Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1CCC(c2nc3cc(Cl)ccc3o2)CN1
InChiKey
NPJRNIZGSITPRO-UHFFFAOYSA-N
Route Signature
e46d945b5bd6a4e1eb4115ec612f15ced3fa3d3744d0f3a2ec8b998bf45a014a
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_4c68ea7589f5e8f8af45b3e0",
"signature": "e46d945b5bd6a4e1eb4115ec612f15ced3fa3d3744d0f3a2ec8b998bf45a014a",
"contentHash": "800a595a2ef68ee11ef659f8c46b463992c296bdceb1d3fb7b4497ecc7b1c14e",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_f6c32599c72e591ca2561bab",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-03294",
"moleculeId": "sa_0eb21885c378c5f97eeda1f5",
"smiles": "CC1CCC(c2nc3cc(Cl)ccc3o2)CN1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_0eb21885c378c5f97eeda1f5",
"inchikey": "NPJRNIZGSITPRO-UHFFFAOYSA-N",
"smiles": "CC1CCC(c2nc3cc(Cl)ccc3o2)CN1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15084",
"routeId": "sa_4c68ea7589f5e8f8af45b3e0",
"moleculeId": "sa_0eb21885c378c5f97eeda1f5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0eb21885c378c5f97eeda1f5",
"inchikey": "NPJRNIZGSITPRO-UHFFFAOYSA-N",
"smiles": "CC1CCC(c2nc3cc(Cl)ccc3o2)CN1"
},
"smiles": "CC1CCC(c2nc3cc(Cl)ccc3o2)CN1",
"reactionStepId": "sa_6ceb4c5f84695a56e91e9e00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140228377A1;0138;1565025\",\"rsmi\":\"CC(C)(C)OC(=O)[N:17]1[CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[o:15]2)[CH2:16]1>CCOC(C)=O.CCOC(C)=O.Cl>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[o:15]2)[CH2:16][NH:17]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:17]1[CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[o:15]2)[CH2:16]1>CCOC(C)=O.CCOC(C)=O.Cl>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[o:15]2)[CH2:16][NH:17]1\"}",
"reactionStep": {
"id": "sa_6ceb4c5f84695a56e91e9e00",
"reactionHash": "f298cec6cec6ba9ce7345333ddd6834da5ed0a699b4bb245a18e2ab132736f14"
},
"children": [
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"routeId": "sa_4c68ea7589f5e8f8af45b3e0",
"moleculeId": "sa_ffc83afbe4597d754f9af039",
"parentId": "15084",
"isLeaf": false,
"molecule": {
"id": "sa_ffc83afbe4597d754f9af039",
"inchikey": "QBJWSICZZYHRGJ-UHFFFAOYSA-N",
"smiles": "CC1CCC(c2nc3cc(Cl)ccc3o2)CN1C(=O)OC(C)(C)C"
},
"smiles": "CC1CCC(c2nc3cc(Cl)ccc3o2)CN1C(=O)OC(C)(C)C",
"reactionStepId": "sa_4af4f73a044ed8b666036ec9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140228377A1;0135;1565024\",\"rsmi\":\"O=[C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:16]1)[NH:7][c:8]1[c:9]([OH:15])[cH:10][cH:11][c:12]([Cl:13])[cH:14]1>Cc1ccccc1.O.O=S(Cl)Cl.c1ccncc1>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[o:15]2)[CH2:16][N:17]1[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]\"},\"mapped_reaction_smiles\":\"O=[C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:16]1)[NH:7][c:8]1[c:9]([OH:15])[cH:10][cH:11][c:12]([Cl:13])[cH:14]1>Cc1ccccc1.O.O=S(Cl)Cl.c1ccncc1>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([c:6]2[n:7][c:8]3[c:9]([cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[o:15]2)[CH2:16][N:17]1[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]\"}",
"reactionStep": {
"id": "sa_4af4f73a044ed8b666036ec9",
"reactionHash": "bfeb6710dbc3b0a1cc224899ad3e77374882f0331e075c718234e95affad0bc5"
},
"children": [
{
"id": "15086",
"routeId": "sa_4c68ea7589f5e8f8af45b3e0",
"moleculeId": "sa_29da8564201c9f91b126e3ee",
"parentId": "15085",
"isLeaf": false,
"molecule": {
"id": "sa_29da8564201c9f91b126e3ee",
"inchikey": "GGIVZUFOUISIFC-UHFFFAOYSA-N",
"smiles": "CC1CCC(C(=O)Nc2cc(Cl)ccc2O)CN1C(=O)OC(C)(C)C"
},
"smiles": "CC1CCC(C(=O)Nc2cc(Cl)ccc2O)CN1C(=O)OC(C)(C)C",
"reactionStepId": "sa_72ce60ac7217594d6318c469",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140228377A1;0132;1565023\",\"rsmi\":\"O[C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:17]1)=[O:7].[NH2:8][c:9]1[c:10]([OH:11])[cH:12][cH:13][c:14]([Cl:15])[cH:16]1>CCO.COc1nc(OC)nc([N+]2(C)CCOCC2)n1.Cl>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[NH:8][c:9]2[c:10]([OH:11])[cH:12][cH:13][c:14]([Cl:15])[cH:16]2)[CH2:17][N:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]\"},\"mapped_reaction_smiles\":\"O[C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:17]1)=[O:7].[NH2:8][c:9]1[c:10]([OH:11])[cH:12][cH:13][c:14]([Cl:15])[cH:16]1>CCO.COc1nc(OC)nc([N+]2(C)CCOCC2)n1.Cl>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[NH:8][c:9]2[c:10]([OH:11])[cH:12][cH:13][c:14]([Cl:15])[cH:16]2)[CH2:17][N:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]\"}",
"reactionStep": {
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"reactionHash": "f088508af4a7f0f8c9c1b0da5dcf2047aded57580d4702905ab18cfa5d2a0ba2"
},
"children": [
{
"id": "15087",
"routeId": "sa_4c68ea7589f5e8f8af45b3e0",
"moleculeId": "sa_d3740ff904e96aea10ddd577",
"parentId": "15086",
"isLeaf": true,
"molecule": {
"id": "sa_d3740ff904e96aea10ddd577",
"inchikey": "SWFNPENEBHAHEB-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)ccc1O"
},
"smiles": "Nc1cc(Cl)ccc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "15088",
"routeId": "sa_4c68ea7589f5e8f8af45b3e0",
"moleculeId": "sa_2398a272fa0d612c6073cb46",
"parentId": "15086",
"isLeaf": false,
"molecule": {
"id": "sa_2398a272fa0d612c6073cb46",
"inchikey": "TZCMQIKRCZLVQN-UHFFFAOYSA-N",
"smiles": "CC1CCC(C(=O)O)CN1C(=O)OC(C)(C)C"
},
"smiles": "CC1CCC(C(=O)O)CN1C(=O)OC(C)(C)C",
"reactionStepId": "sa_3dc8f207b72295678c9a0663",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140228377A1;0129;1565022\",\"rsmi\":\"C[O:8][C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:9]1)=[O:7]>C1CCOC1.O.O.[Li]O>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]\"},\"mapped_reaction_smiles\":\"C[O:8][C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:9]1)=[O:7]>C1CCOC1.O.O.[Li]O>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]\"}",
"reactionStep": {
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"reactionHash": "ab2345a891daa2697a62bcc22c6ebaab7754a331a3815de31a6b036b2bea330b"
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"children": [
{
"id": "15089",
"routeId": "sa_4c68ea7589f5e8f8af45b3e0",
"moleculeId": "sa_90682383c5e5615368b58b03",
"parentId": "15088",
"isLeaf": true,
"molecule": {
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"inchikey": "HDRXORRYMWSTTC-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CCC(C)N(C(=O)OC(C)(C)C)C1"
},
"smiles": "COC(=O)C1CCC(C)N(C(=O)OC(C)(C)C)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
}
]
}
}