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PMC:7291971 / 47113-48711 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T960 54-58 CHEBI:30756;CHEBI:30756 denotes 9-yl
T961 60-84 CHEBI:53233;CHEBI:53233 denotes 3,4-dihydroxyoxolan-2-yl
T962 85-91 CHEBI:29309;CHEBI:29309 denotes methyl
T963 108-129 CHEBI:30756;CHEBI:30756 denotes 6-amino-9H-purin-9-yl
T964 131-133 CHEBI:34018;CHEBI:34018 denotes 4-
T965 133-140 CHEBI:43176;CHEBI:43176 denotes hydroxy
T966 140-141 CHEBI:82321;CHEBI:82321 denotes -
T967 141-142 CHEBI:34018;CHEBI:34018 denotes 5
T968 142-143 CHEBI:82321;CHEBI:82321 denotes -
T969 143-144 CHEBI:17500;CHEBI:17500 denotes (
T970 144-157 CHEBI:24712;CHEBI:24712 denotes hydroxymethyl
T971 158-164 CHEBI:26911;CHEBI:26911 denotes oxolan
T972 164-165 CHEBI:15533;CHEBI:15533 denotes -
T973 165-169 CHEBI:82321;CHEBI:82321 denotes 3-yl
T974 170-173 CHEBI:29354;CHEBI:29354 denotes oxy
T975 174-179 CHEBI:37807;CHEBI:37807 denotes ethyl
T976 186-196 CHEBI:22965;CHEBI:22965 denotes butanamide
T977 210-212 CHEBI:53424;CHEBI:53424 denotes 22
T978 296-301 CHEBI:15377;CHEBI:15377 denotes water
T979 356-364 CHEBI:46787;CHEBI:46787 denotes solvents
T980 415-418 CHEBI:62946;CHEBI:62946 denotes NH3
T981 422-426 CHEBI:32145;CHEBI:32145 denotes MeOH
T982 470-478 CHEBI:46787;CHEBI:46787 denotes solvents
T983 572-578 CHEBI:30563;CHEBI:30563 denotes silica
T984 639-651 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T985 715-723 CHEBI:36357;CHEBI:36357 denotes compound
T986 771-776 CHEBI:15377;CHEBI:15377 denotes water
T987 1336-1339 CHEBI:36927;CHEBI:36927 denotes 13C
T86741 54-58 CHEBI:30756;CHEBI:30756 denotes 9-yl
T58744 60-84 CHEBI:53233;CHEBI:53233 denotes 3,4-dihydroxyoxolan-2-yl
T47857 85-91 CHEBI:29309;CHEBI:29309 denotes methyl
T38462 108-129 CHEBI:30756;CHEBI:30756 denotes 6-amino-9H-purin-9-yl
T83257 131-133 CHEBI:34018;CHEBI:34018 denotes 4-
T64218 133-140 CHEBI:43176;CHEBI:43176 denotes hydroxy
T51011 140-141 CHEBI:82321;CHEBI:82321 denotes -
T77268 141-142 CHEBI:34018;CHEBI:34018 denotes 5
T44485 142-143 CHEBI:82321;CHEBI:82321 denotes -
T32686 143-144 CHEBI:17500;CHEBI:17500 denotes (
T55257 144-157 CHEBI:24712;CHEBI:24712 denotes hydroxymethyl
T66651 158-164 CHEBI:26911;CHEBI:26911 denotes oxolan
T12230 164-165 CHEBI:15533;CHEBI:15533 denotes -
T95331 165-169 CHEBI:82321;CHEBI:82321 denotes 3-yl
T2115 170-173 CHEBI:29354;CHEBI:29354 denotes oxy
T86076 174-179 CHEBI:37807;CHEBI:37807 denotes ethyl
T70057 186-196 CHEBI:22965;CHEBI:22965 denotes butanamide
T84042 210-212 CHEBI:53424;CHEBI:53424 denotes 22
T67269 296-301 CHEBI:15377;CHEBI:15377 denotes water
T97010 356-364 CHEBI:46787;CHEBI:46787 denotes solvents
T83843 415-418 CHEBI:62946;CHEBI:62946 denotes NH3
T7244 422-426 CHEBI:32145;CHEBI:32145 denotes MeOH
T36733 470-478 CHEBI:46787;CHEBI:46787 denotes solvents
T77353 572-578 CHEBI:30563;CHEBI:30563 denotes silica
T73055 639-651 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T11993 715-723 CHEBI:36357;CHEBI:36357 denotes compound
T35043 771-776 CHEBI:15377;CHEBI:15377 denotes water
T3608 1336-1339 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
830 279-282 Chemical denotes TFA MESH:D014269
831 296-301 Chemical denotes water MESH:D014867
832 415-418 Chemical denotes NH3
833 422-426 Chemical denotes MeOH
834 572-582 Chemical denotes silica gel MESH:D058428
835 639-651 Chemical denotes acetonitrile MESH:C032159
836 655-660 Chemical denotes TEAAc
837 771-776 Chemical denotes water MESH:D014867
838 1336-1339 Chemical denotes 13C MESH:C000615229
839 1354-1357 Chemical denotes D2O
840 1552-1563 Chemical denotes C26H38N13O8
841 1525-1529 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T318 210-212 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T319 214-217 http://purl.obolibrary.org/obo/CLO_0001046 denotes 116
T320 555-556 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T321 612-613 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T322 791-797 http://purl.obolibrary.org/obo/CLO_0007698 denotes mg, 38
T323 803-804 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T324 1565-1568 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T875 15-20 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T876 37-58 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T877 39-44 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T878 85-91 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T880 108-129 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T881 110-115 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T882 133-140 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T883 144-157 Chemical denotes hydroxymethyl http://purl.obolibrary.org/obo/CHEBI_24712
T884 170-173 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T885 174-179 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T887 180-185 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T888 186-196 Chemical denotes butanamide http://purl.obolibrary.org/obo/CHEBI_50724
T889 279-282 Chemical denotes TFA http://purl.obolibrary.org/obo/CHEBI_45892
T890 296-301 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T891 356-364 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T892 415-418 Chemical denotes NH3 http://purl.obolibrary.org/obo/CHEBI_16134
T893 422-426 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T894 470-478 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T895 572-578 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T896 639-651 Chemical denotes acetonitrile http://purl.obolibrary.org/obo/CHEBI_38472
T897 661-667 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T898 771-776 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T899 873-875 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T900 890-893 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981
T901 906-908 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T902 920-922 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T903 934-936 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T904 948-950 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T905 974-976 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T906 1000-1002 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T907 1039-1041 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T908 1058-1060 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T909 1097-1099 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T910 1116-1118 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T911 1175-1177 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T912 1234-1236 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T913 1312-1314 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T914 1354-1357 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T342 0-200 Sentence denotes 4.1.12 (2S)-2-amino-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)butanamide (4)
T343 201-351 Sentence denotes Compound 22 (116 mg, 0.10 mmol, 1.00 eq) was treated at room temperature with TFA (1.44 mL) in water (360 μL) and stirred for 3 h at room temperature.
T344 352-435 Sentence denotes The solvents were removed and the residue was treated with 7 M NH3 in MeOH (10 mL).
T345 436-680 Sentence denotes After stirring for 24 h at 30 °C, solvents were removed and the residue was purified by flash column chromatography on a reversed-phase silica gel column C18 (4 g, 40 μm) with a 0–15% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7.
T346 681-872 Sentence denotes The fractions containing the pure compound were pooled, concentrated and lyophilized with water to give 4 (23 mg, 38%) as a white powder with 98% purity determined by HPLC analysis at 260 nm.
T347 873-1335 Sentence denotes 1H NMR (600 MHz, D2O) δ 8.12 (s, 1H), 8.08 (s, 1H), 7.99 (s, 1H), 7.90 (s, 1H), 5.90 (d, J = 2.7 Hz, 1H), 5.79 (d, J = 3.5 Hz, 1H), 4.53 (dd, J = 5.2 Hz, J = 2.7 Hz, 1H), 4.52–4.48 (m, 1H), 4.38 (dd, J = 5.0 Hz, J = 3.6 Hz, 1H), 4.35–4.28 (m, 1H), 4.18–4.07 (m, 3H), 3.98 (td, J = 10.7 Hz, J = 2.6 Hz, 1H), 3.88–3.80 (m, 2H), 3.72 (dd, J = 12.9 Hz, J = 3.5 Hz, 1H), 3.16–2.98 (m, 3H), 2.88–2.76 (m, 2H), 2.62 (dt, J = 14.0 Hz, J = 2.7 Hz, 1H), 2.17–1.98 (m, 2H).
T348 1336-1524 Sentence denotes 13C NMR (150 MHz, D2O) δ 173.0, 155.0 (2C) 152.5, 152.3, 147.8, 147.6, 139.4, 138.7, 118.6, 118.3, 88.9, 86.8, 84.9, 81.8, 79.8, 73.8, 71.1, 69.0, 67.6, 60.4, 55.3, 53.9, 52.6, 52.4, 27.0.
T349 1525-1571 Sentence denotes HRMS (ESI+): m/z calcd for C26H38N13O8 [M+H]+:
T350 1572-1588 Sentence denotes 660.2961, found:
T351 1589-1598 Sentence denotes 660.2966.