Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C[C@@H](CCN1CC(N2CCOC[C@H]2CCO)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1
InChiKey
CIUQAWZEZAFAMC-CJFMBICVSA-N
Route Signature
a7cb5dfb59596e509395f8f81b37f5b9c8ce09337d76a007d0a27f55fd480720
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_8ec173c144c48daf91d62728",
"signature": "a7cb5dfb59596e509395f8f81b37f5b9c8ce09337d76a007d0a27f55fd480720",
"contentHash": "15419913e2373c78e1bfa349366cf9ac3f1b00f0fdaf0383af3159fd272e94dd",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_3bf699546bddf9d1f41fba0c",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00710",
"moleculeId": "sa_c98eb5f828aaa76b07f6154b",
"smiles": "CN(C[C@@H](CCN1CC(N2CCOC[C@H]2CCO)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c98eb5f828aaa76b07f6154b",
"inchikey": "CIUQAWZEZAFAMC-CJFMBICVSA-N",
"smiles": "CN(C[C@@H](CCN1CC(N2CCOC[C@H]2CCO)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9706",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_c98eb5f828aaa76b07f6154b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c98eb5f828aaa76b07f6154b",
"inchikey": "CIUQAWZEZAFAMC-CJFMBICVSA-N",
"smiles": "CN(C[C@@H](CCN1CC(N2CCOC[C@H]2CCO)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1"
},
"smiles": "CN(C[C@@H](CCN1CC(N2CCOC[C@H]2CCO)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1",
"reactionStepId": "sa_d821af95285f1958c5ebf99f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069346A1;0084;850272\",\"rsmi\":\"O=[CH:6][CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:27](=[O:28])[c:29]1[cH:30][c:31]([Br:32])[cH:33][c:34]([C:35]([F:36])([F:37])[F:38])[cH:39]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1.[NH:7]1[CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][C@H:15]2[CH2:16][CH2:17][OH:18])[CH2:19]1>CCN(CC)CC.CO.BC#N.Cl.Cl.[Na+].[Zn+2]>[CH3:1][N:2]([CH2:3][C@@H:4]([CH2:5][CH2:6][N:7]1[CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][C@H:15]2[CH2:16][CH2:17][OH:18])[CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1)[C:27](=[O:28])[c:29]1[cH:30][c:31]([Br:32])[cH:33][c:34]([C:35]([F:36])([F:37])[F:38])[cH:39]1\"},\"mapped_reaction_smiles\":\"O=[CH:6][CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:27](=[O:28])[c:29]1[cH:30][c:31]([Br:32])[cH:33][c:34]([C:35]([F:36])([F:37])[F:38])[cH:39]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1.[NH:7]1[CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][C@H:15]2[CH2:16][CH2:17][OH:18])[CH2:19]1>CCN(CC)CC.CO.BC#N.Cl.Cl.[Na+].[Zn+2]>[CH3:1][N:2]([CH2:3][C@@H:4]([CH2:5][CH2:6][N:7]1[CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][C@H:15]2[CH2:16][CH2:17][OH:18])[CH2:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1)[C:27](=[O:28])[c:29]1[cH:30][c:31]([Br:32])[cH:33][c:34]([C:35]([F:36])([F:37])[F:38])[cH:39]1\"}",
"reactionStep": {
"id": "sa_d821af95285f1958c5ebf99f",
"reactionHash": "fb52ded34abf25573bcbc31484052ce6cb30401866d12113e3258ed7fc85697a"
},
"children": [
{
"id": "9707",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_27771897b269e045b8efd523",
"parentId": "9706",
"isLeaf": false,
"molecule": {
"id": "sa_27771897b269e045b8efd523",
"inchikey": "UNMVUHSNHPGTPH-CYBMUJFWSA-N",
"smiles": "CN(C[C@@H](CC=O)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1"
},
"smiles": "CN(C[C@@H](CC=O)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1",
"reactionStepId": "sa_dbc5049cf54cc4b46cdc50c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069346A1;0108;850279\",\"rsmi\":\"C=[CH:6][CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:15](=[O:16])[c:17]1[cH:18][c:19]([Br:20])[cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1.O=[Os](=O)(=O)=[O:7]>CC(C)=O.C[N+]1([O-])CCOCC1.O.O=S(O)O.[Na+]>[CH3:1][N:2]([CH2:3][C@@H:4]([CH2:5][CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[C:15](=[O:16])[c:17]1[cH:18][c:19]([Br:20])[cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1\"},\"mapped_reaction_smiles\":\"C=[CH:6][CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:15](=[O:16])[c:17]1[cH:18][c:19]([Br:20])[cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1.O=[Os](=O)(=O)=[O:7]>CC(C)=O.C[N+]1([O-])CCOCC1.O.O=S(O)O.[Na+]>[CH3:1][N:2]([CH2:3][C@@H:4]([CH2:5][CH:6]=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[C:15](=[O:16])[c:17]1[cH:18][c:19]([Br:20])[cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1\"}",
"reactionStep": {
"id": "sa_dbc5049cf54cc4b46cdc50c1",
"reactionHash": "30943ef284c467dbc6c395bd403b7492d510799a6673a8515d8ef3b893b1b9d7"
},
"children": [
{
"id": "9708",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_42db6bd3dc142a44dd9502b9",
"parentId": "9707",
"isLeaf": true,
"molecule": {
"id": "sa_42db6bd3dc142a44dd9502b9",
"inchikey": "LDSNYMXLQWETFV-CQSZACIVSA-N",
"smiles": "C=CC[C@H](CN(C)C(=O)c1cc(Br)cc(C(F)(F)F)c1)c1ccc(F)cc1"
},
"smiles": "C=CC[C@H](CN(C)C(=O)c1cc(Br)cc(C(F)(F)F)c1)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9709",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_b09447f6ab7ffdf98f3195fb",
"parentId": "9707",
"isLeaf": true,
"molecule": {
"id": "sa_b09447f6ab7ffdf98f3195fb",
"inchikey": "VUVGYHUDAICLFK-UHFFFAOYSA-N",
"smiles": "[O]=[Os](=[O])(=[O])=[O]"
},
"smiles": "[O]=[Os](=[O])(=[O])=[O]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9710",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_e01f897022072d56fe0af667",
"parentId": "9706",
"isLeaf": false,
"molecule": {
"id": "sa_e01f897022072d56fe0af667",
"inchikey": "YUOOBZKKIYQPGJ-MRVPVSSYSA-N",
"smiles": "OCC[C@@H]1COCCN1C1CNC1"
},
"smiles": "OCC[C@@H]1COCCN1C1CNC1",
"reactionStepId": "sa_dc2fe2e27b2ad733ff765498",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069346A1;0116;850285\",\"rsmi\":\"c1ccc(C(c2ccccc2)[N:12]2[CH2:11][CH:10]([N:9]3[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:5][O:6][CH2:7][CH2:8]3)[CH2:13]2)cc1>CC(=O)O.CCO.O.O.[Pd+2]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH:10]1[CH2:11][NH:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"c1ccc(C(c2ccccc2)[N:12]2[CH2:11][CH:10]([N:9]3[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:5][O:6][CH2:7][CH2:8]3)[CH2:13]2)cc1>CC(=O)O.CCO.O.O.[Pd+2]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH:10]1[CH2:11][NH:12][CH2:13]1\"}",
"reactionStep": {
"id": "sa_dc2fe2e27b2ad733ff765498",
"reactionHash": "a9f98e9edc4e46df4a821b49fb7eaf9380fe0a0efdbc35075f05fa77fee73cae"
},
"children": [
{
"id": "9711",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_17b11fa7c1340d906da36a19",
"parentId": "9710",
"isLeaf": false,
"molecule": {
"id": "sa_17b11fa7c1340d906da36a19",
"inchikey": "CBJMFTSWXDQEGX-HXUWFJFHSA-N",
"smiles": "OCC[C@@H]1COCCN1C1CN(C(c2ccccc2)c2ccccc2)C1"
},
"smiles": "OCC[C@@H]1COCCN1C1CN(C(c2ccccc2)c2ccccc2)C1",
"reactionStepId": "sa_fb1ac8e766840b6713f56ba9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069346A1;0115;850284\",\"rsmi\":\"O=[C:10]1[CH2:11][N:12]([CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1.[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][NH:9]1>CC(=O)O.CO.CN(C)C.BC#N>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH:10]1[CH2:11][N:12]([CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1\"},\"mapped_reaction_smiles\":\"O=[C:10]1[CH2:11][N:12]([CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1.[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][NH:9]1>CC(=O)O.CO.CN(C)C.BC#N>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH:10]1[CH2:11][N:12]([CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26]1\"}",
"reactionStep": {
"id": "sa_fb1ac8e766840b6713f56ba9",
"reactionHash": "3db4afb0267d746eeec4876f218bd9eb5ef8190c29686aa3ba6ae7ffd62ae090"
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"children": [
{
"id": "9712",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_af06f85da4614c85edde9d01",
"parentId": "9711",
"isLeaf": true,
"molecule": {
"id": "sa_af06f85da4614c85edde9d01",
"inchikey": "AVUDXLOVIBJFQA-UHFFFAOYSA-N",
"smiles": "O=C1CN(C(c2ccccc2)c2ccccc2)C1"
},
"smiles": "O=C1CN(C(c2ccccc2)c2ccccc2)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9713",
"routeId": "sa_8ec173c144c48daf91d62728",
"moleculeId": "sa_2b1ddf8134adcfc057d9b735",
"parentId": "9711",
"isLeaf": false,
"molecule": {
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"inchikey": "TVPDWWYLCZDJKD-ZCFIWIBFSA-N",
"smiles": "OCC[C@@H]1COCCN1"
},
"smiles": "OCC[C@@H]1COCCN1",
"reactionStepId": "sa_0018654333ebacbaa2cfb8e4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100069346A1;0114;850283\",\"rsmi\":\"c1ccc(C[N:9]2[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:5][O:6][CH2:7][CH2:8]2)cc1>CC(=O)O.CCO.O.O.[Pd+2]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][NH:9]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:9]2[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:5][O:6][CH2:7][CH2:8]2)cc1>CC(=O)O.CCO.O.O.[Pd+2]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][NH:9]1\"}",
"reactionStep": {
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"children": [
{
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"parentId": "9713",
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"molecule": {
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"inchikey": "ORVPSSNVIVQGDL-CYBMUJFWSA-N",
"smiles": "OCC[C@@H]1COCCN1Cc1ccccc1"
},
"smiles": "OCC[C@@H]1COCCN1Cc1ccccc1",
"reactionStepId": "sa_45b66d448317581ca933cac0",
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"metadata": "{\"annotations\":{\"ID\":\"US20100069346A1;0113;850282\",\"rsmi\":\"CO[C:2](=[O:1])[CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>CCOC(C)=O.CCOCC.O=C(O)O.O=P(O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[K+].[Li+].[Na+]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"CO[C:2](=[O:1])[CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>CCOC(C)=O.CCOCC.O=C(O)O.O=P(O)(O)O.[Al+3].[HH].[HH].[HH].[HH].[K+].[Li+].[Na+]>[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:5][O:6][CH2:7][CH2:8][N:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1\"}",
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"children": [
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"molecule": {
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"smiles": "COC(=O)C[C@@H]1COCCN1Cc1ccccc1"
},
"smiles": "COC(=O)C[C@@H]1COCCN1Cc1ccccc1",
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]
}
]
}
]
}
]
}
]
}
}