Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1nc(CCN2CCCC2)cc1Nc1cc(Nc2ccccc2C(=O)NC)c(Cl)cn1
InChiKey
YYPFFKWDMCZDEA-UHFFFAOYSA-N
Route Signature
b8f369e1154fa43f1d26e74c557ee9bf3e5c11a7380840f3a3e5f50351e3f43c
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_c7e76042829662fc05e42327",
"signature": "b8f369e1154fa43f1d26e74c557ee9bf3e5c11a7380840f3a3e5f50351e3f43c",
"contentHash": "ac24c794ed6c711f264d33677fcd6115bb1180153fe8a2a7bef59e305f1c7af6",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_04b040173ad6bc2394cc3368",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-06098",
"moleculeId": "sa_ccb7067ee48924a1c6e67c63",
"smiles": "CCn1nc(CCN2CCCC2)cc1Nc1cc(Nc2ccccc2C(=O)NC)c(Cl)cn1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_ccb7067ee48924a1c6e67c63",
"inchikey": "YYPFFKWDMCZDEA-UHFFFAOYSA-N",
"smiles": "CCn1nc(CCN2CCCC2)cc1Nc1cc(Nc2ccccc2C(=O)NC)c(Cl)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11506",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_ccb7067ee48924a1c6e67c63",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ccb7067ee48924a1c6e67c63",
"inchikey": "YYPFFKWDMCZDEA-UHFFFAOYSA-N",
"smiles": "CCn1nc(CCN2CCCC2)cc1Nc1cc(Nc2ccccc2C(=O)NC)c(Cl)cn1"
},
"smiles": "CCn1nc(CCN2CCCC2)cc1Nc1cc(Nc2ccccc2C(=O)NC)c(Cl)cn1",
"reactionStepId": "sa_3b0cddd056ef65c031ce4367",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140107131A1;0207;1514626\",\"rsmi\":\"Cl[c:16]1[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]2[c:24]([C:25](=[O:26])[NH:27][CH3:28])[cH:29][cH:30][cH:31][cH:32]2)[cH:33]1.[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH2:15]>C1COCCO1.CC(=O)O.CC(=O)O.O=C(O)O.[Cs+].[Cs+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH:15][c:16]1[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]2[c:24]([C:25](=[O:26])[NH:27][CH3:28])[cH:29][cH:30][cH:31][cH:32]2)[cH:33]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]2[c:24]([C:25](=[O:26])[NH:27][CH3:28])[cH:29][cH:30][cH:31][cH:32]2)[cH:33]1.[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH2:15]>C1COCCO1.CC(=O)O.CC(=O)O.O=C(O)O.[Cs+].[Cs+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH:15][c:16]1[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]2[c:24]([C:25](=[O:26])[NH:27][CH3:28])[cH:29][cH:30][cH:31][cH:32]2)[cH:33]1\"}",
"reactionStep": {
"id": "sa_3b0cddd056ef65c031ce4367",
"reactionHash": "9eacd618f9fb181f0d1dc21b94bf19cc6f3e9ee68e82d89340453e15b7a85e08"
},
"children": [
{
"id": "11507",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_0d172579d79bc9911dfafdb3",
"parentId": "11506",
"isLeaf": false,
"molecule": {
"id": "sa_0d172579d79bc9911dfafdb3",
"inchikey": "BNFBZXVAVRBANV-UHFFFAOYSA-N",
"smiles": "CCn1nc(CCN2CCCC2)cc1N"
},
"smiles": "CCn1nc(CCN2CCCC2)cc1N",
"reactionStepId": "sa_115f5de01ea48a60ecbdae08",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140107131A1;0205;1514625\",\"rsmi\":\"O=[C:7]([CH2:6][c:5]1[n:4][n:3]([CH2:2][CH3:1])[c:14]([NH2:15])[cH:13]1)[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH2:15]\"},\"mapped_reaction_smiles\":\"O=[C:7]([CH2:6][c:5]1[n:4][n:3]([CH2:2][CH3:1])[c:14]([NH2:15])[cH:13]1)[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH2:15]\"}",
"reactionStep": {
"id": "sa_115f5de01ea48a60ecbdae08",
"reactionHash": "8c82712e3d2d282ea543a16c7bba89aa9737f647a209acdc7ab22e5fadc9f070"
},
"children": [
{
"id": "11508",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_1ec3078904c6ae29e31d7ccc",
"parentId": "11507",
"isLeaf": false,
"molecule": {
"id": "sa_1ec3078904c6ae29e31d7ccc",
"inchikey": "OQMKWBZWIAXWJR-UHFFFAOYSA-N",
"smiles": "CCn1nc(CC(=O)N2CCCC2)cc1N"
},
"smiles": "CCn1nc(CC(=O)N2CCCC2)cc1N",
"reactionStepId": "sa_0c7d2112bbc70fe0d865eff9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140107131A1;0203;1514624\",\"rsmi\":\"O=C(C(F)(F)F)[NH:16][c:15]1[n:3]([CH2:2][CH3:1])[n:4][c:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14]1>CO.Cl>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]1[NH2:16]\"},\"mapped_reaction_smiles\":\"O=C(C(F)(F)F)[NH:16][c:15]1[n:3]([CH2:2][CH3:1])[n:4][c:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14]1>CO.Cl>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]1[NH2:16]\"}",
"reactionStep": {
"id": "sa_0c7d2112bbc70fe0d865eff9",
"reactionHash": "70628d71d45e38f69c5c9ea1205b0aff5239ada125f48dfbd3d544fde7bf083a"
},
"children": [
{
"id": "11509",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_bd035dd3754f3cdc7520909a",
"parentId": "11508",
"isLeaf": true,
"molecule": {
"id": "sa_bd035dd3754f3cdc7520909a",
"inchikey": "SVCRLHIYRDANAB-UHFFFAOYSA-N",
"smiles": "CCn1nc(CC(=O)N2CCCC2)cc1NC(=O)C(F)(F)F"
},
"smiles": "CCn1nc(CC(=O)N2CCCC2)cc1NC(=O)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "11510",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_37f6a77bd6fecba6a9c3a886",
"parentId": "11506",
"isLeaf": false,
"molecule": {
"id": "sa_37f6a77bd6fecba6a9c3a886",
"inchikey": "BTYUDXQEYQNBKQ-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl"
},
"smiles": "CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl",
"reactionStepId": "sa_e2dda22da3c1ef01956f8a4d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140107131A1;0146;1514607\",\"rsmi\":\"I[c:8]1[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[Cl:15].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:16][cH:17][cH:18][cH:19]1>C1COCCO1.CC(=O)O.CC(=O)O.O=P(O)(O)O.[K+].[K+].[K+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2Oc2ccccc2P(c2ccccc2)c2ccccc2)cc1>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[Cl:15])[cH:16][cH:17][cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"I[c:8]1[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[Cl:15].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:16][cH:17][cH:18][cH:19]1>C1COCCO1.CC(=O)O.CC(=O)O.O=P(O)(O)O.[K+].[K+].[K+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2Oc2ccccc2P(c2ccccc2)c2ccccc2)cc1>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[Cl:15])[cH:16][cH:17][cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_e2dda22da3c1ef01956f8a4d",
"reactionHash": "b0f4aeabbf5dccb46e67eece7c92765691da3aa5e54244d496228a84c8b4d0da"
},
"children": [
{
"id": "11511",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_81dd95302d03a14727702af2",
"parentId": "11510",
"isLeaf": true,
"molecule": {
"id": "sa_81dd95302d03a14727702af2",
"inchikey": "IWCZLVRNVBSAPH-UHFFFAOYSA-N",
"smiles": "Clc1cc(I)c(Cl)cn1"
},
"smiles": "Clc1cc(I)c(Cl)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11512",
"routeId": "sa_c7e76042829662fc05e42327",
"moleculeId": "sa_c54c147e2492132fa33e5541",
"parentId": "11510",
"isLeaf": true,
"molecule": {
"id": "sa_c54c147e2492132fa33e5541",
"inchikey": "KIMWOULVHFLJIU-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1ccccc1N"
},
"smiles": "CNC(=O)c1ccccc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}