Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#CCCn1cc(NC(=O)c2cnn3cccnc23)c(-c2cc(Cl)ccc2OC(F)F)n1
InChiKey
IIPWJWLOGROPKW-UHFFFAOYSA-N
Route Signature
d5a543ededb49c71c302ea9e7ac8089e1f6d0756127fa72188d774be2de146a8
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_90df5e73c7f400f67f1e4708",
"signature": "d5a543ededb49c71c302ea9e7ac8089e1f6d0756127fa72188d774be2de146a8",
"contentHash": "07461ea7a8bc5cb530c328f5655d20f1aab77fe6f1372c1f1a1d284b5700cb66",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_4898b9e2f732a89f6e3534b0",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-03408",
"moleculeId": "sa_4cd9ca9f37ee2d931935744a",
"smiles": "N#CCCn1cc(NC(=O)c2cnn3cccnc23)c(-c2cc(Cl)ccc2OC(F)F)n1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_4cd9ca9f37ee2d931935744a",
"inchikey": "IIPWJWLOGROPKW-UHFFFAOYSA-N",
"smiles": "N#CCCn1cc(NC(=O)c2cnn3cccnc23)c(-c2cc(Cl)ccc2OC(F)F)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "6839",
"routeId": "sa_90df5e73c7f400f67f1e4708",
"moleculeId": "sa_4cd9ca9f37ee2d931935744a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4cd9ca9f37ee2d931935744a",
"inchikey": "IIPWJWLOGROPKW-UHFFFAOYSA-N",
"smiles": "N#CCCn1cc(NC(=O)c2cnn3cccnc23)c(-c2cc(Cl)ccc2OC(F)F)n1"
},
"smiles": "N#CCCn1cc(NC(=O)c2cnn3cccnc23)c(-c2cc(Cl)ccc2OC(F)F)n1",
"reactionStepId": "sa_e6f1c5568be2b034a6b13cba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237086A1;0689;1924235\",\"rsmi\":\"Br[CH2:4][CH2:3][C:2]#[N:1].[nH:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]3[n:13][cH:14][cH:15][cH:16][n:17]3[n:18][cH:19]2)[c:20](-[c:21]2[c:22]([O:23][CH:24]([F:25])[F:26])[cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[n:32]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[N:1]#[C:2][CH2:3][CH2:4][n:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]3[n:13][cH:14][cH:15][cH:16][n:17]3[n:18][cH:19]2)[c:20](-[c:21]2[c:22]([O:23][CH:24]([F:25])[F:26])[cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[n:32]1\"},\"mapped_reaction_smiles\":\"Br[CH2:4][CH2:3][C:2]#[N:1].[nH:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]3[n:13][cH:14][cH:15][cH:16][n:17]3[n:18][cH:19]2)[c:20](-[c:21]2[c:22]([O:23][CH:24]([F:25])[F:26])[cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[n:32]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[N:1]#[C:2][CH2:3][CH2:4][n:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[c:12]3[n:13][cH:14][cH:15][cH:16][n:17]3[n:18][cH:19]2)[c:20](-[c:21]2[c:22]([O:23][CH:24]([F:25])[F:26])[cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[n:32]1\"}",
"reactionStep": {
"id": "sa_e6f1c5568be2b034a6b13cba",
"reactionHash": "230675068446ba27c2637af99109286c69f77992a2bd73855590da77139f56a7"
},
"children": [
{
"id": "6840",
"routeId": "sa_90df5e73c7f400f67f1e4708",
"moleculeId": "sa_ce88c75f2fff4ab7b4a2386d",
"parentId": "6839",
"isLeaf": true,
"molecule": {
"id": "sa_ce88c75f2fff4ab7b4a2386d",
"inchikey": "CQZIEDXCLQOOEH-UHFFFAOYSA-N",
"smiles": "N#CCCBr"
},
"smiles": "N#CCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6841",
"routeId": "sa_90df5e73c7f400f67f1e4708",
"moleculeId": "sa_d33c45e291d19ce96d42306e",
"parentId": "6839",
"isLeaf": false,
"molecule": {
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"inchikey": "KHCFKCPXXJQHMH-UHFFFAOYSA-N",
"smiles": "O=C(Nc1c[nH]nc1-c1cc(Cl)ccc1OC(F)F)c1cnn2cccnc12"
},
"smiles": "O=C(Nc1c[nH]nc1-c1cc(Cl)ccc1OC(F)F)c1cnn2cccnc12",
"reactionStepId": "sa_e6c61c3e6248c3c49c8a123a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237086A1;0607;1924199\",\"rsmi\":\"C[Si](C)(C)CCOC[n:7]1[n:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:20]2[c:21]3[n:22][cH:23][cH:24][cH:25][n:26]3[n:27][cH:28]2)[c:8]1-[c:9]1[c:10]([O:11][CH:12]([F:13])[F:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]1>CO.Cl>[O:1]=[C:2]([NH:3][c:4]1[cH:5][nH:6][n:7][c:8]1-[c:9]1[c:10]([O:11][CH:12]([F:13])[F:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]1)[c:20]1[c:21]2[n:22][cH:23][cH:24][cH:25][n:26]2[n:27][cH:28]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)CCOC[n:7]1[n:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:20]2[c:21]3[n:22][cH:23][cH:24][cH:25][n:26]3[n:27][cH:28]2)[c:8]1-[c:9]1[c:10]([O:11][CH:12]([F:13])[F:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]1>CO.Cl>[O:1]=[C:2]([NH:3][c:4]1[cH:5][nH:6][n:7][c:8]1-[c:9]1[c:10]([O:11][CH:12]([F:13])[F:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]1)[c:20]1[c:21]2[n:22][cH:23][cH:24][cH:25][n:26]2[n:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_e6c61c3e6248c3c49c8a123a",
"reactionHash": "1739108cec5afac5400d43b6d5246a72059b15b46de940f5e585b7436cde0d5a"
},
"children": [
{
"id": "6842",
"routeId": "sa_90df5e73c7f400f67f1e4708",
"moleculeId": "sa_8165ce34038176631e9b4cb1",
"parentId": "6841",
"isLeaf": false,
"molecule": {
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"inchikey": "PMHWXVXNPIFIHY-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1ncc(NC(=O)c2cnn3cccnc23)c1-c1cc(Cl)ccc1OC(F)F"
},
"smiles": "C[Si](C)(C)CCOCn1ncc(NC(=O)c2cnn3cccnc23)c1-c1cc(Cl)ccc1OC(F)F",
"reactionStepId": "sa_74d8c91936231fb0577f21e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237086A1;0606;1924198\",\"rsmi\":\"Cl[C:14](=[O:15])[c:16]1[c:17]2[n:18][cH:19][cH:20][cH:21][n:22]2[n:23][cH:24]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([NH2:13])[c:25]1-[c:26]1[c:27]([O:28][CH:29]([F:30])[F:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([NH:13][C:14](=[O:15])[c:16]2[c:17]3[n:18][cH:19][cH:20][cH:21][n:22]3[n:23][cH:24]2)[c:25]1-[c:26]1[c:27]([O:28][CH:29]([F:30])[F:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]1\"},\"mapped_reaction_smiles\":\"Cl[C:14](=[O:15])[c:16]1[c:17]2[n:18][cH:19][cH:20][cH:21][n:22]2[n:23][cH:24]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([NH2:13])[c:25]1-[c:26]1[c:27]([O:28][CH:29]([F:30])[F:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([NH:13][C:14](=[O:15])[c:16]2[c:17]3[n:18][cH:19][cH:20][cH:21][n:22]3[n:23][cH:24]2)[c:25]1-[c:26]1[c:27]([O:28][CH:29]([F:30])[F:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]1\"}",
"reactionStep": {
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"reactionHash": "4b7d04a08751b04c6019016a50c4ae615e5e8572fdc27732e98b882cdf7dfbab"
},
"children": [
{
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"routeId": "sa_90df5e73c7f400f67f1e4708",
"moleculeId": "sa_dfcfb6be14eb218030426230",
"parentId": "6842",
"isLeaf": true,
"molecule": {
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"inchikey": "HNOBXHOOORODQT-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1cnn2cccnc12"
},
"smiles": "O=C(Cl)c1cnn2cccnc12",
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{
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"molecule": {
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"inchikey": "YFNLJEFXSCZEQU-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1ncc(N)c1-c1cc(Cl)ccc1OC(F)F"
},
"smiles": "C[Si](C)(C)CCOCn1ncc(N)c1-c1cc(Cl)ccc1OC(F)F",
"reactionStepId": "sa_37d28f6e621b7a2872d26fd4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160237086A1;0605;1924197\",\"rsmi\":\"O=[N+:13]([O-])[c:12]1[cH:11][n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:14]1-[c:15]1[c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]1>CCO.O.Cl.[Fe].N>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([NH2:13])[c:14]1-[c:15]1[c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]1\"},\"mapped_reaction_smiles\":\"O=[N+:13]([O-])[c:12]1[cH:11][n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:14]1-[c:15]1[c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]1>CCO.O.Cl.[Fe].N>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([NH2:13])[c:14]1-[c:15]1[c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22][c:23]([Cl:24])[cH:25]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_2fc328577e23649d9d9634a6",
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"molecule": {
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"smiles": "C[Si](C)(C)CCOCn1ncc([N+](=O)[O-])c1-c1cc(Cl)ccc1OC(F)F"
},
"smiles": "C[Si](C)(C)CCOCn1ncc([N+](=O)[O-])c1-c1cc(Cl)ccc1OC(F)F",
"reactionStepId": "sa_f9d40c6bccc38db10bfe60a6",
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"metadata": "{\"annotations\":{\"ID\":\"US20160237086A1;0604;1924196\",\"rsmi\":\"Br[c:17]1[c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>CC(=O)N(C)C.CC(=O)O.CC(=O)O.CC(C)(C)C(=O)O.CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.O=C(O)O.[K+].[K+].[Pd+2]>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1-[c:17]1[c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>CC(=O)N(C)C.CC(=O)O.CC(=O)O.CC(C)(C)C(=O)O.CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.O=C(O)O.[K+].[K+].[Pd+2]>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1-[c:17]1[c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][cH:24][c:25]([Cl:26])[cH:27]1\"}",
"reactionStep": {
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"smiles": "C[Si](C)(C)CCOCn1cc([N+](=O)[O-])cn1",
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{
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"metadata": "{\"annotations\":{\"ID\":\"US20160237086A1;0603;1924195\",\"rsmi\":\"O=C(O)[C:2](Cl)([F:1])[F:3].[OH:4][c:5]1[c:6]([Br:7])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1>CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+].[Na+]>[F:1][CH:2]([F:3])[O:4][c:5]1[c:6]([Br:7])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O=C(O)[C:2](Cl)([F:1])[F:3].[OH:4][c:5]1[c:6]([Br:7])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1>CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+].[Na+]>[F:1][CH:2]([F:3])[O:4][c:5]1[c:6]([Br:7])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1\"}",
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"smiles": "O=C(O)C(F)(F)Cl"
},
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{
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},
"smiles": "Oc1ccc(Cl)cc1Br",
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}
]
}
]
}
]
}
]
}
]
}
]
}
}