Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)C(C)(C)C)ccc3Cl)nc2cc1Cl
InChiKey
SYKYLWLREXOYMH-UHFFFAOYSA-N
Route Signature
202580708923c79052b1f8f56a92f43f211897128cb37506a7528541d363904d
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_00457a5c60f5f29e71a931b1",
"signature": "202580708923c79052b1f8f56a92f43f211897128cb37506a7528541d363904d",
"contentHash": "03aed60f4e6a81bd8b837699f2281310c852932f28ae6805437a4989af1d17e1",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_996d19d88b804cc7b28a67bf",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02230",
"moleculeId": "sa_174dec813eb919b6a4bbff8b",
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)C(C)(C)C)ccc3Cl)nc2cc1Cl",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_174dec813eb919b6a4bbff8b",
"inchikey": "SYKYLWLREXOYMH-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)C(C)(C)C)ccc3Cl)nc2cc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14696",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_174dec813eb919b6a4bbff8b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_174dec813eb919b6a4bbff8b",
"inchikey": "SYKYLWLREXOYMH-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)C(C)(C)C)ccc3Cl)nc2cc1Cl"
},
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)C(C)(C)C)ccc3Cl)nc2cc1Cl",
"reactionStepId": "sa_9f725897c4d5408354e25ce3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08466186B2;0468;1332855\",\"rsmi\":\"Cl[C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33].[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:34]1)[nH:35]2>C1CCOC1>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34]1)[nH:35]2\"},\"mapped_reaction_smiles\":\"Cl[C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33].[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:34]1)[nH:35]2>C1CCOC1>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34]1)[nH:35]2\"}",
"reactionStep": {
"id": "sa_9f725897c4d5408354e25ce3",
"reactionHash": "e025e6623629a7b2cb8c05df10a1ee56d0fc2da59bca52973c20f849360dee41"
},
"children": [
{
"id": "14697",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_c4a4e8fc10f9a494534f9123",
"parentId": "14696",
"isLeaf": true,
"molecule": {
"id": "sa_c4a4e8fc10f9a494534f9123",
"inchikey": "JVSFQJZRHXAUGT-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C(=O)Cl"
},
"smiles": "CC(C)(C)C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14698",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_2e4a3e4a491abc2b058a9c1c",
"parentId": "14696",
"isLeaf": false,
"molecule": {
"id": "sa_2e4a3e4a491abc2b058a9c1c",
"inchikey": "MZUMVQIHPNVFTD-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CN)ccc3Cl)nc2cc1Cl"
},
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CN)ccc3Cl)nc2cc1Cl",
"reactionStepId": "sa_693394b324216cd75885ab9d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08466186B2;0466;1332854\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:27][CH2:26][c:25]1[cH:24][cH:23][c:21]([Cl:22])[c:20]([NH:19][c:18]2[n:17][c:13]3[c:12]([cH:11][c:10]([N:9]4[CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][CH2:8]4)[c:15]([Cl:16])[cH:14]3)[nH:29]2)[cH:28]1>C1CCOC1.Cl>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:28]1)[nH:29]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:27][CH2:26][c:25]1[cH:24][cH:23][c:21]([Cl:22])[c:20]([NH:19][c:18]2[n:17][c:13]3[c:12]([cH:11][c:10]([N:9]4[CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][CH2:8]4)[c:15]([Cl:16])[cH:14]3)[nH:29]2)[cH:28]1>C1CCOC1.Cl>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:28]1)[nH:29]2\"}",
"reactionStep": {
"id": "sa_693394b324216cd75885ab9d",
"reactionHash": "22cd78c0cfd3d6f63ccc10f17edba5b3eb41a690fc62b8ee1a18450a61311469"
},
"children": [
{
"id": "14699",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_5b6d64ebdbd4535404d54d74",
"parentId": "14698",
"isLeaf": false,
"molecule": {
"id": "sa_5b6d64ebdbd4535404d54d74",
"inchikey": "UWYXPMZVVVNWGB-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)OC(C)(C)C)ccc3Cl)nc2cc1Cl"
},
"smiles": "CN(C)CC1CCCN1c1cc2[nH]c(Nc3cc(CNC(=O)OC(C)(C)C)ccc3Cl)nc2cc1Cl",
"reactionStepId": "sa_0592ab50f32a267f24237023",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08466186B2;0464;1332853\",\"rsmi\":\"S=[C:18]=[N:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]([NH2:36])[c:13]([NH2:17])[cH:14][c:15]1[Cl:16]>CN(C)C=O>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1)[nH:36]2\"},\"mapped_reaction_smiles\":\"S=[C:18]=[N:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]([NH2:36])[c:13]([NH2:17])[cH:14][c:15]1[Cl:16]>CN(C)C=O>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Cl:16])[n:17][c:18]([NH:19][c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1)[nH:36]2\"}",
"reactionStep": {
"id": "sa_0592ab50f32a267f24237023",
"reactionHash": "87a9362eb16a89c055ca92cb90783e1206de040301315e9f2abebbbe451f8f0c"
},
"children": [
{
"id": "14700",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_201ea119ae0f43f547f567b1",
"parentId": "14699",
"isLeaf": true,
"molecule": {
"id": "sa_201ea119ae0f43f547f567b1",
"inchikey": "NGPOVBWHFCJLAB-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCc1ccc(Cl)c(N=C=S)c1"
},
"smiles": "CC(C)(C)OC(=O)NCc1ccc(Cl)c(N=C=S)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14701",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_84e229f7fe56cf1a933c9163",
"parentId": "14699",
"isLeaf": false,
"molecule": {
"id": "sa_84e229f7fe56cf1a933c9163",
"inchikey": "VOQKCWMAUIFRIT-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1c1cc(N)c(N)cc1Cl"
},
"smiles": "CN(C)CC1CCCN1c1cc(N)c(N)cc1Cl",
"reactionStepId": "sa_5c3b2d7ba3052e07da1e22d0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08466186B2;0462;1332852\",\"rsmi\":\"O=[N+:15]([O-])[c:14]1[cH:13][c:11]([Cl:12])[c:10]([N:9]2[CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][CH2:8]2)[cH:18][c:16]1[NH2:17]>CCOC(C)=O.[Ni]>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[c:11]([Cl:12])[cH:13][c:14]([NH2:15])[c:16]([NH2:17])[cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:15]([O-])[c:14]1[cH:13][c:11]([Cl:12])[c:10]([N:9]2[CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][CH2:8]2)[cH:18][c:16]1[NH2:17]>CCOC(C)=O.[Ni]>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[c:11]([Cl:12])[cH:13][c:14]([NH2:15])[c:16]([NH2:17])[cH:18]1\"}",
"reactionStep": {
"id": "sa_5c3b2d7ba3052e07da1e22d0",
"reactionHash": "e43f60424d43e8aa614e8845b0408ba96f79f2bb78306d0971d1dbef570467e4"
},
"children": [
{
"id": "14702",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_02510fd4b20684f8923a84f0",
"parentId": "14701",
"isLeaf": false,
"molecule": {
"id": "sa_02510fd4b20684f8923a84f0",
"inchikey": "HWUDWJALHDLWQA-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1c1cc(N)c([N+](=O)[O-])cc1Cl"
},
"smiles": "CN(C)CC1CCCN1c1cc(N)c([N+](=O)[O-])cc1Cl",
"reactionStepId": "sa_003955a9b8d07885ef969b6f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08466186B2;0460;1332851\",\"rsmi\":\"Cl[c:10]1[cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]1[Cl:20].[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][NH:9]1>CS(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]1[Cl:20]\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]1[Cl:20].[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][NH:9]1>CS(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[c:10]1[cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]1[Cl:20]\"}",
"reactionStep": {
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"reactionHash": "42cb9eeb99c359751a387638c5bc952855936b78fe63a92d77157c6a8c33ffc3"
},
"children": [
{
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"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_d92c28841ba1795016256918",
"parentId": "14702",
"isLeaf": true,
"molecule": {
"id": "sa_d92c28841ba1795016256918",
"inchikey": "FSGTULQLEVAYRS-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)c(Cl)cc1[N+](=O)[O-]"
},
"smiles": "Nc1cc(Cl)c(Cl)cc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "14704",
"routeId": "sa_00457a5c60f5f29e71a931b1",
"moleculeId": "sa_9aa537b86461eba67158a436",
"parentId": "14702",
"isLeaf": true,
"molecule": {
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"inchikey": "SGIJBHQBXMMPRH-UHFFFAOYSA-N",
"smiles": "CN(C)CC1CCCN1"
},
"smiles": "CN(C)CC1CCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
}
]
}
}