Gene denotes high Gene:104137
606 52396-52400 Gene denotes HBGA Gene:3047
607 52330-52334 Gene denotes HBGA Gene:3047
608 51218-51223 Species denotes human Tax:9606
609 51587-51612 Chemical denotes A- and B-tetrasaccharides
610 52152-52157 Chemical denotes L-Fuc
611 52162-52177 Chemical denotes B-trisaccharide
612 51034-51049 Disease denotes gastroenteritis MESH:D005759
613 51308-51317 Disease denotes infection MESH:D007239
621 55603-55613 Gene denotes E-selectin Gene:6401
622 53443-53447 Gene denotes spin Gene:10927
623 53192-53196 Gene denotes spin Gene:10927
624 54571-54575 Gene denotes high Gene:104137
625 54447-54451 Gene denotes high Gene:104137
626 53666-53670 Gene denotes high Gene:104137
627 55541-55556 Chemical denotes polysaccharides MESH:D011134
631 57920-57924 Gene denotes spin Gene:10927
632 56763-56775 Chemical denotes baccatin III MESH:C073950
633 56780-56792 Chemical denotes epothilone A MESH:C093787
635 60681-60685 Gene denotes spin Gene:10927
640 64381-64386 Chemical denotes FK506 MESH:D016559
641 64561-64580 Chemical denotes p-ethoxyiodobenzene
642 64585-64612 Chemical denotes 2-iodo-6-methoxynaphthalene
643 64650-64667 Chemical denotes (4-hydroxyphenyl)
650 64781-64785 Gene denotes spin Gene:10927
651 64750-64752 Chemical denotes 1H
652 64840-64846 Chemical denotes Rf-PEG
653 64860-64874 Chemical denotes 5-fluorouracil MESH:D005472
654 64884-64911 Chemical denotes 1,3-dimethyl-5-fluorouracil
655 64913-64917 Chemical denotes DMFU
659 65461-65474 Gene denotes serum albumin Gene:213
660 65298-65302 Gene denotes high Gene:104137
661 65216-65236 Chemical denotes N-acetyl glucosamine MESH:D000117
663 66723-66727 Gene denotes high Gene:104137
666 67975-67984 Chemical denotes adenosine MESH:D000241
667 68046-68065 Disease denotes Parkinson’s disease MESH:D010300
679 68956-68985 Gene denotes ubiquitin specific protease 7 Gene:7874
680 68987-68991 Gene denotes USP7 Gene:7874
681 69043-69046 Gene denotes p53 Gene:7157
682 69148-69152 Gene denotes USP7 Gene:7874
683 69647-69651 Gene denotes USP7 Gene:7874
684 69862-69866 Gene denotes USP7 Gene:7874
685 69172-69180 Chemical denotes cysteine MESH:D003545
686 69337-69339 Chemical denotes 1H
687 69340-69343 Chemical denotes 15N
688 69444-69452 Chemical denotes Di Lello
689 69017-69022 Disease denotes tumor MESH:D009369
696 70486-70521 Gene denotes Verona integron-encoded MBL (VIM)-2 Gene:100130535
697 70413-70418 Chemical denotes metal MESH:D008670
698 70641-70649 Chemical denotes β-lactam MESH:D047090
699 70450-70453 Disease denotes MBL MESH:C563602
700 70590-70593 Disease denotes MBL MESH:C563602
701 70601-70604 Disease denotes MBL MESH:C563602
704 72413-72423 Chemical denotes lanthanide MESH:D028581
705 72516-72521 Chemical denotes metal MESH:D008670
707 73253-73255 Chemical denotes 1H
719 73715-73719 Chemical denotes EDTA MESH:D004492
720 73732-73746 Chemical denotes deoxythymidine MESH:D013936
721 73748-73755 Chemical denotes dT-EDTA
722 73773-73778 Chemical denotes metal MESH:D008670
723 73792-73796 Chemical denotes Cu2+
724 73800-73804 Chemical denotes Mn2+
725 73818-73825 Chemical denotes dT-EDTA
726 73842-73847 Chemical denotes metal MESH:D008670
727 73933-73948 Chemical denotes oligonucleotide MESH:D009841
728 74347-74354 Chemical denotes dT-EDTA
729 74360-74365 Chemical denotes metal MESH:D008670
742 74550-74561 Gene denotes vasopressin Gene:551
743 74659-74670 Gene denotes vasopressin Gene:551
744 74871-74882 Gene denotes vasopressin Gene:551
745 74509-74520 Chemical denotes Cys-S-S-Cys
746 74571-74574 Chemical denotes His MESH:D006639
747 74575-74579 Chemical denotes Cu2+
748 74580-74583 Chemical denotes His MESH:D006639
749 74714-74718 Chemical denotes Cu2+
750 74727-74729 Chemical denotes 1H
751 74830-74833 Chemical denotes His MESH:D006639
752 74834-74838 Chemical denotes Cu2+
753 74839-74842 Chemical denotes His MESH:D006639
759 75569-75580 Gene denotes thymosin β4 Gene:7114
760 75658-75660 Chemical denotes 1H
761 75661-75664 Chemical denotes 15N
762 75970-75974 Chemical denotes Ni2+
763 76157-76162 Chemical denotes metal MESH:D008670
765 76622-76625 Gene denotes aid Gene:57379
768 77429-77433 Gene denotes pill Gene:8319132
769 77687-77702 Disease denotes crystal defects MESH:D000070657
773 78860-78864 Gene denotes spin Gene:10927
774 79274-79276 Chemical denotes 1H
775 79303-79306 Chemical denotes 13C MESH:C000615229
784 80825-80829 Chemical denotes PMAA MESH:C030613
785 80878-80886 Chemical denotes platinum MESH:D010984
786 80994-81002 Chemical denotes platinum MESH:D010984
787 81106-81114 Chemical denotes platinum MESH:D010984
788 81283-81291 Chemical denotes platinum MESH:D010984
789 81548-81553 Chemical denotes sugar MESH:D000073893
790 80792-80818 Disease denotes fructose hydrophilic block MESH:D006327
791 81053-81065 Disease denotes cytotoxicity MESH:D064420
808 81776-81781 Chemical denotes ester MESH:D004952
809 82121-82145 Chemical denotes Ac-IHVHLQI-CONH2 peptide
810 82193-82197 Chemical denotes Zn2+
811 82198-82201 Chemical denotes HHQ
812 82240-82244 Chemical denotes Zn2+
813 82332-82335 Chemical denotes His MESH:D006639
814 82364-82368 Chemical denotes Zn2+
815 82396-82399 Chemical denotes His MESH:D006639
816 82433-82437 Chemical denotes Zn2+
817 82461-82465 Chemical denotes Zn2+
818 82481-82486 Chemical denotes metal MESH:D008670
819 82623-82642 Chemical denotes histidine nitrogens
820 82682-82692 Chemical denotes histidines MESH:D006639
821 82704-82708 Chemical denotes Zn2+
822 82724-82729 Chemical denotes metal MESH:D008670
823 82730-82741 Chemical denotes imidazolate
825 82931-82935 Gene denotes high Gene:104137
838 83935-83961 Species denotes Mycobacterium tuberculosis Tax:1773
839 83780-83791 Chemical denotes L-Aspartate MESH:D001224
840 83863-83874 Chemical denotes L-aspartate MESH:D001224
841 83896-83905 Chemical denotes β-alanine MESH:D015091
842 83910-83924 Chemical denotes carbon dioxide MESH:D002245
843 84088-84091 Chemical denotes ADC
844 84109-84120 Chemical denotes L-aspartate MESH:D001224
845 84122-84133 Chemical denotes L-aspartate MESH:D001224
846 84185-84196 Chemical denotes L-aspartate MESH:D001224
847 84200-84209 Chemical denotes β-alanine MESH:D015091
848 84243-84254 Chemical denotes L-aspartate MESH:D001224
849 84292-84301 Chemical denotes β-alanine MESH:D015091
856 85214-85217 Gene denotes aid Gene:57379
857 85131-85136 Species denotes human Tax:9606
858 85066-85080 Chemical denotes dithiothreitol MESH:D004229
859 85082-85085 Chemical denotes DTT MESH:D004229
860 85097-85100 Chemical denotes 13C MESH:C000615229
861 85255-85258 Chemical denotes 13C MESH:C000615229
871 86734-86764 Species denotes Human immunodeficiency virus 1 Tax:11676
872 86766-86771 Species denotes HIV-1 Tax:11676
873 86705-86719 Chemical denotes benzodiazepine MESH:D001569
874 86968-86982 Chemical denotes benzodiazepine MESH:D001569
875 87181-87195 Chemical denotes benzodiazepine MESH:D001569
876 87264-87278 Chemical denotes benzodiazepine MESH:D001569
877 87346-87348 Chemical denotes 1H
878 87446-87460 Chemical denotes benzodiazepine MESH:D001569
879 87562-87576 Chemical denotes benzodiazepine MESH:D001569
903 88062-88066 Gene denotes MDM2 Gene:4193
904 88067-88070 Gene denotes p53 Gene:7157
905 88368-88372 Gene denotes MDM2 Gene:4193
906 88373-88376 Gene denotes p53 Gene:7157
907 88556-88560 Gene denotes MDM2 Gene:4193
908 88577-88581 Gene denotes MDM2 Gene:4193
909 88582-88585 Gene denotes p53 Gene:7157
910 88779-88783 Gene denotes MDM2 Gene:4193
911 89233-89237 Gene denotes MDM2 Gene:4193
912 89301-89305 Gene denotes MDM2 Gene:4193
913 88225-88231 Chemical denotes RG7112 MESH:C579783
914 88354-88360 Chemical denotes RG7112 MESH:C579783
915 88476-88482 Chemical denotes RG7112 MESH:C579783
916 88512-88518 Chemical denotes RG7112 MESH:C579783
917 88599-88601 Chemical denotes 1H
918 88602-88605 Chemical denotes 15N
919 88729-88735 Chemical denotes RG7112 MESH:C579783
920 88749-88751 Chemical denotes 1H
921 88752-88755 Chemical denotes 15N
922 88913-88919 Chemical denotes RG7112 MESH:C579783
923 88964-88966 Chemical denotes 1H
924 88967-88970 Chemical denotes 15N
925 88129-88135 Disease denotes cancer MESH:D009369
935 89773-89790 Gene denotes von Hippel–Lindau Gene:7428
936 89792-89795 Gene denotes VHL Gene:7428
937 89851-89857 Gene denotes HIF-1α Gene:3091
938 89962-89968 Gene denotes HIF-1α Gene:3091
939 90018-90022 Gene denotes pVHL Gene:7428
940 90023-90032 Gene denotes elongin C Gene:6921
941 90033-90042 Gene denotes elongin B Gene:6923
942 90162-90166 Gene denotes Carr Gene:407
943 89823-89830 Disease denotes hypoxia MESH:D000860
950 92424-92427 Gene denotes p38 Gene:1432
951 92482-92490 Chemical denotes SB203580 MESH:C093642
952 92577-92585 Chemical denotes SB203580 MESH:C093642
953 92729-92737 Chemical denotes pyridine MESH:C023666
954 92769-92777 Chemical denotes SB203580 MESH:C093642
955 92926-92934 Chemical denotes SB203580 MESH:C093642
963 93844-93848 Gene denotes a 3D Gene:140564
964 94189-94205 Species denotes L. mesenteroides Tax:1245
965 94067-94076 Chemical denotes glycolate MESH:C031149
966 94077-94081 Chemical denotes NAD+ MESH:D009243
967 94144-94151 Chemical denotes glucose MESH:D005947
968 94164-94169 Chemical denotes NADPH MESH:D009249
969 94206-94213 Chemical denotes glucose MESH:D005947
979 94894-94922 Chemical denotes 2-(3′-pyridyl)-benzimidazole
980 94945-94983 Chemical denotes uridine diphosphateN-acetylglucosamine
981 94985-94995 Chemical denotes UDP-GlcNAc
982 95080-95083 Chemical denotes Ile MESH:D007532
983 95085-95088 Chemical denotes Val MESH:D014633
984 95090-95093 Chemical denotes Leu MESH:D007930
985 95106-95109 Chemical denotes Trp MESH:D014364
986 95111-95114 Chemical denotes Phe MESH:D010649
987 95116-95119 Chemical denotes His MESH:D006639
990 95577-95581 Gene denotes Tert Gene:7015
991 95588-95597 Disease denotes Labelling
1006 96793-96796 Gene denotes NS3 Gene:3845
1007 96953-96957 Gene denotes tert Gene:7015
1008 96881-96885 Gene denotes tert Gene:7015
1009 96545-96549 Gene denotes tert Gene:7015
1010 96310-96314 Gene denotes tert Gene:7015
1011 96060-96064 Gene denotes tert Gene:7015
1012 95865-95869 Gene denotes tert Gene:7015
1013 95745-95749 Gene denotes tert Gene:7015
1014 96206-96210 Gene denotes high Gene:104137
1015 96234-96261 Species denotes Bacillus stearothermophilus Tax:1422
1016 96775-96787 Species denotes dengue virus Tax:12637
1017 96041-96043 Chemical denotes 1H
1018 96994-97000 Chemical denotes Val155
1019 97006-97012 Chemical denotes DENpro
1032 97618-97622 Gene denotes NQO2 Gene:4835
1033 97747-97751 Gene denotes NQO2 Gene:4835
1034 97546-97556 Chemical denotes tretazicar MESH:C100099
1035 97558-97597 Chemical denotes (5-(aziridin-1-yl)-2,4-dinitrobenzamide MESH:C100099
1036 97608-97614 Chemical denotes CB1954 MESH:C100099
1037 97725-97735 Chemical denotes tretazicar MESH:C100099
1038 97850-97860 Chemical denotes tretazicar MESH:C100099
1039 97946-97956 Chemical denotes asparagine MESH:D001216
1040 97982-97990 Chemical denotes hydrogen MESH:D006859
1041 98017-98027 Chemical denotes tretazicar MESH:C100099
1042 98042-98051 Chemical denotes aziridine MESH:C033132
1043 98062-98072 Chemical denotes tretazicar MESH:C100099
1058 98536-98540 Gene denotes Brd4 Gene:23476
1059 98598-98602 Gene denotes Brd4 Gene:23476
1060 98755-98759 Gene denotes Brd4 Gene:23476
1061 99613-99617 Gene denotes Brd4 Gene:23476
1062 99618-99621 Gene denotes BD1 Gene:1672
1063 98603-98606 Gene denotes BD1 Gene:1672
1064 98541-98544 Gene denotes BD1 Gene:1672
1065 98668-98686 Chemical denotes triazolopyridazine
1066 98927-98932 Chemical denotes water MESH:D014867
1067 99036-99041 Chemical denotes water MESH:D014867
1068 99143-99161 Chemical denotes triazolopyridazine
1069 99440-99458 Chemical denotes triazolopyridazine
1070 99568-99576 Chemical denotes hydrogen MESH:D006859
1071 99603-99609 Chemical denotes Asn140
1082 100216-100219 Chemical denotes 13C MESH:C000615229
1083 100224-100227 Chemical denotes 15N
1084 100299-100302 Chemical denotes 13C MESH:C000615229
1085 100303-100305 Chemical denotes 1H
1086 100314-100317 Chemical denotes 13C MESH:C000615229
1087 100318-100320 Chemical denotes 1H
1088 100461-100464 Chemical denotes 15N
1089 100465-100468 Chemical denotes 13C MESH:C000615229
1090 100478-100480 Chemical denotes 1H
1091 100481-100483 Chemical denotes 1H
1101 101883-101889 Gene denotes hIFABP Gene:2169
1102 101838-101843 Species denotes human Tax:9606
1103 101105-101107 Chemical denotes 1H
1104 101523-101526 Chemical denotes 15N
1105 101564-101566 Chemical denotes 1H
1106 101662-101670 Chemical denotes hydrogen MESH:D006859
1107 101808-101824 Chemical denotes naphthoate ester
1108 101891-101900 Chemical denotes ketorolac MESH:D020910
1109 101901-101904 Chemical denotes ANS MESH:C027132
1111 102723-102729 Chemical denotes serine MESH:D012694
1120 104543-104551 Species denotes C) media Tax:140785
1123 104394-104397 Chemical denotes 15N
1124 104519-104522 Chemical denotes 13C MESH:C000615229
1125 104524-104527 Chemical denotes 15N
1126 104537-104540 Chemical denotes 15N
1129 104971-104974 Chemical denotes 15N
1131 106383-106388 Species denotes human Tax:9606
1133 106651-106654 Chemical denotes SPs
1138 108550-108552 Chemical denotes 1H
1139 108744-108746 Chemical denotes 1H
1140 108842-108844 Chemical denotes 1H
1141 108921-108923 Chemical denotes 1H
1145 109568-109572 Gene denotes high Gene:104137
1146 109634-109636 Chemical denotes 1H
1147 109744-109750 Chemical denotes helium MESH:D006371
1154 110771-110775 Gene denotes spin Gene:10927
1155 110523-110525 Chemical denotes 1H
1156 110526-110529 Chemical denotes 15N
1157 110533-110535 Chemical denotes 1H
1158 110536-110539 Chemical denotes 13C MESH:C000615229
1159 110610-110612 Chemical denotes 1H
1162 110995-110999 Gene denotes a 2D Gene:11273
1163 110969-110971 Chemical denotes 2D
1166 112446-112448 Gene denotes CS Gene:1431
1167 112187-112190 Disease denotes MDD MESH:D003865
1170 113205-113209 Gene denotes high Gene:104137
1171 112898-112902 Gene denotes high Gene:104137
1173 113562-113566 Gene denotes high Gene:104137
1178 114558-114562 Gene denotes high Gene:104137
1179 114533-114535 Chemical denotes 2D
1180 114751-114754 Chemical denotes 13C MESH:C000615229
1181 114756-114759 Chemical denotes 15N
1183 115595-115599 Gene denotes High Gene:104137
1920 117296-117309 Chemical denotes ethyl acetate MESH:C007650
1921 117409-117411 Chemical denotes 1H
1923 117544-117545 Gene denotes τ Gene:4137
1925 117912-117929 Disease denotes longitudinal axis MESH:C566610
1927 118377-118381 Gene denotes spin Gene:10927
1929 118486-118490 Gene denotes High Gene:104137
1932 118571-118577 Chemical denotes 1H-15N
1933 118655-118672 Chemical denotes 2-phenylimidazole MESH:C059194
1935 119241-119245 Gene denotes high Gene:104137
1937 119564-119568 Gene denotes Spin Gene:10927
1940 120608-120611 Species denotes SAR Tax:2698737
1941 120330-120333 Disease denotes MDD MESH:D003865
2164 123391-123395 Gene denotes BCAA Gene:51742
2165 122147-122151 Gene denotes pill Gene:8319132
2166 123270-123274 Gene denotes high Gene:104137
2167 121580-121584 Gene denotes high Gene:104137
2168 121005-121024 Species denotes Sprague Dawley rats Tax:10116
2169 121184-121203 Species denotes Sprague Dawley rats Tax:10116
2170 121691-121710 Species denotes Sprague-Dawley rats Tax:10116
2171 121885-121892 Species denotes E. coli Tax:562
2172 122279-122290 Species denotes Wistar rats Tax:10116
2173 122816-122824 Species denotes patients Tax:9606
2174 123211-123215 Species denotes mice Tax:10090
2175 123849-123852 Species denotes rat Tax:10116
2176 123979-123990 Species denotes Wistar rats Tax:10116
2177 124049-124057 Species denotes patients Tax:9606
2178 124358-124366 Species denotes patients Tax:9606
2179 124638-124643 Species denotes human Tax:9606
2180 124908-124925 Species denotes Centella asiatica Tax:48106
2181 125075-125094 Species denotes Sprague–Dawley rats Tax:10116
2182 125312-125323 Species denotes Wistar rats Tax:10116
2183 125526-125534 Species denotes patients Tax:9606
2184 125804-125823 Species denotes Sprague-Dawley rats Tax:10116
2185 126102-126106 Species denotes mice Tax:10090
2186 126404-126412 Species denotes patients Tax:9606
2187 126579-126598 Species denotes Sprague Dawley rats Tax:10116
2188 126878-126882 Species denotes mice Tax:10090
2189 127416-127427 Species denotes Wistar rats Tax:10116
2190 127630-127641 Species denotes Wistar rats Tax:10116
2191 123893-123895 Gene denotes AA Gene:351
2192 120855-120864 Chemical denotes Isoniazid MESH:D007538
2193 121027-121029 Chemical denotes 1H
2194 121041-121043 Chemical denotes 1H
2195 121052-121055 Chemical denotes 13C MESH:C000615229
2196 121068-121076 Chemical denotes Naproxen MESH:D009288
2197 121078-121086 Chemical denotes Naproxen MESH:D009288
2198 121123-121130 Chemical denotes choline MESH:D002794
2199 121170-121180 Chemical denotes tryptophan MESH:D014364
2200 121206-121208 Chemical denotes 1H
2201 121231-121240 Chemical denotes Cisplatin MESH:D002945
2202 121276-121283 Chemical denotes alanine MESH:D000409
2203 121285-121292 Chemical denotes betaine MESH:D001622
2204 121294-121301 Chemical denotes glucose MESH:D005947
2205 121303-121312 Chemical denotes glutamine MESH:D005973
2206 121314-121321 Chemical denotes lactate MESH:D019344
2207 121327-121334 Chemical denotes leucine MESH:D007930
2208 121355-121362 Chemical denotes alanine MESH:D000409
2209 121364-121371 Chemical denotes acetate MESH:D000085
2210 121373-121380 Chemical denotes citrate MESH:D019343
2211 121382-121389 Chemical denotes glucose MESH:D005947
2212 121391-121398 Chemical denotes glycine MESH:D005998
2213 121400-121416 Chemical denotes guanidinoacetate MESH:C004946
2214 121418-121427 Chemical denotes hippurate MESH:C030514
2215 121433-121440 Chemical denotes lactate MESH:D019344
2216 121489-121498 Chemical denotes cisplatin MESH:D002945
2217 121516-121518 Chemical denotes 1H
2218 121713-121715 Chemical denotes 1H
2219 121727-121730 Chemical denotes 13C MESH:C000615229
2220 121738-121741 Chemical denotes 13C MESH:C000615229
2221 121754-121764 Chemical denotes Ampicillin MESH:D000667
2222 121895-121897 Chemical denotes 1H
2223 121898-121901 Chemical denotes 31P
2224 121990-122001 Chemical denotes citric acid MESH:D019343
2225 122020-122031 Chemical denotes glutathione MESH:D005978
2226 122080-122082 Chemical denotes 1H
2227 122104-122107 Chemical denotes 13C MESH:C000615229
2228 122179-122190 Chemical denotes citric acid MESH:D019343
2229 122231-122240 Chemical denotes glutamate MESH:D018698
2230 122242-122251 Chemical denotes glutamine MESH:D005973
2231 122256-122261 Chemical denotes BCAAs MESH:D000597
2232 122293-122295 Chemical denotes 1H
2233 122317-122320 Chemical denotes 13C MESH:C000615229
2234 122434-122445 Chemical denotes citric acid MESH:D019343
2235 122535-122544 Chemical denotes cisplatin MESH:D002945
2236 122566-122572 Chemical denotes Ptac2S
2237 122609-122611 Chemical denotes 1H
2238 122633-122636 Chemical denotes 13C MESH:C000615229
2239 122644-122652 Chemical denotes 13C-HMBC
2240 122660-122671 Chemical denotes Gemcitabine MESH:C056507
2241 122672-122683 Chemical denotes carboplatin MESH:D016190
2242 122685-122687 Chemical denotes GC
2243 122724-122731 Chemical denotes formate MESH:C030544
2244 122736-122743 Chemical denotes acetate MESH:D000085
2245 122856-122858 Chemical denotes 1H
2246 122887-122889 Chemical denotes 1H
2247 122898-122901 Chemical denotes 13C MESH:C000615229
2248 122925-122936 Chemical denotes Doxorubicin MESH:D004317
2249 122938-122941 Chemical denotes DOX MESH:D004317
2250 122943-122954 Chemical denotes dexrazoxane MESH:D064730
2251 122956-122959 Chemical denotes DEX MESH:D064730
2252 122962-122965 Chemical denotes DOX MESH:D004317
2253 122976-122979 Chemical denotes ATP MESH:D000255
2254 123035-123038 Chemical denotes DEX MESH:D064730
2255 123120-123122 Chemical denotes 1H
2256 123144-123152 Chemical denotes Curcumin MESH:D003474
2257 123154-123162 Chemical denotes Curcumin MESH:D003474
2258 123325-123336 Chemical denotes citric acid MESH:D019343
2259 123410-123416 Chemical denotes ketone MESH:D007659
2260 123428-123439 Chemical denotes cholesterol MESH:D002784
2261 123445-123452 Chemical denotes choline MESH:D002794
2262 123457-123467 Chemical denotes fatty acid MESH:D005227
2263 123481-123483 Chemical denotes 1H
2264 123662-123673 Chemical denotes citric acid MESH:D019343
2265 123739-123741 Chemical denotes 1H
2266 123753-123771 Chemical denotes Melamine Melamine
2267 123795-123802 Chemical denotes glucose MESH:D005947
2268 123804-123812 Chemical denotes nitrogen MESH:D009584
2269 123855-123857 Chemical denotes 1H
2270 123874-123891 Chemical denotes Aristolochic acid MESH:C000228
2271 123898-123915 Chemical denotes Aristolochic acid MESH:C000228
2272 123993-123995 Chemical denotes 1H
2273 124006-124015 Chemical denotes Rituximab MESH:D000069283
2274 124098-124107 Chemical denotes rituximab MESH:D000069283
2275 124193-124202 Chemical denotes succinate MESH:D019802
2276 124204-124211 Chemical denotes taurine MESH:D013654
2277 124213-124220 Chemical denotes lactate MESH:D019344
2278 124222-124230 Chemical denotes pyruvate MESH:D019289
2279 124235-124244 Chemical denotes aspartate MESH:D001224
2280 124247-124249 Chemical denotes 1H
2281 124261-124274 Chemical denotes Levetiracetam MESH:D000077287
2282 124276-124287 Chemical denotes Lamotrigine MESH:D000077213
2283 124289-124299 Chemical denotes Topiramate MESH:D000077236
2284 124380-124393 Chemical denotes levetiracetam MESH:D000077287
2285 124395-124406 Chemical denotes lamotrigine MESH:D000077213
2286 124411-124421 Chemical denotes topiramate MESH:D000077236
2287 124486-124488 Chemical denotes 1H
2288 124524-124533 Chemical denotes Ruthenium MESH:D012428
2289 124576-124581 Chemical denotes lipid MESH:D008055
2290 124683-124686 Chemical denotes GSH MESH:D005978
2291 124727-124736 Chemical denotes cisplatin MESH:D002945
2292 124761-124766 Chemical denotes lipid MESH:D008055
2293 124851-124856 Chemical denotes 1D-1H
2294 124863-124865 Chemical denotes 1H
2295 124872-124874 Chemical denotes 2D
2296 124875-124877 Chemical denotes 1H
2297 124878-124889 Chemical denotes 1H-TOCSY-1H
2298 124998-125009 Chemical denotes citric acid MESH:D019343
2299 125097-125099 Chemical denotes 1H
2300 125128-125146 Chemical denotes 1,3,4-thiadiazoles MESH:C058949
2301 125171-125179 Chemical denotes glycerol MESH:D005990
2302 125201-125208 Chemical denotes betaine MESH:D001622
2303 125252-125263 Chemical denotes myoinositol MESH:D007294
2304 125276-125279 Chemical denotes DMH MESH:D004111
2305 125326-125328 Chemical denotes 1H
2306 125537-125539 Chemical denotes 1H
2307 125561-125564 Chemical denotes 13C MESH:C000615229
2308 125673-125684 Chemical denotes citric acid MESH:D019343
2309 125826-125828 Chemical denotes 1H
2310 125995-125999 Chemical denotes GABA MESH:D005680
2311 126004-126011 Chemical denotes glycine MESH:D005998
2312 126138-126140 Chemical denotes 1H
2313 126158-126168 Chemical denotes 1H-gCOSY1H
2314 126169-126193 Chemical denotes 1H-TOCSY [87] Acyclovir
2315 126195-126207 Chemical denotes Pyrazinamide MESH:D011718
2316 126209-126218 Chemical denotes Isoniazid MESH:D007538
2317 126220-126236 Chemical denotes Sulfamethoxazole MESH:D013420
2318 126415-126417 Chemical denotes 1H
2319 126528-126539 Chemical denotes methylamine MESH:C027451
2320 126601-126603 Chemical denotes 1H
2321 126620-126630 Chemical denotes Adriamycin MESH:D004317
2322 126674-126694 Chemical denotes trimethylamine oxide MESH:C005855
2323 126696-126700 Chemical denotes TMAO MESH:C005855
2324 126703-126710 Chemical denotes taurine MESH:D013654
2325 126712-126726 Chemical denotes trimethylamine MESH:C023336
2326 126734-126743 Chemical denotes hippurate MESH:C030514
2327 126745-126757 Chemical denotes trigonelline MESH:C009560
2328 126759-126766 Chemical denotes citrate MESH:D019343
2329 126771-126785 Chemical denotes 2-oxoglutarate MESH:D007656
2330 126885-126887 Chemical denotes 1H
2331 127177-127179 Chemical denotes 1H
2332 127218-127221 Chemical denotes 13C MESH:C000615229
2333 127233-127245 Chemical denotes Erythromycin MESH:D004917
2334 127247-127259 Chemical denotes Erythromycin MESH:D004917
2335 127270-127281 Chemical denotes citric acid MESH:D019343
2336 127307-127317 Chemical denotes fatty acid MESH:D005227
2337 127430-127432 Chemical denotes 1H
2338 127714-127716 Chemical denotes 1H
2339 127771-127773 Chemical denotes 1H
2340 127833-127841 Chemical denotes naringin MESH:C005274
2341 127843-127850 Chemical denotes sucrose MESH:D013395
2342 127858-127865 Chemical denotes glucose MESH:D005947
2343 127872-127875 Chemical denotes 13C MESH:C000615229
2344 127927-127935 Chemical denotes naringin MESH:C005274
2345 127937-127950 Chemical denotes neohesperidin MESH:C546526
2346 127961-127968 Chemical denotes glucose MESH:D005947
2347 127970-127977 Chemical denotes sucrose MESH:D013395
2348 127979-127987 Chemical denotes limonene MESH:D000077222
2349 127989-127998 Chemical denotes narirutin MESH:C500601
2350 128004-128014 Chemical denotes synephrine MESH:D013578
2351 128018-128020 Chemical denotes 1H
2352 121499-121513 Disease denotes nephrotoxicity MESH:D007674
2353 122365-122371 Disease denotes cancer MESH:D009369
2354 122801-122814 Disease denotes breast cancer MESH:D001943
2355 123239-123256 Disease denotes metabolic defects MESH:D008659
2356 123923-123936 Disease denotes renal lesions MESH:D007674
2357 124063-124083 Disease denotes rheumatoid arthritis MESH:D001172
2358 124475-124483 Disease denotes epilepsy MESH:D004827
2359 124603-124623 Disease denotes human ovarian cancer MESH:D010051
2360 124644-124660 Disease denotes embryonic kidney MESH:D007674
2361 124948-124985 Disease denotes Centella asiatica promotes glycolysis MESH:C564972
2362 125020-125066 Disease denotes decreases gluconeogenesis and lipid metabolism MESH:D052439
2363 125288-125291 Disease denotes CRC MESH:D015179
2364 125293-125310 Disease denotes colorectal cancer MESH:D015179
2365 125516-125525 Disease denotes depressed MESH:D000275
2366 126118-126135 Disease denotes hypobaric hypoxia MESH:D000860
2367 126381-126403 Disease denotes tuberculous meningitis MESH:D014390
2368 126570-126578 Disease denotes diabetic MESH:D003920
2369 126803-126808 Disease denotes tumor MESH:D009369
2370 126812-126834 Disease denotes gastric adenocarcinoma MESH:D013274
2371 127336-127347 Disease denotes dysfunction MESH:D009461
2372 127574-127582 Disease denotes toxicity MESH:D064420
2373 122095-122103 CellLine denotes H-COSY1H CVCL:Z499
2374 122308-122316 CellLine denotes H-COSY1H CVCL:Z499
2375 122624-122632 CellLine denotes H-COSY1H CVCL:Z499
2376 122878-122886 CellLine denotes H-COSY1H CVCL:Z499
2377 123023-123027 CellLine denotes H9C2 CVCL:0286
2378 123102-123106 CellLine denotes H9C2 CVCL:0286
2379 123725-123730 CellLine denotes HepG2 CVCL:0027
2380 124596-124601 CellLine denotes A2780 CVCL:0134
2381 124629-124636 CellLine denotes HEK-293 CVCL:0045
2382 124716-124721 CellLine denotes A2780 CVCL:0134
2383 124747-124752 CellLine denotes A2780 CVCL:0134
2384 125552-125560 CellLine denotes H-COSY1H CVCL:Z499
2385 127209-127217 CellLine denotes H-COSY1H CVCL:Z499
2395 128370-128374 Gene denotes BRAF Gene:673
2396 128515-128520 Gene denotes BCL-2 Gene:596
2397 128607-128611 Gene denotes CDK4 Gene:1019
2398 128731-128735 Gene denotes FLT3 Gene:2322
2399 128847-128852 Gene denotes BACE1 Gene:23621
2400 129175-129186 Gene denotes CDK 1, 2, 4 Gene:983
2401 128947-128952 Gene denotes HSP90 Gene:3320
2402 128393-128397 Gene denotes high Gene:104137
2403 128375-128380 Mutation denotes V600E rs113488022
2405 128205-128209 Chemical denotes FBDD
2407 129299-129302 Gene denotes Dan Gene:4681
2421 130623-130625 Gene denotes CS Gene:1431
2422 132436-132440 Gene denotes spin Gene:10927
2423 129959-129963 Gene denotes spin Gene:10927
2424 132300-132304 Gene denotes pill Gene:8319132
2425 129515-129519 Gene denotes High Gene:104137
2426 131134-131137 Species denotes SAR Tax:2698737
2427 132176-132181 Species denotes human Tax:9606
2428 129611-129613 Chemical denotes 2D
2429 129632-129634 Chemical denotes 2D
2430 129717-129719 Chemical denotes 1H
2431 130964-130968 Chemical denotes FBDD
2432 131948-131953 Chemical denotes metal MESH:D008670
2433 130406-130409 Disease denotes MDD MESH:D003865

LitCovid-PD-GO-BP

Id Subject Object Predicate Lexical cue
T1 100937-100945 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T2 104481-104492 http://purl.obolibrary.org/obo/GO_0016049 denotes cell growth
T3 104486-104492 http://purl.obolibrary.org/obo/GO_0040007 denotes growth
T4 106193-106205 http://purl.obolibrary.org/obo/GO_0016791 denotes phosphatases
T5 106672-106686 http://purl.obolibrary.org/obo/GO_0019068 denotes viral assembly
T6 112643-112652 http://purl.obolibrary.org/obo/GO_0023052 denotes in signal
T7 119409-119422 http://purl.obolibrary.org/obo/GO_0006412 denotes translational
T8 120380-120389 http://purl.obolibrary.org/obo/GO_0023052 denotes Signaling
T9 120918-120928 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T10 120954-120971 http://purl.obolibrary.org/obo/GO_0007268 denotes neurotransmission
T11 121123-121141 http://purl.obolibrary.org/obo/GO_0019695 denotes choline metabolism
T12 121131-121141 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T13 121156-121166 http://purl.obolibrary.org/obo/GO_0009056 denotes catabolism
T14 121648-121658 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T15 121855-121864 http://purl.obolibrary.org/obo/GO_0009056 denotes breakdown
T16 121941-121956 http://purl.obolibrary.org/obo/GO_0006955 denotes immune response
T17 121978-121988 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T18 121990-122007 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T19 122020-122041 http://purl.obolibrary.org/obo/GO_0006750 denotes glutathione synthesis
T20 122032-122041 http://purl.obolibrary.org/obo/GO_0009058 denotes synthesis
T21 122179-122196 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T22 122434-122451 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T23 123325-123342 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T24 123344-123354 http://purl.obolibrary.org/obo/GO_0006096 denotes glycolysis
T25 123359-123374 http://purl.obolibrary.org/obo/GO_0006094 denotes gluconeogenesis
T26 123397-123406 http://purl.obolibrary.org/obo/GO_0009058 denotes synthesis
T27 123457-123478 http://purl.obolibrary.org/obo/GO_0006631 denotes fatty acid metabolism
T28 123468-123478 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T29 123589-123598 http://purl.obolibrary.org/obo/GO_0009058 denotes synthesis
T30 123603-123614 http://purl.obolibrary.org/obo/GO_0032259 denotes methylation
T31 123662-123679 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T32 123691-123701 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T33 123781-123791 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T34 124576-124592 http://purl.obolibrary.org/obo/GO_0006629 denotes lipid metabolism
T35 124582-124592 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T36 124782-124795 http://purl.obolibrary.org/obo/GO_0070085 denotes glycosylation
T37 124975-124985 http://purl.obolibrary.org/obo/GO_0006096 denotes glycolysis
T38 124998-125015 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T39 125030-125045 http://purl.obolibrary.org/obo/GO_0006094 denotes gluconeogenesis
T40 125050-125066 http://purl.obolibrary.org/obo/GO_0006629 denotes lipid metabolism
T41 125056-125066 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T42 125171-125190 http://purl.obolibrary.org/obo/GO_0006071 denotes glycerol metabolism
T43 125180-125190 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T44 125385-125395 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T45 125431-125441 http://purl.obolibrary.org/obo/GO_0065007 denotes regulation
T46 125644-125654 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T47 125673-125690 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T48 125706-125716 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T49 125920-125930 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T50 126004-126021 http://purl.obolibrary.org/obo/GO_0016934 denotes glycine receptors
T51 126004-126021 http://purl.obolibrary.org/obo/GO_0016933 denotes glycine receptors
T52 126486-126496 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T53 126555-126566 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolisms
T54 127270-127287 http://purl.obolibrary.org/obo/GO_0006099 denotes citric acid cycle
T55 127307-127327 http://purl.obolibrary.org/obo/GO_0019395 denotes fatty acid oxidation
T56 127362-127372 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T57 127505-127515 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T58 127522-127541 http://purl.obolibrary.org/obo/GO_0009060 denotes aerobic respiration
T59 127530-127541 http://purl.obolibrary.org/obo/GO_0045333 denotes respiration
T60 127530-127541 http://purl.obolibrary.org/obo/GO_0007585 denotes respiration
T61 131514-131522 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T62 132163-132172 http://purl.obolibrary.org/obo/GO_0009058 denotes synthesis
T77349 334-349 http://purl.obolibrary.org/obo/GO_0042493 denotes drug resistance
T41965 613-629 http://purl.obolibrary.org/obo/GO_0016032 denotes Viral infections
T25274 3221-3229 http://purl.obolibrary.org/obo/GO_0007612 denotes learning
T41226 9957-9965 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T32700 10116-10124 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T6950 13953-13961 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T20318 19286-19309 http://purl.obolibrary.org/obo/GO_0006644 denotes phospholipid metabolism
T95169 19299-19309 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T97670 20736-20746 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T44461 23683-23693 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T28937 25826-25849 http://purl.obolibrary.org/obo/GO_0036272 denotes response to gemcitabine
T71924 30859-30869 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T68745 30882-30892 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T3745 30898-30914 http://purl.obolibrary.org/obo/GO_0006629 denotes lipid metabolism
T18679 30904-30914 http://purl.obolibrary.org/obo/GO_0008152 denotes metabolism
T93601 31093-31102 http://purl.obolibrary.org/obo/GO_0023052 denotes in signal
T97672 37167-37182 http://purl.obolibrary.org/obo/GO_0006605 denotes protein targets
T83902 38609-38617 http://purl.obolibrary.org/obo/GO_0007610 denotes behavior
T79912 47586-47595 http://purl.obolibrary.org/obo/GO_0023052 denotes in signal
T6249 52864-52872 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T89047 53843-53851 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T16144 56641-56649 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T55554 57330-57338 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T99470 57763-57771 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T11659 58731-58744 http://purl.obolibrary.org/obo/GO_0006412 denotes translational
T93302 69017-69033 http://purl.obolibrary.org/obo/GO_0051726 denotes tumor suppressor
T21092 70155-70170 http://purl.obolibrary.org/obo/GO_0006605 denotes protein targets
T68138 76078-76086 http://purl.obolibrary.org/obo/GO_0015297 denotes exchange
T51549 81032-81038 http://purl.obolibrary.org/obo/GO_0098739 denotes uptake
T68041 81032-81038 http://purl.obolibrary.org/obo/GO_0098657 denotes uptake
T564 82914-82929 http://purl.obolibrary.org/obo/GO_0016049 denotes cellular growth
T496 82923-82929 http://purl.obolibrary.org/obo/GO_0040007 denotes growth
T3606 92418-92422 http://purl.obolibrary.org/obo/GO_0004707 denotes MAPK
T66733 92637-92641 http://purl.obolibrary.org/obo/GO_0004707 denotes MAPK
T42258 92804-92808 http://purl.obolibrary.org/obo/GO_0004707 denotes MAPK
T6077 92939-92943 http://purl.obolibrary.org/obo/GO_0004707 denotes MAPK

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T1 334-349 Phenotype denotes drug resistance http://purl.obolibrary.org/obo/HP_0020174
T2 351-357 Phenotype denotes Cancer http://purl.obolibrary.org/obo/HP_0002664
T3 6416-6435 Phenotype denotes Alzheimer’s disease http://purl.obolibrary.org/obo/HP_0002511
T4 6594-6613 Phenotype denotes Alzheimer’s disease http://purl.obolibrary.org/obo/HP_0002511
T5 25908-25921 Phenotype denotes breast cancer http://purl.obolibrary.org/obo/HP_0003002
T6 26681-26694 Phenotype denotes breast cancer http://purl.obolibrary.org/obo/HP_0003002
T7 28056-28073 Phenotype denotes ovarian carcinoma http://purl.obolibrary.org/obo/HP_0025318
T8 41481-41487 Phenotype denotes cancer http://purl.obolibrary.org/obo/HP_0002664
T9 41580-41588 Phenotype denotes melanoma http://purl.obolibrary.org/obo/HP_0002861
T10 41650-41678 Phenotype denotes chronic lymphocytic leukemia http://purl.obolibrary.org/obo/HP_0005550
T11 69017-69022 Phenotype denotes tumor http://purl.obolibrary.org/obo/HP_0002664
T12 81156-81162 Phenotype denotes cancer http://purl.obolibrary.org/obo/HP_0002664
T13 81196-81209 Phenotype denotes breast cancer http://purl.obolibrary.org/obo/HP_0003002
T14 81221-81232 Phenotype denotes lung cancer http://purl.obolibrary.org/obo/HP_0100526
T15 86740-86756 Phenotype denotes immunodeficiency http://purl.obolibrary.org/obo/HP_0002721
T16 88129-88135 Phenotype denotes cancer http://purl.obolibrary.org/obo/HP_0002664
T17 89823-89830 Phenotype denotes hypoxia http://purl.obolibrary.org/obo/HP_0012418
T18 107168-107177 Phenotype denotes Whitehead http://purl.obolibrary.org/obo/HP_0025250
T19 107576-107585 Phenotype denotes Whitehead http://purl.obolibrary.org/obo/HP_0025250
T20 108940-108956 Phenotype denotes highly sensitive http://purl.obolibrary.org/obo/HP_0041092
T21 120884-120900 Phenotype denotes oxidative stress http://purl.obolibrary.org/obo/HP_0025464
T22 121671-121687 Phenotype denotes oxidative stress http://purl.obolibrary.org/obo/HP_0025464
T23 122061-122077 Phenotype denotes oxidative stress http://purl.obolibrary.org/obo/HP_0025464
T24 122365-122371 Phenotype denotes cancer http://purl.obolibrary.org/obo/HP_0002664
T25 122801-122814 Phenotype denotes breast cancer http://purl.obolibrary.org/obo/HP_0003002
T26 123003-123019 Phenotype denotes oxidative stress http://purl.obolibrary.org/obo/HP_0025464
T27 124063-124083 Phenotype denotes rheumatoid arthritis http://purl.obolibrary.org/obo/HP_0001370
T28 124475-124483 Phenotype denotes epilepsy http://purl.obolibrary.org/obo/HP_0001250
T29 124609-124623 Phenotype denotes ovarian cancer http://purl.obolibrary.org/obo/HP_0100615
T30 125304-125310 Phenotype denotes cancer http://purl.obolibrary.org/obo/HP_0002664
T31 126128-126135 Phenotype denotes hypoxia http://purl.obolibrary.org/obo/HP_0012418
T32 126393-126403 Phenotype denotes meningitis http://purl.obolibrary.org/obo/HP_0001287
T33 127386-127402 Phenotype denotes oxidative stress http://purl.obolibrary.org/obo/HP_0025464

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T1 0-60 Sentence denotes NMR as a “Gold Standard” Method in Drug Design and Discovery
T2 62-70 Sentence denotes Abstract
T3 71-224 Sentence denotes Studying disease models at the molecular level is vital for drug development in order to improve treatment and prevent a wide range of human pathologies.
T4 225-350 Sentence denotes Microbial infections are still a major challenge because pathogens rapidly and continually evolve developing drug resistance.
T5 351-473 Sentence denotes Cancer cells also change genetically, and current therapeutic techniques may be (or may become) ineffective in many cases.
T6 474-612 Sentence denotes The pathology of many neurological diseases remains an enigma, and the exact etiology and underlying mechanisms are still largely unknown.
T7 613-933 Sentence denotes Viral infections spread and develop much more quickly than does the corresponding research needed to prevent and combat these infections; the present and most relevant outbreak of SARS-CoV-2, which originated in Wuhan, China, illustrates the critical and immediate need to improve drug design and development techniques.
T8 934-999 Sentence denotes Modern day drug discovery is a time-consuming, expensive process.
T9 1000-1105 Sentence denotes Each new drug takes in excess of 10 years to develop and costs on average more than a billion US dollars.
T10 1106-1176 Sentence denotes This demonstrates the need of a complete redesign or novel strategies.
T11 1177-1303 Sentence denotes Nuclear Magnetic Resonance (NMR) has played a critical role in drug discovery ever since its introduction several decades ago.
T12 1304-1416 Sentence denotes In just three decades, NMR has become a “gold standard” platform technology in medical and pharmacology studies.
T13 1417-1529 Sentence denotes In this review, we present the major applications of NMR spectroscopy in medical drug discovery and development.
T14 1530-1632 Sentence denotes The basic concepts, theories, and applications of the most commonly used NMR techniques are presented.
T15 1633-1729 Sentence denotes We also summarize the advantages and limitations of the primary NMR methods in drug development.
T16 1731-1733 Sentence denotes 1.
T17 1734-1746 Sentence denotes Introduction
T18 1747-1843 Sentence denotes The unexpected SARS-CoV-2/COVID-19 outbreak, with over 34 million confirmed cases globally (Oct.
T19 1844-2030 Sentence denotes 2020) and the struggle for survival in the absence of a proven and efficient treatments, emphasizes the critical need to develop effective, novel, and rapid drug discovery methodologies.
T20 2031-2165 Sentence denotes Even though the pharmaceutical industry works constantly to discover and develop novel drugs, the process is still slow and expensive.
T21 2166-2319 Sentence denotes The cost of introducing a new drug has increased steadily, with current cost estimates predicting that a future drug will cost in excess of $2.6 billion.
T22 2320-2474 Sentence denotes The typical development cost is usually spread out over the course of 14 years [1,2,3], making investment even more difficult (i.e., cost recovery delay).
T23 2475-2646 Sentence denotes This high investment barrier for drug development is a result of numerous testing phases (Scheme 1), with each phase requiring a statistically significant number of cases.
T24 2647-2810 Sentence denotes Although there are several other substantial costs to drug development, that discussion of experimental methods to reduce costs is beyond the scope of this review.
T25 2811-2965 Sentence denotes The emergence of a pandemic and the emergencies it creates worldwide understandably drive and motivate the rapid development and/or optimization of drugs.
T26 2966-3050 Sentence denotes However, patient safety and subsequent earned public trust is a primary requirement.
T27 3051-3306 Sentence denotes Drug redirecting/repurposing (Scheme 1) is an efficient short-cut method in disease treatment that utilizes existing tools, and combines artificial intelligence, machine learning algorithms, and experimental NMR techniques (i.e., “from Bench to Bedside”).
T28 3307-3418 Sentence denotes This process must be relatively rapid and efficient to have any benefit to patients and the health-care system.
T29 3419-3604 Sentence denotes Compared to mass spectrometry and high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) is another powerful technique with several unique advantages [5,6,7,8].
T30 3605-3805 Sentence denotes NMR is intrinsically quantitative, and it provides several different approaches that are routinely utilized to identify and structurally elucidate molecules of interest [9,10,11,12,13,14,15,16,17,18].
T31 3806-4119 Sentence denotes In contrast to mass spectrometry, NMR is non-destructive, non-invasive, has extremely high reproducibility permitting researchers to acquire measurements under different experimental conditions (e.g., temperature, time points, and concentrations) often while the same sample is inside the magnet [19,20,21,22,23].
T32 4120-4303 Sentence denotes NMR can be used in reaction kinetic studies while several consecutive measurements are taken, and while spectral changes (function of the reaction time) are analyzed [24,25,26,27,28].
T33 4304-4367 Sentence denotes Moreover, molecules are studied at the atomic level [29,30,31].
T34 4368-4578 Sentence denotes Unlike other analytical tools, NMR provides dynamic information, and NMR experiments can be carried out under physiological conditions (e.g., atmospheric pressure, temperature, and different pH values) [32,33].
T35 4579-4722 Sentence denotes This is especially important in medical drug design since one must understand the interactions between an enzyme of interest and the ligand(s).
T36 4723-4893 Sentence denotes NMR provides information on the binding affinity of such ligands, details/location of the binding site, and associated structural changes following binding [32,33,34,35].
T37 4894-5023 Sentence denotes These biophysical details are essential when evaluating the potential efficacy of a drug, and during any subsequent optimization.
T38 5024-5121 Sentence denotes The available literature [32,33,34,36] highlights the practicality of NMR in drug design studies.
T39 5122-5337 Sentence denotes For these reasons, NMR spectroscopy is highly sought after in drug development [37,38,39,40,41], for both molecule identification [11,13,14,18,42,43,44,45,46] and structural elucidation [15,16,17,45,47,48,49,50,51].
T40 5338-5553 Sentence denotes NMR has been successfully applied in stereochemistry [52,53,54,55,56] and isomer determination [57,58,59,60,61], in drug-protein interactions studies [62,63,64], and in the evaluation of drug toxicity [65,66,67,68].
T41 5554-5684 Sentence denotes The use of NMR in drug design is not restricted to academic laboratories and gained interest from those in development industries.
T42 5685-5808 Sentence denotes The use of NMR in drug development increased in the late ‘80s, as seen in both scientific and patent literature (Figure 1).
T43 5809-5924 Sentence denotes While scientific interest in NMR is still growing, the number of patents has been decreasing since the early 2000s.
T44 5925-6072 Sentence denotes The top applicants of NMR in pharmaceutical patents are Bristol Myers, AstraZeneca, and Wyeth, with 146, 104, and 67 patent families, respectively.
T45 6073-6228 Sentence denotes In addition to the advantages provided by NMR, it is often used with complementary methods such as X-ray crystallography, HPLC, and mass spectrometry [69].
T46 6229-6436 Sentence denotes An example of this is found in work by Wyss et al. [36], where they combined X-ray crystallography with NMR fragment-based screening to create the first inhibitor candidate for BACE-1 in Alzheimer’s disease.
T47 6437-6622 Sentence denotes BACE-1 is a membrane-anchored aspartic acid protease and is responsible for the production of amyloid beta peptides in neurons related to the progression of Alzheimer’s disease [36,70].
T48 6623-6837 Sentence denotes Using NMR fragment-based screening, Wyss et al. identified isothiourea as binding to BACE-1 and confirmed this observation with the X-ray crystal structure of the complex of a ligand-efficient isothiourea fragment.
T49 6838-6987 Sentence denotes Information obtained from these experiments aided in design optimization, resulting in the selection of iminopyrimidinones as BACE-1 inhibitors [36].
T50 6988-7086 Sentence denotes This is a perfect example of using different complementary methods to maximize scientific outcome.
T51 7087-7184 Sentence denotes However, in order to be efficient, one must know the advantages and disadvantages of each method.
T52 7185-7309 Sentence denotes One of the major issues regarding NMR is the effective size restriction when measuring targets such as proteins above 40kDa.
T53 7310-7513 Sentence denotes Recent progress has extended this mass limit; an example of this is the resolved structure of chaperone SecB in complex with unstructured proPhoA (PDB ID 5JTL) with a total mass of 119kDa using NMR [71].
T54 7514-7671 Sentence denotes In this review, we present practical guideline to use NMR techniques in drug design studies and provide examples of the successful use of NMR in drug-design.
T55 7673-7675 Sentence denotes 2.
T56 7676-7711 Sentence denotes An Introduction to NMR Spectroscopy
T57 7712-7849 Sentence denotes NMR is a versatile tool for studying biomolecules of all kinds and is a unique regarding the biophysical analysis of drugs [72,73,74,75].
T58 7850-8095 Sentence denotes The basic feature of NMR lies in the fact that it inductively detects the Larmor precession of individual nuclei (i.e., spins) which vary because of different atomic, electronic, and chemical environments (i.e., structural atomic relationships).
T59 8096-8180 Sentence denotes Initially, the sample is placed in a strong, static, and homogeneous magnetic field.
T60 8181-8287 Sentence denotes Because spins contain angular momentum, they exhibit Larmor precessions around this static magnetic field.
T61 8288-8455 Sentence denotes A net magnetization builds up over time as the spin population (represented by different energy levels) is minutely differential in the presence of the magnetic field.
T62 8456-8598 Sentence denotes These levels are dictated by the spin quantum number and can be roughly thought of as different orientations with respect to the static field.
T63 8599-8815 Sentence denotes Subsequently, induced electromagnetic fields at radiofrequencies (called RF pulses) are applied transverse to the plane of the static magnetic field, and the net or bulk magnetization undergoes an effective rotation.
T64 8816-8995 Sentence denotes The bulk coherence moves into the transverse plane and the subsequent coherently precessing magnetization vectors induce a detectable alternating voltage in the NMR receiver coil.
T65 8996-9137 Sentence denotes This tiny alternating voltage is amplified and converted from an analog time domain signal to a frequency reading via Fourier transformation.
T66 9138-9368 Sentence denotes These signals are recorded in response to the induced radio-wave pulses (Figure 2) and are representative of the Larmor frequencies that are converted into normalized values termed chemical shifts in order to be field independent.
T67 9369-9580 Sentence denotes This is the final, representative spectroscopic signature of the chemical and magnetic environment of the atom, and it provides detailed atomic resolution information about the molecular structure [76,77,78,79].
T68 9581-9757 Sentence denotes A wealth of information can be derived from the NMR signal made up components such as the chemical shift position, signal linewidth, and observed couplings/multiplet structure.
T69 9758-9983 Sentence denotes The signal contains precise details about the chemical environment of the involved and interacting spins in the structure of the molecule, dynamics of the spins in various timescales, conformational exchange, etc. [80,81,82].
T70 9984-10053 Sentence denotes Any change in the environment of the associated spin can be observed.
T71 10054-10171 Sentence denotes These changes include molecular binding, interactions, and/or exchange between different conformations [20,83,84,85].
T72 10172-10466 Sentence denotes Thus, NMR has been used to study a wide range of functional molecules such as natural products [86,87,88], saccharides [89,90], metabolites [91,92], DNA [93,94], and proteins [95], and its use as an analytical tool in drug design research has increased immensely in recent years (see Figure 1).
T73 10467-10547 Sentence denotes As NMR is non-destructive in nature, the same sample can be analyzed repeatedly.
T74 10548-10821 Sentence denotes NMR can be performed first and then submitted to mass spectrometry (MS); however, the addition of common deuterated NMR solvents (such as D2O) can perturb MS results and should be avoided (e.g., tube-in-tube or by using non-deuterated solvent and running the NMR unlocked).
T75 10822-11006 Sentence denotes In fact, high-performance liquid chromatography (HPLC), ion-trap MS and NMR have been combined to detect the effects of drugs demonstration in urine and blood serum samples [69,96,97].
T76 11007-11186 Sentence denotes Corcoran and Spraul [98] emphasize that liquid chromatography (LC), MS, and NMR utilized in parallel give comprehensive structural data on molecules of novel drugs in development.
T77 11187-11356 Sentence denotes In the following subsections we briefly describe NMR methods that have been used in drug design, and then discuss how NMR principles are used in drug discovery research.
T78 11358-11362 Sentence denotes 2.1.
T79 11363-11395 Sentence denotes One Dimensional NMR Spectroscopy
T80 11396-11495 Sentence denotes The one-dimensional (1D) experiment is by far the most common NMR experiment used for drug studies.
T81 11496-11678 Sentence denotes The 1D acquisition takes the least amount of time, has one of the simplest hardware requirements, and therefore, in most cases, 1D-NMR is more attractive for high throughput studies.
T82 11679-11852 Sentence denotes One dimensional NMR spectroscopy normally incorporates a preparation period, some form of induced excitation to form coherence, and lastly, a signal “read” detection period.
T83 11853-11964 Sentence denotes The preparation period can be modified according to the needs of the experiment or the specifics of the sample.
T84 11965-12134 Sentence denotes Simple 1D NMR is capable of rapidly producing high-quality spectra of drugs and their targets while revealing how the drugs and targets may interact at the atomic level.
T85 12135-12342 Sentence denotes 1D 1H-NMR is extremely effective in drug design studies because it has a (relatively) high sensitivity, it is non-destructive, and because hydrogen atoms are extremely abundant in most molecules of interest.
T86 12343-12508 Sentence denotes Therefore the resulting spectra usually contains a large amount of relevant information and this wealth of data can be acquired in a relatively short period of time.
T87 12509-12660 Sentence denotes The basic 1D 1H-NMR, along with 1D 13C-NMR, 1D 15N-NMR, and 1D 31P-NMR, and their respective uses in drug design/discovery are briefly discussed below.
T88 12662-12668 Sentence denotes 2.1.1.
T89 12669-12678 Sentence denotes 1D 1H-NMR
T90 12679-12880 Sentence denotes The 1H hydrogen isotope is NMR visible, has the highest gyromagnetic ratio (apart from tritium) of all of NMR active nuclei, and is combined with a vast natural abundance in organic chemical compounds.
T91 12881-12956 Sentence denotes This makes the 1D-1H-NMR experiment the most commonly applied NMR approach.
T92 12957-13149 Sentence denotes Moreover, many software databases [99,100,101,102] are well established for 1H-NMR spectra therefore assisting with processing, analyzing, and identifying the detected molecules automatically.
T93 13150-13317 Sentence denotes Since almost all drug discovery and drug development studies are performed on samples dissolved in water, many different solvent suppression methods have been applied.
T94 13318-13361 Sentence denotes The most common is presaturation [103,104].
T95 13362-13462 Sentence denotes The key point of this method is to use a low power induced field at the specific frequency of water.
T96 13463-13530 Sentence denotes This effectively averages out any coherence of the water resonance.
T97 13531-13780 Sentence denotes The experiment is simple for common hardware to perform and easy to set up; however, presaturation has a substantial disadvantage in that signals resonating close to the solvent signal will show decreased intensity [103,104] or may be lost entirely.
T98 13781-13902 Sentence denotes This is due to the fact the even selective pulses or very low power pulses also excite some area around the water signal.
T99 13903-14075 Sentence denotes Also suppressed hydrogen from H2O in solution can exchange with atoms of interest in the molecule and effectively bleed the suppressive spin state to any neighboring atoms.
T100 14076-14228 Sentence denotes The water signal itself is usually broad, so a wider area of suppression is not necessarily undesirable but affects more of the molecule(s) of interest.
T101 14229-14362 Sentence denotes More recent water suppression techniques have been developed such as those based on a scheme known as excitation sculpting [105,106].
T102 14363-14536 Sentence denotes The basic pulse sequence consists of a double pulsed field gradient echo (DPFGE) in each of which a selective component pulse is flanked by two pulsed field gradients [107].
T103 14537-14595 Sentence denotes The particular elements differ for different applications.
T104 14596-14908 Sentence denotes In the case of water suppression known as WATER suppression by GrAdient Tailored Excitation (WATERGATE), this involves an initial encoding gradient along with the middle element; a combination of two selective 90° rotations on the water along with a central non-selective 180° excitation of all resonances [108].
T105 14909-15039 Sentence denotes This is predicated in that water experiences a 360° rotation (effectively nothing) while all other spins experience 180° rotation.
T106 15040-15150 Sentence denotes The application of the second refocusing gradient does not rephase the water and therefore removes the signal.
T107 15151-15239 Sentence denotes The reader is referred to the detailed literature [103,104,109] for further information.
T108 15240-15475 Sentence denotes In principle, a water suppression element (or many elements combined) can be incorporated in any existing pulse sequence to enhance the performance, and it has been implemented in various 1D, 2D, and triple resonance 3D/4D experiments.
T109 15476-15654 Sentence denotes Although 1H is the most sensitive nucleus for NMR yielding strong, sharp signals within a few minutes [110], chemical shift dispersion of 1H is quite narrow (only around 10 ppm).
T110 15655-15760 Sentence denotes This has prompted the consideration of other nuclei such as 13C, 15N, or 31P for resolution improvements.
T111 15762-15768 Sentence denotes 2.1.2.
T112 15769-15779 Sentence denotes 1D 13C-NMR
T113 15780-15909 Sentence denotes Compared with 1H, 13C has a much higher chemical shift dispersion (~200 ppm), however the natural abundance of 13C is low (1.1%).
T114 15910-16074 Sentence denotes Additionally, the gyromagnetic ratio is ~4 times weaker than 1H and therefore 13C spectra are far more difficult to obtain especially for less concentrated samples.
T115 16075-16536 Sentence denotes There are some polarization transfer techniques such as Distortionless Enhancement by Polarization Transfer (DEPT) or Insensitive Nuclei Enhanced by Polarization Transfer (INEPT), which can enhance signal intensity by starting the magnetization on a higher sensitivity and abundance proton and then transferring magnetization to the less sensitive carbon nuclei for subsequent direct detection [111], but this requires additional hardware and acquisition times.
T116 16537-16620 Sentence denotes The use of 1D 13C in drug design studies was illustrated by Tsujimoto et al. [112].
T117 16621-16768 Sentence denotes The goal of the study was to examine if a metabolomics approach based on 1H and 13C offers significant improvements when comparing potential drugs.
T118 16769-16943 Sentence denotes The authors prepared a total of 40 samples with five different citrus-type crude drugs (kijitsu, tohi, chimpi, kippi and seihi) and measured 1D 1H and 1D 13C for each sample.
T119 16944-17216 Sentence denotes While 1H-NMR spectra allowed the identification of three compounds (naringin, sucrose, and β-glucose), using 13C-NMR allowed unambiguous identification of eight additional compounds (naringin, neohesperidin, α- and β-glucose, sucrose, limonene, narirutin, and synephrine).
T120 17217-17377 Sentence denotes The added signal resolution from 13C-NMR spectra allowed researchers to obtain better structural information about the compounds than from 1H-NMR spectra alone.
T121 17379-17385 Sentence denotes 2.1.3.
T122 17386-17396 Sentence denotes 1D 15N-NMR
T123 17397-17516 Sentence denotes In comparison to the previous example, 15N has a lower shift dispersion (~100ppm) than 13C, but higher than that of 1H.
T124 17517-17669 Sentence denotes Here, the situation is unfortunately severely limited due to an even lower natural abundance (0.37%) and a gyromagnetic ratio ~10 times smaller than 1H.
T125 17670-17751 Sentence denotes This means that 15N’s combined sensitivity is around 260,000 times lower than 1H.
T126 17752-17918 Sentence denotes As a result, isotopic enrichment of 15N combined with 1H-mediated enhancement via indirect detection is often needed in order to obtain a satisfactory 1D 15N spectra.
T127 17919-17996 Sentence denotes Similar to 13C, a few methods are available to overcome such low sensitivity.
T128 17997-18171 Sentence denotes One of them focuses on tagging molecules with carboxyl groups using 15N-ethanolamine and later detecting the signal using a 2D heteronuclear correlation NMR experiment [113].
T129 18172-18259 Sentence denotes Currently, novel approaches such as “smart isotope labeling” have been developed [114].
T130 18260-18519 Sentence denotes Also, the SOFAST (Band-Selective Optimized Flip Angle Short Transient) technique can help but results in substantial hardware considerations/drawbacks and often increased concentrations, and/or dramatically longer experiments are still required [115,116,117].
T131 18520-18557 Sentence denotes Promising methods are on the horizon.
T132 18558-18844 Sentence denotes These methods include 15N heteronuclear signal enhancement via Signal Amplification by Reversible Exchange in SHield Enables Alignment Transfer to Heteronuclei (SABRE-SHEATH); however, more work and research are required before such methods can be applied for biomedical purposes [118].
T133 18846-18852 Sentence denotes 2.1.4.
T134 18853-18863 Sentence denotes 1D 31P-NMR
T135 18864-19075 Sentence denotes With a natural abundance of 100% and a gyromagnetic ratio of about 2.5 times smaller than 1H, one may think that phosphorus could be broadly used for NMR experiments regarding the drug discovery and development.
T136 19076-19214 Sentence denotes However, the application of 31P is limited due to the fact that most of the molecules of interest simply do not contain a phosphorus atom.
T137 19215-19378 Sentence denotes Therefore 31P-NMR is usually applicable for studies related to energy, phospholipid metabolism (ATP, NADP), and/or characterization of changes in DNA [94,119,120].
T138 19379-19557 Sentence denotes For example, Overall et al. conducted an experiment in which they showed that 31P solid-state NMR can be used for quantitative analysis of DNA dynamics within live bacteria [94].
T139 19558-19719 Sentence denotes For that, the researchers first prepared untreated cultures of E. coli, and measured them using a Hartmann-Hahn 1H to 31P cross-polarization (31P CP) experiment.
T140 19720-19825 Sentence denotes Afterwards, they measured E. coli treated with ampicillin and maculatin 1.1 (Mac1.1) in a similar manner.
T141 19826-20130 Sentence denotes Spectra obtained from treated bacteria compared to those obtained from untreated bacteria showed alterations in the lineshape, reduced signal intensity at the spectrum’s edges, and a shift in spectral density towards 0 ppm which indicated the increased dynamics of the phosphorus from nucleic acids [94].
T142 20131-20207 Sentence denotes Over time, several innovations have been applied to expand the usage of 31P.
T143 20208-20309 Sentence denotes Like in 13C and 15N labeling of specific biological compounds, incorporation of 31P can also be used.
T144 20310-20527 Sentence denotes In order to achieve that, 2-chloro-4,4,5,5-tetramethyldioxaphospholane (CTMDP) can be used for tagging lipids containing hydroxyl, aldehyde, and carboxyl groups that can later be detected with better resolution [121].
T145 20528-20669 Sentence denotes Another fairly recent method enables toxicological screening of 31P in living cells for several hours without affecting cell viability [122].
T146 20670-20827 Sentence denotes This specific method can be used to observe the changes in energy metabolism in real-time while enabling the evaluation of the effects of administered drugs.
T147 20829-20833 Sentence denotes 2.2.
T148 20834-20868 Sentence denotes Multi-Dimensional NMR Spectroscopy
T149 20869-21042 Sentence denotes NMR experiments are not limited to one-dimensional direct acquisition; they can be extended to multidimensional methods including 2D, 3D, 4D, and even higher dimensionality.
T150 21043-21154 Sentence denotes The focus of this section is common 2D NMR experiments that have been used in drug design and drug development.
T151 21155-21372 Sentence denotes A brief description of Correlation Spectroscopy (COSY), Total Correlation Spectroscopy (TOCSY), and Heteronuclear Multiple Bond Correlation (HMBC), along with their uses in drug design and discovery will be presented.
T152 21374-21380 Sentence denotes 2.2.1.
T153 21381-21394 Sentence denotes 2D 1H,1H-COSY
T154 21395-21472 Sentence denotes COSY is one of the simplest and most frequently used 2D NMR experiment [123].
T155 21473-21573 Sentence denotes It shows the homonuclear coupling of nuclei (i.e., 1H-1H) separated by up to several covalent bonds.
T156 21574-21777 Sentence denotes The pulse sequence consists of a 90° excitation pulse followed by a specific evolution time (t1), a second pulse, and finally a measurement period (t2, not to be confused with relaxation rates or times).
T157 21778-21953 Sentence denotes The second pulse can be 90° or 45° or 135°, depending upon the specific requirements, and respectively yield COSY [124], COSY-45 or COSY-135 functionality (see [125,126,127]).
T158 21954-22122 Sentence denotes A two-dimensional Fourier Transform (FT) yields the final spectra and shows the frequencies for proton (1H) or carbon (in the case of carbon detection) along both axes.
T159 22123-22342 Sentence denotes There are two types of peaks; (I) Diagonal peaks, which represent the peaks of the conventional 1D spectra, and (II) cross-peaks, which have different values in the two frequency axes and are therefore off the diagonal.
T160 22343-22512 Sentence denotes These off diagonal cross-peaks are the most important pieces of information as they mark correlations between pairs of nuclei due to through bond magnetization transfer.
T161 22513-22672 Sentence denotes This helps in identifying which atoms are connected [128], critical for structural elucidation of both known molecules and unknown molecules in solution [129].
T162 22673-22865 Sentence denotes By implementing phase-cycling [130,131], it is also possible to distinguish different types of coupling and yields further helpful information about the chemical structure of a molecule [132].
T163 22866-22959 Sentence denotes As an example, the use of the COSY experiment was presented in the work of Zheng et al. [88].
T164 22960-23171 Sentence denotes The main goal of their work was to investigate potential biological differences and compare the pharmacological effects between Danggui (an herbal drug used in traditional Chinese medicine) and European Danggui.
T165 23172-23306 Sentence denotes For that, Zheng et al. treated blood deficiency rats with Danggui and European Danggui and collected samples of their serum and urine.
T166 23307-23466 Sentence denotes The samples were later measured using 1H-CPMG-NMR, 1H-NOESYPRESAT-1D, 1H,1H-COSY, and 1H,13C-HSQC, and then compared to equivalent spectra from untreated rats.
T167 23467-23703 Sentence denotes The results showed that exposure to Danggui and European Danggui altered the levels of 18 different metabolites, such as lactate, nicotinamide, glycerol and formate, which were involved in a total of seven different metabolism pathways.
T168 23704-23877 Sentence denotes Additionally, it was proven that Danggui and European Danggui have different chemical compositions, with Danggui having better blood-enriching effects than European Danggui.
T169 23879-23885 Sentence denotes 2.2.2.
T170 23886-23900 Sentence denotes 2D 1H,1H-TOCSY
T171 23901-24078 Sentence denotes Total Correlation Spectroscopy (TOCSY) also originally known as the Homonuclear Hartmann Hahn (HOHAHA) experiment can be considered an extension of the 2D 1H,1H-COSY experiment.
T172 24079-24317 Sentence denotes The difference between the two experiments is that a TOCSY experiment will show multiple cross-peaks including indirectly coupled nuclei (i.e., longer range via scalar coupling) throughout the J-coupled spin system of a chemical compound.
T173 24318-24477 Sentence denotes The basic pulse sequence of the TOCSY consists of excitation by a 90° pulse, followed by a free variable evolution period which encodes the indirect dimension.
T174 24478-24607 Sentence denotes This is normally followed by an isotropic mixing sequence to transfer magnetization between spins via the strong scalar coupling.
T175 24608-24734 Sentence denotes The mixing generates in-phase magnetization throughout a spin coupled network of the associated nuclei during the mixing time.
T176 24735-24775 Sentence denotes Lastly, a direct detection is performed.
T177 24776-25011 Sentence denotes A major advantage of the TOCSY experiment is that it detects in-phase magnetization (i.e., pure absorptive line-shape) which is far easier to analyze compared to the anti-phase information in the phase sensitivity COSY-type experiment.
T178 25012-25257 Sentence denotes The isotropic mixing is usually performed using a composite pulse scheme such as WALTZ, MLEV or DIPSI [133,134] pulse train, and can be sandwiched between two z-filters [135] where isotropic mixing is performed on the longitudinal magnetization.
T179 25258-25388 Sentence denotes The most obvious advantage of TOCSY is that all cross-peaks of the same spin system can be observed for whole spin system at once.
T180 25389-25501 Sentence denotes This is useful for identifying the complete network of spins and reducing the ambiguity of any spectral overlap.
T181 25502-25665 Sentence denotes The TOCSY experiment can be produced as 1D with a relatively shorter time and easier analysis compared to 2D but lacks the benefit of multi-dimensional resolution.
T182 25666-25774 Sentence denotes The 2D TOCSY is usually done to resolve spectra overlap [50] when first identifying molecules [136,137,138].
T183 25775-26006 Sentence denotes For example, Jiang et al. used this to predict the response to gemcitabine-carboplatin (GC) chemotherapy in patients with metastatic breast cancer who were previously exposed to treatment with both anthracyclines and taxanes [137].
T184 26007-26123 Sentence denotes For that, researchers collected serum samples from 29 patients prior to treatment and measured them using 1D 1H-NMR.
T185 26124-26270 Sentence denotes Additionally, they conducted 2D NMR experiments such as the 1H,1H-COSY, 1,1H-TOCSY, 1H,13C-HSQC, and 1H,13C-HMBC to help assign serum metabolites.
T186 26271-26517 Sentence denotes After receiving the treatment with gemcitabine-carboplatin, patients were divided into four groups based on the results from the computed tomography: complete response (CR), partial response (PR), stable disease (SD), or progressive disease (PD).
T187 26518-26942 Sentence denotes After comparing NMR results prior to the treatment with the outcome of chemotherapy, the researchers observed lower baseline levels of serum format and acetate in breast cancer patients who progressed with the disease than in those who achieved a clinical benefit from therapy, indicating that those two biomarkers could be used to distinguish between patients who will benefit from GC treatment from those who do not [137].
T188 26944-26950 Sentence denotes 2.2.3.
T189 26951-26965 Sentence denotes 2D 1H,13C-HSQC
T190 26966-27202 Sentence denotes 2D- Heteronuclear Single Quantum Coherence (HSQC) experiments are commonly used to help resolve spectral overlap [139] while providing 13C information without the inherent sensitivity losses involved in 13C direct detection (see below).
T191 27203-27299 Sentence denotes HSQC shows the correlations between directly coupled nuclei [140], e.g., 1H-13C or 1H-15N [140].
T192 27300-27446 Sentence denotes As such, an HSQC spectrum will show clean peaks for each unique proton directly connected to the heteronuclear nuclear atom of interest [140,141].
T193 27447-27618 Sentence denotes In 1H,13C/15N HSQC experiments, the magnetization is transferred from the more sensitive nucleus (I:1H) to the less sensitive nucleus (S:13C/15N) [142,143,144] (Figure 3).
T194 27619-27808 Sentence denotes This is especially useful when applying NMR spectroscopy to drug design, as most drugs are organic (i.e., contain carbon atoms), and the relative abundance of 13C (1.1%) is quite low [143].
T195 27809-27937 Sentence denotes By transferring sensitivity from 1H to 13C, one can circumvent the long experimental time required for 1D 13C experiments [143].
T196 27938-28094 Sentence denotes For example, De Castro et al. [145] studied Ptac2S and its related cytotoxicity to the cisplatin-resistant epithelial ovarian carcinoma (EOC), Skov-3 cells.
T197 28095-28236 Sentence denotes In the study, they used NMR spectroscopy and multi-variate statistical analysis to observe how Skov-3 cells reacted to treatment with Ptac2S.
T198 28237-28465 Sentence denotes In particular, they used 1H,13C-HSQC along with 1H-COSY and Heteronuclear Multiple Bond Correlation (HMBC), and the Human Metabolome Database to assign the chemical shifts of the lipid metabolites present in the studied samples.
T199 28466-28578 Sentence denotes Interestingly, Skov-3 cells treated with Ptac2S produced more pyruvate than Skov-3 cells treated with cisplatin.
T200 28579-28738 Sentence denotes The authors also noticed an unexpected difference in lipid metabolite expression levels between the cells treated with Ptac2S and those treated with cisplatin.
T201 28739-28862 Sentence denotes These results provide a possible explanation for how Ptac2S is able to overcome cisplatin resistance in Skov-3 cells [145].
T202 28864-28870 Sentence denotes 2.2.4.
T203 28871-28886 Sentence denotes 2D 1H, 13C-HMBC
T204 28887-29104 Sentence denotes Heteronuclear 2D experiments are useful for transferring magnetization from sensitive nuclei (i.e., 1H) to less sensitive nuclei (i.e., 13C) [146] thereby reducing the time needed for the acquisition of spectra [147].
T205 29105-29222 Sentence denotes Heteronuclear Single Quantum Coherence (HSQC) will only show one cross peak for each coupled pair [92,128] of nuclei.
T206 29223-29403 Sentence denotes This makes HSQCs useful for assigning the backbone of proteins [148] and in metabolites of complex biofluids [149], whose 1D 1H-NMR spectra can suffer from severe spectral overlap.
T207 29404-29637 Sentence denotes The HMBC technique, while similar to HSQC, is an example of a heteronuclear 2D experiment that reveals correlations between nuclei separated by two or more chemical bonds while also suppressing one-bond correlations at the same time.
T208 29638-29774 Sentence denotes This experiment combined with HSQC is often used to assign NMR spectra for studied molecules in drug design experiments [65,66,137,145].
T209 29775-29993 Sentence denotes As an example, HMBC was used in a recent study by Xu et al. [66] to investigate the changes in the metabolic profiles of rats treated with different dosages of the “RenqingMangjue” pill, a traditional Tibetan medicine.
T210 29994-30244 Sentence denotes In this study, the rats were divided into four groups based on the amount of “RenqingMangjue” administered: low dose group (LD)-83.33 mg/kg/day, middle dose group (MD)-333.33 mg/kg/day, high dose group (HD)-1333.33 mg/kg/day and a control group (NC).
T211 30245-30489 Sentence denotes After 15 days of consecutive administration, half of the rat population was used to collect samples such as serum, kidney, and liver tissue, while the other half underwent an additional 15 days of recovery before the same samples were acquired.
T212 30490-30704 Sentence denotes The samples were measured using 1H-NMR CPMG (an experiment used to suppress signals from larger molecules, see below) [150,151,152] along with 1H,1H-COSY, 1H,13C-HSQC, and 1H,13C-HMBC used for molecules assignment.
T213 30705-30975 Sentence denotes The obtained spectra showed that the “RenqingMangjue” pill alters many metabolites, which are related to a variety of metabolic pathways including energy metabolism, amino acid metabolism, and lipid metabolism indicating potentially harmful effects on kidneys and liver.
T214 30977-30983 Sentence denotes 2.2.5.
T215 30984-31018 Sentence denotes Relaxation-Edited NMR Spectroscopy
T216 31019-31173 Sentence denotes Relaxation in NMR is a phenomenon describing the time dependence involved in signal intensity after an induced RF (radiofrequency) pulse is applied [153].
T217 31174-31374 Sentence denotes After application of a 90° RF pulse, the bulk magnetization will move to the transverse (xy) plane and will gradually return to its original equilibrium position along the longitudinal (z) axis [154].
T218 31375-31442 Sentence denotes This process is described in Figure 4, and is termed T1 relaxation.
T219 31443-31562 Sentence denotes The details are beyond the scope of the manuscript and interested readers are directed to [155] and references therein.
T220 31563-31653 Sentence denotes Relaxation times for NMR are even more complicated and exist in two categories: T1 and T2.
T221 31654-31765 Sentence denotes T1 refers to the rate of longitudinal (or spin-lattice) Z-axis relaxation as the system returns to equilibrium.
T222 31766-31921 Sentence denotes A second component also contributes, i.e., T2 relaxation and refers to the rate of transverse (or spin-spin) relaxation [154] which occurs in the XY plane.
T223 31922-32037 Sentence denotes T2 is independent of the longitudinal relaxation (T1) and represents the loss of coherence in the precessing spins.
T224 32038-32177 Sentence denotes Therefore NMR relaxation spectroscopy can be based on T1 and/or T2 [156], and is collectively referred to as “relaxation edited NMR” [157].
T225 32178-32268 Sentence denotes T1-based methods typically measure and compare the T1 times of the free and bound ligands.
T226 32269-32491 Sentence denotes A common way to measure the T1 value of a small molecule is the inversion recovery experiment [158,159], although other experiments are also available such as ultrafast NMR T1 [160] and saturation inversion recovery [161].
T227 32492-32623 Sentence denotes In general, the shorter T1 the relaxation time the less intense the peak signal will be and the broader the signal linewidth [162].
T228 32624-32856 Sentence denotes The T1 values of free and bound ligand will differ depending on how strongly the ligand binds because molecular interactions with the target will influence the ligand’s molecular motion, and hence, its longitudinal relaxation [156].
T229 32857-33070 Sentence denotes Bound ligands will have smaller T1 values than in their free form because, overall, they will experience slower molecular motion upon interacting with a target [163] therefore behaving like a much larger molecule.
T230 33071-33250 Sentence denotes They can (depending on molecule size) also display a negative NOE difference spectrum (transferred NOE) [164], whereas non-binding ligands normally show small-positive NOEs [156].
T231 33251-33384 Sentence denotes For binding ligands to display negative NOEs, their T1 values must be comparatively longer than the 1/koff value of the target [156].
T232 33385-33522 Sentence denotes T1 relaxation times can be easily used to screen small molecules as ligands for DNA [165] and serve as a basis for HTS experiments [166].
T233 33523-33778 Sentence denotes An experiment related to drug design that utilized 1D and 2D relaxation edited NMR was done by Hajduk et al. [167] in which he and others used 1D and 2D relaxation edited NMR techniques to detect ligands that bind to FK506 binding protein and stromelysin.
T234 33779-33915 Sentence denotes One year earlier, Liu et al. [157] used relaxation edited one-and two-dimensional 1H-NMR spectroscopy to characterize biological fluids.
T235 33916-34051 Sentence denotes Tang et al. [168] extended this by applying relaxation edited NMR Spectroscopy to improve the detection of metabolites in blood plasma.
T236 34052-34261 Sentence denotes More recently, Jaremko et al. commented on available models used to interpret 15N protein relaxation data [169], and even used deficient 15N relaxation data to rapidly calculate the dynamics of proteins [170].
T237 34262-34371 Sentence denotes The T2 relaxation experiment relies on so-called Carr–Purcell–Meiboom–Gill (CPMG) building blocks (Figure 5).
T238 34372-34430 Sentence denotes This pulse sequence is explained with the following steps:
T239 34431-34514 Sentence denotes First, application of a 90° RF pulse creates a transverse (xy plane) magnetization.
T240 34515-34611 Sentence denotes Second, a spin-echo period (delay-180°-delay block) is responsible for Mx/y magnetization decay.
T241 34612-34670 Sentence denotes This period is repeated “n’’ times (CPMG building blocks).
T242 34671-34921 Sentence denotes It is essential to point out that every NMR experiment involving a large number of pulses (e. g. due to the repeating building blocks) is likely to be sensitive to hardware restrictions and small miscalibrations of the duration of the applied pulses.
T243 34922-35117 Sentence denotes To attenuate the unwanted effects of miscalibrations, Meiboom and Gill modified the previously used Carr–Purcell sequence [171] by changing the phase of the applied 180° pulses from x to y [172].
T244 35118-35198 Sentence denotes This procedure can be used to measure T2 relaxation times of any type of nuclei.
T245 35199-35361 Sentence denotes For instance, in the case of 13C, all pulses and acquisitions are applied on 13C channel, while broadband proton decoupling is applied during all pulse sequences.
T246 35362-35422 Sentence denotes It works analogically for different NMR-active nuclei [173].
T247 35423-35609 Sentence denotes In a typical CPMG experiment, the effective transverse relaxation rate, R2,eff, is typically measured by fitting the signal decay as a function of a variable number of CPMG blocks [174].
T248 35610-35790 Sentence denotes The experimental half-height linewidth (d) of a given resonance signal is directly related to T2* (also called as ‘effective’ or “observed’’) by the following equation:(1) d=1π T2*
T249 35791-35972 Sentence denotes T2 represents the transverse relaxation times, and additional broadening comes from the magnetic field inhomogeneities (T2inh), which must be taken into account. (2) 1T2*=1T2+1T2inh
T250 35973-36071 Sentence denotes T2 measurements of ligands are also useful for determining the binding nature of a small molecule.
T251 36072-36242 Sentence denotes The T2 values of small molecules are quite large compared to those of bigger molecules (i.e., proteins) mostly because macromolecules have more spin-spin diffusion [175].
T252 36243-36453 Sentence denotes Bound ligands will, therefore, display shorter T2 values than non-binding ligands because they interact with the target (i.e., protein), adopting similar vibrational and rotational energies to the target [176].
T253 36454-36604 Sentence denotes This interaction is represented by the resonance line broadening in the binding ligand’s spectrum when a receptor is introduced into the sample [156].
T254 36605-36872 Sentence denotes Given the sizable difference of T2 values of binding and non-binding ligands, one can utilize 1D relaxation-edited experiments to distinguish the binding ligands from the non-binding ligands efficiently and effectively based on the differences in the T2 values [167].
T255 36873-36955 Sentence denotes These and other related relaxation edited experiments prove useful in drug design.
T256 36956-37202 Sentence denotes Relaxation edited NMR spectroscopy takes advantage of an inherent atomic property (i.e., the return of bulk magnetization back to equilibrium [177]), so no molecular enrichment (e.g., 15N isotopic enrichment of protein targets) is required [167].
T257 37203-37437 Sentence denotes Furthermore, the slow time scale of NMR relaxation allows the user to manipulate the external conditions (i.e., length and power of pulse) to increase the resolution of targets and potential drugs [155] in NMR drug design experiments.
T258 37438-37654 Sentence denotes However, this slow timescale also sets the lower limit at which NMR drug design experiments can be performed [155], meaning that any external manipulations cannot decrease experimental time below a certain threshold.
T259 37655-37721 Sentence denotes This varies based on the drugs and targets used in the experiment.
T260 37722-37968 Sentence denotes Low drug solubility is also a challenge, as the ligands must be at a sufficiently high concentration to allow detection via NMR, although the use of organic solvents has helped to attenuate this effect in relaxation edited NMR spectroscopy [156].
T261 37969-38060 Sentence denotes For examples of experiments that use different NMR techniques mentioned above, see Table 1.
T262 38062-38064 Sentence denotes 3.
T263 38065-38116 Sentence denotes NMR Methods for Drug Discovery and Drug Development
T264 38117-38214 Sentence denotes As stated, NMR spectroscopy can be fundamental in studying how drugs interact with their targets.
T265 38215-38378 Sentence denotes This has been done mainly via the Fragment Based Drug Design (FBDD) approach, which has two sub-approaches: target- (i.e., protein) based, or ligand- (drug) based.
T266 38379-38522 Sentence denotes Target based screening monitors how the target responds to binding molecules in a method called Structure Activity Relationship (“SAR”) by NMR.
T267 38523-38813 Sentence denotes Ligand (drug)-based screening methods provide ways to observe the binding/non-binding behavior of the drug in approaches such as Saturation Transfer Difference (STD) and other Nuclear Overhauser Effect (NOE) type methods, diffusion-based methods, relaxation-based methods (i.e., T1 and T2).
T268 38814-38929 Sentence denotes Target based screening, ligand (drug) based screening, and their respective methods, are discussed in detail below.
T269 38931-38935 Sentence denotes 3.1.
T270 38936-38976 Sentence denotes NMR in Fragment Based Drug Design (FBDD)
T271 38977-39090 Sentence denotes NMR-based drug discovery can be broadly classified into two groups: chemical and biological (in-cell) categories.
T272 39091-39211 Sentence denotes One of the principal methods of drug discovery using NMR spectroscopy is called fragment-based drug design (FBDD) [194].
T273 39212-39308 Sentence denotes In-cell NMR (biological) based drug discovery techniques will be discussed later in this review.
T274 39309-39477 Sentence denotes FBDD was first reported in 1996 [195] and used throughout the late 1990s as evidenced by the use of keywords related to FBDD in papers published during this time [196].
T275 39478-39581 Sentence denotes The use of FBDD as a viable drug screening technique began to be widely adopted in the mid-2000s [197].
T276 39582-39671 Sentence denotes High Throughput Screening (HTS) is another technique widely used in drug discovery [198].
T277 39672-39789 Sentence denotes HTS analyzes molecules from a chemical library to see which ones are suitable leads [198,199,200,201] (see Figure 6).
T278 39790-40098 Sentence denotes FBDD techniques will screen against a carefully designed fragment library composed of a few thousand molecules (for details on the choice of compounds and design of fragment libraries, see [202,203]) and identified hits are further developed via fragment growing, fragment merging, or fragment linking [194].
T279 40099-40208 Sentence denotes For examples of drugs derived from the FBDD approach that are currently in clinical trials, refer to Table 2.
T280 40209-40401 Sentence denotes HTS has been productive in drug design [204,205], but the method is time and resource intensive [206] and expensive [206] because of the numerous molecules to be examined (~100 million) [207].
T281 40402-40474 Sentence denotes Furthermore, the success rate is only estimated to be at ~50% [204,208].
T282 40475-40721 Sentence denotes Unlike traditional HTS, which can survey a large number of molecules ranging from a few hundred thousand to a few million [209], FBDD usually surveys a few thousand molecules (~1000–15000) from libraries with greater chemical diversity [209,210].
T283 40722-40865 Sentence denotes FBDD is a main-stream screening technique for drug discovery [207,209,211,212,213,214,215,216] and NMR is standard for many FBDD studies [209].
T284 40866-41047 Sentence denotes Additional methods and techniques such as SPR, X-ray crystallography [209,217,218,219,220] etc. have also been used in FBDD studies, accompanied or unaccompanied by NMR experiments.
T285 41048-41127 Sentence denotes For examples of FBDD derived drugs using methods besides NMR, refer to Table 2.
T286 41128-41331 Sentence denotes At the time of writing, and to the best of our knowledge, there are three Food and Drug Administration (FDA)-approved drugs derived from the FBDD approach [221], and over 30 are in clinical trials [222].
T287 41332-41407 Sentence denotes The first marketed drug derived via the FBDD approach is vemurafenib [223].
T288 41408-41595 Sentence denotes Vemurafenib is also the first drug approved for treatment of BRAF-mutant cancer [224], and is reported to exhibit significant clinical benefit for patients with metastatic melanoma [224].
T289 41596-41814 Sentence denotes Venetoclax, a common drug used to treat patients with chronic lymphocytic leukemia [225], is considered the second drug to be discovered using the FBDD approach [221], and ribociclib, a CDK4 inhibitor, the third [221].
T290 41815-41958 Sentence denotes The names, structures, targets/applications, and clinical status of vemurafenib, venetoclax, ribociclib, and other drugs are listed in Table 2.
T291 41959-42106 Sentence denotes As mentioned, NMR spectroscopy can be used in FBDD in two different ways: (1) target (or receptor) based screening, and (2) ligand-based screening.
T292 42107-42212 Sentence denotes With the stated advantages and disadvantages, researchers must select based on their available compounds.
T293 42214-42220 Sentence denotes 3.1.1.
T294 42221-42243 Sentence denotes Target Based Screening
T295 42244-42382 Sentence denotes Target based screening typically utilizes the “SAR by NMR” (structure-activity-relationship by nuclear magnetic resonance) approach [246].
T296 42383-42467 Sentence denotes SAR is primarily used to identify and develop extremely tight-binding ligands [247].
T297 42468-42663 Sentence denotes The ligand to target binding is traditionally monitored via chemical shift changes [247] using a correlation spectroscopy such as 1H-15N HSQC starting with the target and no ligand present [248].
T298 42664-42748 Sentence denotes Multiple spectra for the target are recorded in the presence and absence of ligands.
T299 42749-42911 Sentence denotes The binding ligand will cause chemical shift perturbations in the target, and these perturbations are often easily visualized by overlaying the two spectra [247].
T300 42912-43046 Sentence denotes For example Hajduk et al. investigated the binding interactions of 2-phenylimidazole with the FKBP protein as shown in Figure 7 [249].
T301 43047-43256 Sentence denotes From the overlaid spectra, chemical shift changes are measured, and from the molecular location, extent, and rate of the chemical shift changes, the binding site and affinity of the ligand is calculated [250].
T302 43257-43500 Sentence denotes Then, by following a procedure completely analogous to that of FBDD (see Figure 6), a ligand developed from multiple fragments can be optimized for the binding site of interest, again by monitoring the changes in chemical shifts of the target.
T303 43501-43642 Sentence denotes Several examples of the successful applications of SAR by NMR in drug design research are replete in the scientific literature [204,251,252].
T304 43643-43823 Sentence denotes SAR by NMR spectroscopy allows researchers to observe directly ligand binding [247] in both solution state and solid-state spectra [253], increasing the method’s versatility [254].
T305 43824-43920 Sentence denotes It works particularly well for targeting proteins with adjacent “subpocket” binding sites [248].
T306 43921-44020 Sentence denotes Furthermore, SAR by NMR is cost-effective when combined with HTS (High Throughput Screening) [255].
T307 44021-44196 Sentence denotes SAR by NMR can also be used even when atomic peak assignments in spectra are unknown, though it is much more powerful when the resonance frequency of each atom is known [254].
T308 44197-44525 Sentence denotes The main limitation of SAR by NMR, however, is its inability to distinguish between multiple binding modes (i.e., cleavage of covalent bonds or allosteric changes), and if multiple binding modes are present, it can be difficult to pinpoint the “true” binding site of the ligand solely using data obtained using SAR by NMR [254].
T309 44527-44533 Sentence denotes 3.1.2.
T310 44534-44560 Sentence denotes NMR Ligand-Based Screening
T311 44561-44647 Sentence denotes Ligand-based screening, the second approach of NMR in FBDD, has three main categories:
T312 44648-44818 Sentence denotes 1) Saturation Transfer Difference (STD) and Nuclear Overhauser Effect (NOE) type methods, based on 2) diffusion methods, or 3) relaxation-based methods (i.e., T1 and T2).
T313 44820-44826 Sentence denotes 3.1.3.
T314 44827-44863 Sentence denotes Saturation Transfer Difference (STD)
T315 44864-45055 Sentence denotes Saturation Transfer Difference (STD) NMR depends on the Nuclear Overhauser Effect (NOE), which is often used to enhance the sensitivity of less sensitive nuclei such as 13C and 15N [256,257].
T316 45056-45185 Sentence denotes This increase in sensitivity is possible because of dipolar coupling (i.e., through space interactions of separate nuclei) [257].
T317 45186-45532 Sentence denotes The increase in sensitivity is actually brought about by applying a long, low power radiofrequency pulse that selectively saturates the magnetization [256] of a specific chemical group (i.e., the methyl groups on a protein), which is then given time to transfer to another chemical group via the NOE dipolar coupling within a few angstroms [258].
T318 45533-45693 Sentence denotes The transfer in magnetization is easily visualized on a NMR spectrum that takes the differences in the signal intensities from before and after the irradiation.
T319 45694-45840 Sentence denotes This new spectrum is called a “difference spectrum”, and it reveals what chemical groups interact with the irradiated signal [259] (see Figure 8).
T320 45841-45965 Sentence denotes STD NMR is an application of NOE used to probe the binding of ligands to a specific site within the targeted proteins [256].
T321 45966-46046 Sentence denotes A generic example of detecting ligand binding via STD is presented in Figure 9a.
T322 46047-46362 Sentence denotes The STD NMR method follows the same concepts as a normal NOE experiment: a spectrum of the ligand in the free, non-binding form is recorded, the ligand is allowed to bind to the protein, which has a functional group of interest (i.e., methyls) with a saturated signal from a previous selective radiofrequency pulse.
T323 46363-46567 Sentence denotes The saturated signal travels to the ligand, increasing the intensity of a signal on the ligand spectrum and finally a difference spectrum is used to determine precisely which sections of the ligands bind.
T324 46568-46647 Sentence denotes The difference in peak intensities proves the presence of ligand binding [260].
T325 46648-46753 Sentence denotes Water-Ligand Observed through Gradient Spectroscopy (WaterLOGSY) is a second type of STD (see Figure 9b).
T326 46754-46950 Sentence denotes The main difference with normal STD NMR is that water is the saturated signal [261], and instead of observing lower peak intensities, peak inversions indicate the presence of ligand binding [209].
T327 46951-47129 Sentence denotes For STD NMR to work properly, the ligand concentration must be in large excess (often 100–1000 fold) over the receptor so that effective saturation transfer can take place [260].
T328 47130-47252 Sentence denotes This means that for STD NMR, and WaterLOGSY, only small amounts (µg) of protein are required to get results [261,262,263].
T329 47253-47417 Sentence denotes This is advantageous for researchers, as they can perform STD NMR on a protein of interest, and preserve the rest of the unused sample for future/other experiments.
T330 47418-47482 Sentence denotes Also, the same sample can be used for multiple NMR measurements.
T331 47483-47692 Sentence denotes STD NMR facilitates the differentiation of binding ligands from non-binding ligands because the change in signal (as determined by the difference spectrum) is easy to measure and observe, as shown in Figure 9.
T332 47693-47774 Sentence denotes WaterLOGSY has been extended to study ligand interactions with DNA and RNA [261].
T333 47775-47966 Sentence denotes There are additional NOE-type experiments (trNOE, INPHARMA, SALMON, etc.) used for drug design, and specific details regarding individual methods are found in the scientific literature [264].
T334 47967-48113 Sentence denotes With the pressing search for new antiviral drugs, any techniques for identifying and characterizing novel leads has become increasingly important.
T335 48114-48349 Sentence denotes Benie et al. [265] described the use of saturation transfer difference (STD) NMR spectroscopy [262,266,267,268,269,270,271] to identify and characterize the binding of an antiviral compound to native human rhinovirus serotype 2 (HRV2).
T336 48350-48555 Sentence denotes The experiments demonstrated that it is possible to subject targets of the size and complexity of whole viruses (for a model of an HRV2 particle cut open, cf. the table of contents) to STD NMR experiments.
T337 48556-48798 Sentence denotes The principles of STD NMR have been known for many years [267,268] but it was only recently that the potential of this technique for screening libraries for compounds with binding activity toward protein receptors has been realized [262,266].
T338 48799-48891 Sentence denotes The technique also permitted the analysis of epitopes of ligands bound to receptor proteins.
T339 48892-49024 Sentence denotes Previous NMR studies of virus-ligand interactions used chemical shift titrations, which required very large quantities of the virus.
T340 49025-49087 Sentence denotes This approach was unworkable when studying pathogenic viruses.
T341 49088-49360 Sentence denotes Benie et al. [265] demonstrated that solution state STD methodology not only reduces the amount of virus required by approximately 2 orders of magnitude, but also allows for the identification and characterization of virus-ligand interactions with atomic resolution [272].
T342 49361-49574 Sentence denotes The very large size of viruses makes them particularly attractive for studies by STD NMR, as they inherently yield large line widths allowing for easy irradiation of the virus without affecting the ligand protons.
T343 49575-49745 Sentence denotes Furthermore, because of the larger correlation time of a virus in comparison to an average-sized protein, spin diffusion, and thus saturation transfer, is very efficient.
T344 49746-49986 Sentence denotes The large line width has additional benefits not just for STD-based NMR methods but also for transfer NOESY spectra, as protons from the virus capsid are invisible in the NMR spectra (for an example of a transfer NOESY spectrum, see [265]).
T345 49987-50091 Sentence denotes Moreover, competitive STD titration experiments can be used to determine the Kd value of a ligand [271].
T346 50092-50217 Sentence denotes Analysis of the STD spectra using the group epitope mapping method [271] allows for the determination of the binding epitope.
T347 50218-50340 Sentence denotes STD NMR methods can considerably speed up the determination of the binding epitope for potential antiviral lead compounds.
T348 50341-50543 Sentence denotes Simple STD NMR experiments provide substantial information on the binding of ligands to native viruses and require very small amounts of the virus with measurement times in the range of tens of minutes.
T349 50544-50790 Sentence denotes This allows for a high throughput of ligand samples without significant consumption of viral material because it remains unaffected by the experiments and is easily separated from the low molecular weight ligands by ultra-filtration subsequently.
T350 50791-50903 Sentence denotes In addition to the detection of binding, a complete mapping of the ligand-binding epitope can be achieved [265].
T351 50904-51074 Sentence denotes Noroviruses (NV) are non-enveloped, single-stranded, positive-sense RNA viruses that are the major cause of epidemic outbreaks of gastroenteritis worldwide [273,274,275].
T352 51075-51203 Sentence denotes The viral coat consists of a single protein, VP1, which assembles into a capsid with overall icosahedral symmetry [276,277,278].
T353 51204-51332 Sentence denotes Attachment of human noroviruses to histo-blood group antigens (HBGAs) is thought to be critical for the infection process [279].
T354 51333-51443 Sentence denotes The protruding domains of the VP1 proteins, called P-domains, harbor highly conserved binding sites for HBGAs.
T355 51444-51696 Sentence denotes STD NMR-based epitope mapping was used [262,271] to identify structural features of different core types critical for the binding of synthetic A- and B-tetrasaccharides [280] to virus-like particles (VLPs) of a highly homologous GII.4 strain (Ast6139).
T356 51697-51823 Sentence denotes STD NMR experiments provide a robust and straightforward technique for obtaining ligand binding epitopes at atomic resolution.
T357 51824-51958 Sentence denotes Comparing binding epitopes of related ligands then delivers critical information about structural requirements for ligand recognition.
T358 51959-52126 Sentence denotes Conversely, comparison of binding epitopes of a given ligand binding to wild type, and to mutant proteins reveals the importance of individual amino acids for binding.
T359 52127-52347 Sentence denotes STD NMR experiments with L-Fuc and B-trisaccharide in the presence of wild type and mutant VLPs yield virtually identical binding epitopes and suggest that these two mutations do not significantly alter HBGA recognition.
T360 52348-52617 Sentence denotes The STD NMR approach to characterize binding of HBGA ligands to noroviruses has employed VLPs as targets and thus taken advantage of the large size of VLPs yielding excellent signal-to-noise ratios of the corresponding STD NMR spectra, as demonstrated previously [281].
T361 52619-52625 Sentence denotes 3.1.4.
T362 52626-52676 Sentence denotes Transferred NOE (tr-NOE) in Ligand Based Screening
T363 52677-52775 Sentence denotes The application of the transferred NOE (Tr-NOE) effect was first demonstrated by Bothner-By [282].
T364 52776-52937 Sentence denotes The Tr-NOE is the nuclear Overhauser effect between ligand spins, which are in chemical exchange between the bound and unbound form with the protein or receptor.
T365 52938-53026 Sentence denotes Ligands, which are a mixture of target molecules, are small in size (below 500–1000 Da).
T366 53027-53207 Sentence denotes Since they are usually low molecular weight molecules, they exhibit much shorter correlation times when compared to the receptor and have slow NOE build-ups with no spin diffusion.
T367 53208-53274 Sentence denotes This is the reason they show small positive NOEs in the free form.
T368 53275-53427 Sentence denotes When binding to a protein receptor, the situation changes, where the ligand acquires large correlation times in the bound state with rapid NOE build-up.
T369 53428-53521 Sentence denotes Then they show spin diffusion and a strong negative NOE, which is termed the transferred NOE.
T370 53522-53692 Sentence denotes Signals arising from the protein are usually not observed for large proteins as they are generally kept low in concentration, with ligands in a high excess concentration.
T371 53693-53784 Sentence denotes In addition, most of the time protein signals are suppressed by their very short T2 period.
T372 53785-54153 Sentence denotes It is worthwhile to mention that ligands that are in fast exchange between the bound and the free form (dissociation constants ranging from μM to mM) get enough bound time to transfer the negative NOE from the protein complex to the population of the free molecules, yet usually retain the chemical shift of the free molecule along with the relaxation characteristics.
T373 54154-54338 Sentence denotes In order to observe tr-NOEs, the following condition have to be fulfilled:(3) |Nb∂b|≫|Nf∂f| where N and ∂ represent the number of molecules and the cross-relaxation rate, respectively.
T374 54339-54409 Sentence denotes The subscript b and f represent the bound and free form, respectively.
T375 54410-54511 Sentence denotes Therefore, to observe the tr-NOEs, a high excess concentration of ligands over protein is maintained.
T376 54512-54790 Sentence denotes On the other hand, if the ligand concentration is kept too high, the excess free ligand in solution will exhibit positive NOE, which can result in a significant reduction of the tr-NOESY enhancements due to negative NOE developed by the very small concentration of bound ligand.
T377 54791-54948 Sentence denotes Hence, the preparation of the sample becomes tricky and an optimum ratio between 10–30 to 1 is maintained while considering the dissociation constant values.
T378 54949-55063 Sentence denotes The binding of a ligand to a receptor protein can easily be identified by observing the sign and size of the NOEs.
T379 55064-55231 Sentence denotes There are some distinct experimental features for the discrimination between tr-NOEs from the bound state and NOEs of the ligand in free states like the build-up rate.
T380 55232-55327 Sentence denotes For tr-NOEs, this is in the range of 50 to 100 ms, whereas for small ligands it is much longer.
T381 55328-55456 Sentence denotes There have been various instances of experimental implementations to quickly determine the binding activity of ligand libraries.
T382 55457-55620 Sentence denotes One example was to find the ligand molecule among a library of 10 similar structure polysaccharides that is bioactive in binding with recombinant E-selectin [283].
T383 55621-55706 Sentence denotes This is a protein present in an IgG chimera with a molecular weight of about 220 kDa.
T384 55707-55756 Sentence denotes In this case, two 2D NOESY spectra were recorded.
T385 55757-56009 Sentence denotes The NOESY spectra for the ligand library was measured at several temperatures and it was found that most of the 10 compounds exhibited the weak positive NOEs at 310 K, which was then chosen to differentiate between trNOEs showing large negative values.
T386 56010-56162 Sentence denotes The trNOESY spectra of the ligand library in the presence of protein was recorded at different ratios, such as 5:1, 8:1, 12:1, 15:1, and 20:1, at 310 K.
T387 56163-56266 Sentence denotes In all the ratios, trNOEs were observed; however, the ratio of 15:1 represented the best-case scenario.
T388 56268-56274 Sentence denotes 3.1.5.
T389 56275-56320 Sentence denotes The INPHARMA Method for Pharmacophore Mapping
T390 56321-56539 Sentence denotes The INPHARMA method (see Figure 10) was designed to determine the relative orientation between two competitive ligands in the receptor-binding pocket through the observation of inter-ligand NOE between the two ligands.
T391 56540-56676 Sentence denotes It is a tr-NOE in nature as it is mediated by the bound conformation of the competing ligands and in exchange with the receptor protein.
T392 56677-56852 Sentence denotes The first example was competitive binding and observation of inter-ligand NOE between baccatin III and epothilone A in the presence of tubulin, which acts as a receptor [284].
T393 56853-56928 Sentence denotes Since the observation is on the ligand site, it provides unique advantages.
T394 56929-57020 Sentence denotes The detailed conformation of a ligand-protein complex can be addressed by conventional NMR.
T395 57021-57129 Sentence denotes However, it is time-consuming and demands full solving of the structure and there is also a size limitation.
T396 57130-57185 Sentence denotes From that aspect, ligand-based methods are more useful.
T397 57186-57382 Sentence denotes The only limiting fact is that it should fulfill all the conditions of tr-NOE explained previously in terms of dissociation constant (Kd), fast exchange regime, and proper ligand to protein ratio.
T398 57383-57490 Sentence denotes Then, information on the ligand structure can be derived from tr-NOE build up as a function of mixing time.
T399 57491-57568 Sentence denotes This can be readily explained using the originally proposed schematics [284].
T400 57569-57683 Sentence denotes The NOESY spectrum of a mixture of the two ligands A and B in the presence of the common receptor (T) is recorded.
T401 57684-57935 Sentence denotes Under the situation that each of A and B exhibit competitive binding in a fast exchange regime with the receptor T, intermolecular tr-NOE peaks between the two ligands A and B can then be observed in the NOESY spectrum due to extensive spin diffusion.
T402 57936-58079 Sentence denotes During the NOESY mixing time, the first proton of ligand A (HA) binds to receptor T, which results in transfers of magnetization from HA to HT.
T403 58080-58264 Sentence denotes Subsequently, the complex AT dissociates as they fulfill the dissociation constant range, which creates the opportunity for ligand B to bind to the receptor T at the same binding site.
T404 58265-58370 Sentence denotes This results in the transfer of the magnetization of HT, which had been originally coming from HA, to HB.
T405 58371-58516 Sentence denotes As a result, an inter-molecular correlation HA–HB can be seen, and this inter-molecular NOE will be a function of mixing time as described above.
T406 58517-58653 Sentence denotes The detailed analysis of such intermolecular NOE peaks helps in assessing the relative orientation of each ligand in the binding pocket.
T407 58655-58661 Sentence denotes 3.1.6.
T408 58662-58705 Sentence denotes Diffusion Based Spectroscopy in Drug Design
T409 58706-58824 Sentence denotes Diffusion is the random, translational motion of molecules in solution as a consequence of their thermal energy [285].
T410 58825-58988 Sentence denotes This type of motion is often referred to as “Brownian motion”, a motion that describes molecular movement induced by random collisions between the molecules [286].
T411 58989-59188 Sentence denotes In the presence of a concentration gradient, molecules will naturally move from places of higher concentration to places of lower concentration [287] after a period of time, t, as shown in Figure 11.
T412 59189-59249 Sentence denotes Fick’s Law can be used to model this type of movement [288].
T413 59250-59449 Sentence denotes The distribution of the diffusing molecules is accurately represented by a Gaussian curve, a normal distribution centered at a single point, which gradually “flattens” as t approaches infinity [213].
T414 59450-59545 Sentence denotes The extent to which a molecule diffuses is directly related to its shape, size, and mass [285].
T415 59546-59779 Sentence denotes In homogeneous isotropic solutions, the root mean square distance (zrms) traveled by a molecule is given by following equation [289,290]:zrms=(2Dt)12  where D is the diffusion coefficient of the molecule, and t is the diffusion time.
T416 59780-60134 Sentence denotes Making the assumption that the molecules are solid rigid spheres, the value of D can be calculated according to the famous Einstein-Stokes equation (Equation (2)):(4) D=kbT6πηrs  where kb is the Boltzmann’s constant (1.3807 × 10−23 J/K), T is the absolute temperature, η is the solution viscosity, and rs is the hydrodynamic radius of the molecule [290].
T417 60135-60377 Sentence denotes Equation (1) and Equation (2), however, are not universally applicable; they only apply to molecules that are freely diffusing in isotropic, homogeneous solutions, and importantly that can be accurately described as hard, rigid spheres [285].
T418 60378-60590 Sentence denotes Different molecular geometries and additional modes of diffusion (i.e., restricted and anisotropic) require more advanced mathematics and theory [291,292], but the essential concepts of diffusion remain the same.
T419 60591-60741 Sentence denotes The earliest pulse sequence used to measure diffusion in NMR spectroscopy is the gradient spin echo sequence (SE), developed by Stejskal et al. [293].
T420 60742-60786 Sentence denotes The SE pulse sequence is shown in Figure 12.
T421 60787-60973 Sentence denotes The SE pulse sequence uses a gradient (G) of the externally applied magnetic field, (pulsed field gradient), the first after the 90° pulse, and the other after the 180° refocusing pulse.
T422 60974-61105 Sentence denotes The first gradient pulse (G1) labels or gradient-encodes the NMR-active nuclei based on their physical position in the sample tube.
T423 61106-61252 Sentence denotes If the molecules diffuse during the time period they are not in the correct position to experience the second gradient which re-focuses the spins.
T424 61253-61309 Sentence denotes This is detected via NMR as a signal intensity decrease.
T425 61310-61502 Sentence denotes After a diffusion time (∆), the second gradient pulse is applied to decode the spatial labeling of NMR-active nuclei, obtaining a well-defined spectra of diffusing molecules in solution [294].
T426 61503-61657 Sentence denotes Additional NMR sequences are available for diffusion experiments [295], and are detailed in more comprehensive reviews dealing with the subject [296,297].
T427 61658-62094 Sentence denotes The signal intensity of the diffusing molecules depends on three factors, as described by Equation (3) [294]:(5) I=I0e−Dγ2g2δ2  where I is the observed intensity, I0 the reference intensity (unattenuated signal intensity), D is, of course, the diffusion coefficient referred to earlier, γ is the gyromagnetic ratio of the observed nucleus, g is the strength of the gradient, δ the length of the gradient, and ∆ the diffusion time [294].
T428 62095-62283 Sentence denotes From Equation (3), it is easy to see that the signal intensity decreases exponentially with time, so it is vital to optimize the values of g, δ, and ∆ for diffusion NMR measurements [294].
T429 62284-62450 Sentence denotes The drug design approach based on diffusion NMR is basically a screening technique used to differentiate the binding ligands (drug) from non-binding components [264].
T430 62451-62682 Sentence denotes Ligands able to bind should have significantly different diffusion coefficients (D) compared to non-binding ligands [297], i.e., the diffusion coefficients of binding ligands will be smaller than those of non-binding ligands [264].
T431 62683-62793 Sentence denotes Thus, diffusion-based NMR is a way of effectively “filtering” and identifying which ligands are binding [264].
T432 62794-62894 Sentence denotes Diffusion-based NMR spectroscopy has advantages in ligand based screening applied to drug discovery.
T433 62895-63029 Sentence denotes For example, Diffusion Ordered Spectroscopy (DOSY) does not require prior separation/purification of the ligand/target solution [298].
T434 63030-63442 Sentence denotes Diffusion based NMR allows simultaneous determination of diffusion coefficients in multicomponent systems containing large molecules (i.e., proteins) and possible binding partners (i.e., small drug compounds) [285], and no special labeling or contrasting agents are required, though their use is not exclusively inhibited (for an example of the use of labeled compounds in diffusion NMR spectroscopy, see [299]).
T435 63443-63561 Sentence denotes A problem occurs when there is significant chemical shift overlap between the binding molecule signals and the target.
T436 63562-63736 Sentence denotes This situation makes it hard to distinguish the NMR signals [300], and the calculations typically assign an intermediate value to the diffusion rate (i.e., one gets a smear).
T437 63737-63869 Sentence denotes Multidimensional diffusion NMR pulse sequences are available [301], which may help resolve spectral overlap in 1D experiments [300].
T438 63870-63968 Sentence denotes Another issue is that molecules in chemical databases may have generally low solubility [302,303].
T439 63969-64111 Sentence denotes Low solubility decreases the overall signal intensity and therefore makes accurately measuring diffusion experiments far more difficult [304].
T440 64112-64284 Sentence denotes There are many examples demonstrating the successful application of diffusion NMR in examining drugs of pharmaceutical interest [305], and ligand-target interactions [167].
T441 64285-64443 Sentence denotes Hajduk et al. [167] exploited the changes in diffusion rates to detect ligands that bind to the FK506 binding protein and the catalytic domain of stromelysin.
T442 64444-64709 Sentence denotes Nishimura et al. [306] utilized DOSY, in combination with NOESY to determine the orientation of two guest molecules, p-ethoxyiodobenzene and 2-iodo-6-methoxynaphthalene, within a host composed of a tetrakis(4-hydroxyphenyl)-cavitand and a tetra(4-pyridyl)-cavitand.
T443 64710-64941 Sentence denotes Furthermore, Matthias et al. [307] used 1H molecular diffusion and 19F spin diffusion to probe the drug loading properties of the Rf-PEG hydrogel for 5-fluorouracil (FU) and 1,3-dimethyl-5-fluorouracil (DMFU), two anticancer drugs.
T444 64942-65094 Sentence denotes DOSY can be combined with Saturation Transfer Difference (STD, discussed earlier in this review) to yield new insights about ligand-target interactions.
T445 65095-65247 Sentence denotes Kramer et al. [308] combined STD with DOSY to analyze a mixture composed of wheat germ agglutinin and two derivatives of N-acetyl glucosamine (ligands).
T446 65248-65352 Sentence denotes Using this new technique they were able to obtain high quality spectra of the components in the mixture.
T447 65353-65475 Sentence denotes Tanoli et al. [309] also combined STD and DOSY to explore the interactions of smaller molecules with bovine serum albumin.
T448 65476-65617 Sentence denotes These are just a few examples to show that diffusion NMR spectroscopy has played, and will continue to play, a prominent role in drug design.
T449 65619-65623 Sentence denotes 3.2.
T450 65624-65680 Sentence denotes NMR and In Silico Screening-Two Complementary Approaches
T451 65681-65891 Sentence denotes In silico (virtual) screening is now a standard technique in drug design and discovery [310] that has been in use since at least 1991 [311], though the exact origin of the phrase “in silico” is not clear [312].
T452 65892-66261 Sentence denotes The nearly ubiquitous use of virtual screening is due to its efficiency in searching massive chemical databases in order to generate lead molecules [313] that inhibit protein-protein interactions [314], and its ability to help identity ligand (drug) binding sites on the target of interest [310] to lend insight to the mechanisms of action for lead compounds [315,316].
T453 66262-66480 Sentence denotes Virtual screening is often accompanied by in vitro or in vivo techniques for pharmacology drug research [312], to increase drug throughput, helping to reduce the time and cost of developing novel drug candidates [317].
T454 66481-66595 Sentence denotes Virtual screening has also been used to identify candidates for anti-viral drugs [318] and anticancer drugs [319].
T455 66596-66676 Sentence denotes Several chemical databases are available both for public and academic use [320].
T456 66677-66857 Sentence denotes Virtual screening is properly identified as a high-throughput screening (HTS) technique [321], though using its full capacity as an HTS technique is not required for most purposes.
T457 66858-67138 Sentence denotes Virtual screening requires a minimum of two inputs, (1) a three-dimensional model of the ligand (drug), and (2) a three-dimensional model of the receptor (protein) [322], the latter generated from the atomic studies of proteins via X-ray crystallography or NMR spectroscopy [323].
T458 67139-67436 Sentence denotes Virtual screening is not a truly “stand-alone” technique and has often been combined with additional biophysical techniques besides NMR spectroscopy and/or X-ray crystallography [324], such as differential scanning fluorimetry [325], fluorescence polarization, and surface plasmon resonance [324].
T459 67437-67609 Sentence denotes In this section, we briefly introduce how virtual screening has been combined with NMR spectroscopy, and how they are complementary approaches to each other in drug design.
T460 67610-67804 Sentence denotes The complete details of how virtual screening works, and how it applies to drug design outside of its combination with NMR is well documented in additional reviews [310,322,326,327,328,329,330].
T461 67805-68072 Sentence denotes A prime example of the complementarity between NMR screening and virtual docking is found in the work of Chen et al. [331], in which the authors sought to target the A2A adenosine receptor (A2AAR) protein, a drug target for the treatment of Parkinson’s disease [332].
T462 68073-68238 Sentence denotes They used virtual screening and an NMR-based screening method against the same 500 molecules in a fragment library so they could compare the results of both methods.
T463 68239-68510 Sentence denotes The virtual screen successfully predicted (based on calculated binding affinities) four out of the five orthosteric ligands discovered by NMR that were within the top 5% of the fragment library, showing that the two separate methods can give similar and reliable results.
T464 68511-68815 Sentence denotes Later on, Chen et al. discovered that virtual screening picked up three additional fragments that remained undetected by the NMR-based method, and were, in fact, A2AAR ligands; this shows that though neither method is flawless, they are still perfectly complementary approaches for drug design [322,331].
T465 68816-69053 Sentence denotes In another scientific work that integrated NMR with virtual screening, Di Lello et al. [333] found small molecular inhibitors of the enzyme ubiquitin specific protease 7 (USP7), a key regulator of the tumor suppressor protein, p53 [334].
T466 69054-69198 Sentence denotes A fragment screen by NMR revealed a series of small molecules that bind in the active site of USP7 near the catalytic cysteine (amino acid 223).
T467 69199-69443 Sentence denotes A ligand-based virtual screen utilizing the fastROCS program identified ~30 hit molecules, several of which were further characterized by 1H-15N TROSY chemical shift perturbation and line broadening to probe the binding site of the active hits.
T468 69444-69661 Sentence denotes Di Lello. also tested the active compounds against EOL-1 cells to verify the hits as identified by virtual screening and further characterized by NMR, showing that the active compounds do indeed inhibit USP7 activity.
T469 69662-69908 Sentence denotes Through additional study of the active molecules and further optimization of their structures, they eventually discovered a series of ligands that bind in the “palm” region of the catalytic domain of USP7, inhibiting its catalytic activity [333].
T470 69909-70061 Sentence denotes This study clearly demonstrates that NMR screening-based techniques can be combined with virtual screening to find viable drugs for targets of interest.
T471 70062-70311 Sentence denotes Additional examples of the successful integration of NMR and virtual screening as applied to protein targets are also found in the literature, further demonstrating the practicality and complementarity of virtual screening and NMR [329,335,336,337].
T472 70312-70729 Sentence denotes For example, Li et al. [338] used virtual screening filtered by NMR to identify and characterize non-metal chelating metallo-β-lactamase (MBL) inhibitors, and in particular, Verona integron-encoded MBL (VIM)-2, when previously there were no clinically significant inhibitors of MBL, since MBL enzymes hydrolyse many, if not all, β-lactam antibacterials compounds specifically designed to inhibit their activity [339].
T473 70730-70851 Sentence denotes Furthermore, Shan et al. [340] and Bertini et al. [337] both used virtual screening and NMR, in their respective studies.
T474 70852-71046 Sentence denotes Through the combined use of NMR and virtual screening, Shan et al. was able to identify, design, and synthesize novel PDZ domain inhibitors, which are proteins implicated in tumorigenesis [340].
T475 71047-71218 Sentence denotes Bertini et al. was able to combine NMR to study the interaction of ligands with metalloproteinases, using known inhibitors of metalloproteinases as a starting point [337].
T476 71219-71410 Sentence denotes While HSQC NOESY NMR data provided structural and spatial constraints for the proposed 3D models, virtual screening was used to refine the models, and to probe the ligand-protein interaction.
T477 71411-71647 Sentence denotes In each case (i.e., ligand-protein interaction), Bertini et al. was able to obtain a well-defined ligand conformation in the protein binding site, thus offering a viable alternative to other approaches described in the literature [337].
T478 71648-71810 Sentence denotes Clearly, combining virtual screening with NMR-based methods is advantageous in studying how ligands (drugs) bind and interact with targets (proteins) of interest.
T479 71812-71816 Sentence denotes 3.3.
T480 71817-71857 Sentence denotes Paramagnetic Resonance in Drug Discovery
T481 71858-72072 Sentence denotes Paramagnetic NMR (PNMR) can also play a prominent role in drug discovery [341], as PNMR can provide key structural information in situations where crystal structures cannot due to the weak binding of ligands [341].
T482 72073-72190 Sentence denotes PNMR can be used to quantify the binding between ligands and large biomolecules such as proteins, DNA, and RNA [342].
T483 72191-72477 Sentence denotes PNMR depends on the presence of a group (called the paramagnetic center) with an unpaired electron [343], and since many naturally occurring biomolecules and organic compounds lack a paramagnetic center, one such as caged lanthanide (CLaNP) [344], must be introduced artificially [341].
T484 72478-72663 Sentence denotes Once the paramagnetic center (often a metal ion) is present, paramagnetic effects can be used to measure the distance and the relative orientation (i.e., angle) between molecules [345].
T485 72664-72753 Sentence denotes This information is crucial when it comes to determining how ligands and substrates bind.
T486 72754-72850 Sentence denotes Thus, PNMR is quite a useful technique for drug discovery when a paramagnetic center is present.
T487 72851-73084 Sentence denotes The most relevant consequence of PNMR for drug discovery is paramagnetic relaxation enhancement (PRE), although there are a number of studies demonstrating the use of pseudocontact shift (PCS) effect in drug discovery research [341].
T488 73085-73328 Sentence denotes Paramagnetic relaxation enhancement (PRE) is proportional to the inverse sixth power of the distance between the paramagnetic center and the nucleus of interest (i.e., 1H), although it does not reveal anything about relative orientation [341].
T489 73329-73405 Sentence denotes PRE can give quantitative information in the range of 10–25 Angstroms [346].
T490 73406-73593 Sentence denotes Several researchers have taken advantage of this outstanding property to study the structural and dynamic properties of complex biomolecular machineries in their native environment [347].
T491 73594-73949 Sentence denotes For example, Iwahara et al. (2003) demonstrated that a protein’s binding polarity to DNA can be determined by PRE, using EDTA-derivatized deoxythymidine (dT-EDTA) with a chelated metal ion (such as Cu2+ or Mn2+) as a probe. dT-EDTA with a chelated metal ion is a convenient choice, as it can be inserted into any position of a synthesized oligonucleotide.
T492 73950-74073 Sentence denotes With data derived from the PRE effect, one can easily determine the polarity of the protein (or drug) binding to DNA [348].
T493 74074-74381 Sentence denotes Several researchers have investigated DNA as a drug target [349], and the study of Iwahara et al. clearly demonstrates, and even indicates, that PRE can potentially be used to study the interactions between a drug and DNA [348], provided that a paramagnetic center such as dT-EDTA or a metal ion is present.
T494 74382-74490 Sentence denotes Brasuń et al. [350] also used PRE derived distances between a paramagnetic center and a nucleus of interest.
T495 74491-74671 Sentence denotes They replaced the Cys-S-S-Cys bridge found in oxytocin and vasopressin with the His-Cu2+-His motif to investigate if doing so would alter the stability of oxytocin and vasopressin.
T496 74672-74883 Sentence denotes They determined the distances between the Cu2+ ion and 1H nuclei (possible because of PRE), and used these values to generate three-dimensional models of the His-Cu2+-His motifs in both oxytocin and vasopressin.
T497 74884-75206 Sentence denotes In doing so, they indicated that such an approach using PRE can help in designing new biologically active compounds [350], and hence in drug discovery research, as many drug discovery studies require a reliable models for the successful generations of hit-lead molecules, especially in the case of in silico docking [351].
T498 75207-75302 Sentence denotes This study again proves the usefulness of PRE, and therefore, PNMR, in drug discovery research.
T499 75303-75444 Sentence denotes In two additional studies, Huang et al. [352,353] used PRE in their individual studies of protein binding and protein dynamics, respectively.
T500 75445-75608 Sentence denotes In the Huang et al. case [352], these authors used PRE to establish a model of the binding between the G-actin protein, and thymosin β4, an actin- binding protein.
T501 75609-75777 Sentence denotes Using PRE determined constraints (distances) and 1H-15N HSQC, they were able to establish a well-converging docking structure of the G-actin/thymonsin β4 complex [352].
T502 75778-76002 Sentence denotes On the other hand Huang et al. [353] did not measure protein binding, but studied the conformational changes and dynamics of select large membrane proteins utilizing 19F-NMR spectroscopy, and Ni2+ as the paramagnetic center.
T503 76003-76518 Sentence denotes Through a series of extensive experiments, they showed that conformational exchange rates of membrane proteins can be determined from measurements of the metal-enhanced longitudinal relaxation (i.e., PRE) of the 19F nuclei [353], thus yielding additional information (i.e., protein conformation dynamics) that could be utilized in drug discovery projects targeting proteins (i.e., understanding how the protein changes shape based on its environment can be used to find potential binding sites for drug candidates).
T504 76519-76782 Sentence denotes All these examples prove that PNMR is powerful approach in drug discovery research, given that PRE can aid in generating trustworthy models of interacting molecules, and that it can help researchers understand better how the molecules interact in the first place.
T505 76784-76788 Sentence denotes 3.4.
T506 76789-76822 Sentence denotes Solid State NMR in Drug Discovery
T507 76823-76973 Sentence denotes Since the late 1970s solid state NMR (ssNMR) has demonstrated its usefulness in complex biomolecular systems such as collagen or lipid bilayers [354].
T508 76974-77223 Sentence denotes However, over the past years ssNMR has gained attention in the field of drug design and is slowly becoming a commonly used technique as its proving to be a powerful tool for structural analysis of membrane proteins and amyloid fibrils [354,355,356].
T509 77224-77302 Sentence denotes ssNMR is becoming a more attractive alternative for several different reasons.
T510 77303-77448 Sentence denotes One of them is the fact that it enables the characterization of a chemical compound in a solid-state form such as in a tablet/pill [356,357,358].
T511 77449-78092 Sentence denotes Moreover, ssNMR is not only restricted to analyzing the chemical structure but it can also provide insight into the physical properties of a compound such as polymorphism (different crystalline structures of the same compound), disorder (crystal defects and amorphous solids in the compound) or the presence of cocrystals (multicomponent crystal made of a compound and one or more small organic molecules) [356,357]. ssNMR can also be used to quantify the amount of crystalline against the amount of amorphous material in the sample to establish phase purity (the amount of desired phase separated from other, undesirable phase) [356,357,358].
T512 78093-78173 Sentence denotes ssNMR differs from liquid state NMR by the presence of anisotropic interactions.
T513 78174-78269 Sentence denotes In liquids NMR these effects are averaged to zero as a consequence of rapid molecular tumbling.
T514 78270-78627 Sentence denotes In solid state however, the molecules are not tumbling rapidly and the residual effects of anisotropic (orientation depended) interactions such as anisotropic chemical shift, magnetic dipolar coupling, and quadrupolar coupling could be observed in the form of broad peaks, with could be much wider than the chemical shift range of the nucleus [355,358,359].
T515 78628-78813 Sentence denotes As a results, there has been a constant effort to improve the sensitivity and resolution of solid state NMR spectra, which increased the potential of ssNMR in future applications [360].
T516 78814-78919 Sentence denotes One of the methods that works for nuclei with spin value of I = 1/2 is called magic-angle spinning (MAS).
T517 78920-79038 Sentence denotes It increases the resolution by rapidly rotating the sample around a fixed (or so-called magic) angle of 54.736° [360].
T518 79039-79130 Sentence denotes This method can be combined with decoupling, to remove the dipolar couplings between spins.
T519 79131-79317 Sentence denotes This is done by applying radiofrequency pulses or cross-polarization (CP) transfer of magnetization from abundant and sensitive nuclei such as 1H to less sensitive such as 13C [328,333].
T520 79318-79395 Sentence denotes A broader comparison between ssNMR and liquid state NMR is provided in [361].
T521 79396-79485 Sentence denotes As mentioned before, ssNMR can provide information about membranes and membrane proteins.
T522 79486-79918 Sentence denotes For this reason, ssNMR can be used to detect interactions of ligands with receptors embedded to the membrane which enables the mapping of binding site of a receptor by utilizing CP-MAS (cross-polarization magic-angle spinning) NMR and site specific mutagenesis [355]. ssNMR can provide the conformation of ligands bound to the receptor which can then be used to optimize future drug in terms of better affinity and efficiency [355].
T523 79919-80076 Sentence denotes Since ssNMR is also applicable to amyloid research, it can be used for probing polypeptide structures of amyloid and intermolecular contacts between fibrils.
T524 80077-80192 Sentence denotes The potential is for the design a drug that will inhibit the process of aggregation of proteins and peptides [355].
T525 80193-80403 Sentence denotes Lastly, since ssNMR gains insight into physical properties of a chemical compound it can be used for control of the process of formulation and processing of a drug to help assess the purity of a compound [358].
T526 80404-80567 Sentence denotes An example of ssNMR application related to drug design is the work of Callari et al., who monitored the effect of drug loading on the properties of micelles [362].
T527 80568-80754 Sentence denotes Polymer micelles are widely used as nano-carries for drug delivery, but so far the effects of drug loading on the morphology of a drug carrier had not been thoroughly investigated [362].
T528 80755-80908 Sentence denotes They created a model consisting of a fructose hydrophilic block and a PMAA block (micelle), to which a different amount of platinum complex was anchored.
T529 80909-81066 Sentence denotes The results from this experiment showed that micelles loaded with a higher amount of platinum complex had reduced cellular uptake, release, and cytotoxicity.
T530 81067-81300 Sentence denotes The micelles with a lower load (LL) of platinum complex were more effective at targeting cancer cells (of cell lines MDA-MB-231 (breast cancer) and A549 (lung cancer) than the micelles with a higher load (HL) of the platinum complex.
T531 81301-81434 Sentence denotes This is evidenced by the lower IC50 (half maximal inhibitory concentration) values of the LL micelles as compared to the HL micelles.
T532 81435-81587 Sentence denotes Both of those results could be related to the micellar structure and their potential for interaction between the sugar moieties and the cell wall [362].
T533 81588-81793 Sentence denotes Another example of practical application of ssNMR is the work of Lee and colleagues [363] in which they investigated the structure of a designed zinc-binding amyloid fibril that catalyzed ester hydrolysis.
T534 81794-81927 Sentence denotes Metals ions such as zinc where found to affect the process of protein aggregation which resulted in arise of amyloid like structures.
T535 81928-82086 Sentence denotes Therefore, understanding the processes of aggregation and the factors related to them is crucial for creation of new drugs for amyloid related diseases [364].
T536 82087-82215 Sentence denotes In the experiment Lee et al. used Ac-IHVHLQI-CONH2 peptide (referred as HHQ) to form fibrils with varying Zn2+:HHQ molar ratios.
T537 82216-82446 Sentence denotes The results showed that Zn2+-bound HHQ fibrils form parallel-in-register form of packing β-strand in each sheet and His residues are coordinated to Zn2+ via Nδ1, while half of the His residues are also coordinated to Zn2+ via Nε2.
T538 82447-82505 Sentence denotes Additionally, Zn2+ binds in a 1:1 metal ion/peptide ratio.
T539 82506-82669 Sentence denotes After further analysis using structural bioinformatics, it was concluded that each zinc ion was coordinated by three histidine nitrogens from two adjacent strands.
T540 82670-82754 Sentence denotes Half of all histidines bridged to Zn2+ ions forming a metal–imidazolate chain [363].
T541 82756-82760 Sentence denotes 3.5.
T542 82761-82790 Sentence denotes NMR Validation in Drug Design
T543 82791-82974 Sentence denotes A “hit” is a molecule identified from a screening technique (HTS, FBDD, etc) as having a desirable effect (i.e., decreased cellular growth, high affinity score) on a target [365,366].
T544 82975-83156 Sentence denotes However, the question of whether the activity is related to actual binding to the target, or to interference with one of the components of the assay readout mechanism, is uncertain.
T545 83157-83193 Sentence denotes Thus, a validation step is required.
T546 83194-83357 Sentence denotes Hit-validation is therefore the process of confirming, or validating, that the molecule(s) identified previously have on target activity and selectivity [367,368].
T547 83358-83446 Sentence denotes One of the highest-impacts of NMR on drug discovery is the use as a hit-validation tool.
T548 83447-83619 Sentence denotes Though the hit-validation or confirmation of drugs is mostly limited to the solution state [369], this aspect of NMR truly is a “gold standard” technique in drug discovery.
T549 83620-83962 Sentence denotes NMR by itself is a powerful tool for drug validation as in the case of Sharma et al. (2012) [370] who sought to identify potential drug-like inhibitors against L-Aspartate α-Decarboxylase (ADC) an enzyme responsible for the decarboxylation of L-aspartate in order to generate β-alanine and carbon dioxide [371], in Mycobacterium tuberculosis.
T550 83963-84070 Sentence denotes They began with known inhibitors of ADC, and developed a protocol to measure the enzymatic activity of ADC.
T551 84071-84363 Sentence denotes Upon addition of ADC to a solution of L-aspartate, L-aspartate gradually disappeared because ADC was converted to L-aspartate to β-alanine; therefore the peak intensity of L-aspartate decreased, and the peak intensity of β-alanine increased in the presence of ADC (no inhibitor drug present).
T552 84364-84592 Sentence denotes Using this newly developed NMR-based protocol allowed direct measurement of ADC enzymatic activity, and Sharma et al. were able to confirm the enzymatic inhibiting activity of seven previously discovered inhibitors of ADC [370].
T553 84593-84730 Sentence denotes This study demonstrated that NMR can be an effective validation tool for known drugs and for new drugs generated by a screening approach.
T554 84731-84817 Sentence denotes NMR is also able to remove false positives that emerge from biochemical screens [372].
T555 84818-85154 Sentence denotes For example, an aptly named technique called A La Assay to detect Reactive Molecules by Nuclear Magnetic Resonance (ALARM NMR) is able to eliminate false positives from HTS methods [373], and in the presence of a test compound or mixture, measures dithiothreitol (DTT)-dependent 13C chemical shift changes of the human La antigen [373].
T556 85155-85382 Sentence denotes Dahlin et al. provided an updated protocol of ALARM NMR to aid researchers in the production of the 13C-labeled La antigen reporter protein, in testing compounds with the La protein, and in the analysis of obtained NMR spectra.
T557 85383-85452 Sentence denotes Using ALARM NMR prioritized hits identified from HTS screening [374].
T558 85453-85781 Sentence denotes An example of ALARM NMR is found in the work of Dahlin et al., where they used this technique to test molecules that were assumed to be inhibitors of histone acetyltransferase (HAT) inhibitors, and from their studies, actually discovered that 65% (15 out of 23) of the most commonly reported HAT inhibitors were actually faulty.
T559 85782-85894 Sentence denotes They were actually nonselective interference compounds, not necessarily specific to the inhibition of HAT [375].
T560 85895-86074 Sentence denotes Thus, ALARM NMR (and NMR in general) served as a useful validation method, especially for unvalidated hits identified from biochemical screens [372] or other screening techniques.
T561 86075-86214 Sentence denotes The last example highlights the need for cross validation, or the combination of two or more techniques to verify identified chemical hits.
T562 86215-86281 Sentence denotes Of course, NMR is not the sole technique used for drug validation.
T563 86282-86524 Sentence denotes Most often, NMR drug validation is coupled with additional methods [367] such as surface plasmon resonance (SPR) [376,377] X-ray crystallography [377,378,379], isothermal calorimetry (ITC) [379], UV-Vis and/or fluorescence spectroscopy [380].
T564 86525-86692 Sentence denotes The work of Goudreau et al. is an excellent example of combining NMR with another biophysical technique, in this case X-ray crystallography, for drug validation [378].
T565 86693-86866 Sentence denotes A series of benzodiazepine inhibitors of Human immunodeficiency virus 1 (HIV-1) was identified using an in vitro capsid assembly assay, and further characterized by 19F-NMR.
T566 86867-87063 Sentence denotes Analysis of the chemical shift perturbation and line broadening effect on the 19F-NMR spectra of the benzodiazepine inhibitors revealed the specificity and reversibility of the binding inhibitors.
T567 87064-87207 Sentence denotes The same set of 19F-NMR spectra were used to identify the N-terminal domain of the capsid as the binding site of the benzodiazepine inhibitors.
T568 87208-87371 Sentence denotes The specific amino acids involved in the binding of the benzodiazepine inhibitors were identified from the chemical shift perturbation of 1H,15N-TROSY NMR spectra.
T569 87372-87594 Sentence denotes Later, use of X-ray co-crystallography confirmed binding locations of the benzodiazepine inhibitors and their binding modes, which was useful for further development and optimization of the benzodiazepine inhibitors [378].
T570 87595-87729 Sentence denotes The work of Goudreau et al. therefore showed how NMR could be used as a co-validation technique with another biophysical method [378].
T571 87730-87877 Sentence denotes NMR can be also coupled with multiple biophysical techniques to validate a molecule’s ability to inhibit protein-protein interactions (PPIs) [367].
T572 87878-88183 Sentence denotes An example of the combination of NMR with SPR and X-ray crystallography can be found in the work of Fry et al., where the authors sought to understand how the nutlin molecule inhibits MDM2-p53, a protein-protein interaction that has been an important cancer therapy target for several years [381,382,383].
T573 88184-88428 Sentence denotes Fry et al. [377] gradually deconstructed RG7112, the first nutlin molecule to enter clinical trials [384], into 11 fragments so they could study the inhibitory effect of RG7112 on the MDM2-p53 interaction by SPR, NMR, and X-ray crystallography.
T574 88429-88598 Sentence denotes SPR was used to determine the Kd values of the RG7112 fragments and confirmed that RG7112 and some of its fragments do bind to MDM2, inhibiting the MDM2-p53 interaction.
T575 88599-88704 Sentence denotes 1H,15N-HSQC NMR chemical shift perturbation was also used to assess and verify binding identified by SPR.
T576 88705-88895 Sentence denotes Of the six fragments of RG7112 confirmed by 1H,15N-HSQC NMR as binding to MDM2, SPR showed binding for five of them; thus, the two separate techniques were in good agreement with each other.
T577 88896-89102 Sentence denotes The fragments of RG7112 that were confirmed to bind by both SPR and 1H,15N-HSQC NMR were further studied with X-ray crystallography, which can tell precisely where and how the molecules bind to the protein.
T578 89103-89320 Sentence denotes Using co-crystallization, Fry et al. were able to obtain structures for several of the verified binding fragments in complex with MDM2 and were able to visualize the binding of the fragments to the MDM2 protein [377].
T579 89321-89506 Sentence denotes NMR is obviously a powerful drug binding validation tool, but it becomes much more powerful when coupled with additional biophysical techniques, as seen in the work of Fry et al. [377].
T580 89507-89718 Sentence denotes Dias et al. [379] took a similar approach as Fry et al. [377] in that they took known inhibitors of a protein-protein interaction, and dissected them into individual fragments to assess a protein’s drug-ability.
T581 89719-89859 Sentence denotes The interaction studied was that between the proteins von Hippel–Lindau (VHL), and the alpha subunit of hypoxia-inducible factor 1 (HIF-1α).
T582 89860-90049 Sentence denotes Twelve compounds (known inhibitors and derived fragments) were developed using a crystal structure of HIF-1α peptide bound to the stable multiprotein complex pVHL-elongin C:elongin B (VCB).
T583 90050-90291 Sentence denotes Each of these compounds was screened using three separate NMR techniques, Saturation Transfer Difference (STD), Carr–Purcell–Meiboom–Gill (CPMG) relaxation experiments, and WaterLOGSY (to assess drug binding and to predict drug binding mode.
T584 90292-90535 Sentence denotes Each compound that was unambiguously detected (i.e., the molecule was identified as successfully binding by at least two of the three NMR methods of STD, CPMG, and WaterLOGSY) was subjected to further analysis by ITC and X-ray crystallography.
T585 90536-90703 Sentence denotes ITC was used to determine the dissociation constants of binding molecules, and X-ray crystallography was used to confirm the binding mode predicted by the NMR studies.
T586 90704-90953 Sentence denotes Generally speaking, the designed fragments had similar ligands efficacies compared to the parent molecules but had much higher dissociation constants (Kd values), meaning that the fragments bound less tightly than the original parent molecule [379].
T587 90954-91319 Sentence denotes With this example, it is possible to see the strength of using NMR as its own hit-validation tool (i.e., three different NMR techniques were used for screening compounds [379]), and yet, the follow-up of NMR studies with ITC and X-ray crystallography was useful in providing a basis for assessing the drug-ability of a protein-protein interaction [385,386,387,388].
T588 91320-91482 Sentence denotes Thus, it is clear to see that NMR is a prominent method of hit-validation in drug discovery research, especially in combination with other biophysical techniques.
T589 91484-91488 Sentence denotes 3.6.
T590 91489-91546 Sentence denotes Other Methods Used to Determine the Drug-Target Complexes
T591 91547-91701 Sentence denotes Substantial progress has been made in the NMR field over the past 5–10 years, and various methods were established to determine the drug-target complexes.
T592 91702-91843 Sentence denotes Most of them utilize either NOE or chemical shift perturbations (CSP) although in silico models/programs, using NMR-derivate data also exist.
T593 91845-91851 Sentence denotes 3.6.1.
T594 91852-91861 Sentence denotes DIRECTION
T595 91862-92049 Sentence denotes One of the methods called difference of inversion recovery rate with and without target irradiation (DIRECTION) is used to map pharmacophores and can be an alternative to STD experiments.
T596 92050-92206 Sentence denotes This method uses the difference between longitudinal relaxation rates of ligand protons with- and with-out irradiation of the protons of the target protein.
T597 92207-92301 Sentence denotes The DIRECTION approach, however cannot be used for slowly exchanging (strong binding) ligands.
T598 92302-92501 Sentence denotes The practical approach of this method was demonstrated on the experiment when analyzed the interactions between p38 MAPK (p38 a mitogen-activated protein kinase) and its inhibitor-SB203580 [389,390].
T599 92502-92688 Sentence denotes The results from this experiment showed that protons H1, H4, H5, and H6 of SB203580, are in close neighborhood with the protons of p38 MAPK when compared with H2, H3, and methyl protons.
T600 92689-92809 Sentence denotes It indicates that two aromatic rings (a pyridine ring and fluorophenyl ring) of SB203580 interact tightly with p38 MAPK.
T601 92810-92958 Sentence denotes The results were later confirmed with proton density map of each ligand’s proton, based on the crystal structure of SB203580–p38 MAPK complex [391].
T602 92959-93125 Sentence denotes Moreover, the same authors already created a new and improved protein–ligand docking method by combining the DIRECTION obtained NMR data with docking software. [392].
T603 93127-93133 Sentence denotes 3.6.2.
T604 93134-93138 Sentence denotes ILOE
T605 93139-93250 Sentence denotes A second method that can be used to map pharmacophores is called inter-ligand nuclear Overhauser effect (ILOE).
T606 93251-93476 Sentence denotes This 2D NMR experiment detects when two ligands bind simultaneously to adjacent sites on a protein surface although both of the ligands do not have to bind to the same binding pocket (opposite to INPHARMA, see above) [5,393].
T607 93477-93677 Sentence denotes A negative ligand−ligand NOE signal will be created when ligands bind in close proximity to each other whereas ligands that do not bind will show no NOEs, or at most very weak positive ones [372,394].
T608 93678-93771 Sentence denotes ILOE also enables determination of the ligand orientations with respect to one another [393].
T609 93772-93896 Sentence denotes As in the case of INPHARMA, ILOE can be utilized even in the absence of a 3D protein structure and used with large proteins.
T610 93897-94027 Sentence denotes Additionally, ILOE differs from INPHARMA in mixing times—for ILOE the mixing times are typically in the range of 600–800 ms [345].
T611 94028-94296 Sentence denotes Application of ILOE was first shown on glycolate+NAD+ in the presence of porcine heart lactatedehydrogenase, and by glucose-6-phosphate+NADPH in the presence of L. mesenteroides glucose-6-phosphatedehydrogenase and from that time it has been widely used [393,395,396].
T612 94298-94304 Sentence denotes 3.6.3.
T613 94305-94312 Sentence denotes SOS-NMR
T614 94313-94576 Sentence denotes A third method called structural information using Overhauser effects and selective labeling (SOS-NMR), relies of STD experiments performed on ligand complexes with different protein samples that have been fully deuterated excluding a specific type of amino acid.
T615 94577-94819 Sentence denotes In other words, the data obtained by SOS-NMR gives insight into the ligand-binding amino acid composition and when taken into consideration the 3D structure of targeted protein can be used to establish the structure of protein-ligand complex.
T616 94820-94997 Sentence denotes This approach has been demonstrated using two complexes—FKBP complexed to 2-(3′-pyridyl)-benzimidazole and MurA complexed to uridine diphosphateN-acetylglucosamine (UDP-GlcNAc).
T617 94998-95079 Sentence denotes The results showed that for FKBP and MurA, only four and three amino acids (FKBP:
T618 95080-95105 Sentence denotes Ile, Val, Leu, Met; MurA:
T619 95106-95224 Sentence denotes Trp, Phe, His) were needed to be selectively protonated in perdeuterated samples to establish the ligand-binding site.
T620 95225-95337 Sentence denotes Additionally, on average only 6 amino acids were required for accurate identification of ligand-binding surface.
T621 95338-95440 Sentence denotes According to authors SOS-NMR can greatly improve the early stages of the drug discovery process [397].
T622 95441-95568 Sentence denotes Moreover, combining SOS-NMR with other methods can even further increase chances for a positive outcome of an experiment [398].
T623 95570-95576 Sentence denotes 3.6.4.
T624 95577-95597 Sentence denotes Tert-butyl Labelling
T625 95598-95679 Sentence denotes A completely different approach to this topic was taken by Chen et al. [399,400].
T626 95680-95860 Sentence denotes Instead of using isotope labeling, Chen’s group decided to use a tert-butyl group contained within ligand-1 to obtain structural information about the protein-ligand complex [400].
T627 95861-96007 Sentence denotes The tert-butyl group formed an intense singlet in 1.0 to 1.5 ppm range thanks to rapid methyl rotation and methyl reorientation within that group.
T628 96008-96291 Sentence denotes When compared with the protein’s 1H-NMR signal, the tert-butyl signal tended to be much narrower and resulted in easy detection without the need for isotopic enrichment even in protein complexes of high molecular mass such as Bacillus stearothermophilus DnaB hexamer (320 kDa) [399].
T629 96292-96471 Sentence denotes Additionally, the tert-butyl group produces intense NOESY cross peaks that can be observed even in the situations where normally cross-peaks of the proteins are barely detectable.
T630 96472-96562 Sentence denotes This is partially because the signal corresponded to nine protons within tert-butyl group.
T631 96563-96677 Sentence denotes Those aspects enable measurements of pseudo-contact shifts generated by paramagnetic tags attached to the protein.
T632 96678-96742 Sentence denotes As a result, it allows positioning of the ligand on the protein.
T633 96743-96898 Sentence denotes An example of this approach, is dengue virus NS2B-NS3 protease from serotype 2 (referred as DENpro) in complexed with ligand containing a tert-butyl group.
T634 96899-97019 Sentence denotes The result of this experiment showed NOEs between the tert-butyl group of ligand-1 and residue Val155 from DENpro [400].
T635 97021-97027 Sentence denotes 3.6.5.
T636 97028-97034 Sentence denotes SALMON
T637 97035-97212 Sentence denotes Solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy (SALMON) is another method based on the data obtained via nuclear Overhauser effect.
T638 97213-97471 Sentence denotes This method utilizes WaterLOGSY [401] to probe for solvent accessibility to the ligand and determine the orientation of the ligand by analyzing signal changes in WaterLOGSY spectra (positive signal from unbound ligand vs. negative for protein-bound ligands).
T639 97472-97663 Sentence denotes This method was first used to determine the orientation of prodrug called tretazicar ((5-(aziridin-1-yl)-2,4-dinitrobenzamide) known as CB1954 in NQO2 (quinone oxidoreductase 2) binding site.
T640 97664-97879 Sentence denotes Previous attempts had been made to obtain the orientation of tretazicar bounded to NQO2, however the results obtained from X-ray crystallography were inconclusive as two orientations of tretazicar could be possible.
T641 97880-98106 Sentence denotes The information obtained via SALMON showed that the side chain of asparagine at position 161 formed a hydrogen bond with 2-nitrogroup of tretazicar, and that the aziridine moiety of tretazicar pointed toward the solvent [401].
T642 98108-98114 Sentence denotes 3.6.6.
T643 98115-98130 Sentence denotes LOGSY Titration
T644 98131-98249 Sentence denotes Another variant of WaterLOGSY method called LOGSY utilizes the titration slopes as a measure of solvent accessibility.
T645 98250-98332 Sentence denotes The titration slopes are created by a constant increase of protein concentrations.
T646 98333-98477 Sentence denotes This method also provides more insight into the process of ligand solvation by checking the influence of protein concentration onto the process.
T647 98478-98639 Sentence denotes This approach was used on the bromodomain 1 of protein 4 (Brd4-BD1) by mapping epitopes of two ligands interacting with Brd4-BD1 and predicting ligands position.
T648 98640-98760 Sentence denotes The results showed that the triazolopyridazine moiety of both ligands was implanted into the binding pocket of the Brd4.
T649 98761-98937 Sentence denotes Additionally, the results from LOGSY titration showed that methyl-group 1 of ligand 1, aromatic proton 8 of ligand 2 and aromatic proton 8 of ligand 1 exhibit strong water NOE.
T650 98938-99167 Sentence denotes This information enabled researchers to utilize a chemical replacement strategy (substitute bound water molecules by suitable functional groups) for aromatic proton 8 in a series of ligands containing the triazolopyridazine ring.
T651 99168-99306 Sentence denotes Those protons were replaced with an amino or aminomethyl groups and as a result, the binding affinity of those ligands increased 100-fold.
T652 99307-99628 Sentence denotes Finally, the results obtained from X-ray crystallography for ligands with such modifications allowed to find the binding mode of the triazolopyridazine ring of ligand 1 (with methyl group pointing internally) and the substituted amino group was found to create hydrogen bond to the side chain of Asn140 of Brd4-BD1 [402].
T653 99630-99636 Sentence denotes 3.6.7.
T654 99637-99692 Sentence denotes Nuclear Magnetic Resonance Molecular Replacement (NMR2)
T655 99693-99900 Sentence denotes The most recent approach called Nuclear Magnetic Resonance Molecular Replacement (NMR2) utilizes spatial data obtained through solution-state NMR in order to locate the binding pocket of a complex structure.
T656 99901-100071 Sentence denotes For that, it uses a receptor model, e.g., a X-ray structure of a homolog, to conduct an analysis and at the same time excluding the need for protein resonance assignment.
T657 100072-100141 Sentence denotes To conduct an experiment using such an approach requires a few steps.
T658 100142-100236 Sentence denotes First, either the protein or ligand used in the complex must be uniformly 13C and 15N labeled.
T659 100237-100326 Sentence denotes Then, an experiment to assign the ligand is needed such as 2D 13C,1H-HMQC or 13C,1H-HMBC.
T660 100327-100490 Sentence denotes The next step is the evaluation of ligand intra- and ligand–protein intermolecular distances through NOE cross peaks obtained from F1-15N,13C-filtered 1H,1H-NOESY.
T661 100491-100669 Sentence denotes Lastly, choosing a proper input structure is required which can be either X-ray or NMR structures in apo form, with another bound ligand, or a homolog to the protein of interest.
T662 100670-100839 Sentence denotes Then the NMR2 program analyzes for all possible partial assignments (such as methyl groups of a protein) and calculates the complex structures for all options [403,404].
T663 100840-100972 Sentence denotes This method was already successfully used to resolve complex structures in case of slow and fast exchange ligands [403,404,405,406].
T664 100974-100980 Sentence denotes 3.6.8.
T665 100981-100986 Sentence denotes HECSP
T666 100987-101104 Sentence denotes In silico methods combined with NMR derived information can also be used to determine accurate drug-target complexes.
T667 101105-101240 Sentence denotes 1H empirical chemical shift perturbation (HECSP) is an empirical model that is based on chemical shift perturbation (CSP) of a protein.
T668 101241-101384 Sentence denotes CSP represents the change in chemical shifts in a protein due to alteration of its chemical environment (which can happen upon ligand binding).
T669 101385-101544 Sentence denotes The CSP of a target protein is obtained by a series of 2D HSQC experiments with a set of ligand titrations involving samples that contain 15N-labelled protein.
T670 101545-101622 Sentence denotes The calculation of 1H-CSPs inside the protein are based on four contributors:
T671 101623-101712 Sentence denotes 1) ring current, 2) electric field, 3) hydrogen bonding, and last 4) magnetic anisotropy.
T672 101713-101913 Sentence denotes To show the value of the HECSP model two CSP examples were used: apo-neocarzinostatin (apoNCS)-naphthoate ester complex, and human intestinal fatty acid binding protein (hIFABP)-ketorolac-ANS complex.
T673 101914-102105 Sentence denotes The results from the experiment showed that HECSP model can distinguish native ligand from decoys and more clearly define protein-ligand complex structures with NMR derived information [407].
T674 102107-102113 Sentence denotes 3.6.9.
T675 102114-102121 Sentence denotes SAMPLEX
T676 102122-102303 Sentence denotes Another program that can utilize CSP called Smoothed Automatic Mapping of Protein from Listed Extremes (SAMPLEX) can help to determine the interaction surface of proteins complexes.
T677 102304-102461 Sentence denotes SAMPLEX takes the chemical shifts of the protein of interests in both the free and bound state and corresponding 3D structure of a protein in the free state.
T678 102462-102645 Sentence denotes The programs returns a confidence value for each residue to be in a perturbed or unperturbed state (0.05 as being in a perturbed state, −0.05 as remaining in their unperturbed state).
T679 102646-102794 Sentence denotes This approach was tested on five examples, one of which was Subtilisin BPN’ (serine protease) complexed with its inhibitor–chymotrypsin inhibitor 2.
T680 102795-102933 Sentence denotes The results showed that residue 2, and residues 56–62 of chymotrypsin inhibitor-2 were perturbed and residue 63 was in an ambiguous state.
T681 102934-103040 Sentence denotes To compare, the X-ray crystallography data showed residues 50 and 54–61 to be involved in the interaction.
T682 103041-103217 Sentence denotes For subtilisin BPN’ the program predicted residues 33, 97, 99–109, 126-128, 141, 154–156, 167–171 and 218–219 to perturbed and residues 65, 98 and 220 to be in ambiguous state.
T683 103218-103373 Sentence denotes That information was also confronted with the X-ray crystallography data which shown residues 99–104, 125–128, 154–157, 167, 218–221 to be perturbed [408].
T684 103375-103377 Sentence denotes 4.
T685 103378-103400 Sentence denotes In-Cell NMR Approaches
T686 103401-103580 Sentence denotes The interactions between targets (proteins) and ligands (small molecules) can be analyzed independently of the biological systems by using ‘cell-based’ NMR drug design approaches.
T687 103581-103732 Sentence denotes Three basic approaches [409] are as follows: (1) Compound-detected in-cell NMR, (2) Target-detected in-cell NMR, and (3) Reporter-detected in-cell NMR.
T688 103733-103917 Sentence denotes These methods, with the exception of compound detected in-cell NMR, differ according to the isotopically labeled structure (protein, cell structure, etc.), which enables NMR detection.
T689 103918-103990 Sentence denotes A cartoon representation of each of these methods is given in Figure 13.
T690 103992-103996 Sentence denotes 4.1.
T691 103997-104026 Sentence denotes Compound-Detected In-Cell NMR
T692 104027-104171 Sentence denotes STD NMR is a technique that lies within the compound-detected in-cell NMR method but does not require isotope-labelling of the studied compound.
T693 104172-104265 Sentence denotes However isotopic labelling of the compound may be used to enhance the quality of the spectra.
T694 104267-104271 Sentence denotes 4.2.
T695 104272-104299 Sentence denotes Target-Detected In-Cell NMR
T696 104300-104415 Sentence denotes In the target-detected in-cell NMR only the target of interest is isotopically labeled (i.e., 15N labeled protein).
T697 104416-104558 Sentence denotes For instance, target proteins can be isotopically labeled during cell growth in isotopically enriched (13C, 15N, or both 15N/13C) media [410].
T698 104559-104625 Sentence denotes The cell type and the labeling method may vary across experiments.
T699 104626-104813 Sentence denotes Different cell types, including bacteria [411], oocytes [412], yeast cells [413], mammalian cells [414], HeLa cells [415] and even insect cells [416] have been reported in the literature.
T700 104814-104948 Sentence denotes The fact that in-cell NMR applies to more than one cell type testifies of the versatility and potential application of this technique.
T701 104949-105067 Sentence denotes In terms of labeling, 15N is one of the most commonly used approaches [417] when the targets of interest are proteins.
T702 105068-105165 Sentence denotes Recently, 19F labeling has been reported as a useful probe for protein-ligand interactions [418].
T703 105166-105267 Sentence denotes It was shown that 19F can reveal information about the dynamics of protein-ligand interactions [419].
T704 105268-105469 Sentence denotes Methyl groups [420] have also been used as probes for proteins and complexes in vivo [420], proving that labeling specific chemical groups instead of the entire biomolecule (i.e., protein) is feasible.
T705 105471-105475 Sentence denotes 4.3.
T706 105476-105505 Sentence denotes Reporter-Detected In-Cell NMR
T707 105506-105621 Sentence denotes In-cell NMR extends beyond proteins, and has been applied successfully to DNA [93,421] and RNA molecules [422,423].
T708 105622-105703 Sentence denotes Telomeric repeats have also been studied using target detected in-cell NMR [424].
T709 105704-105893 Sentence denotes The reporter-detected in-cell NMR technique isotopically labels neither the ligand nor the target, but rather a receptor that indirectly measures the effects of ligand-target binding [409].
T710 105894-105954 Sentence denotes The “reporter” varies according to the experimental context.
T711 105955-106106 Sentence denotes For instance, Dose et al. [425] used acetylation- and deacetylation-based assays to monitor the activity of histone deacetylase and acetyl-transferase.
T712 106107-106229 Sentence denotes Thongwichian et al. [426] used peptide-based reporters to identify active kinases and phosphatases in cellular conditions.
T713 106230-106395 Sentence denotes Lastly, Doura et al. [427] designed a 19F probe that operates in biological conditions in order to study the adherence and dynamics of proteins found in human blood.
T714 106397-106425 Sentence denotes 4.4. “In-Virus” NMR Strategy
T715 106426-106641 Sentence denotes In many viruses and phages, scaffolding proteins (SPs) are required to ensure the correct organization of coat proteins (CPs) and other minor capsid proteins into a precursor structure, called a procapsid [428,429].
T716 106642-106820 Sentence denotes Although SPs are critical for viral assembly and therefore potential therapeutic targets their structural properties (with only a few exceptions [430,431]) are poorly understood.
T717 106821-106971 Sentence denotes The size limitation of NMR can be used advantageously as a filter to identify disordered segments even in very large supramolecular protein complexes.
T718 106972-107114 Sentence denotes In this way, NMR can provide a unique perspective on the dynamic and disordered elements of macromolecules not accessible by other techniques.
T719 107115-107524 Sentence denotes The procapsid encapsulation experiments described by Whitehead et al. [432] were conceptually analogous to in-cell NMR experiments [433,434,435] in which signals from small proteins, or flexible segments of proteins, can be observed when they are incorporated inside living cells, as long as the isotope-labeled proteins of interest do not interact strongly with other large cellular components [433,434,435].
T720 107525-107796 Sentence denotes The so called ‘‘in-virus’’ NMR strategy applied by Whitehead et al. [432] could be more generally used to study the dynamic properties of macromolecules encapsulated into virus particles, including cargo molecules encased in viral capsids for nanotechnology applications.
T721 107797-107948 Sentence denotes Additionally, such studies could assess the level of interaction of cargo molecules with the virus and probe the release properties of cargo NMR [432].
T722 107950-107952 Sentence denotes 5.
T723 107953-107966 Sentence denotes Final Remarks
T724 107967-108068 Sentence denotes As we have attempted to emphasize and demonstrate, NMR has a powerful and unique role in drug design.
T725 108069-108224 Sentence denotes NMR provides detailed structural information about a molecule along with kinetic information over extended time periods, i.e., not just a snapshot [24,25].
T726 108225-108404 Sentence denotes Moreover, NMR is quantitative and highly reproducible, allowing applications in diverse fields such as relaxometry, combinatorial chemistry, fluxomics, and targeted analysis [91].
T727 108405-108549 Sentence denotes NMR can be combined with other analytical techniques, such as mass spectrometry “in tandem” analysis of the molecules of interest [436,437,438].
T728 108550-108743 Sentence denotes 1H 1D-NMR is used particularly in the analysis of metabolites, while the strength and intensity of the recorded signals is directly proportional to the concentration of the sample [44,439,440].
T729 108744-108831 Sentence denotes 1H 1D-NMR can also be used to follow “real-time” analysis of different molecules [441].
T730 108832-109038 Sentence denotes In the 1D 1H-NMR experiment, there are no polarization transfer techniques required (the 1H atom is already highly sensitive) and covers a spread of interesting nuclei in the molecule(s) being studied [91].
T731 109039-109217 Sentence denotes Assuming that the sample can be stored stably for extended periods of time, the non-destructive nature of NMR permits the re-use on the sample for different experiments [50,442].
T732 109218-109326 Sentence denotes Aiding in the reproducibility of NMR [91], sample-recycling offers a significant advantage of NMR [443,444].
T733 109327-109454 Sentence denotes While always important in drug design, sensitivity and resolution of NMR are two major factors that need special consideration.
T734 109455-109597 Sentence denotes Since both factors improve with increasing magnetic field strength, we have seen a spike in the demand for ultra-high-field NMR spectrometers.
T735 109598-109957 Sentence denotes Recently, 28.2 T (i.e., 1.2 GHz for 1H) magnets have become commercially available, and with recent advances in magnet technology, such as liquid helium recycling and magnetic field shielding [91], NMR has begun to offer far better resolution and higher sensitivity while reducing the substantial costs of maintaining the instruments compared to past decades.
T736 109958-110244 Sentence denotes Other steps have been taken to enhance the sensitivity of NMR including: the development of cryoprobes increasing the signal to noise ratio 3 to 4 times, and micro-coil probes that not only increased sensitivity but also reduced the amount of sample required for the measurements [445].
T737 110245-110372 Sentence denotes From another perspective, one can further optimize the process of obtaining spectra by using different methods of measurements.
T738 110373-110554 Sentence denotes One of these, called SOFAST, helps to reduce the delay between scans resulting in lowering acquisition time for 2D experiments such as HMQC utilizing 1H,15N or 1H,13C [117,446,447].
T739 110555-110836 Sentence denotes The basic principle of this method is to use selective 1H pulses that will excite only a small portion of the available nuclei pool, while the unperturbed spins provide a magnetization “heat sink” thus improving the spin-lattice relaxation (T1) rate via dipolar interactions [446].
T740 110837-110935 Sentence denotes These methods can be highly efficient when studying drug binding and molecular interactions [117].
T741 110936-111091 Sentence denotes Another method, called ultrafast 2D NMR, enables obtaining a 2D spectra within a single scan but with the associated cost of reduced sensitivity [117,448].
T742 111092-111302 Sentence denotes The principle of this method is to divide the sample into n number of fractions, and apply the appropriate incremental aspect to each fraction, while recording them all simultaneously within the one scan [448].
T743 111303-111427 Sentence denotes This method has been applied to many metabolomic studies [177,447,449] as well as in the analysis of natural products [450].
T744 111428-111531 Sentence denotes The difficulty is that the effective concentration of the sample is lowered by the fractionation level.
T745 111532-111636 Sentence denotes The more slices the sample is split into, the greater the reduction of combined signal that is obtained.
T746 111637-111811 Sentence denotes Lastly, a method termed non-uniform sampling (NUS) may provide an advantage by reducing the total time for measurement while maintaining the same resolution of spectra [117].
T747 111812-111913 Sentence denotes NUS effectively skips over parts of the total dataset, collecting only around 20 to 30% of the total.
T748 111914-112064 Sentence denotes Usually sections containing higher concentrations of signal (over noise) are emphasized in the selection scheme, known as non-linear data acquisition.
T749 112065-112400 Sentence denotes These methods reconstruct the complete data subset by applying various algorithms such as multidimensional decomposition (MDD), which essentially separates the sets of multidimensional data into one dimensional problems that are much easier to solve given the common process of signal overlapping in multidimensional NMR spectra [117].
T750 112401-112630 Sentence denotes Other algorithms such as compressed sensing (CS), Maximum entropy method (Max Ent) and Iterative soft threshold (IST) each have their own advantages but all focus on decreasing the time needed for collection of spectra [117,451].
T751 112631-112698 Sentence denotes The cost is in signal to noise, as no gain is ever absolutely free.
T752 112699-112881 Sentence denotes The inherent advantages of NMR do not eliminate the disadvantages (Table 3), which are namely being limited for some nuclei, and inherent insensitivity for many types of experiments.
T753 112882-113007 Sentence denotes NMR can provide high quality resolution and sensitivity for some experiments [91,452] but the application can be challenging.
T754 113008-113327 Sentence denotes When the experiments become multidimensional, there is often a tradeoff between the improved higher resolution and/or the resulting sensitivity and/or the amount of time an experiment takes, i.e., high-quality spectra for multidimensional experiments take much longer than their simple 1D counterparts [117] (Scheme 2).
T755 113328-113452 Sentence denotes One must always choose between resolution, sensitivity, and the amount time; as you can only ever have two out of the three.
T756 113453-113638 Sentence denotes Unfortunately, in the real world, when working with NMR spectroscopy, we are mainly forced to choose between high or low precision data (Scheme 2) with fixed available instrument times.
T757 113639-113732 Sentence denotes Scheme 2 can be useful, when choosing NMR technique and/or method/approaches in drug studies.
T758 113733-114005 Sentence denotes It shows the general representation of different NMR techniques and method/approaches in cost-time matrix, bearing in mind that the exact position in the matrix can be influenced by the environmental conditions, pulse sequence and sample preparation (e.g., concentration).
T759 114006-114106 Sentence denotes Regarding, NMR methods/approaches, the exact position depends on the choice of proper NMR technique.
T760 114107-114206 Sentence denotes For the purposes of Scheme 2, the 2D techniques were chosen as described in the practical examples.
T761 114207-114389 Sentence denotes Nevertheless, with relatively short times and at low cost, we can acquire numerous data sets and therefore the low precision can be partially compensated for by statistical analysis.
T762 114390-114589 Sentence denotes Fortunately, significant efforts have been undertaken to reduce the amount of time it takes to record multidimensional spectra, especially for 2D NMR, and still obtain high quality spectra (Table 3).
T763 114590-114675 Sentence denotes Novel pulse sequences have been developed to decouple nuclei in Pure-shift NMR [117].
T764 114676-114806 Sentence denotes Dynamic Nuclear Polarization (DNP) can induce hyper-polarization in atoms (13C, 15N) with an inherently low sensitivity [453,454].
T765 114807-115010 Sentence denotes Parahydrogen-Induced Polarization (PHIP) and Signal Amplification by Reversible Exchange (SABRE) are other polarization techniques used to increase the sensitivity of inherently insensitive nuclei [455].
T766 115012-115014 Sentence denotes 6.
T767 115015-115026 Sentence denotes Conclusions
T768 115027-115132 Sentence denotes NMR has become a “gold standard” method in drug design due to its speed, simplicity, and reproducibility.
T769 115133-115261 Sentence denotes The standardized ppm scale allows one to compare all NMR results and gather them in databases for the common use of researchers.
T770 115262-115454 Sentence denotes Although sample labeling was limiting in the beginning, it has now become a strength of NMR that permits the observation of big molecules and/or biomolecular processes “through the door lock”.
T771 115455-115594 Sentence denotes NMR is the only analytical technique that permits qualitative and quantitative analysis without previous sample purification or separation.
T772 115595-115737 Sentence denotes High precision NMR data still requires long experiment times and has elevated costs; however, these will no doubt be alleviated in the future.
T773 115739-115754 Sentence denotes Acknowledgments
T774 115755-115868 Sentence denotes The authors would like to thank King Abdullah University of Science and Technology (KAUST) for financial support.
T775 115870-115890 Sentence denotes Author Contributions
T776 115891-115986 Sentence denotes A.-H.E. designed the outline of the manuscript, and offered numerous suggestions for each part.
T777 115987-116086 Sentence denotes B.G.P. contributed to Section 3 and Section 4 of this paper, and provided English editing services.
T778 116087-116130 Sentence denotes K.S. arranged and organized the references.
T779 116131-116250 Sentence denotes K.S. and K.C. designed the figures representing common NMR mechanisms and concepts, as well as the NMR pulse sequences.
T780 116251-116409 Sentence denotes R.T.M., M.J., and L.J. contributed their NMR expertise to make “An Introduction to NMR Spectroscopy” (Section 2) scientifically correct and reader accessible.
T781 116410-116534 Sentence denotes M.D. and F.A. created the figures in the Introduction and made valuable revisions for the final remarks section (Section 5).
T782 116535-116639 Sentence denotes J.I.L. did extensive research and added the information regarding NMR as it applies to studying viruses.
T783 116640-116733 Sentence denotes M.D. and J.I.L. developed and contributed to all parts, especially the final remarks section.
T784 116734-116810 Sentence denotes All authors have read and agreed to the published version of the manuscript.
T785 116812-116819 Sentence denotes Funding
T786 116820-116863 Sentence denotes This research received no external funding.
T787 116865-116886 Sentence denotes Conflicts of Interest
T788 116887-116931 Sentence denotes The authors declare no conflict of interest.
T789 116933-116960 Sentence denotes Figures, Schemes and Tables
T790 116961-117018 Sentence denotes Scheme 1 Schematic representation of drug discovery [4].
T791 117019-117070 Sentence denotes Numerical data were reported from Meigs et al. [3].
T792 117071-117216 Sentence denotes Figure 1 Data search results for: “NMR” and “Drug design” in Scopus (blue) (www.scopus.com) and Orbit patent (orange) (www.orbit.com) databases.
T793 117217-117275 Sentence denotes Figure 2 The most simplified layout of an NMR experiment.
T794 117276-117318 Sentence denotes The NMR spectrum of ethyl acetate Table 1.
T795 117319-117371 Sentence denotes H chemical shift assignments is shown as an example.
T796 117372-117458 Sentence denotes The chemical structure and simulated 1H-NMR spectrum were created using ChemDraw 18.1.
T797 117459-117496 Sentence denotes Figure 3 The pulse sequence of HSQC.
T798 117497-117539 Sentence denotes I and S represent two heteronuclear spins.
T799 117540-117589 Sentence denotes The τ is (1/4J) where J is the coupling constant.
T800 117590-117666 Sentence denotes The thick and thin bars represent the 180° and 90° pulse respectively [142].
T801 117667-117765 Sentence denotes Figure 4 RF (radiofrequency) pulse causes the bulk magnetization to move to the transverse plane.
T802 117766-118039 Sentence denotes Over time (ms to seconds, and in extreme cases, minutes [155]), the bulk magnetization will decrease in the transverse plane, and increase in the longitudinal axis, returning to its original, equilibrium value. (A) represents T1 relaxation and (B) represents T2 relaxation.
T803 118040-118070 Sentence denotes Figure 5 CPMG pulse sequence.
T804 118071-118160 Sentence denotes First, a 90° RF pulse is applied and results in transverse magnetization in the xy plane.
T805 118161-118229 Sentence denotes Then a 180°y pulse is applied to re-phase the magnetization vectors.
T806 118230-118394 Sentence denotes After 180°y, the vectors who were faster during the dephasing are overtaken by the slower vectors, which results in re-phasing and generation of a spin-echo signal.
T807 118395-118434 Sentence denotes This process is repeated several times.
T808 118435-118551 Sentence denotes Figure 6 Underlying mechanisms of (A) Traditional High-throughput Screening, and (B) Fragment Based Drug Discovery.
T809 118552-118673 Sentence denotes Figure 7 Overlaid 1H-15N-HSQC for FKBP in the absence (black contours) and presence (red contours) of 2-phenylimidazole.
T810 118674-118723 Sentence denotes Adapted with permission from Hajduk et al. [249].
T811 118724-118790 Sentence denotes Figure 8 Basic layout of the different NOE effect on NMR signals.
T812 118791-118863 Sentence denotes Figure 9 Illustration of STD NMR (a) and WaterLOGSY (b) in drug design.
T813 118864-118910 Sentence denotes Copied with permission from Robson-Tull [209].
T814 118911-118980 Sentence denotes Figure 10 Schematic representation of the principle of the INPHARMA.
T815 118981-119129 Sentence denotes The inter-ligand NOEs observed between two competitive ligands A (in green) and B (in blue), which bind consecutively to the same target receptor T.
T816 119130-119163 Sentence denotes The figure is adapted from [284].
T817 119164-119367 Sentence denotes Figure 11 Visual representation of how molecules diffuse in solution from a high concentration to a low concentration across an arbitrarily defined point (x = 0) after some period of time (t = ∞) [289].
T818 119368-119552 Sentence denotes The red arrow indicates the direction of translational motion as the molecules (green) move from an area of higher concentration (left) to an area of lower concentration (right) [287].
T819 119553-119628 Sentence denotes Figure 12 Spin echo (SE) sequence, as discovered by Stejskal et al. [293].
T820 119629-119833 Sentence denotes G1 is the first gradient pulse applied after the first 90° pulse, and G2 is the second gradient pulse applied after the first 180° pulse. δ and ∆ are the gradient length, and diffusion time, respectively.
T821 119834-119999 Sentence denotes Figure 13 Representation of different in-cell NMR techniques. (A) Target-detected in-cell NMR, (B) compound-detected in-cell NMR, (C) Reporter-detected in-cell NMR.
T822 120000-120066 Sentence denotes The red color is the isotopically labeled component of the system.
T823 120067-120102 Sentence denotes Adapted with permission from [409].
T824 120103-120193 Sentence denotes Scheme 2 Analysis of the cost and time between different NMR methods used in drug design.
T825 120194-120644 Sentence denotes Meaning of some of the acronyms are listed below: SOFAST—Band-Selective Optimized Flip Angle Short Transient; NUS—Non-uniform sampling; MDD—Multidimensional Decomposition; CS—Compressed Signaling; MAX ENT—Maximum Entropy; IST—Iterative Soft Threshold; STD—Saturation Transfer Difference; PNMR—Paramagnetic NMR; ALARM—A La Assay to detect Reactive Molecules; ssNMR—Solid State NMR; FBDD—Fragment Based Drug Design; SAR—Structure Activity Relationship.
T826 120645-120778 Sentence denotes Table 1 Recent pharmacological studies complemented with NMR approaches for evaluating the efficacy/safety of new or existing drugs.
T827 120779-120854 Sentence denotes Tested Substance Evaluated Effect NMR Experiments Used in the Study Ref.
T828 120855-121025 Sentence denotes Isoniazid (INH) INH induces oxidative stress, disturbs energy metabolism, and causes disorders in neurotransmission and neuromodulation processes in Sprague Dawley rats.
T829 121027-121067 Sentence denotes 1H-NMR CPMG1H,1H-TOCSY1H,13C-HSQC [178]
T830 121068-121204 Sentence denotes Naproxen Naproxen induces a disturbance in energy and choline metabolism, and promotes catabolism of tryptophan in Sprague Dawley rats.
T831 121206-121230 Sentence denotes 1H-NOESYPRESAT-1D [179]
T832 121231-121514 Sentence denotes Cisplatin (CP) Identification of six serum (alanine, betaine, glucose, glutamine, lactate, and leucine) and eight urinary (alanine, acetate, citrate, glucose, glycine, guanidinoacetate, hippurate, and lactate) metabolites that can be used as biomarkers for cisplatin nephrotoxicity.
T833 121516-121529 Sentence denotes 1H-NMR [180]
T834 121530-121711 Sentence denotes Shell of Herpetospermum caudigerum Wall (SHCW) A high dosage of SHCW causes the disturbance of energy and amino acid metabolism and induces oxidative stress in Sprague-Dawley rats.
T835 121713-121753 Sentence denotes 1H-NMR CPMG1H,13C-HSQC1H,13C-TOCSY [86]
T836 121754-121893 Sentence denotes Ampicillin, Maculatin 1.1 Both antibiotics cause destabilization of membrane integrity and increase breakdown of nucleic acids in E. coli.
T837 121895-121910 Sentence denotes 1H-31P CP [94]
T838 121911-122078 Sentence denotes Emodin Emodin can affect the immune response and interrupt energy metabolism (citric acid cycle) along with glutathione synthesis, which can lead to oxidative stress.
T839 122080-122129 Sentence denotes 1H-NMR CPMG1H,1H-COSY1H,13C-HMBC1H,13C-HSQC [65]
T840 122130-122291 Sentence denotes “RenqingMangjue” pill (RMP) RMP can disturb the citric acid cycle in cells, and decreases levels of glutamate, glutamine and BCAAs in the plasma of Wistar rats.
T841 122293-122342 Sentence denotes 1H-NMR CPMG1H,1H-COSY1H,13C-HSQC1H-13C HMBC [66]
T842 122343-122551 Sentence denotes Ptac2S Ptac2S limits cancer cell (Skov-3) proliferation by reducing the efficiency of the citric acid cycle and induces changes in cell membranes in a shorter period of time (6h) compared to cisplatin (24h).
T843 122552-122607 Sentence denotes Additionally, Ptac2S may inhibit lactate dehydrogenase.
T844 122609-122659 Sentence denotes 1H-NMR CPMG1H,1H-COSY1H,13C-HSQC1H,13C-HMBC [145]
T845 122660-122854 Sentence denotes Gemcitabine-carboplatin (GC) Identification of two biomarkers (formate and acetate) that can predict a positive response in MBC (metastatic breast cancer) patients treated with GC chemotherapy.
T846 122856-122924 Sentence denotes 1H-NMR CPMG1H JRES1H,1H-COSY1H,1H-TOCSY1H,13C-HSQC1H,13C-HMBC [137]
T847 122925-123034 Sentence denotes Doxorubicin (DOX)/dexrazoxane (DEX) DOX decreases ATP production and induces oxidative stress in H9C2 cells.
T848 123035-123118 Sentence denotes DEX counteracts those changes, having a cardioprotective effect on H9C2 cell lines.
T849 123120-123143 Sentence denotes 1H-NOESYPRESAT-1D [67]
T850 123144-123284 Sentence denotes Curcumin Curcumin shows antihyperlipidemic effects on C57BL/6Slac mice by partially restoring metabolic defects induced by a high-fat diet.
T851 123285-123479 Sentence denotes Affected metabolic pathways include the citric acid cycle, glycolysis and gluconeogenesis, ketogenesis of BCAA, synthesis of ketone bodies and cholesterol, and choline and fatty acid metabolism.
T852 123481-123527 Sentence denotes 1H-NOESYPRESAT-1D1H-1H TOCSY1H,13C-HSQC [136]
T853 123528-123737 Sentence denotes Formosanin C (FC) Formosanin C shows the ability to inhibit synthesis and methylation of DNA as well as reducing the activity of the citric acid cycle and energy metabolism in the mitochondria of HepG2 cells.
T854 123739-123752 Sentence denotes 1H-NMR [181]
T855 123753-123853 Sentence denotes Melamine Melamine disrupts metabolism of glucose, nitrogen, and protein in the liver of Wistar rat.
T856 123855-123873 Sentence denotes 1H-NMR CPMG [182]
T857 123874-123991 Sentence denotes Aristolochic acid (AA) Aristolochic acid causes renal lesions and a disorder in tubular reabsorption in Wistar rats.
T858 123993-124005 Sentence denotes 1H-NMR [68]
T859 124006-124108 Sentence denotes Rituximab Evaluating response outcome for patients with rheumatoid arthritis, treated with rituximab.
T860 124109-124245 Sentence denotes Identification of metabolites changes between responders and non-responders such as succinate, taurine, lactate, pyruvate and aspartate.
T861 124247-124260 Sentence denotes 1H-NMR [183]
T862 124261-124422 Sentence denotes Levetiracetam, Lamotrigine, Topiramate No distinction between metabolite profiles of serum from patients treated with levetiracetam, lamotrigine and topiramate.
T863 124423-124484 Sentence denotes Could not evaluate response of initial treatment of epilepsy.
T864 124486-124510 Sentence denotes 1H-NOESYPRESAT-1D [184]
T865 124511-124712 Sentence denotes Hexacationic Ruthenium Metallaprism Metallaprism mainly affects lipid metabolism in A2780 (human ovarian cancer) and HEK-293 (human embryonic kidney) cells, and increases GSH levels in all cell lines.
T866 124713-124840 Sentence denotes In A2780cisR (cisplatin resistant A2780) cells, lipid biogenesis and glycosylation are affected by treatment with metallaprism.
T867 124842-124907 Sentence denotes HR-MAS:a)1D-1H NOESY-1H CPMGb)2D-1H,1H-TOCSY-1H J-resolved [138]
T868 124908-125095 Sentence denotes Centella asiatica extract Extract from Centella asiatica promotes glycolysis, boosts the citric acid cycle and decreases gluconeogenesis and lipid metabolism in T2DM Sprague–Dawley rats.
T869 125097-125115 Sentence denotes 1H-NMR CPMG [185]
T870 125116-125324 Sentence denotes VR24, VR27 (1,3,4-thiadiazoles) VR24 and VR27 improve glycerol metabolism, decrease betaine levels, and normalize the altered level of myoinositol in serum of DMH-induced CRC (colorectal cancer) Wistar rats.
T871 125326-125344 Sentence denotes 1H-NMR CPMG [186]
T872 125345-125535 Sentence denotes Xiaoyaosan Xiaoyaosan regulates energy metabolism, can play an important role in the regulation of the nervous system, and might restore the balance in gut microbiota of depressed patients.
T873 125537-125576 Sentence denotes 1H-NMR CPMG1H,1H-COSY1H,13C-HMQC [187]
T874 125577-125717 Sentence denotes Sini decoction (SND) SND may restore balance in myocardial energy metabolism, and regulate the citric acid cycle and amino acid metabolism.
T875 125718-125824 Sentence denotes Identification of 10 biomarkers showing potential efficiency of SND administration in Sprague-Dawley rats.
T876 125826-125839 Sentence denotes 1H-NMR [188]
T877 125840-126136 Sentence denotes Fu Fang Jin Jing Oral Liquid (FJJOL) with Herba Rhodiol FJJOL regulates energy metabolism of brain tissue, can affect the function of neurons abundant in GABA and glycine receptors, and may help to maintain the membrane integrity of the cells in Kunming-strain mice exposed to hypobaric hypoxia.
T878 126138-126183 Sentence denotes 1H-NOESYPRESAT-1D1H,1H-gCOSY1H,1H-TOCSY [87]
T879 126184-126413 Sentence denotes Acyclovir, Pyrazinamide, Isoniazid, Sulfamethoxazole Evaluating the efficacy (determined by the concentration of a drug able to reach the therapeutic site) of four drugs in cerebrospinal fluid of tuberculous meningitis patients.
T880 126415-126449 Sentence denotes 1H-NOESYPRESAT-1D1H,1H-COSY [189]
T881 126450-126599 Sentence denotes Genipin Genipin can recover energy metabolism to normal levels, and regulate methylamine and amino acid metabolisms of diabetic Sprague Dawley rats.
T882 126601-126619 Sentence denotes 1H-NOESY-1D [190]
T883 126620-126883 Sentence denotes Adriamycin (ADR) Identification of seven biomarkers: trimethylamine oxide (TMAO), taurine, trimethylamine (TMA), hippurate, trigonelline, citrate and 2-oxoglutarate that can predict tumor’s (gastric adenocarcinoma) response to ADR treatment in BALB/c-nu/nu mice.
T884 126885-126909 Sentence denotes 1H-NOESYPRESAT-1D [191]
T885 126910-127111 Sentence denotes Danggui/European Danggui Comparison between Danggui and European Danggui showed that Danggui has a different chemical composition and provides a better enriching effect on blood than European Danggui.
T886 127112-127175 Sentence denotes Identification of 18 metabolites affected by Danggui treatment.
T887 127177-127232 Sentence denotes 1H-NMR CPMG1H-NOESYPRESAT-1D1H,1H-COSY1H,13C-HSQC [88]
T888 127233-127428 Sentence denotes Erythromycin Erythromycin decreases citric acid cycle activity, enhances fatty acid oxidation, causes dysfunction in amino acid metabolism, and creates oxidative stress in livers of Wistar rats.
T889 127430-127461 Sentence denotes 1H-NMR CPMG1H-NMR BPPLED [192]
T890 127462-127642 Sentence denotes Fuzi/Gancao Fuzi causes a shift in energy metabolism (from aerobic respiration to anaerobic), induces membrane toxicity, and disrupts the balance of gut microbiota of Wistar rats.
T891 127643-127712 Sentence denotes Administrating Fuzi with Gancao diminishes the toxic effects of Fuzi.
T892 127714-127732 Sentence denotes 1H-NOESY-1D [193]
T893 127733-128016 Sentence denotes Kijitsu, Tohi, Chimpi, Kippi, Seihi 1H-NMR spectra enabled the identification of three compounds (naringin, sucrose, and β-glucose), and 13C-NMR enabled the identification of eight compounds (naringin, neohesperidin, ɑ- and β-glucose, sucrose, limonene, narirutin, and synephrine).
T894 128018-128038 Sentence denotes 1H-NMR13C-NMR [112]
T895 128039-128219 Sentence denotes Table 2 The names, structures, targets, FBDD optimization strategy used, biophysical techniques used, and status in clinical trials of select drugs derived from the FBDD approach.
T896 128220-128334 Sentence denotes Drug (Company) Target Original Fragment(s) * Advanced Molecule and Progress in Clinical Trials Techniques Used
T897 128335-128465 Sentence denotes Vemurafenib (Plexxikon) [224,226] BRAF-V600E Approved high-concentration biochemical fragment screening, X-ray crystallography
T898 128466-128559 Sentence denotes Venetoclax (AbbVie, Genetech) [227,228,229,230] BCL-2 Approved NMR, X-ray crystallography
T899 128560-128681 Sentence denotes Ribociclib (Novartis Europharm Limited) [231] CDK4 and 6 Information Not Available Approved Information not Available
T900 128682-128814 Sentence denotes PLX3397 (Plexxikon) [232,233,234] FMS, KIT, and FLT3-ITD Phase 3 X-ray crystallography, Structure Confirmed by NMR, MS, and HPLC
T901 128815-128917 Sentence denotes Verubecestat (Merck) [235,236] BACE1 Phase 3 NMR, X-ray crystallography, inhibition of cathepsin D
T902 128918-129024 Sentence denotes Onalespib (Astex) [237,238] HSP90 Phase 2 X-ray crystallography, isothermal titration calorimetry, NMR
T903 129025-129148 Sentence denotes AZD5099 [239,240] Topoisomerase II Phase 1 NMR, Surface Plasmon Resonance, isothermal calorimetry, X-ray cystallography
T904 129149-129235 Sentence denotes AT7519 [241,242,243,244] CDK 1, 2, 4, and 5 Phase 2 NMR, MS, X-ray crystallography
T905 129236-129328 Sentence denotes * Structures for some of the fragments are taken directly from Dan Erlanson’s blog at [245].
T906 129329-129419 Sentence denotes Table 3 Advantages and limitations of different NMR techniques developed in recent years.
T907 129420-129460 Sentence denotes NMR Technique Advantages Disadvantages
T908 129461-129618 Sentence denotes 1D-NMR Ability to identify simple chemical compounds.High quality resolution and sensitivity for many 1D experiments.Less time consuming compared to 2D NMR.
T909 129620-129813 Sentence denotes Compared to 2D NMR less details can be obtained for more complex molecules.For nuclei other than 1H and 19F, relative sensitivity is fairly low—requires extra labeling to obtain better spectra.
T910 129814-129994 Sentence denotes 2D NMR Ability to identify complex molecules and observe different interactions between the nuclei, e.g., correlations between all spins in one spin system using TOCSY experiment.
T911 129996-130056 Sentence denotes Requires long times to obtain a proper spectra (up to days).
T912 130057-130117 Sentence denotes Ultrafast 2D NMR Greatly reduces time to obtain 2D spectra.
T913 130119-130139 Sentence denotes Reduced sensitivity.
T914 130140-130195 Sentence denotes SOFAST Significantly reduces acquisition time of HMQC.
T915 130197-130222 Sentence denotes Relatively low resolution
T916 130223-130302 Sentence denotes NUS Lowers the time of measurement while keeping the same level of resolution.
T917 130304-130405 Sentence denotes Requires use of reconstruction algorithms since missing data points can lead to artifacts in spectra.
T918 130406-130536 Sentence denotes MDD Multidimensional data are “broken” to one dimensional, which are easier to analyze.Ability to resolve overlapping resonances.
T919 130539-130622 Sentence denotes Data must be (approximately) symmetrical (Lorentzian shape) to obtain good spectra.
T920 130623-130663 Sentence denotes CS Good reconstruction of weaker peaks.
T921 130665-130722 Sentence denotes Large computational costs, low performance on noisy data.
T922 130723-130774 Sentence denotes MAX ENT Significant reduction in acquisition time.
T923 130776-130863 Sentence denotes Nominally Lorentzian peak shapes may be distorted, and peak intensities may be altered.
T924 130864-130912 Sentence denotes IST Greatly reduced time to obtain NMR spectra.
T925 130914-130963 Sentence denotes Requires a grid of uniformly sampled data points.
T926 130964-131070 Sentence denotes FBDD Often makes stronger binding ligands from weakly binding fragments.Less time and resource intensive.
T927 131072-131133 Sentence denotes Can be used only for small fragments of compound of interest.
T928 131134-131186 Sentence denotes SAR Direct observation of target binding to ligand.
T929 131187-131233 Sentence denotes Several types of NMR experiments are possible.
T930 131235-131338 Sentence denotes Inability to distinguish binding modes, difficult to gage the “true” binding site of ligand to protein.
T931 131339-131448 Sentence denotes STD Only requires a small amount of sample.Highly reproducible.Allows direct observations of ligand binding.
T932 131450-131524 Sentence denotes Only works for ligands with low binding affinity (fast chemical exchange).
T933 131525-131564 Sentence denotes Inability to distinguish binding modes.
T934 131565-131641 Sentence denotes In cell NMR In vivo studies are possible, can focus on specific cell parts.
T935 131643-131687 Sentence denotes Special labeling techniques may be required.
T936 131688-131733 Sentence denotes Spectra may be more challenging to interpret.
T937 131734-131903 Sentence denotes In silico + NMR Can model protein drug interactions, helps speed up and reduce cost of drug delivery Protein models need to be validated through experimental approach.
T938 131904-132047 Sentence denotes PNMR Can observe proteins interacting with metal ions, long observation distance (10-25 angstroms) between paramagnetic left and nearby atoms.
T939 132049-132090 Sentence denotes Paramagnetic left required in the system.
T940 132091-132201 Sentence denotes ALARM NMR Elimination of false positives from HTS methods It requires synthesis of human La antigen protein.
T941 132202-132365 Sentence denotes ssNMR Enables the characterization of a chemical compound in a solid-state form such as a tablet/pill.Provides insight into the physical properties of a compound.
T942 132367-132454 Sentence denotes Significant broadening of the spectral lineshapes due to anisotropic spin interactions.
T943 132455-132543 Sentence denotes Relaxation editing Noticeable difference in spectra of binding and non-binding ligands.
T944 132545-132613 Sentence denotes Sets the lower limit of time for which experiments can be performed.