Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)CCc1ccc2cccc(N3CCN(CCc4ccc(OCCCN5CCCCCC5)cc4)CC3)c2n1
InChiKey
XQBVWPSKNWZNJZ-UHFFFAOYSA-N
Route Signature
8d34b43506ef5b9d1fecefc4a7930476c0c5b201a76f6b5dabfe200f661b65b5
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_6b7d75324a76865016499cab",
"signature": "8d34b43506ef5b9d1fecefc4a7930476c0c5b201a76f6b5dabfe200f661b65b5",
"contentHash": "a1c3f7850e9f3e9cca51945f3e046571f32370c1c31ef6a814d51ea3f3de6957",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_131c1e0297d27d1171888f33",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-07453",
"moleculeId": "sa_edf45a3b87bec84e06cbefbb",
"smiles": "COC(=O)CCc1ccc2cccc(N3CCN(CCc4ccc(OCCCN5CCCCCC5)cc4)CC3)c2n1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_edf45a3b87bec84e06cbefbb",
"inchikey": "XQBVWPSKNWZNJZ-UHFFFAOYSA-N",
"smiles": "COC(=O)CCc1ccc2cccc(N3CCN(CCc4ccc(OCCCN5CCCCCC5)cc4)CC3)c2n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11742",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_edf45a3b87bec84e06cbefbb",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_edf45a3b87bec84e06cbefbb",
"inchikey": "XQBVWPSKNWZNJZ-UHFFFAOYSA-N",
"smiles": "COC(=O)CCc1ccc2cccc(N3CCN(CCc4ccc(OCCCN5CCCCCC5)cc4)CC3)c2n1"
},
"smiles": "COC(=O)CCc1ccc2cccc(N3CCN(CCc4ccc(OCCCN5CCCCCC5)cc4)CC3)c2n1",
"reactionStepId": "sa_5ce9e3ed93a0d60a8c9a6e76",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181950A1;0216;736151\",\"rsmi\":\"CS(=O)(=O)O[CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[cH:32][cH:33]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][NH:14][CH2:34][CH2:35]3)[cH:36][cH:37][cH:38][c:39]2[cH:40][cH:41]1>CC#N.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][CH2:23][CH2:24][N:25]5[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]5)[cH:32][cH:33]4)[CH2:34][CH2:35]3)[cH:36][cH:37][cH:38][c:39]2[cH:40][cH:41]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[cH:32][cH:33]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][NH:14][CH2:34][CH2:35]3)[cH:36][cH:37][cH:38][c:39]2[cH:40][cH:41]1>CC#N.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][c:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][CH2:23][CH2:24][N:25]5[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]5)[cH:32][cH:33]4)[CH2:34][CH2:35]3)[cH:36][cH:37][cH:38][c:39]2[cH:40][cH:41]1\"}",
"reactionStep": {
"id": "sa_5ce9e3ed93a0d60a8c9a6e76",
"reactionHash": "4ecaf9d0e18052108a2fa3d2be2b33f1d7c9e2d9bbd81ae9b9ebdb9cfa329c5f"
},
"children": [
{
"id": "11743",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_11fd0c55749e94d247927c4c",
"parentId": "11742",
"isLeaf": false,
"molecule": {
"id": "sa_11fd0c55749e94d247927c4c",
"inchikey": "ALBFMRSACHZUPV-UHFFFAOYSA-N",
"smiles": "COC(=O)CCc1ccc2cccc(N3CCNCC3)c2n1"
},
"smiles": "COC(=O)CCc1ccc2cccc(N3CCNCC3)c2n1",
"reactionStepId": "sa_1d07ff1af8ae0b9bf46ed1a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181950A1;0215;736150\",\"rsmi\":\"CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][N:11]([c:10]2[c:9]3[n:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21][c:20]3[cH:19][cH:18][cH:17]2)[CH2:16][CH2:15]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[cH:17][cH:18][cH:19][c:20]2[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][N:11]([c:10]2[c:9]3[n:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21][c:20]3[cH:19][cH:18][cH:17]2)[CH2:16][CH2:15]1>CO.ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[cH:17][cH:18][cH:19][c:20]2[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_1d07ff1af8ae0b9bf46ed1a8",
"reactionHash": "290fe0d3a76154e40cfae71679e2b1ae7068e139293c3050e82f3a59551ab401"
},
"children": [
{
"id": "11744",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_01a2ba512c542b3c130cf68d",
"parentId": "11743",
"isLeaf": false,
"molecule": {
"id": "sa_01a2ba512c542b3c130cf68d",
"inchikey": "GLBVKBVKMDTLHW-UHFFFAOYSA-N",
"smiles": "COC(=O)CCc1ccc2cccc(N3CCN(C(=O)OC(C)(C)C)CC3)c2n1"
},
"smiles": "COC(=O)CCc1ccc2cccc(N3CCN(C(=O)OC(C)(C)C)CC3)c2n1",
"reactionStepId": "sa_4c7340815f025b97473f790c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181950A1;0214;736149\",\"rsmi\":\"O=S(=O)(O[c:10]1[c:9]2[n:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:29][cH:28][c:27]2[cH:26][cH:25][cH:24]1)C(F)(F)F.[NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1>C1CCOC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]3)[cH:24][cH:25][cH:26][c:27]2[cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(O[c:10]1[c:9]2[n:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:29][cH:28][c:27]2[cH:26][cH:25][cH:24]1)C(F)(F)F.[NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1>C1CCOC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]2[c:10]([N:11]3[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]3)[cH:24][cH:25][cH:26][c:27]2[cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_4c7340815f025b97473f790c",
"reactionHash": "6a2715c02bd3843363add4be39e9b9094d8360aa21bdcccbe8fa1378d9bd9ce0"
},
"children": [
{
"id": "11745",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_04c50a88932aa2c9d9b979b4",
"parentId": "11744",
"isLeaf": true,
"molecule": {
"id": "sa_04c50a88932aa2c9d9b979b4",
"inchikey": "CWXPZXBSDSIRCS-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCNCC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11746",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_4aeec7b79bd878b1a1f0efd3",
"parentId": "11744",
"isLeaf": true,
"molecule": {
"id": "sa_4aeec7b79bd878b1a1f0efd3",
"inchikey": "OHALUVNZNOTXNH-UHFFFAOYSA-N",
"smiles": "COC(=O)CCc1ccc2cccc(OS(=O)(=O)C(F)(F)F)c2n1"
},
"smiles": "COC(=O)CCc1ccc2cccc(OS(=O)(=O)C(F)(F)F)c2n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "11747",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_78f2f75e3dd35ab320d768f1",
"parentId": "11742",
"isLeaf": false,
"molecule": {
"id": "sa_78f2f75e3dd35ab320d768f1",
"inchikey": "ANXQAAOXTPLUES-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)OCCc1ccc(OCCCN2CCCCCC2)cc1"
},
"smiles": "CS(=O)(=O)OCCc1ccc(OCCCN2CCCCCC2)cc1",
"reactionStepId": "sa_1b2e946fed503c6113a89c3f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181950A1;0201;736140\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23][cH:24]1>CCN(C(C)C)C(C)C.ClCCl.O=C(O)O.[Na+]>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23][cH:24]1>CCN(C(C)C)C(C)C.ClCCl.O=C(O)O.[Na+]>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_1b2e946fed503c6113a89c3f",
"reactionHash": "defa428a4cac2c332460002fd293ccda37874549a8480f1e1a18e1eabe872f57"
},
"children": [
{
"id": "11748",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_7dff38ddddeba5932b803bf3",
"parentId": "11747",
"isLeaf": true,
"molecule": {
"id": "sa_7dff38ddddeba5932b803bf3",
"inchikey": "AGVZCYKFZGQBPX-UHFFFAOYSA-N",
"smiles": "OCCc1ccc(OCCCN2CCCCCC2)cc1"
},
"smiles": "OCCc1ccc(OCCCN2CCCCCC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11749",
"routeId": "sa_6b7d75324a76865016499cab",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "11747",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
}