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PMC:7291971 / 44379-45856 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T926 9-11 CHEBI:53424;CHEBI:53424 denotes 22
T927 93-98 CHEBI:15377;CHEBI:15377 denotes water
T928 133-141 CHEBI:46787;CHEBI:46787 denotes solvents
T929 198-203 CHEBI:15377;CHEBI:15377 denotes water
T930 221-228 CHEBI:15377;CHEBI:15377 denotes aqueous
T931 229-233 CHEBI:48607;CHEBI:48607 denotes LiOH
T932 234-242 CHEBI:75958;CHEBI:75958 denotes solution
T933 340-347 CHEBI:15377;CHEBI:15377 denotes aqueous
T934 348-351 CHEBI:17883;CHEBI:17883 denotes HCl
T935 352-360 CHEBI:75958;CHEBI:75958 denotes solution
T936 366-373 CHEBI:46787;CHEBI:46787 denotes solvent
T937 479-485 CHEBI:30563;CHEBI:30563 denotes silica
T938 546-558 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T939 622-630 CHEBI:36357;CHEBI:36357 denotes compound
T940 678-683 CHEBI:15377;CHEBI:15377 denotes water
T941 1215-1218 CHEBI:36927;CHEBI:36927 denotes 13C
T17648 9-11 CHEBI:53424;CHEBI:53424 denotes 22
T7216 93-98 CHEBI:15377;CHEBI:15377 denotes water
T10240 133-141 CHEBI:46787;CHEBI:46787 denotes solvents
T70971 198-203 CHEBI:15377;CHEBI:15377 denotes water
T82680 221-228 CHEBI:15377;CHEBI:15377 denotes aqueous
T99687 229-233 CHEBI:48607;CHEBI:48607 denotes LiOH
T12422 234-242 CHEBI:75958;CHEBI:75958 denotes solution
T45037 340-347 CHEBI:15377;CHEBI:15377 denotes aqueous
T26603 348-351 CHEBI:17883;CHEBI:17883 denotes HCl
T15792 352-360 CHEBI:75958;CHEBI:75958 denotes solution
T22239 366-373 CHEBI:46787;CHEBI:46787 denotes solvent
T42331 479-485 CHEBI:30563;CHEBI:30563 denotes silica
T43871 546-558 CHEBI:38472;CHEBI:38472 denotes acetonitrile
T83104 622-630 CHEBI:36357;CHEBI:36357 denotes compound
T77066 678-683 CHEBI:15377;CHEBI:15377 denotes water
T3324 1215-1218 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
792 77-80 Chemical denotes TFA MESH:D014269
793 93-98 Chemical denotes water MESH:D014867
794 198-203 Chemical denotes water MESH:D014867
795 229-233 Chemical denotes LiOH
796 348-351 Chemical denotes HCl MESH:D006851
797 479-485 Chemical denotes silica MESH:D012822
798 497-500 Chemical denotes C18 MESH:C109760
799 546-558 Chemical denotes acetonitrile MESH:C032159
800 562-567 Chemical denotes TEAAc
801 678-683 Chemical denotes water MESH:D014867
802 1215-1218 Chemical denotes 13C MESH:C000615229
803 1233-1236 Chemical denotes D2O
804 1431-1442 Chemical denotes C26H37N12O9
805 1404-1408 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T308 9-11 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T309 462-463 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T310 519-520 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T311 710-711 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T312 1444-1447 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T812 77-80 Chemical denotes TFA http://purl.obolibrary.org/obo/CHEBI_45892
T813 93-98 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T814 133-141 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T815 198-203 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T816 229-233 Chemical denotes LiOH http://purl.obolibrary.org/obo/CHEBI_33979
T817 234-242 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T818 348-351 Chemical denotes HCl http://purl.obolibrary.org/obo/CHEBI_17883
T819 352-360 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T820 366-373 Chemical denotes solvent http://purl.obolibrary.org/obo/CHEBI_46787
T821 479-485 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T822 546-558 Chemical denotes acetonitrile http://purl.obolibrary.org/obo/CHEBI_38472
T823 568-574 Chemical denotes buffer http://purl.obolibrary.org/obo/CHEBI_35225
T824 678-683 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T825 780-782 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T826 797-800 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981
T827 813-815 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T828 827-829 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T829 841-843 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T830 855-857 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T831 881-883 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T832 907-909 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T833 965-967 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T834 984-986 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T835 1043-1045 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T836 1099-1101 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T837 1164-1166 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T838 1191-1193 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T839 1233-1236 Chemical denotes D2O http://purl.obolibrary.org/obo/CHEBI_41981

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T324 0-108 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 109-168 Sentence denotes After stirring for 3 h, solvents were removed under vacuum.
T326 169-260 Sentence denotes The residue was dissolved in water (0.5 mL) and 2 M aqueous LiOH solution (4 mL) was added.
T327 261-361 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 362-587 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 588-779 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 780-1214 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 1215-1403 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 1404-1450 Sentence denotes HRMS (ESI+): m/z calcd for C26H37N12O9 [M+H]+:
T333 1451-1467 Sentence denotes 661.2806, found:
T334 1468-1477 Sentence denotes 661.2811.