Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(C(=O)Nc2ccc(NCCc3ccccn3)cc2)c(N2CCCCC2)n1
InChiKey
QJJMHNFFKOIETB-UHFFFAOYSA-N
Route Signature
6596c063ea32a575aebbfc0c71667370c5a8a782e8229809be4bd0ff536abdce
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d2f963b85ee7c448aec0794d",
"signature": "6596c063ea32a575aebbfc0c71667370c5a8a782e8229809be4bd0ff536abdce",
"contentHash": "7da096560405db16144fe277dfb4bc20627246b657619a3e2594f268babb5c2c",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_e3f2be04dc01a027455c9b6b",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00796",
"moleculeId": "sa_6f43daeb60b54d9fc0eb00fd",
"smiles": "Cc1ccc(C(=O)Nc2ccc(NCCc3ccccn3)cc2)c(N2CCCCC2)n1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_6f43daeb60b54d9fc0eb00fd",
"inchikey": "QJJMHNFFKOIETB-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)Nc2ccc(NCCc3ccccn3)cc2)c(N2CCCCC2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13790",
"routeId": "sa_d2f963b85ee7c448aec0794d",
"moleculeId": "sa_6f43daeb60b54d9fc0eb00fd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6f43daeb60b54d9fc0eb00fd",
"inchikey": "QJJMHNFFKOIETB-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)Nc2ccc(NCCc3ccccn3)cc2)c(N2CCCCC2)n1"
},
"smiles": "Cc1ccc(C(=O)Nc2ccc(NCCc3ccccn3)cc2)c(N2CCCCC2)n1",
"reactionStepId": "sa_968001040088641a271cc4f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040133008A1;0603;170601\",\"rsmi\":\"CC(C)(C)OC(=O)[N:19]([c:18]1[cH:17][cH:16][c:15]([NH:14][C:12]([c:11]2[c:4]([N:5]3[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[n:3][c:2]([CH3:1])[cH:31][cH:30]2)=[O:13])[cH:29][cH:28]1)[CH2:20][CH2:21][c:22]1[n:23][cH:24][cH:25][cH:26][cH:27]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][cH:17][c:18]([NH:19][CH2:20][CH2:21][c:22]3[n:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29]2)[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:19]([c:18]1[cH:17][cH:16][c:15]([NH:14][C:12]([c:11]2[c:4]([N:5]3[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[n:3][c:2]([CH3:1])[cH:31][cH:30]2)=[O:13])[cH:29][cH:28]1)[CH2:20][CH2:21][c:22]1[n:23][cH:24][cH:25][cH:26][cH:27]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][cH:17][c:18]([NH:19][CH2:20][CH2:21][c:22]3[n:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29]2)[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_968001040088641a271cc4f1",
"reactionHash": "caeea844189f2094e7276596df911584f4786cc4a293bd4b7147cf848a5235d2"
},
"children": [
{
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"routeId": "sa_d2f963b85ee7c448aec0794d",
"moleculeId": "sa_c74dec7038f0e590dad30ce4",
"parentId": "13790",
"isLeaf": false,
"molecule": {
"id": "sa_c74dec7038f0e590dad30ce4",
"inchikey": "KYEKKMOQWGEWAM-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)Nc2ccc(N(CCc3ccccn3)C(=O)OC(C)(C)C)cc2)c(N2CCCCC2)n1"
},
"smiles": "Cc1ccc(C(=O)Nc2ccc(N(CCc3ccccn3)C(=O)OC(C)(C)C)cc2)c(N2CCCCC2)n1",
"reactionStepId": "sa_6be26aff908936f717d9ddf7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040133008A1;0601;170600\",\"rsmi\":\"Cl[c:31]1[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]3[n:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[cH:4][cH:3][c:2]([CH3:1])[n:38]1.[NH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1>C1CCOC1.CCOC(C)=O.O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]3[n:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[c:31]([N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[n:38]1\"},\"mapped_reaction_smiles\":\"Cl[c:31]1[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]3[n:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[cH:4][cH:3][c:2]([CH3:1])[n:38]1.[NH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1>C1CCOC1.CCOC(C)=O.O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]3[n:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[c:31]([N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[n:38]1\"}",
"reactionStep": {
"id": "sa_6be26aff908936f717d9ddf7",
"reactionHash": "b77fa4854fa7a2b64064108f01e548fa006e46317e50ce22e80004852557e68b"
},
"children": [
{
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"routeId": "sa_d2f963b85ee7c448aec0794d",
"moleculeId": "sa_6a0de4c39b276213037d4459",
"parentId": "13791",
"isLeaf": false,
"molecule": {
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"inchikey": "MQDIJTLBHUBIOJ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)Nc2ccc(N(CCc3ccccn3)C(=O)OC(C)(C)C)cc2)c(Cl)n1"
},
"smiles": "Cc1ccc(C(=O)Nc2ccc(N(CCc3ccccn3)C(=O)OC(C)(C)C)cc2)c(Cl)n1",
"reactionStepId": "sa_7dae88d659c2cd8f138373fc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040133008A1;0599;170599\",\"rsmi\":\"O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:33][c:31]1[Cl:32])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]2[n:17][cH:18][cH:19][cH:20][cH:21]2)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]1>CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.O.O.On1nnc2ccccc21>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]3[n:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[c:31]([Cl:32])[n:33]1\"},\"mapped_reaction_smiles\":\"O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:33][c:31]1[Cl:32])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]2[n:17][cH:18][cH:19][cH:20][cH:21]2)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]1>CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.O.O.On1nnc2ccccc21>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([N:13]([CH2:14][CH2:15][c:16]3[n:17][cH:18][cH:19][cH:20][cH:21]3)[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[c:31]([Cl:32])[n:33]1\"}",
"reactionStep": {
"id": "sa_7dae88d659c2cd8f138373fc",
"reactionHash": "e1f593ce18bf84fd6659ae5005e4399efc69602da533edea993e29c91b242737"
},
"children": [
{
"id": "13793",
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"moleculeId": "sa_52c7a874637740e28aaaae23",
"parentId": "13792",
"isLeaf": true,
"molecule": {
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"inchikey": "ACQXHCHKMFYDPM-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)O)c(Cl)n1"
},
"smiles": "Cc1ccc(C(=O)O)c(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "13794",
"routeId": "sa_d2f963b85ee7c448aec0794d",
"moleculeId": "sa_1d7983b32651bed0e6295bfd",
"parentId": "13792",
"isLeaf": false,
"molecule": {
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"inchikey": "GOESIEZFHDMACA-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N(CCc1ccccn1)c1ccc(N)cc1"
},
"smiles": "CC(C)(C)OC(=O)N(CCc1ccccn1)c1ccc(N)cc1",
"reactionStepId": "sa_b9ffc810898c02780d76b07c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040133008A1;0586;170597\",\"rsmi\":\"O=[N+:21]([O-])[c:20]1[cH:19][cH:18][c:17]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][c:11]2[n:12][cH:13][cH:14][cH:15][cH:16]2)[cH:23][cH:22]1>C.CCO.Cl[Fe](Cl)Cl.NN.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][c:11]1[n:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O=[N+:21]([O-])[c:20]1[cH:19][cH:18][c:17]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][c:11]2[n:12][cH:13][cH:14][cH:15][cH:16]2)[cH:23][cH:22]1>C.CCO.Cl[Fe](Cl)Cl.NN.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][c:11]1[n:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:22][cH:23]1\"}",
"reactionStep": {
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"reactionHash": "a6397bb1a893a3d1e7b73d8527119172a2d120ecb5c1f94bf3a5890cec3b5e13"
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"children": [
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"moleculeId": "sa_d8970c7a45d9cbb43d463f05",
"parentId": "13794",
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"molecule": {
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"inchikey": "HHMWSQPWRDKMQI-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N(CCc1ccccn1)c1ccc([N+](=O)[O-])cc1"
},
"smiles": "CC(C)(C)OC(=O)N(CCc1ccccn1)c1ccc([N+](=O)[O-])cc1",
"reactionStepId": "sa_d29599cd3faa6cddb3ca5a39",
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"metadata": "{\"annotations\":{\"ID\":\"US20040133008A1;0583;170596\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]([CH2:9][CH2:10][c:11]1[n:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1>C1CCOC1.CCN(CC)CC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][c:11]1[n:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]([CH2:9][CH2:10][c:11]1[n:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1>C1CCOC1.CCN(CC)CC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][c:11]1[n:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1\"}",
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"molecule": {
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"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
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{
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},
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{
"id": "13799",
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"smiles": "NCCc1ccccn1"
},
"smiles": "NCCc1ccccn1",
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}
]
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]
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]
}
]
},
{
"id": "13800",
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"molecule": {
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"inchikey": "NQRYJNQNLNOLGT-UHFFFAOYSA-N",
"smiles": "C1CCNCC1"
},
"smiles": "C1CCNCC1",
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}
]
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]
}
}