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PMC:7571312 / 98671-100615 JSONTXT

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LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T1 1296-1299 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T1 158-159 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T2 1002-1010 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T3 1002-1010 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T4 1283-1284 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T5 1296-1299 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum
T6 1900-1902 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T7 1936-1941 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T36398 33-36 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T68180 67-73 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T23806 74-80 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T43660 81-86 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T81179 109-119 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T16323 123-130 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T59723 131-140 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T83326 131-133 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T54917 134-140 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T90295 143-154 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T63164 160-168 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T59444 172-182 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T35775 177-182 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T40975 214-217 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T93872 248-254 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T74567 255-261 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T69512 262-267 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T20884 290-300 Chemical denotes 2-oxoethyl http://purl.obolibrary.org/obo/CHEBI_46886
T5959 301-310 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T56743 334-341 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T53389 363-380 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T42433 376-380 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T4011 381-388 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T75071 405-413 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T51684 480-488 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T36338 528-535 Chemical denotes toluene http://purl.obolibrary.org/obo/CHEBI_17578
T93903 588-601 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T66847 602-606 Chemical denotes salt http://purl.obolibrary.org/obo/CHEBI_24866|http://purl.obolibrary.org/obo/CHEBI_26710
T48542 622-625 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T25345 642-650 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T18497 686-693 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T14391 694-700 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_16881|http://purl.obolibrary.org/obo/CHEBI_35581
T25234 703-718 Chemical denotes carboxylic acid http://purl.obolibrary.org/obo/CHEBI_33575
T15706 714-718 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T72172 912-917 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T37051 935-942 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T9365 962-975 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T51737 970-975 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T21849 1028-1033 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T33310 1072-1077 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T79743 1097-1105 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T76543 1226-1234 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T18868 1235-1250 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T41848 1400-1402 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T47509 1417-1422 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T15859 1435-1437 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T42303 1461-1463 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T6599 1506-1508 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38218 1532-1534 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T14852 1558-1560 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T83387 1577-1579 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79575 1603-1605 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94704 1617-1619 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T84391 1631-1633 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T97905 1645-1647 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T3346 1672-1674 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41450 1699-1701 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T49284 1726-1728 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2691 1753-1755 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T53090 1805-1807 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55404 1819-1821 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40430 1857-1859 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T20957 1900-1902 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T557 0-154 Sentence denotes N-[(1S)-2-[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide
T558 155-577 Sentence denotes To a solution of tert-butyl [(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]carbamate (200 mg, 0.38 mmol) in dioxane (4 mL) was added 4 M hydrochloric acid/dioxane (4 mL), and the solution was stirred at an ambient temperature for 2 h before removing the solvents in vacuo, azeotroping the residue with toluene (2 × 10 mL), and drying in vacuo for 1 h.
T559 578-866 Sentence denotes The crude hydrochloride salt was taken into DMF (3 mL), and the solution was cooled to 0 °C before adding 4-methoxy-indole-2-carboxylic acid (73 mg, 0.38 mmol), collidine (125 μL, 0.95 mmol), and HATU (144 mg, 0.38 mmol) in order, and the resulting suspension was stirred at 0 °C for 6 h.
T560 867-988 Sentence denotes The reaction was quenched by the addition of water (20 mL), and the mixture was extracted with diethyl ether (3 × 50 mL).
T561 989-1312 Sentence denotes The combined organics were washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered, and the solvents were removed in vacuo to yield the crude product, which was purified by Biotage flash chromatography, eluting with 1–3% methanol/dichloromethane to afford the title compound as a pale brown gum, 90 mg, 39%.
T562 1313-1399 Sentence denotes The product was contaminated with ∼20% of another diastereomer from the previous step.
T563 1400-1944 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 9.59 (s, 1H), 8.13 (d, J = 6.6 Hz, 1H), 7.21–7.32 (m, 5H), 7.11 (t, J = 8.0 Hz, 1H), 7.02 (d, J = 1.5 Hz, 1H), 6.94 (d, J = 8.3 Hz, 1H), 6.72–6.78 (m, 1H), 6.42 (d, J = 7.8 Hz, 1H), 5.97 (s, 1H), 4.73 (m, 1H), 4.64 (m, 1H), 4.53 (d, J = 11.6 Hz, 1H), 4.46 (d, J = 11.6 Hz, 1H), 4.26 (d, J = 17.2 Hz, 1H), 4.15 (d, J = 17.4 Hz, 1H), 3.87 (s, 3H), 3.08–3.16 (m, 2H), 2.27–2.38 (m, 1H), 1.92 (m, 1H), 1.49–1.84 (m, 9H), 1.26–1.42 (m, 1H), 0.98–1.23 (m, 4H), 0.78–0.98 (m, 2H); MS (APCI+) for C34H42N4O6m/z 603.2 (M + H)+.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1867 1290-1299 Species denotes brown gum Tax:338536
1868 912-917 Chemical denotes water MESH:D014867
1869 1028-1033 Chemical denotes water MESH:D014867
1870 1046-1051 Chemical denotes brine MESH:C017082
1871 1072-1077 Chemical denotes MgSO4 MESH:D008278
1872 1226-1234 Chemical denotes methanol MESH:D000432
1873 1235-1250 Chemical denotes dichloromethane MESH:D008752