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PMC:7291971 / 57187-58835 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1146 51-66 CHEBI:50488;CHEBI:50488 denotes dihydroxyoxolan
T1147 69-71 CHEBI:53233;CHEBI:53233 denotes yl
T1148 72-78 CHEBI:16625;CHEBI:16625 denotes methyl
T1149 111-115 CHEBI:30756;CHEBI:30756 denotes 9-yl
T1150 116-118 CHEBI:17500;CHEBI:17500 denotes -4
T1151 118-119 CHEBI:34018;CHEBI:34018 denotes -
T1152 119-126 CHEBI:43176;CHEBI:43176 denotes hydroxy
T1153 126-130 CHEBI:17500;CHEBI:17500 denotes -5-(
T1154 130-143 CHEBI:24712;CHEBI:24712 denotes hydroxymethyl
T1155 144-150 CHEBI:26911;CHEBI:26911 denotes oxolan
T1156 150-156 CHEBI:15533;CHEBI:15533 denotes -3-yl]
T1157 156-159 CHEBI:29354;CHEBI:29354 denotes oxy
T1158 160-165 CHEBI:37807;CHEBI:37807 denotes ethyl
T1159 166-171 CHEBI:46882;CHEBI:46882 denotes amino
T1160 172-185 CHEBI:30772;CHEBI:30772 denotes butanoic acid
T1161 266-271 CHEBI:15377;CHEBI:15377 denotes water
T1162 309-317 CHEBI:46787;CHEBI:46787 denotes solvents
T1163 374-379 CHEBI:15377;CHEBI:15377 denotes water
T1164 397-401 CHEBI:48607;CHEBI:48607 denotes LiOH
T1165 402-409 CHEBI:15377;CHEBI:15377 denotes aqueous
T1166 410-418 CHEBI:75958;CHEBI:75958 denotes solution
T1167 520-523 CHEBI:17883;CHEBI:17883 denotes HCl
T1168 524-531 CHEBI:15377;CHEBI:15377 denotes aqueous
T1169 532-540 CHEBI:75958;CHEBI:75958 denotes solution
T1170 542-550 CHEBI:46787;CHEBI:46787 denotes Solvents
T1171 657-663 CHEBI:30563;CHEBI:30563 denotes silica
T1172 724-736 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T1173 800-808 CHEBI:36357;CHEBI:36357 denotes compound
T1174 856-861 CHEBI:15377;CHEBI:15377 denotes water
T1175 866-877 CHEBI:47032;CHEBI:47032 denotes 1,4-dioxane
T1176 1385-1388 CHEBI:36927;CHEBI:36927 denotes 13C
T67979 51-66 CHEBI:50488;CHEBI:50488 denotes dihydroxyoxolan
T32544 69-71 CHEBI:53233;CHEBI:53233 denotes yl
T12991 72-78 CHEBI:16625;CHEBI:16625 denotes methyl
T86322 111-115 CHEBI:30756;CHEBI:30756 denotes 9-yl
T2693 116-118 CHEBI:17500;CHEBI:17500 denotes -4
T25161 118-119 CHEBI:34018;CHEBI:34018 denotes -
T69413 119-126 CHEBI:43176;CHEBI:43176 denotes hydroxy
T26102 126-130 CHEBI:17500;CHEBI:17500 denotes -5-(
T20939 130-143 CHEBI:24712;CHEBI:24712 denotes hydroxymethyl
T70312 144-150 CHEBI:26911;CHEBI:26911 denotes oxolan
T56764 150-156 CHEBI:15533;CHEBI:15533 denotes -3-yl]
T75470 156-159 CHEBI:29354;CHEBI:29354 denotes oxy
T3995 160-165 CHEBI:37807;CHEBI:37807 denotes ethyl
T67962 166-171 CHEBI:46882;CHEBI:46882 denotes amino
T85476 172-185 CHEBI:30772;CHEBI:30772 denotes butanoic acid
T88015 266-271 CHEBI:15377;CHEBI:15377 denotes water
T32144 309-317 CHEBI:46787;CHEBI:46787 denotes solvents
T73518 374-379 CHEBI:15377;CHEBI:15377 denotes water
T36371 397-401 CHEBI:48607;CHEBI:48607 denotes LiOH
T62284 402-409 CHEBI:15377;CHEBI:15377 denotes aqueous
T5176 410-418 CHEBI:75958;CHEBI:75958 denotes solution
T58294 520-523 CHEBI:17883;CHEBI:17883 denotes HCl
T17055 524-531 CHEBI:15377;CHEBI:15377 denotes aqueous
T68995 532-540 CHEBI:75958;CHEBI:75958 denotes solution
T64029 542-550 CHEBI:46787;CHEBI:46787 denotes Solvents
T62206 657-663 CHEBI:30563;CHEBI:30563 denotes silica
T74306 724-736 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T36288 800-808 CHEBI:36357;CHEBI:36357 denotes compound
T43085 856-861 CHEBI:15377;CHEBI:15377 denotes water
T91454 866-877 CHEBI:47032;CHEBI:47032 denotes 1,4-dioxane
T2736 1385-1388 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
991 248-251 Chemical denotes TFA MESH:D014269
992 266-271 Chemical denotes water MESH:D014867
993 374-379 Chemical denotes water MESH:D014867
994 397-401 Chemical denotes LiOH
995 520-523 Chemical denotes HCl MESH:D006851
996 657-663 Chemical denotes silica MESH:D012822
997 675-678 Chemical denotes C18 MESH:C109760
998 724-736 Chemical denotes acetonitrile MESH:C032159
999 740-745 Chemical denotes TEAAc
1000 856-861 Chemical denotes water MESH:D014867
1001 866-877 Chemical denotes 1,4-dioxane MESH:C025223
1002 1385-1388 Chemical denotes 13C MESH:C000615229
1003 1403-1406 Chemical denotes D2O
1004 1602-1613 Chemical denotes C26H37N12O9
1005 1575-1579 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T345 640-641 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T346 697-698 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T347 889-891 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T348 896-898 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T349 904-905 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T350 1615-1618 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T52186 24-45 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T71124 26-31 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T91179 72-78 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T191 94-115 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T25223 96-101 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T4835 119-126 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T67895 130-143 Chemical denotes hydroxymethyl http://purl.obolibrary.org/obo/CHEBI_24712
T64132 156-159 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T8624 160-165 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T3060 166-171 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T19597 172-185 Chemical denotes butanoic acid http://purl.obolibrary.org/obo/CHEBI_30772
T17443 181-185 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T55499 248-251 Chemical denotes TFA http://purl.obolibrary.org/obo/CHEBI_45892
T92108 266-271 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T27273 309-317 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T83132 374-379 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T14764 397-401 Chemical denotes LiOH http://purl.obolibrary.org/obo/CHEBI_33979
T93820 410-418 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T54370 520-523 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T6531 532-540 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T80709 657-663 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T66891 724-736 Chemical denotes acetonitrile http://purl.obolibrary.org/obo/CHEBI_38472
T91062 746-752 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T90091 856-861 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T17933 866-877 Chemical denotes 1,4-dioxane http://purl.obolibrary.org/obo/CHEBI_47032
T66670 870-877 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T88233 974-976 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T216 991-994 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981
T68989 1007-1009 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T82560 1021-1023 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T81404 1035-1037 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T12372 1049-1051 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28362 1075-1077 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98794 1101-1103 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T15115 1120-1122 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T89279 1158-1160 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T92999 1177-1179 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T58256 1196-1198 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T40105 1252-1254 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T12935 1289-1291 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T229 1403-1406 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T397 0-189 Sentence denotes 4.1.20 4-({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(2-[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)amino)butanoic acid (8)
T398 190-282 Sentence denotes Compound 25 (140 mg, 0.15 mmol, 1.00 eq) was treated with TFA (1.37 mL) and water (0.34 mL).
T399 283-344 Sentence denotes After stirring for 5.5 h, solvents were removed under vacuum.
T400 345-438 Sentence denotes The residue was dissolved in water (0.5 mL) and 2 M LiOH aqueous solution (3.5 mL) was added.
T401 439-541 Sentence denotes After stirring at 0 °C for 30 min, pH was adjusted to ≈3 or 4 by addition of 1 M HCl aqueous solution.
T402 542-765 Sentence denotes Solvents were removed under vacuum and the residue was purified by flash column chromatography on a reversed-phase silica gel column C18 (4 g, 40 μm) with a 0–20% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7.
T403 766-973 Sentence denotes The fractions containing the pure compound were pooled, concentrated and lyophilized with water and 1,4-dioxane to give 8 (35 mg, 36%) as a white powder with 99% purity determined by HPLC analysis at 260 nm.
T404 974-1384 Sentence denotes 1H NMR (600 MHz, D2O) δ 8.24 (s, 1H), 8.13 (s, 1H), 8.05 (s, 1H), 8.01 (s, 1H), 5.98 (d, J = 4.3 Hz, 1H), 5.94 (d, J = 4.6 Hz, 1H), 4.68–4.59 (m, 1H), 4.51–4.44 (m, 2H), 4.44–4.38 (m, 1H), 4.38–4.30 (m, 1H), 4.23–4.15 (m, 1H), 4.09–3.95 (m, 2H), 3.91 (dd, J = 12.9, J = 2.7 Hz, 1H), 3.80 (dd, J = 12.9, J = 3.8 Hz, 1H), 3.69–3.33 (m, 4H), 3.20 (m, 2H), 2.29 (td, J = 7.0 Hz, J = 2.7 Hz, 2H), 2.02–1.85 (m, 2H).
T405 1385-1574 Sentence denotes 13C NMR (150 MHz, D2O) δ 174.5, 154.9 (2C), 152.5, 152.3, 147.7, 147.5, 139.3, 138.5, 118.6, 118.3, 89.0, 86.9, 84.8, 81.8, 80.1, 73.9, 71.1, 69.0, 67.8, 60.3, 56.2, 55.3, 53.8, 52.5, 26.1.
T406 1575-1621 Sentence denotes HRMS (ESI+): m/z calcd for C26H37N12O9 [M+H]+:
T407 1622-1638 Sentence denotes 661.2806, found:
T408 1639-1648 Sentence denotes 661.2811.