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PMC:7571312 / 68240-69742 JSONTXT

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LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T533 108-109 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T534 229-232 http://purl.obolibrary.org/obo/CLO_0001360 denotes 412
T535 533-536 http://purl.obolibrary.org/obo/CLO_0053733 denotes 1:1
T536 541-544 http://purl.obolibrary.org/obo/CLO_0009952 denotes sat
T537 635-643 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T538 635-643 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T539 734-735 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T540 780-782 http://purl.obolibrary.org/obo/CL_0000453 denotes LC
T541 803-806 http://purl.obolibrary.org/obo/CLO_0001000 denotes 3–5
T542 966-967 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T543 1237-1239 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T544 1292-1294 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T545 1329-1334 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T37154 0-2 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T37988 36-42 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T40575 45-48 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T87309 79-85 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T15226 86-92 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T71708 110-118 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T84983 137-142 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T723 145-151 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T70140 163-179 Chemical denotes pyrrolidin-2-one http://purl.obolibrary.org/obo/CHEBI_36592
T48078 180-193 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T8628 217-220 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T92797 221-224 Chemical denotes Leu http://purl.obolibrary.org/obo/CHEBI_15603|http://purl.obolibrary.org/obo/CHEBI_25017|http://purl.obolibrary.org/obo/CHEBI_30006
T24507 250-253 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T64579 295-297 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T4261 341-349 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T97970 469-476 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T81782 553-559 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T74303 599-612 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T61396 599-604 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T89842 605-612 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T65022 692-697 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T8881 780-782 Chemical denotes LC http://purl.obolibrary.org/obo/CHEBI_73582
T68823 797-801 Chemical denotes SiO2 http://purl.obolibrary.org/obo/CHEBI_30563
T743 808-816 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T78694 817-827 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T745 855-857 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T61338 859-878 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T3870 891-897 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T57417 900-903 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T92113 934-940 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T3316 941-947 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T18208 980-982 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73895 988-992 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T54705 1018-1020 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T9003 1032-1034 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95148 1056-1058 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46407 1081-1083 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29864 1106-1108 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48792 1120-1122 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T760 1134-1136 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T761 1148-1150 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38397 1162-1164 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72464 1176-1178 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T73628 1190-1192 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T33402 1204-1206 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T766 1292-1294 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T68140 1371-1374 Chemical denotes H2O http://purl.obolibrary.org/obo/CHEBI_15377

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T420 0-107 Sentence denotes N2-(tert-Butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide
T421 108-317 Sentence denotes A solution of (3S)-3-[(2S)-2-amino-4-chloro-3-oxobutyl]pyrrolidin-2-one hydrochloride (391 mg, 1.6 mmol) and Boc-Leu-OH (412 mg, 1.8 mmol) in DMF (9 mL) was placed under an atmosphere of N2 and cooled to 0 °C.
T422 318-455 Sentence denotes This clear pale yellow solution was successively treated with HATU (678 mg, 1.8 mmol) followed by N-methylmorpholine (0.41 mL, 3.7 mmol).
T423 456-621 Sentence denotes The reaction mixture gradually became opaque and after 1 h was quenched with 1:1 ice/sat aqueous NaHCO3 (40 mL) and extracted three times with ethyl acetate (40 mL).
T424 622-749 Sentence denotes The combined organics were washed once with brine (30 mL), dried over MgSO4, filtered, and concentrated to give a yellow syrup.
T425 750-979 Sentence denotes This material was purified by LC (50 g 230–400 SiO2, 3–5% methanol/chloroform) to afford 636 mg (40%) of N2-(tert-butoxycarbonyl)-N1-((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-l-leucinamide as a white foam.
T426 980-1337 Sentence denotes 1H NMR (DMSO-d6) δ 8.47 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.04 (d, J = 8 Hz, 1H), 4.60 (d, J = 16 Hz, 1H), 4.53 (d, J = 16 Hz, 1H), 4.40 (m, 1H), 3.90 (m, 1H), 3.16 (m, 1H), 3.08 (m, 1H), 2.24 (m, 1H), 2.10 (m, 1H), 1.98 (m, 1H), 1.63 (m, 2H), 1.45–1.37 (m, 11 H), 0.89 (d, J = 4 Hz, 3H), 0.85 (d, J = 4 Hz, 3H); MS (ESI+) for C19H32ClN3O5m/z 418.1 (M + H)+.
T427 1338-1403 Sentence denotes Anal. calcd for C19H32ClN3O5·0.6 H2O: C, 53.22; H, 7.81; N, 9.80.
T428 1404-1438 Sentence denotes Found: C, 53.00; H, 7.65; N, 9.54.
T429 1439-1502 Sentence denotes HRMS (ESI+) calcd for C19H32ClN3O5+H1 418.2103, found 418.2091.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1492 217-220 Gene denotes Boc Gene:91653
1493 1471-1476 Species denotes O5+H1 Tax:2491878
1494 553-559 Chemical denotes NaHCO3 MESH:D017693
1495 599-612 Chemical denotes ethyl acetate MESH:C007650
1496 666-671 Chemical denotes brine MESH:C017082
1497 692-697 Chemical denotes MgSO4 MESH:D008278
1498 797-801 Chemical denotes SiO2
1499 808-816 Chemical denotes methanol MESH:D000432
1500 817-827 Chemical denotes chloroform MESH:D002725
1501 1354-1366 Chemical denotes C19H32ClN3O5
1502 1371-1374 Chemical denotes H2O
1503 1376-1377 Chemical denotes C MESH:D002244
1504 1395-1396 Chemical denotes N MESH:D009584
1505 1411-1412 Chemical denotes C MESH:D002244
1506 1430-1431 Chemical denotes N MESH:D009584
1507 1439-1443 Disease denotes HRMS