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PMC:7291971 / 44175-45856 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T910 52-71 CHEBI:53233;CHEBI:53233 denotes 3,4-dihydroxyoxolan
T911 74-76 CHEBI:53233;CHEBI:53233 denotes yl
T912 108-110 CHEBI:30756;CHEBI:30756 denotes 9H
T913 111-121 CHEBI:30756;CHEBI:30756 denotes purin-9-yl
T914 123-125 CHEBI:17500;CHEBI:17500 denotes 4-
T915 125-132 CHEBI:43176;CHEBI:43176 denotes hydroxy
T916 133-134 CHEBI:34018;CHEBI:34018 denotes 5
T917 134-136 CHEBI:17500;CHEBI:17500 denotes -(
T918 136-149 CHEBI:24712;CHEBI:24712 denotes hydroxymethyl
T919 150-156 CHEBI:26911;CHEBI:26911 denotes oxolan
T920 156-157 CHEBI:15533;CHEBI:15533 denotes -
T921 157-158 CHEBI:53233;CHEBI:53233 denotes 3
T922 158-161 CHEBI:15533;CHEBI:15533 denotes -yl
T923 162-165 CHEBI:29354;CHEBI:29354 denotes oxy
T924 166-171 CHEBI:37807;CHEBI:37807 denotes ethyl
T925 179-199 CHEBI:86228;CHEBI:86228 denotes 2-azaniumylbutanoate
T926 213-215 CHEBI:53424;CHEBI:53424 denotes 22
T927 297-302 CHEBI:15377;CHEBI:15377 denotes water
T928 337-345 CHEBI:46787;CHEBI:46787 denotes solvents
T929 402-407 CHEBI:15377;CHEBI:15377 denotes water
T930 425-432 CHEBI:15377;CHEBI:15377 denotes aqueous
T931 433-437 CHEBI:48607;CHEBI:48607 denotes LiOH
T932 438-446 CHEBI:75958;CHEBI:75958 denotes solution
T933 544-551 CHEBI:15377;CHEBI:15377 denotes aqueous
T934 552-555 CHEBI:17883;CHEBI:17883 denotes HCl
T935 556-564 CHEBI:75958;CHEBI:75958 denotes solution
T936 570-577 CHEBI:46787;CHEBI:46787 denotes solvent
T937 683-689 CHEBI:30563;CHEBI:30563 denotes silica
T938 750-762 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T939 826-834 CHEBI:36357;CHEBI:36357 denotes compound
T940 882-887 CHEBI:15377;CHEBI:15377 denotes water
T941 1419-1422 CHEBI:36927;CHEBI:36927 denotes 13C
T77495 52-71 CHEBI:53233;CHEBI:53233 denotes 3,4-dihydroxyoxolan
T7135 74-76 CHEBI:53233;CHEBI:53233 denotes yl
T35703 108-110 CHEBI:30756;CHEBI:30756 denotes 9H
T50990 111-121 CHEBI:30756;CHEBI:30756 denotes purin-9-yl
T26796 123-125 CHEBI:17500;CHEBI:17500 denotes 4-
T4175 125-132 CHEBI:43176;CHEBI:43176 denotes hydroxy
T65952 133-134 CHEBI:34018;CHEBI:34018 denotes 5
T10649 134-136 CHEBI:17500;CHEBI:17500 denotes -(
T3672 136-149 CHEBI:24712;CHEBI:24712 denotes hydroxymethyl
T60171 150-156 CHEBI:26911;CHEBI:26911 denotes oxolan
T38256 156-157 CHEBI:15533;CHEBI:15533 denotes -
T3560 157-158 CHEBI:53233;CHEBI:53233 denotes 3
T94233 158-161 CHEBI:15533;CHEBI:15533 denotes -yl
T42442 162-165 CHEBI:29354;CHEBI:29354 denotes oxy
T43064 166-171 CHEBI:37807;CHEBI:37807 denotes ethyl
T8061 179-199 CHEBI:86228;CHEBI:86228 denotes 2-azaniumylbutanoate
T17648 213-215 CHEBI:53424;CHEBI:53424 denotes 22
T7216 297-302 CHEBI:15377;CHEBI:15377 denotes water
T10240 337-345 CHEBI:46787;CHEBI:46787 denotes solvents
T70971 402-407 CHEBI:15377;CHEBI:15377 denotes water
T82680 425-432 CHEBI:15377;CHEBI:15377 denotes aqueous
T99687 433-437 CHEBI:48607;CHEBI:48607 denotes LiOH
T12422 438-446 CHEBI:75958;CHEBI:75958 denotes solution
T45037 544-551 CHEBI:15377;CHEBI:15377 denotes aqueous
T26603 552-555 CHEBI:17883;CHEBI:17883 denotes HCl
T15792 556-564 CHEBI:75958;CHEBI:75958 denotes solution
T22239 570-577 CHEBI:46787;CHEBI:46787 denotes solvent
T42331 683-689 CHEBI:30563;CHEBI:30563 denotes silica
T43871 750-762 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T83104 826-834 CHEBI:36357;CHEBI:36357 denotes compound
T77066 882-887 CHEBI:15377;CHEBI:15377 denotes water
T3324 1419-1422 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
792 281-284 Chemical denotes TFA MESH:D014269
793 297-302 Chemical denotes water MESH:D014867
794 402-407 Chemical denotes water MESH:D014867
795 433-437 Chemical denotes LiOH
796 552-555 Chemical denotes HCl MESH:D006851
797 683-689 Chemical denotes silica MESH:D012822
798 701-704 Chemical denotes C18 MESH:C109760
799 750-762 Chemical denotes acetonitrile MESH:C032159
800 766-771 Chemical denotes TEAAc
801 882-887 Chemical denotes water MESH:D014867
802 1419-1422 Chemical denotes 13C MESH:C000615229
803 1437-1440 Chemical denotes D2O
804 1635-1646 Chemical denotes C26H37N12O9
805 1608-1612 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T308 213-215 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T309 666-667 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T310 723-724 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T311 914-915 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T312 1648-1651 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T800 29-50 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T801 31-36 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T802 77-83 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T804 100-121 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T805 102-107 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T806 125-132 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T807 136-149 Chemical denotes hydroxymethyl http://purl.obolibrary.org/obo/CHEBI_24712
T808 162-165 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T809 166-171 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T811 172-177 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T812 281-284 Chemical denotes TFA http://purl.obolibrary.org/obo/CHEBI_45892
T813 297-302 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T814 337-345 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T815 402-407 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T816 433-437 Chemical denotes LiOH http://purl.obolibrary.org/obo/CHEBI_33979
T817 438-446 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T818 552-555 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T819 556-564 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T820 570-577 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T821 683-689 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T822 750-762 Chemical denotes acetonitrile http://purl.obolibrary.org/obo/CHEBI_38472
T823 772-778 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T824 882-887 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T825 984-986 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T826 1001-1004 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981
T827 1017-1019 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T828 1031-1033 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T829 1045-1047 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T830 1059-1061 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T831 1085-1087 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T832 1111-1113 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T833 1169-1171 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T834 1188-1190 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T835 1247-1249 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T836 1303-1305 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T837 1368-1370 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T838 1395-1397 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T839 1437-1440 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T323 0-203 Sentence denotes 4.1.10 (2S)-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)-2-azaniumylbutanoate (2)
T324 204-312 Sentence denotes Compound 22 (86 mg, 75.3 μmol, 1.00 eq) was treated at room temperature with TFA (830 μL) in water (210 μL).
T325 313-372 Sentence denotes After stirring for 3 h, solvents were removed under vacuum.
T326 373-464 Sentence denotes The residue was dissolved in water (0.5 mL) and 2 M aqueous LiOH solution (4 mL) was added.
T327 465-565 Sentence denotes After stirring at 0 °C for 30 min, pH ≈ 3 or 4 was adjusted by addition of 1 M aqueous HCl solution.
T328 566-791 Sentence denotes The solvent was 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 0–15% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7.
T329 792-983 Sentence denotes The fractions containing the pure compound were pooled, concentrated and lyophilized with water to give 2 (16 mg, 32%) as a white powder with 99% purity determined by HPLC analysis at 260 nm.
T330 984-1418 Sentence denotes 1H NMR (600 MHz, D2O) δ 8.11 (s, 1H), 8.05 (s, 1H), 7.98 (s, 1H), 7.86 (s, 1H), 5.89 (d, J = 2.5 Hz, 1H), 5.77 (d, J = 3.3 Hz, 1H), 4.51–4.47 (m, 2H), 4.36 (dd, J = 5.1 Hz, J = 3.4 Hz, 1H), 4.34–4.29 (m, 1H), 4.14–4.08 (m, 2H), 3.97 (td, J = 10.6 Hz, J = 2.4 Hz, 1H), 3.89–3.80 (m, 3H), 3.71 (dd, J = 13.0, J = 3.4 Hz, 1H), 3.15–3.04 (m, 2H), 3.03–2.81 (m, 2H), 2.76 (d, J = 14.2 Hz, 1H), 2.58 (d, J = 13.8 Hz, 1H), 2.14–1.99 (m, 2H).
T331 1419-1607 Sentence denotes 13C NMR (150 MHz, D2O) δ 174.5, 154.9 (2C) 152.5, 152.2, 147.7, 147.5, 139.3, 138.5, 118.5, 118.2, 89.0, 86.8, 84.8, 81.7, 80.0, 73.9, 71.1, 68.9, 67.7, 60.3, 56.2, 55.3, 53.8, 52.5, 26.1.
T332 1608-1654 Sentence denotes HRMS (ESI+): m/z calcd for C26H37N12O9 [M+H]+:
T333 1655-1671 Sentence denotes 661.2806, found:
T334 1672-1681 Sentence denotes 661.2811.