Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC(O)CO)ccn45)cccc32)n1
InChiKey
GSZCBMFOSHKWOI-UHFFFAOYSA-N
Route Signature
2658de3c6f86cad1909eec7ea262a012e7209b0a839a26ea0042556eaab4a074
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_94f79a041809a876277c4582",
"signature": "2658de3c6f86cad1909eec7ea262a012e7209b0a839a26ea0042556eaab4a074",
"contentHash": "3ba4ddb447dcb15c3a989d95fdcf719f5cc7b5eb51cc79af197a2bf751547cbf",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_2512d1e6757cc9144d871780",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02501",
"moleculeId": "sa_f60f75eddccd8efeb855b403",
"smiles": "Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC(O)CO)ccn45)cccc32)n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_f60f75eddccd8efeb855b403",
"inchikey": "GSZCBMFOSHKWOI-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC(O)CO)ccn45)cccc32)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10745",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_f60f75eddccd8efeb855b403",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f60f75eddccd8efeb855b403",
"inchikey": "GSZCBMFOSHKWOI-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC(O)CO)ccn45)cccc32)n1"
},
"smiles": "Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC(O)CO)ccn45)cccc32)n1",
"reactionStepId": "sa_cec5bde7113acf14c85853da",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09174981B2;0687;1686374\",\"rsmi\":\"CC1(C)[O:26][CH:25]([CH2:24][O:23][c:22]2[cH:21][c:20]3[n:19][cH:18][c:17]([C:15]([NH:14][c:13]4[c:12]5[c:10]([CH3:11])[n:9][n:8]([CH2:7][c:6]6[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:36]6)[c:35]5[cH:34][cH:33][cH:32]4)=[O:16])[n:31]3[cH:30][cH:29]2)[CH2:27][O:28]1>O.O=C(O)C(F)(F)F>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]([NH:14][C:15](=[O:16])[c:17]4[cH:18][n:19][c:20]5[cH:21][c:22]([O:23][CH2:24][CH:25]([OH:26])[CH2:27][OH:28])[cH:29][cH:30][n:31]45)[cH:32][cH:33][cH:34][c:35]23)[n:36]1\"},\"mapped_reaction_smiles\":\"CC1(C)[O:26][CH:25]([CH2:24][O:23][c:22]2[cH:21][c:20]3[n:19][cH:18][c:17]([C:15]([NH:14][c:13]4[c:12]5[c:10]([CH3:11])[n:9][n:8]([CH2:7][c:6]6[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:36]6)[c:35]5[cH:34][cH:33][cH:32]4)=[O:16])[n:31]3[cH:30][cH:29]2)[CH2:27][O:28]1>O.O=C(O)C(F)(F)F>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]([NH:14][C:15](=[O:16])[c:17]4[cH:18][n:19][c:20]5[cH:21][c:22]([O:23][CH2:24][CH:25]([OH:26])[CH2:27][OH:28])[cH:29][cH:30][n:31]45)[cH:32][cH:33][cH:34][c:35]23)[n:36]1\"}",
"reactionStep": {
"id": "sa_cec5bde7113acf14c85853da",
"reactionHash": "cacc4f8fb1c48fb48a1eaf8250e1c1dd736fcd2bfd11d09ef922e99db610214f"
},
"children": [
{
"id": "10746",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_38aa31a083403570d32f183e",
"parentId": "10745",
"isLeaf": false,
"molecule": {
"id": "sa_38aa31a083403570d32f183e",
"inchikey": "JGKIVFKUQIXCRI-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC6COC(C)(C)O6)ccn45)cccc32)n1"
},
"smiles": "Cc1cccc(Cn2nc(C)c3c(NC(=O)c4cnc5cc(OCC6COC(C)(C)O6)ccn45)cccc32)n1",
"reactionStepId": "sa_2d6cfb5b84b0a990be7c0d38",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09174981B2;0686;1686373\",\"rsmi\":\"O[C:15](=[O:16])[c:17]1[cH:18][n:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH:25]3[CH2:26][O:27][C:28]([CH3:29])([CH3:30])[O:31]3)[cH:32][cH:33][n:34]12.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]([NH2:14])[cH:35][cH:36][cH:37][c:38]23)[n:39]1>CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]([NH:14][C:15](=[O:16])[c:17]4[cH:18][n:19][c:20]5[cH:21][c:22]([O:23][CH2:24][CH:25]6[CH2:26][O:27][C:28]([CH3:29])([CH3:30])[O:31]6)[cH:32][cH:33][n:34]45)[cH:35][cH:36][cH:37][c:38]23)[n:39]1\"},\"mapped_reaction_smiles\":\"O[C:15](=[O:16])[c:17]1[cH:18][n:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH:25]3[CH2:26][O:27][C:28]([CH3:29])([CH3:30])[O:31]3)[cH:32][cH:33][n:34]12.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]([NH2:14])[cH:35][cH:36][cH:37][c:38]23)[n:39]1>CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]([NH:14][C:15](=[O:16])[c:17]4[cH:18][n:19][c:20]5[cH:21][c:22]([O:23][CH2:24][CH:25]6[CH2:26][O:27][C:28]([CH3:29])([CH3:30])[O:31]6)[cH:32][cH:33][n:34]45)[cH:35][cH:36][cH:37][c:38]23)[n:39]1\"}",
"reactionStep": {
"id": "sa_2d6cfb5b84b0a990be7c0d38",
"reactionHash": "52e110dc307aa5919ef7787626766f7b95d2ded1baf335b585bc743dacace0d0"
},
"children": [
{
"id": "10747",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_28624a27afa8bce2e0b94ef0",
"parentId": "10746",
"isLeaf": false,
"molecule": {
"id": "sa_28624a27afa8bce2e0b94ef0",
"inchikey": "FPEYDBWXOQJGJH-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cn2nc(C)c3c(N)cccc32)n1"
},
"smiles": "Cc1cccc(Cn2nc(C)c3c(N)cccc32)n1",
"reactionStepId": "sa_ca77be097f6d2a713669882d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09174981B2;0734;1686401\",\"rsmi\":\"O=[N+:18]([O-])[c:17]1[c:12]2[c:10]([CH3:11])[n:9][n:8]([CH2:7][c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:19]3)[c:13]2[cH:14][cH:15][cH:16]1>CCO.O[Pd]O>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]2[cH:14][cH:15][cH:16][c:17]3[NH2:18])[n:19]1\"},\"mapped_reaction_smiles\":\"O=[N+:18]([O-])[c:17]1[c:12]2[c:10]([CH3:11])[n:9][n:8]([CH2:7][c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:19]3)[c:13]2[cH:14][cH:15][cH:16]1>CCO.O[Pd]O>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][c:10]([CH3:11])[c:12]3[c:13]2[cH:14][cH:15][cH:16][c:17]3[NH2:18])[n:19]1\"}",
"reactionStep": {
"id": "sa_ca77be097f6d2a713669882d",
"reactionHash": "923abb27f289a973e6fa7f0c5feea506942450b15f46710c832977c590dd8096"
},
"children": [
{
"id": "10748",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_46dce72f05b3bf4417ffe42c",
"parentId": "10747",
"isLeaf": true,
"molecule": {
"id": "sa_46dce72f05b3bf4417ffe42c",
"inchikey": "LTULZFCVAWXEKT-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cn2nc(C)c3c([N+](=O)[O-])cccc32)n1"
},
"smiles": "Cc1cccc(Cn2nc(C)c3c([N+](=O)[O-])cccc32)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10749",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_f33e1511ffdfb6362ac53571",
"parentId": "10746",
"isLeaf": false,
"molecule": {
"id": "sa_f33e1511ffdfb6362ac53571",
"inchikey": "NYWKLBBPHXZAAE-UHFFFAOYSA-N",
"smiles": "CC1(C)OCC(COc2ccn3c(C(=O)O)cnc3c2)O1"
},
"smiles": "CC1(C)OCC(COc2ccn3c(C(=O)O)cnc3c2)O1",
"reactionStepId": "sa_b3a39ea317e9613d818fe59d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09174981B2;0685;1686372\",\"rsmi\":\"CC[O:17][C:15]([c:14]1[cH:13][n:12][c:11]2[cH:10][c:9]([O:8][CH2:7][CH:6]3[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:21]3)[cH:20][cH:19][n:18]21)=[O:16]>C1CCOC1.CCO.ClCCl.O.O.O.[Li+].O>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][c:11]3[n:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[n:18]3[cH:19][cH:20]2)[O:21]1\"},\"mapped_reaction_smiles\":\"CC[O:17][C:15]([c:14]1[cH:13][n:12][c:11]2[cH:10][c:9]([O:8][CH2:7][CH:6]3[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:21]3)[cH:20][cH:19][n:18]21)=[O:16]>C1CCOC1.CCO.ClCCl.O.O.O.[Li+].O>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][O:8][c:9]2[cH:10][c:11]3[n:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[n:18]3[cH:19][cH:20]2)[O:21]1\"}",
"reactionStep": {
"id": "sa_b3a39ea317e9613d818fe59d",
"reactionHash": "4e803b2685b48fb5f287c116a3eeaa35ae0c397ec24a38dc3c4f636c50dd2dbf"
},
"children": [
{
"id": "10750",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_3c100a74750dde725491ed13",
"parentId": "10749",
"isLeaf": false,
"molecule": {
"id": "sa_3c100a74750dde725491ed13",
"inchikey": "RGILLICMLOJOGQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc2cc(OCC3COC(C)(C)O3)ccn12"
},
"smiles": "CCOC(=O)c1cnc2cc(OCC3COC(C)(C)O3)ccn12",
"reactionStepId": "sa_1300f48f3c5af43a47b07d08",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09174981B2;0684;1686371\",\"rsmi\":\"O=[CH:7][CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][c:9]1[cH:10][c:11]([O:12][CH2:13][CH:14]2[CH2:15][O:16][C:17]([CH3:18])([CH3:19])[O:20]2)[cH:21][cH:22][n:23]1>CCO.CCOC(C)=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([O:12][CH2:13][CH:14]3[CH2:15][O:16][C:17]([CH3:18])([CH3:19])[O:20]3)[cH:21][cH:22][n:23]12\"},\"mapped_reaction_smiles\":\"O=[CH:7][CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:8][c:9]1[cH:10][c:11]([O:12][CH2:13][CH:14]2[CH2:15][O:16][C:17]([CH3:18])([CH3:19])[O:20]2)[cH:21][cH:22][n:23]1>CCO.CCOC(C)=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([O:12][CH2:13][CH:14]3[CH2:15][O:16][C:17]([CH3:18])([CH3:19])[O:20]3)[cH:21][cH:22][n:23]12\"}",
"reactionStep": {
"id": "sa_1300f48f3c5af43a47b07d08",
"reactionHash": "b2acf2b02acce1ccde52dc5b1d2ed914b89c120173ca19d23a22b5a082eb1390"
},
"children": [
{
"id": "10751",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_ef55ab2d5ad26117256c3ecb",
"parentId": "10750",
"isLeaf": true,
"molecule": {
"id": "sa_ef55ab2d5ad26117256c3ecb",
"inchikey": "DWXKSCKBUSAOKS-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(Cl)C=O"
},
"smiles": "CCOC(=O)C(Cl)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10752",
"routeId": "sa_94f79a041809a876277c4582",
"moleculeId": "sa_1ad62c27b61d9e6184c5dfe2",
"parentId": "10750",
"isLeaf": true,
"molecule": {
"id": "sa_1ad62c27b61d9e6184c5dfe2",
"inchikey": "OXYIHRSZXWMHPH-UHFFFAOYSA-N",
"smiles": "CC1(C)OCC(COc2ccnc(N)c2)O1"
},
"smiles": "CC1(C)OCC(COc2ccnc(N)c2)O1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}