PMC:7291971 / 9126-12304
Annnotations
LitCovid-PMC-OGER-BB
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| T177 | 24-35 | CHEBI:17544;CHEBI:17544 | denotes | bisubstrate |
| T178 | 36-45 | CHEBI:36357;CHEBI:36357 | denotes | compounds |
| T179 | 92-95 | GO:0008541 | denotes | cap |
| T180 | 101-116 | GO:0006272 | denotes | ′-O-methylation |
| T181 | 179-188 | CHEBI:22260;CHEBI:22260 | denotes | adenosine |
| T182 | 207-215 | CHEBI:23357;CHEBI:23357 | denotes | cofactor |
| T183 | 227-236 | CHEBI:22260;CHEBI:22260 | denotes | adenosine |
| T184 | 271-282 | CHEBI:37807;CHEBI:37807 | denotes | ethyl group |
| T185 | 389-399 | CHEBI:22260;CHEBI:22260 | denotes | adenosines |
| T186 | 501-516 | CHEBI:32863;CHEBI:32863 | denotes | secondary amine |
| T187 | 541-547 | CHEBI:24433;CHEBI:24433 | denotes | groups |
| T188 | 701-714 | GO:0006119 | denotes | O-methylation |
| T189 | 839-843 | CHEBI:33250;CHEBI:33250 | denotes | atom |
| T190 | 875-885 | CHEBI:50325;CHEBI:50325 | denotes | side chain |
| T191 | 892-894 | CHEBI:17865;CHEBI:17865 | denotes | α- |
| T192 | 894-899 | CHEBI:46882;CHEBI:46882 | denotes | amino |
| T193 | 899-900 | CHEBI:17865;CHEBI:17865 | denotes | - |
| T194 | 900-905 | CHEBI:35701;CHEBI:35701 | denotes | ester |
| T195 | 914-916 | CHEBI:17865;CHEBI:17865 | denotes | α- |
| T196 | 916-921 | CHEBI:46882;CHEBI:46882 | denotes | amino |
| T197 | 921-922 | CHEBI:17865;CHEBI:17865 | denotes | - |
| T198 | 922-927 | CHEBI:29337;CHEBI:29337 | denotes | amide |
| T199 | 1062-1077 | CHEBI:32863;CHEBI:32863 | denotes | secondary amine |
| T200 | 1081-1094 | CHEBI:23447;CHEBI:23447 | denotes | dinucleosides |
| T201 | 1152-1175 | CHEBI:53325;CHEBI:53325 | denotes | nitrobenzenesulfonamide |
| T202 | 1225-1237 | CHEBI:86063;CHEBI:86063 | denotes | dinucleoside |
| T203 | 1298-1299 | CHEBI:7586;CHEBI:7586 | denotes | N |
| T204 | 1299-1300 | CHEBI:75508;CHEBI:75508 | denotes | - |
| T205 | 1300-1315 | CHEBI:57472;CHEBI:57472 | denotes | arylsulfonamide |
| T206 | 1344-1360 | CHEBI:67079;CHEBI:67079 | denotes | antitumor agents |
| T207 | 1382-1392 | CHEBI:35222;CHEBI:35222 | denotes | inhibitors |
| T208 | 1446-1457 | CHEBI:29785;CHEBI:29785 | denotes | nitro group |
| T209 | 1526-1532 | CHEBI:30396;CHEBI:30396 | denotes | phenyl |
| T210 | 1555-1564 | CHEBI:36357;CHEBI:36357 | denotes | compounds |
| T211 | 1595-1606 | CHEBI:29785;CHEBI:29785 | denotes | nitro group |
| T212 | 1663-1670 | CHEBI:33543;CHEBI:33543 | denotes | sulfone |
| T213 | 1676-1691 | CHEBI:50728;CHEBI:50728 | denotes | methylene group |
| T214 | 1727-1734 | CHEBI:33543;CHEBI:33543 | denotes | sulfone |
| T215 | 1789-1802 | CHEBI:23447;CHEBI:23447 | denotes | dinucleosides |
| T216 | 1818-1819 | CHEBI:7586;CHEBI:7586 | denotes | N |
| T217 | 1819-1820 | CHEBI:75508;CHEBI:75508 | denotes | - |
| T218 | 1820-1835 | CHEBI:57472;CHEBI:57472 | denotes | arylsulfonamide |
| T219 | 1865-1878 | CHEBI:23447;CHEBI:23447 | denotes | dinucleosides |
| T220 | 1888-1893 | CHEBI:32031;CHEBI:32031 | denotes | K2CO3 |
| T221 | 1932-1937 | CHEBI:32031;CHEBI:32031 | denotes | K2CO3 |
| T222 | 1969-1972 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
| T223 | 2027-2031 | CHEBI:16236;CHEBI:16236 | denotes | AcOH |
| T224 | 2099-2102 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
| T225 | 2129-2136 | CHEBI:15377;CHEBI:15377 | denotes | aqueous |
| T226 | 2137-2145 | CHEBI:75958;CHEBI:75958 | denotes | solution |
| T227 | 2146-2150 | CHEBI:48607;CHEBI:48607 | denotes | LiOH |
| T228 | 2179-2182 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
| T229 | 2217-2220 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
| T230 | 2247-2250 | CHEBI:62946;CHEBI:62946 | denotes | NH3 |
| T231 | 2251-2255 | CHEBI:32145;CHEBI:32145 | denotes | MeOH |
| T232 | 2279-2292 | CHEBI:62946;CHEBI:62946 | denotes | 1-bromobutane |
| T233 | 2340-2342 | CHEBI:17824;CHEBI:17824 | denotes | 1- |
| T234 | 2342-2347 | CHEBI:47265;CHEBI:47265 | denotes | bromo |
| T235 | 2347-2363 | CHEBI:17824;CHEBI:17824 | denotes | -3-phenylpropane |
| T236 | 2495-2498 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
| T237 | 2583-2590 | CHEBI:15377;CHEBI:15377 | denotes | aqueous |
| T238 | 2591-2599 | CHEBI:75958;CHEBI:75958 | denotes | solution |
| T239 | 2600-2604 | CHEBI:32145;CHEBI:32145 | denotes | LiOH |
| T240 | 2652-2665 | CHEBI:23447;CHEBI:23447 | denotes | dinucleosides |
| T241 | 2729-2734 | CHEBI:32031;CHEBI:32031 | denotes | K2CO3 |
| T242 | 2770-2773 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
| T243 | 2825-2838 | CHEBI:23447;CHEBI:23447 | denotes | dinucleosides |
| T244 | 2850-2873 | CHEBI:75508;CHEBI:75508 | denotes | 4-chlorobenzenesulfonyl |
| T245 | 2874-2882 | CHEBI:17996;CHEBI:17996 | denotes | chloride |
| T246 | 2922-2924 | CHEBI:86228;CHEBI:86228 | denotes | 4- |
| T247 | 2924-2930 | CHEBI:47853;CHEBI:47853 | denotes | chloro |
| T248 | 2930-2950 | CHEBI:86228;CHEBI:86228 | denotes | -3-nitrobenzaldehyde |
| T249 | 2952-2956 | CHEBI:16236;CHEBI:16236 | denotes | AcOH |
| T250 | 3021-3041 | CHEBI:28105;CHEBI:28105 | denotes | 4-chlorobenzaldehyde |
| T251 | 3043-3047 | CHEBI:28619;CHEBI:28619 | denotes | AcOH |
| T252 | 3112-3115 | CHEBI:15377;CHEBI:15377 | denotes | H2O |
LitCovid-PD-FMA-UBERON
| Id | Subject | Object | Predicate | Lexical cue | fma_id |
|---|---|---|---|---|---|
| T46 | 96-99 | Body_part | denotes | RNA | http://purl.org/sig/ont/fma/fma67095 |
| T47 | 608-611 | Body_part | denotes | RNA | http://purl.org/sig/ont/fma/fma67095 |
| T48 | 786-796 | Body_part | denotes | amino acid | http://purl.org/sig/ont/fma/fma82739 |
| T49 | 2050-2057 | Body_part | denotes | h, (ii) | http://purl.org/sig/ont/fma/fma278665 |
| T50 | 2117-2124 | Body_part | denotes | h, (ii) | http://purl.org/sig/ont/fma/fma278665 |
| T51 | 2235-2242 | Body_part | denotes | h, (ii) | http://purl.org/sig/ont/fma/fma278665 |
LitCovid-PubTator
| Id | Subject | Object | Predicate | Lexical cue | tao:has_database_id |
|---|---|---|---|---|---|
| 109 | 1865-1878 | Chemical | denotes | dinucleosides | |
| 110 | 1969-1972 | Chemical | denotes | H2O | |
| 111 | 2099-2102 | Chemical | denotes | H2O | |
| 112 | 2179-2182 | Chemical | denotes | H2O | |
| 113 | 2217-2220 | Chemical | denotes | H2O | |
| 114 | 2495-2498 | Chemical | denotes | H2O | |
| 115 | 2600-2604 | Chemical | denotes | LiOH | |
| 124 | 2652-2665 | Chemical | denotes | dinucleosides | |
| 125 | 2677-2679 | Chemical | denotes | Ns | MESH:D009584 |
| 126 | 2684-2688 | Chemical | denotes | NEt3 | |
| 127 | 2690-2693 | Chemical | denotes | DMF | |
| 128 | 2729-2734 | Chemical | denotes | K2CO3 | MESH:C037593 |
| 129 | 2736-2739 | Chemical | denotes | DMF | |
| 130 | 2766-2769 | Chemical | denotes | TFA | MESH:D014269 |
| 131 | 2770-2773 | Chemical | denotes | H2O | |
| 146 | 2825-2838 | Chemical | denotes | dinucleosides | |
| 147 | 2850-2882 | Chemical | denotes | 4-chlorobenzenesulfonyl chloride | |
| 148 | 2884-2888 | Chemical | denotes | NEt3 | |
| 149 | 2890-2896 | Chemical | denotes | CH2Cl2 | |
| 150 | 2922-2950 | Chemical | denotes | 4-chloro-3-nitrobenzaldehyde | |
| 151 | 2952-2956 | Chemical | denotes | AcOH | |
| 152 | 2958-2961 | Chemical | denotes | DCE | |
| 153 | 2983-2993 | Chemical | denotes | NaBH(OAc)3 | |
| 154 | 3021-3041 | Chemical | denotes | 4-chlorobenzaldehyde | MESH:C052044 |
| 155 | 3043-3047 | Chemical | denotes | AcOH | |
| 156 | 3049-3052 | Chemical | denotes | DCE | |
| 157 | 3074-3084 | Chemical | denotes | NaBH(OAc)3 | |
| 158 | 3108-3111 | Chemical | denotes | TFA | MESH:D014269 |
| 159 | 3112-3115 | Chemical | denotes | H2O | |
| 181 | 179-188 | Chemical | denotes | adenosine | MESH:D000241 |
| 182 | 227-236 | Chemical | denotes | adenosine | MESH:D000241 |
| 183 | 332-344 | Chemical | denotes | dinucleoside | |
| 184 | 389-399 | Chemical | denotes | adenosines | MESH:D000241 |
| 185 | 441-442 | Chemical | denotes | N | MESH:D009584 |
| 186 | 511-516 | Chemical | denotes | amine | MESH:D000588 |
| 187 | 830-838 | Chemical | denotes | nitrogen | MESH:D009584 |
| 188 | 892-905 | Chemical | denotes | α-amino-ester | |
| 189 | 914-927 | Chemical | denotes | α-amino-amide | |
| 190 | 1072-1077 | Chemical | denotes | amine | MESH:D000588 |
| 191 | 1081-1094 | Chemical | denotes | dinucleosides | |
| 192 | 1152-1175 | Chemical | denotes | nitrobenzenesulfonamide | |
| 193 | 1225-1237 | Chemical | denotes | dinucleoside | |
| 194 | 1298-1315 | Chemical | denotes | N-arylsulfonamide | |
| 195 | 1446-1451 | Chemical | denotes | nitro | |
| 196 | 1489-1492 | Chemical | denotes | CF3 | |
| 197 | 1595-1600 | Chemical | denotes | nitro | |
| 198 | 1663-1670 | Chemical | denotes | sulfone | MESH:D013450 |
| 199 | 1727-1734 | Chemical | denotes | sulfone | MESH:D013450 |
| 200 | 1789-1802 | Chemical | denotes | dinucleosides | |
| 201 | 1818-1835 | Chemical | denotes | N-arylsulfonamide |
LitCovid-PD-MONDO
| Id | Subject | Object | Predicate | Lexical cue | mondo_id |
|---|---|---|---|---|---|
| T32 | 2677-2679 | Disease | denotes | Ns | http://purl.obolibrary.org/obo/MONDO_0009735 |
LitCovid-PD-CLO
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| T67 | 352-355 | http://purl.obolibrary.org/obo/CLO_0001562 | denotes | a 2 |
| T68 | 352-355 | http://purl.obolibrary.org/obo/CLO_0001563 | denotes | a 2 |
| T69 | 522-523 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T70 | 786-802 | http://purl.obolibrary.org/obo/PR_000018263 | denotes | amino acid chain |
| T71 | 1150-1151 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T72 | 1186-1187 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T73 | 1250-1251 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T74 | 1494-1496 | http://purl.obolibrary.org/obo/CLO_0052906 | denotes | Cl |
| T75 | 1674-1675 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T76 | 1766-1774 | http://purl.obolibrary.org/obo/CLO_0001658 | denotes | activity |
| T77 | 1885-1886 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T78 | 1923-1924 | http://purl.obolibrary.org/obo/CLO_0001021 | denotes | b |
| T79 | 1948-1952 | http://purl.obolibrary.org/obo/CLO_0002105 | denotes | C, 2 |
| T80 | 1948-1952 | http://purl.obolibrary.org/obo/CLO_0051742 | denotes | C, 2 |
| T81 | 1975-1980 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T82 | 2004-2006 | http://purl.obolibrary.org/obo/CLO_0001302 | denotes | 34 |
| T83 | 2019-2025 | http://purl.obolibrary.org/obo/CLO_0004316 | denotes | (i) 21 |
| T84 | 2045-2049 | http://purl.obolibrary.org/obo/CLO_0002105 | denotes | C, 2 |
| T85 | 2045-2049 | http://purl.obolibrary.org/obo/CLO_0051742 | denotes | C, 2 |
| T86 | 2074-2078 | http://purl.obolibrary.org/obo/CLO_0002105 | denotes | C, 2 |
| T87 | 2074-2078 | http://purl.obolibrary.org/obo/CLO_0051742 | denotes | C, 2 |
| T88 | 2105-2110 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T89 | 2185-2190 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T90 | 2200-2202 | http://purl.obolibrary.org/obo/CLO_0001000 | denotes | 35 |
| T91 | 2223-2228 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T92 | 2320-2324 | http://purl.obolibrary.org/obo/CLO_0037284 | denotes | C, 4 |
| T93 | 2391-2395 | http://purl.obolibrary.org/obo/CLO_0037284 | denotes | C, 4 |
| T94 | 2501-2506 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T95 | 2508-2512 | http://purl.obolibrary.org/obo/CLO_0002140 | denotes | C, 6 |
| T96 | 2508-2512 | http://purl.obolibrary.org/obo/CLO_0051387 | denotes | C, 6 |
| T97 | 2508-2512 | http://purl.obolibrary.org/obo/CLO_0051684 | denotes | C, 6 |
| T98 | 2508-2512 | http://purl.obolibrary.org/obo/CLO_0051685 | denotes | C, 6 |
| T99 | 2508-2512 | http://purl.obolibrary.org/obo/CLO_0051686 | denotes | C, 6 |
| T100 | 2529-2534 | http://purl.obolibrary.org/obo/CLO_0003588 | denotes | h, 28 |
| T101 | 2619-2621 | http://purl.obolibrary.org/obo/CLO_0001313 | denotes | 36 |
| T102 | 2674-2675 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T103 | 2680-2682 | http://purl.obolibrary.org/obo/CLO_0052906 | denotes | Cl |
| T104 | 2718-2719 | http://purl.obolibrary.org/obo/CLO_0001021 | denotes | b |
| T105 | 2757-2759 | http://purl.obolibrary.org/obo/CLO_0001407 | denotes | 52 |
| T106 | 2776-2781 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T107 | 2788-2791 | http://purl.obolibrary.org/obo/CLO_0003607 | denotes | h–5 |
| T108 | 2847-2848 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
| T109 | 2915-2916 | http://purl.obolibrary.org/obo/CLO_0001021 | denotes | b |
| T110 | 2999-3004 | http://purl.obolibrary.org/obo/CLO_0002096 | denotes | C, 16 |
| T111 | 3090-3095 | http://purl.obolibrary.org/obo/CLO_0002096 | denotes | C, 16 |
| T112 | 3118-3123 | http://purl.obolibrary.org/obo/CLO_0001196 | denotes | 2, 25 |
| T113 | 3133-3135 | http://purl.obolibrary.org/obo/CLO_0001382 | denotes | 48 |
LitCovid-PD-CHEBI
| Id | Subject | Object | Predicate | Lexical cue | chebi_id |
|---|---|---|---|---|---|
| T104 | 136-139 | Chemical | denotes | SAM | http://purl.obolibrary.org/obo/CHEBI_15414|http://purl.obolibrary.org/obo/CHEBI_67040 |
| T106 | 179-188 | Chemical | denotes | adenosine | http://purl.obolibrary.org/obo/CHEBI_16335 |
| T107 | 203-206 | Chemical | denotes | SAM | http://purl.obolibrary.org/obo/CHEBI_15414|http://purl.obolibrary.org/obo/CHEBI_67040 |
| T109 | 207-215 | Chemical | denotes | cofactor | http://purl.obolibrary.org/obo/CHEBI_23357 |
| T110 | 227-236 | Chemical | denotes | adenosine | http://purl.obolibrary.org/obo/CHEBI_16335 |
| T111 | 271-282 | Chemical | denotes | ethyl group | http://purl.obolibrary.org/obo/CHEBI_37807 |
| T112 | 271-276 | Chemical | denotes | ethyl | http://purl.obolibrary.org/obo/CHEBI_62801 |
| T113 | 277-282 | Chemical | denotes | group | http://purl.obolibrary.org/obo/CHEBI_24433 |
| T114 | 359-364 | Chemical | denotes | ethyl | http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801 |
| T116 | 365-370 | Chemical | denotes | amino | http://purl.obolibrary.org/obo/CHEBI_46882 |
| T117 | 389-399 | Chemical | denotes | adenosines | http://purl.obolibrary.org/obo/CHEBI_22260 |
| T118 | 501-516 | Chemical | denotes | secondary amine | http://purl.obolibrary.org/obo/CHEBI_32863 |
| T119 | 511-516 | Chemical | denotes | amine | http://purl.obolibrary.org/obo/CHEBI_32952 |
| T120 | 786-796 | Chemical | denotes | amino acid | http://purl.obolibrary.org/obo/CHEBI_33709 |
| T121 | 786-791 | Chemical | denotes | amino | http://purl.obolibrary.org/obo/CHEBI_46882 |
| T122 | 792-796 | Chemical | denotes | acid | http://purl.obolibrary.org/obo/CHEBI_37527 |
| T123 | 810-813 | Chemical | denotes | SAM | http://purl.obolibrary.org/obo/CHEBI_15414|http://purl.obolibrary.org/obo/CHEBI_67040 |
| T125 | 830-843 | Chemical | denotes | nitrogen atom | http://purl.obolibrary.org/obo/CHEBI_25555|http://purl.obolibrary.org/obo/CHEBI_29351 |
| T127 | 839-843 | Chemical | denotes | atom | http://purl.obolibrary.org/obo/CHEBI_33250 |
| T128 | 894-899 | Chemical | denotes | amino | http://purl.obolibrary.org/obo/CHEBI_46882 |
| T129 | 900-905 | Chemical | denotes | ester | http://purl.obolibrary.org/obo/CHEBI_35701 |
| T130 | 916-921 | Chemical | denotes | amino | http://purl.obolibrary.org/obo/CHEBI_46882 |
| T131 | 922-927 | Chemical | denotes | amide | http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988 |
| T133 | 1062-1077 | Chemical | denotes | secondary amine | http://purl.obolibrary.org/obo/CHEBI_32863 |
| T134 | 1072-1077 | Chemical | denotes | amine | http://purl.obolibrary.org/obo/CHEBI_32952 |
| T135 | 1372-1381 | Chemical | denotes | antiviral | http://purl.obolibrary.org/obo/CHEBI_22587 |
| T136 | 1382-1392 | Chemical | denotes | inhibitors | http://purl.obolibrary.org/obo/CHEBI_35222 |
| T137 | 1446-1457 | Chemical | denotes | nitro group | http://purl.obolibrary.org/obo/CHEBI_29785 |
| T138 | 1452-1457 | Chemical | denotes | group | http://purl.obolibrary.org/obo/CHEBI_24433 |
| T139 | 1494-1496 | Chemical | denotes | Cl | http://purl.obolibrary.org/obo/CHEBI_23116 |
| T140 | 1526-1532 | Chemical | denotes | phenyl | http://purl.obolibrary.org/obo/CHEBI_30396 |
| T141 | 1595-1606 | Chemical | denotes | nitro group | http://purl.obolibrary.org/obo/CHEBI_29785 |
| T142 | 1601-1606 | Chemical | denotes | group | http://purl.obolibrary.org/obo/CHEBI_24433 |
| T143 | 1663-1670 | Chemical | denotes | sulfone | http://purl.obolibrary.org/obo/CHEBI_35850 |
| T144 | 1676-1691 | Chemical | denotes | methylene group | http://purl.obolibrary.org/obo/CHEBI_50728 |
| T145 | 1676-1685 | Chemical | denotes | methylene | http://purl.obolibrary.org/obo/CHEBI_29357|http://purl.obolibrary.org/obo/CHEBI_29358 |
| T147 | 1686-1691 | Chemical | denotes | group | http://purl.obolibrary.org/obo/CHEBI_24433 |
| T148 | 1727-1734 | Chemical | denotes | sulfone | http://purl.obolibrary.org/obo/CHEBI_35850 |
| T149 | 1888-1893 | Chemical | denotes | K2CO3 | http://purl.obolibrary.org/obo/CHEBI_131526 |
| T150 | 1895-1897 | Chemical | denotes | KI | http://purl.obolibrary.org/obo/CHEBI_74559|http://purl.obolibrary.org/obo/CHEBI_8346 |
| T152 | 1899-1902 | Chemical | denotes | DMF | http://purl.obolibrary.org/obo/CHEBI_17741 |
| T153 | 1932-1937 | Chemical | denotes | K2CO3 | http://purl.obolibrary.org/obo/CHEBI_131526 |
| T154 | 1939-1942 | Chemical | denotes | DMF | http://purl.obolibrary.org/obo/CHEBI_17741 |
| T155 | 1965-1968 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T156 | 1969-1972 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
| T157 | 2027-2031 | Chemical | denotes | AcOH | http://purl.obolibrary.org/obo/CHEBI_15366 |
| T158 | 2095-2098 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T159 | 2099-2102 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
| T160 | 2137-2145 | Chemical | denotes | solution | http://purl.obolibrary.org/obo/CHEBI_75958 |
| T161 | 2146-2150 | Chemical | denotes | LiOH | http://purl.obolibrary.org/obo/CHEBI_33979 |
| T162 | 2175-2178 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T163 | 2179-2182 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
| T164 | 2213-2216 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T165 | 2217-2220 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
| T166 | 2247-2250 | Chemical | denotes | NH3 | http://purl.obolibrary.org/obo/CHEBI_16134 |
| T167 | 2251-2255 | Chemical | denotes | MeOH | http://purl.obolibrary.org/obo/CHEBI_17790 |
| T168 | 2300-2303 | Chemical | denotes | NMP | http://purl.obolibrary.org/obo/CHEBI_17188|http://purl.obolibrary.org/obo/CHEBI_25608|http://purl.obolibrary.org/obo/CHEBI_7307 |
| T171 | 2342-2347 | Chemical | denotes | bromo | http://purl.obolibrary.org/obo/CHEBI_22927|http://purl.obolibrary.org/obo/CHEBI_47265 |
| T173 | 2371-2374 | Chemical | denotes | NMP | http://purl.obolibrary.org/obo/CHEBI_17188|http://purl.obolibrary.org/obo/CHEBI_25608|http://purl.obolibrary.org/obo/CHEBI_7307 |
| T176 | 2411-2417 | Chemical | denotes | methyl | http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309 |
| T178 | 2441-2444 | Chemical | denotes | NMP | http://purl.obolibrary.org/obo/CHEBI_17188|http://purl.obolibrary.org/obo/CHEBI_25608|http://purl.obolibrary.org/obo/CHEBI_7307 |
| T181 | 2491-2494 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T182 | 2495-2498 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
| T183 | 2591-2599 | Chemical | denotes | solution | http://purl.obolibrary.org/obo/CHEBI_75958 |
| T184 | 2600-2604 | Chemical | denotes | LiOH | http://purl.obolibrary.org/obo/CHEBI_33979 |
| T185 | 2677-2679 | Chemical | denotes | Ns | http://purl.obolibrary.org/obo/CHEBI_33349|http://purl.obolibrary.org/obo/CHEBI_33355 |
| T187 | 2680-2682 | Chemical | denotes | Cl | http://purl.obolibrary.org/obo/CHEBI_23116 |
| T188 | 2684-2688 | Chemical | denotes | NEt3 | http://purl.obolibrary.org/obo/CHEBI_35026 |
| T189 | 2690-2693 | Chemical | denotes | DMF | http://purl.obolibrary.org/obo/CHEBI_17741 |
| T190 | 2725-2727 | Chemical | denotes | KI | http://purl.obolibrary.org/obo/CHEBI_74559|http://purl.obolibrary.org/obo/CHEBI_8346 |
| T192 | 2729-2734 | Chemical | denotes | K2CO3 | http://purl.obolibrary.org/obo/CHEBI_131526 |
| T193 | 2736-2739 | Chemical | denotes | DMF | http://purl.obolibrary.org/obo/CHEBI_17741 |
| T194 | 2766-2769 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T195 | 2770-2773 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
| T196 | 2874-2882 | Chemical | denotes | chloride | http://purl.obolibrary.org/obo/CHEBI_17996 |
| T197 | 2884-2888 | Chemical | denotes | NEt3 | http://purl.obolibrary.org/obo/CHEBI_35026 |
| T198 | 2924-2930 | Chemical | denotes | chloro | http://purl.obolibrary.org/obo/CHEBI_47853 |
| T199 | 2952-2956 | Chemical | denotes | AcOH | http://purl.obolibrary.org/obo/CHEBI_15366 |
| T200 | 2958-2961 | Chemical | denotes | DCE | http://purl.obolibrary.org/obo/CHEBI_27789 |
| T201 | 3021-3041 | Chemical | denotes | 4-chlorobenzaldehyde | http://purl.obolibrary.org/obo/CHEBI_28105 |
| T202 | 3043-3047 | Chemical | denotes | AcOH | http://purl.obolibrary.org/obo/CHEBI_15366 |
| T203 | 3049-3052 | Chemical | denotes | DCE | http://purl.obolibrary.org/obo/CHEBI_27789 |
| T204 | 3108-3111 | Chemical | denotes | TFA | http://purl.obolibrary.org/obo/CHEBI_45892 |
| T205 | 3112-3115 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
LitCovid-PD-GO-BP
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| T24 | 105-116 | http://purl.obolibrary.org/obo/GO_0032259 | denotes | methylation |
| T25 | 703-714 | http://purl.obolibrary.org/obo/GO_0032259 | denotes | methylation |
| T26 | 1852-1861 | http://purl.obolibrary.org/obo/GO_0009058 | denotes | Synthesis |
| T27 | 2639-2648 | http://purl.obolibrary.org/obo/GO_0009058 | denotes | Synthesis |
| T28 | 2812-2821 | http://purl.obolibrary.org/obo/GO_0009058 | denotes | Synthesis |
2_test
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| 32563813-30615835-29105574 | 1394-1396 | 30615835 | denotes | 19 |
| 32563813-31559005-29105575 | 1397-1399 | 31559005 | denotes | 20 |
LitCovid-sentences
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| T61 | 0-45 | Sentence | denotes | 2.1 Rational design of bisubstrate compounds |
| T62 | 46-300 | Sentence | denotes | In order to mimic the transition state of the cap RNA 2′-O-methylation, the design of the SAM mimetics relies on the coupling of the adenosine moiety of the SAM cofactor to another adenosine modified at 2′-O-position with an ethyl group to form the link. |
| T63 | 301-412 | Sentence | denotes | Thus, we first synthesized the dinucleoside 1 with a 2′-O-ethyl amino link between both adenosines (Scheme 2 ). |
| T64 | 413-624 | Sentence | denotes | The major advantage of this N-containing linker is the possibility to functionalize the secondary amine with a large variety of groups which may lead to additional binding with specific sites of RNA 2′-O-MTases. |
| T65 | 625-849 | Sentence | denotes | According to the schematic representation of the transition state of the 2′-O-methylation (Scheme 1), an accurate mimic was represented by compound 2 with the α-amino acid chain of the SAM branched to the nitrogen atom [16]. |
| T66 | 850-978 | Sentence | denotes | We further modified this side chain under α-amino-ester form or α-amino-amide form to result in compounds 3 and 4, respectively. |
| T67 | 979-1106 | Sentence | denotes | Then instead of polar modifications, we introduced hydrophobic substituents on the secondary amine in dinucleosides 5, 6 and 7. |
| T68 | 1107-1238 | Sentence | denotes | Finally we chose to obtain compound 9 with a nitrobenzenesulfonamide moiety as a structural particular element of the dinucleoside. |
| T69 | 1239-1401 | Sentence | denotes | Indeed, as a global observation in medicinal chemistry the N-arylsulfonamide motif is regularly found in antitumor agents as in some antiviral inhibitors [19,20]. |
| T70 | 1402-1625 | Sentence | denotes | Further, we explored the combination of the nitro group with another substituent (MeO, CF3, Cl) at diverse positions in the phenyl ring resulting in the compounds 10–13 and we also removed the nitro group in 14 (Scheme 3 ). |
| T71 | 1626-1842 | Sentence | denotes | In addition, we chose to replace the sulfone by a methylene group in 15–16 (Scheme 4 ) to assess the sulfone contribution to the inhibitory activity obtained with dinucleosides containing the N-arylsulfonamide motif. |
| T72 | 1843-2629 | Sentence | denotes | Scheme 2 Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8. |
| T73 | 2630-2802 | Sentence | denotes | Scheme 3 Synthesis of dinucleosides 10–13. (a) Ns-Cl, NEt3, DMF, 25 °C, 3.5 h, 40–72%; (b) 17, KI, K2CO3, DMF, 50 °C, 24 h, 43–52%; (c) TFA/H2O 8/2, 25 °C, 3 h–5 h, 13–20%. |
| T74 | 2803-3178 | Sentence | denotes | Scheme 4 Synthesis of dinucleosides 14–16. (a) 4-chlorobenzenesulfonyl chloride, NEt3, CH2Cl2, 0 °C, 3 h, 90%. (b) (i) 4-chloro-3-nitrobenzaldehyde, AcOH, DCE, 40 °C, 20 min; (ii) NaBH(OAc)3, 40 °C, 16 h, 87%. (c) (i) 4-chlorobenzaldehyde, AcOH, DCE, 40 °C, 20 min. (ii) NaBH(OAc)3, 40 °C, 16 h, 72%. (d) TFA/H2O 8/2, 25 °C, 3 h, 48% for 14; 6 h, 25% for 15; 6 h, 37% for 16. |
MyTest
| Id | Subject | Object | Predicate | Lexical cue |
|---|---|---|---|---|
| 32563813-30615835-29105574 | 1394-1396 | 30615835 | denotes | 19 |
| 32563813-31559005-29105575 | 1397-1399 | 31559005 | denotes | 20 |