Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOc1ncnc(Nc2cc(OCc3c(OC)ccc(F)c3F)c(OC)cc2Cl)c1[N+](=O)[O-]
InChiKey
UBNMQWKSJHHWRU-UHFFFAOYSA-N
Route Signature
2c2f477306a9202bc2274e3a73c9660054f3ed70d8fcfa5f30e010f25d545a8e
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_26a0d7577b80f88799339a1c",
"signature": "2c2f477306a9202bc2274e3a73c9660054f3ed70d8fcfa5f30e010f25d545a8e",
"contentHash": "97f8288f9b528224d7947b759efd39b02d759ac2b1f4bc6cd7080c8b84679fa5",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_76f532dd6706da58636ba817",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-05276",
"moleculeId": "sa_2fa5434d30d9430a609739bd",
"smiles": "CCOc1ncnc(Nc2cc(OCc3c(OC)ccc(F)c3F)c(OC)cc2Cl)c1[N+](=O)[O-]",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_2fa5434d30d9430a609739bd",
"inchikey": "UBNMQWKSJHHWRU-UHFFFAOYSA-N",
"smiles": "CCOc1ncnc(Nc2cc(OCc3c(OC)ccc(F)c3F)c(OC)cc2Cl)c1[N+](=O)[O-]"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "7629",
"routeId": "sa_26a0d7577b80f88799339a1c",
"moleculeId": "sa_2fa5434d30d9430a609739bd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2fa5434d30d9430a609739bd",
"inchikey": "UBNMQWKSJHHWRU-UHFFFAOYSA-N",
"smiles": "CCOc1ncnc(Nc2cc(OCc3c(OC)ccc(F)c3F)c(OC)cc2Cl)c1[N+](=O)[O-]"
},
"smiles": "CCOc1ncnc(Nc2cc(OCc3c(OC)ccc(F)c3F)c(OC)cc2Cl)c1[N+](=O)[O-]",
"reactionStepId": "sa_76ceb2028f20de0b0df40c4d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100112090A1;0315;872016\",\"rsmi\":\"Cl[c:4]1[c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH:10][c:11]2[c:12]([Cl:13])[cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH2:20][c:21]3[c:22]([F:23])[c:24]([F:25])[cH:26][cH:27][c:28]3[O:29][CH3:30])[cH:31]2)[n:32][cH:33][n:34]1.[CH3:1][CH2:2][OH:3]>CN1CCCC1=O.Cl.[Na+]>[CH3:1][CH2:2][O:3][c:4]1[c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH:10][c:11]2[c:12]([Cl:13])[cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH2:20][c:21]3[c:22]([F:23])[c:24]([F:25])[cH:26][cH:27][c:28]3[O:29][CH3:30])[cH:31]2)[n:32][cH:33][n:34]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH:10][c:11]2[c:12]([Cl:13])[cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH2:20][c:21]3[c:22]([F:23])[c:24]([F:25])[cH:26][cH:27][c:28]3[O:29][CH3:30])[cH:31]2)[n:32][cH:33][n:34]1.[CH3:1][CH2:2][OH:3]>CN1CCCC1=O.Cl.[Na+]>[CH3:1][CH2:2][O:3][c:4]1[c:5]([N+:6](=[O:7])[O-:8])[c:9]([NH:10][c:11]2[c:12]([Cl:13])[cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH2:20][c:21]3[c:22]([F:23])[c:24]([F:25])[cH:26][cH:27][c:28]3[O:29][CH3:30])[cH:31]2)[n:32][cH:33][n:34]1\"}",
"reactionStep": {
"id": "sa_76ceb2028f20de0b0df40c4d",
"reactionHash": "264e360ffc73ed5747d66883a26b95a8322f68d10dd7184afb9b16e0c3895da8"
},
"children": [
{
"id": "7630",
"routeId": "sa_26a0d7577b80f88799339a1c",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "7629",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7631",
"routeId": "sa_26a0d7577b80f88799339a1c",
"moleculeId": "sa_75ef21955744e125c3f8a766",
"parentId": "7629",
"isLeaf": false,
"molecule": {
"id": "sa_75ef21955744e125c3f8a766",
"inchikey": "RHGXNUQSHKPTEM-UHFFFAOYSA-N",
"smiles": "COc1cc(Cl)c(Nc2ncnc(Cl)c2[N+](=O)[O-])cc1OCc1c(OC)ccc(F)c1F"
},
"smiles": "COc1cc(Cl)c(Nc2ncnc(Cl)c2[N+](=O)[O-])cc1OCc1c(OC)ccc(F)c1F",
"reactionStepId": "sa_a132b1d04aa9bcdc63236f78",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100112090A1;0315;872015\",\"rsmi\":\"Cl[c:9]1[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]1[N+:16](=[O:17])[O-:18].[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH2:8])[cH:19][c:20]1[O:21][CH2:22][c:23]1[c:24]([F:25])[c:26]([F:27])[cH:28][cH:29][c:30]1[O:31][CH3:32]>CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]2[N+:16](=[O:17])[O-:18])[cH:19][c:20]1[O:21][CH2:22][c:23]1[c:24]([F:25])[c:26]([F:27])[cH:28][cH:29][c:30]1[O:31][CH3:32]\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]1[N+:16](=[O:17])[O-:18].[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH2:8])[cH:19][c:20]1[O:21][CH2:22][c:23]1[c:24]([F:25])[c:26]([F:27])[cH:28][cH:29][c:30]1[O:31][CH3:32]>CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]2[N+:16](=[O:17])[O-:18])[cH:19][c:20]1[O:21][CH2:22][c:23]1[c:24]([F:25])[c:26]([F:27])[cH:28][cH:29][c:30]1[O:31][CH3:32]\"}",
"reactionStep": {
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"reactionHash": "21e706ce8fe53ac6be6c7d29cd14d7cc17c88de9f80aedd122309f93891d8566"
},
"children": [
{
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"moleculeId": "sa_7cdf256abc3afc7faedfc083",
"parentId": "7631",
"isLeaf": true,
"molecule": {
"id": "sa_7cdf256abc3afc7faedfc083",
"inchikey": "HCTISZQLTGAYOX-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1c(Cl)ncnc1Cl"
},
"smiles": "O=[N+]([O-])c1c(Cl)ncnc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "7633",
"routeId": "sa_26a0d7577b80f88799339a1c",
"moleculeId": "sa_115e5d4dba7490ee44ddd93b",
"parentId": "7631",
"isLeaf": false,
"molecule": {
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"inchikey": "ZFYIZMQVAVZXKV-UHFFFAOYSA-N",
"smiles": "COc1cc(Cl)c(N)cc1OCc1c(OC)ccc(F)c1F"
},
"smiles": "COc1cc(Cl)c(N)cc1OCc1c(OC)ccc(F)c1F",
"reactionStepId": "sa_3c4dc503ce06daaac521af37",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100112090A1;0175;871941\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[c:5]([Cl:6])[cH:4][c:3]([O:2][CH3:1])[c:10]([O:11][CH2:12][c:13]2[c:14]([F:15])[c:16]([F:17])[cH:18][cH:19][c:20]2[O:21][CH3:22])[cH:9]1>Br[Ni]Br.C1CCOC1.CO.O=C(O)O.B.[Na+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH2:8])[cH:9][c:10]1[O:11][CH2:12][c:13]1[c:14]([F:15])[c:16]([F:17])[cH:18][cH:19][c:20]1[O:21][CH3:22]\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[c:5]([Cl:6])[cH:4][c:3]([O:2][CH3:1])[c:10]([O:11][CH2:12][c:13]2[c:14]([F:15])[c:16]([F:17])[cH:18][cH:19][c:20]2[O:21][CH3:22])[cH:9]1>Br[Ni]Br.C1CCOC1.CO.O=C(O)O.B.[Na+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH2:8])[cH:9][c:10]1[O:11][CH2:12][c:13]1[c:14]([F:15])[c:16]([F:17])[cH:18][cH:19][c:20]1[O:21][CH3:22]\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_e6776d2c31806fb973734675",
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"isLeaf": false,
"molecule": {
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"inchikey": "WHGUKAGAHDNEDB-UHFFFAOYSA-N",
"smiles": "COc1cc(Cl)c([N+](=O)[O-])cc1OCc1c(OC)ccc(F)c1F"
},
"smiles": "COc1cc(Cl)c([N+](=O)[O-])cc1OCc1c(OC)ccc(F)c1F",
"reactionStepId": "sa_50c69b1053018270c1cbff4a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100112090A1;0173;871940\",\"rsmi\":\"O=[N+:21]([OH:22])[O-:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][O:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[cH:20][cH:24]1>CC(=O)OC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][O:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]1\"},\"mapped_reaction_smiles\":\"O=[N+:21]([OH:22])[O-:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][O:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[cH:20][cH:24]1>CC(=O)OC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][O:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]1\"}",
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"children": [
{
"id": "7635",
"routeId": "sa_26a0d7577b80f88799339a1c",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "7634",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "7636",
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"moleculeId": "sa_731786d14727e582f3ecfc16",
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"molecule": {
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"inchikey": "UVVPFLHAEUAZOP-UHFFFAOYSA-N",
"smiles": "COc1cc(Cl)ccc1OCc1c(OC)ccc(F)c1F"
},
"smiles": "COc1cc(Cl)ccc1OCc1c(OC)ccc(F)c1F",
"reactionStepId": "sa_6513566966690a0c64bf4788",
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"metadata": "{\"annotations\":{\"ID\":\"US20100112090A1;0171;871939\",\"rsmi\":\"Cl[CH2:11][c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[c:8]1[F:9].[OH:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[cH:20][cH:21]1>CN(C)C=O.O.O=C(O)O.I.[K+].[K+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][O:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:11][c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[c:8]1[F:9].[OH:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[cH:20][cH:21]1>CN(C)C=O.O.O=C(O)O.I.[K+].[K+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][O:12][c:13]1[c:14]([O:15][CH3:16])[cH:17][c:18]([Cl:19])[cH:20][cH:21]1\"}",
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"molecule": {
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"smiles": "COc1ccc(F)c(F)c1CCl"
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"metadata": "{\"annotations\":{\"ID\":\"US20100112090A1;0170;871938\",\"rsmi\":\"O=S(Cl)[Cl:12].O[CH2:11][c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[c:8]1[F:9]>Cc1ccccc1.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][Cl:12]\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:12].O[CH2:11][c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([F:7])[c:8]1[F:9]>Cc1ccccc1.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[CH2:11][Cl:12]\"}",
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{
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{
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"smiles": "COc1cc(Cl)ccc1O"
},
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}
]
}
]
}
]
}
]
}
]
}
}