Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCO[C@@H]1CN(c2nc(C(=O)O)c(CC)o2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1
InChiKey
ZSTGSWANAOPJNO-GXTWGEPZSA-N
Route Signature
6a242df13140e0486cb876d2b47c9720367fe6bc4e0dbee4ce999848a19bddfc
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_fd6301d55d29dab3ba23d843",
"signature": "6a242df13140e0486cb876d2b47c9720367fe6bc4e0dbee4ce999848a19bddfc",
"contentHash": "034fe1e076dd3a2b9fb250228a93880c44f3c43a21fac4c77fea49393a1bf4f7",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_b4b5e1ee58adecfe987d92e7",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02504",
"moleculeId": "sa_c04320971b341293e94a850c",
"smiles": "CCCO[C@@H]1CN(c2nc(C(=O)O)c(CC)o2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c04320971b341293e94a850c",
"inchikey": "ZSTGSWANAOPJNO-GXTWGEPZSA-N",
"smiles": "CCCO[C@@H]1CN(c2nc(C(=O)O)c(CC)o2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10753",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_c04320971b341293e94a850c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c04320971b341293e94a850c",
"inchikey": "ZSTGSWANAOPJNO-GXTWGEPZSA-N",
"smiles": "CCCO[C@@H]1CN(c2nc(C(=O)O)c(CC)o2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1"
},
"smiles": "CCCO[C@@H]1CN(c2nc(C(=O)O)c(CC)o2)CC[C@@H]1NC(=O)c1nc(Cl)c(CC)[nH]1",
"reactionStepId": "sa_58d28072708f3fe89335ef4a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;1368;1564996\",\"rsmi\":\"CCCC[O:13][C:11]([c:10]1[n:9][c:8]([N:7]2[CH2:6][C@@H:5]([O:4][CH2:3][CH2:2][CH3:1])[C@@H:20]([NH:21][C:22](=[O:23])[c:24]3[n:25][c:26]([Cl:27])[c:28]([CH2:29][CH3:30])[nH:31]3)[CH2:19][CH2:18]2)[o:17][c:14]1[CH2:15][CH3:16])=[O:12]>C1CCOC1.CO.[Li+].O>[CH3:1][CH2:2][CH2:3][O:4][C@@H:5]1[CH2:6][N:7]([c:8]2[n:9][c:10]([C:11](=[O:12])[OH:13])[c:14]([CH2:15][CH3:16])[o:17]2)[CH2:18][CH2:19][C@@H:20]1[NH:21][C:22](=[O:23])[c:24]1[n:25][c:26]([Cl:27])[c:28]([CH2:29][CH3:30])[nH:31]1\"},\"mapped_reaction_smiles\":\"CCCC[O:13][C:11]([c:10]1[n:9][c:8]([N:7]2[CH2:6][C@@H:5]([O:4][CH2:3][CH2:2][CH3:1])[C@@H:20]([NH:21][C:22](=[O:23])[c:24]3[n:25][c:26]([Cl:27])[c:28]([CH2:29][CH3:30])[nH:31]3)[CH2:19][CH2:18]2)[o:17][c:14]1[CH2:15][CH3:16])=[O:12]>C1CCOC1.CO.[Li+].O>[CH3:1][CH2:2][CH2:3][O:4][C@@H:5]1[CH2:6][N:7]([c:8]2[n:9][c:10]([C:11](=[O:12])[OH:13])[c:14]([CH2:15][CH3:16])[o:17]2)[CH2:18][CH2:19][C@@H:20]1[NH:21][C:22](=[O:23])[c:24]1[n:25][c:26]([Cl:27])[c:28]([CH2:29][CH3:30])[nH:31]1\"}",
"reactionStep": {
"id": "sa_58d28072708f3fe89335ef4a",
"reactionHash": "6e4f1b06551a62c0b71ec37a180c3175113262b05892cc30fb27c2487f691240"
},
"children": [
{
"id": "10754",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_5c9e05c63a265c70762a9ad6",
"parentId": "10753",
"isLeaf": false,
"molecule": {
"id": "sa_5c9e05c63a265c70762a9ad6",
"inchikey": "BJBHUOWZOPPXKG-FUHWJXTLSA-N",
"smiles": "CCCCOC(=O)c1nc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](OCCC)C2)oc1CC"
},
"smiles": "CCCCOC(=O)c1nc(N2CC[C@H](NC(=O)c3nc(Cl)c(CC)[nH]3)[C@H](OCCC)C2)oc1CC",
"reactionStepId": "sa_a06e92acb947aff5556d5321",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;1366;1564995\",\"rsmi\":\"O[C:19](=[O:20])[c:21]1[n:22][c:23]([Cl:24])[c:25]([CH2:26][CH3:27])[nH:28]1.[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[c:9]([CH2:10][CH3:11])[o:12][c:13]([N:14]2[CH2:15][CH2:16][C@H:17]([NH2:18])[C@H:29]([O:30][CH2:31][CH2:32][CH3:33])[CH2:34]2)[n:35]1>CC(=O)N(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[c:9]([CH2:10][CH3:11])[o:12][c:13]([N:14]2[CH2:15][CH2:16][C@H:17]([NH:18][C:19](=[O:20])[c:21]3[n:22][c:23]([Cl:24])[c:25]([CH2:26][CH3:27])[nH:28]3)[C@H:29]([O:30][CH2:31][CH2:32][CH3:33])[CH2:34]2)[n:35]1\"},\"mapped_reaction_smiles\":\"O[C:19](=[O:20])[c:21]1[n:22][c:23]([Cl:24])[c:25]([CH2:26][CH3:27])[nH:28]1.[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[c:9]([CH2:10][CH3:11])[o:12][c:13]([N:14]2[CH2:15][CH2:16][C@H:17]([NH2:18])[C@H:29]([O:30][CH2:31][CH2:32][CH3:33])[CH2:34]2)[n:35]1>CC(=O)N(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[c:9]([CH2:10][CH3:11])[o:12][c:13]([N:14]2[CH2:15][CH2:16][C@H:17]([NH:18][C:19](=[O:20])[c:21]3[n:22][c:23]([Cl:24])[c:25]([CH2:26][CH3:27])[nH:28]3)[C@H:29]([O:30][CH2:31][CH2:32][CH3:33])[CH2:34]2)[n:35]1\"}",
"reactionStep": {
"id": "sa_a06e92acb947aff5556d5321",
"reactionHash": "1319fe8e43bdd15c7eb7168278002da4297be80d0a2f5caae7c323184eb0a99b"
},
"children": [
{
"id": "10755",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_0c24e3801f357839e7e8df89",
"parentId": "10754",
"isLeaf": false,
"molecule": {
"id": "sa_0c24e3801f357839e7e8df89",
"inchikey": "SIPMTCWRWYOAHL-DZGCQCFKSA-N",
"smiles": "CCCCOC(=O)c1nc(N2CC[C@H](N)[C@H](OCCC)C2)oc1CC"
},
"smiles": "CCCCOC(=O)c1nc(N2CC[C@H](N)[C@H](OCCC)C2)oc1CC",
"reactionStepId": "sa_58797efd7e24e2f3012ffa69",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;1364;1564994\",\"rsmi\":\"O=C(OCc1ccccc1)[NH:18][C@H:17]1[CH2:16][CH2:15][N:14]([c:13]2[o:12][c:9]([CH2:10][CH3:11])[c:8]([C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7])[n:25]2)[CH2:24][C@H:19]1[O:20][CH2:21][CH2:22][CH3:23]>CO.[Pd]>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[c:9]([CH2:10][CH3:11])[o:12][c:13]([N:14]2[CH2:15][CH2:16][C@H:17]([NH2:18])[C@H:19]([O:20][CH2:21][CH2:22][CH3:23])[CH2:24]2)[n:25]1\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[NH:18][C@H:17]1[CH2:16][CH2:15][N:14]([c:13]2[o:12][c:9]([CH2:10][CH3:11])[c:8]([C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7])[n:25]2)[CH2:24][C@H:19]1[O:20][CH2:21][CH2:22][CH3:23]>CO.[Pd]>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[c:9]([CH2:10][CH3:11])[o:12][c:13]([N:14]2[CH2:15][CH2:16][C@H:17]([NH2:18])[C@H:19]([O:20][CH2:21][CH2:22][CH3:23])[CH2:24]2)[n:25]1\"}",
"reactionStep": {
"id": "sa_58797efd7e24e2f3012ffa69",
"reactionHash": "3421525cc520f56541268ea256dc706c52e6449ce11bc074c39d297cde0c9466"
},
"children": [
{
"id": "10756",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_25f107b53263e43cf50ec1d0",
"parentId": "10755",
"isLeaf": true,
"molecule": {
"id": "sa_25f107b53263e43cf50ec1d0",
"inchikey": "DYDWAXOOOMCCBZ-RBBKRZOGSA-N",
"smiles": "CCCCOC(=O)c1nc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OCCC)C2)oc1CC"
},
"smiles": "CCCCOC(=O)c1nc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OCCC)C2)oc1CC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10757",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_9bc8b08abdf7525102dd4467",
"parentId": "10754",
"isLeaf": false,
"molecule": {
"id": "sa_9bc8b08abdf7525102dd4467",
"inchikey": "WBRFPIVOPOBICF-UHFFFAOYSA-N",
"smiles": "CCc1[nH]c(C(=O)O)nc1Cl"
},
"smiles": "CCc1[nH]c(C(=O)O)nc1Cl",
"reactionStepId": "sa_f145be2dbb2bb8ad8b26d359",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0267;1564753\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:11]1)=[O:9]>CO.ClCCl.[Li+].O>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[OH:10])[nH:11]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[n:6][c:4]([Cl:5])[c:3]([CH2:2][CH3:1])[nH:11]1)=[O:9]>CO.ClCCl.[Li+].O>[CH3:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6][c:7]([C:8](=[O:9])[OH:10])[nH:11]1\"}",
"reactionStep": {
"id": "sa_f145be2dbb2bb8ad8b26d359",
"reactionHash": "17bf90cc2e29a1b93adad9c3beb9855c8d9b28d5e254875cc053de9bb17da259"
},
"children": [
{
"id": "10758",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_0ffae542729eb49e4bfd3649",
"parentId": "10757",
"isLeaf": false,
"molecule": {
"id": "sa_0ffae542729eb49e4bfd3649",
"inchikey": "KNQZWWOAZXSMTG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1nc(Cl)c(CC)[nH]1"
},
"smiles": "CCOC(=O)c1nc(Cl)c(CC)[nH]1",
"reactionStepId": "sa_9add913b41fde2dc06ad7c95",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08927588B2;0265;1564752\",\"rsmi\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:10]([CH2:11][CH3:12])[nH:13]1>ClC(Cl)Cl.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Cl:9])[c:10]([CH2:11][CH3:12])[nH:13]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:10]([CH2:11][CH3:12])[nH:13]1>ClC(Cl)Cl.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Cl:9])[c:10]([CH2:11][CH3:12])[nH:13]1\"}",
"reactionStep": {
"id": "sa_9add913b41fde2dc06ad7c95",
"reactionHash": "8ac4f168cb7d53155176d18af2cdf84b0660857106b9bf17ae887dbbc6f00fa8"
},
"children": [
{
"id": "10759",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_a576f9b9a2caa305053d217d",
"parentId": "10758",
"isLeaf": true,
"molecule": {
"id": "sa_a576f9b9a2caa305053d217d",
"inchikey": "JRNVZBWKYDBUCA-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Cl"
},
"smiles": "O=C1CCC(=O)N1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10760",
"routeId": "sa_fd6301d55d29dab3ba23d843",
"moleculeId": "sa_249834358f82e299278170ed",
"parentId": "10758",
"isLeaf": true,
"molecule": {
"id": "sa_249834358f82e299278170ed",
"inchikey": "QFBQZDDWPFZPSS-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ncc(CC)[nH]1"
},
"smiles": "CCOC(=O)c1ncc(CC)[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}