Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C[C@@H](CCN1CC(N2CCC(C(=O)N3CCC3)CC2)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1
InChiKey
OFWACLABIZNOCB-HSZRJFAPSA-N
Route Signature
0ec84879363f9b94ce03449dcafb450abcf29a0b698f8b1b6885d09b73492ebd
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_b6c97c7a71399c779e89e55f",
"signature": "0ec84879363f9b94ce03449dcafb450abcf29a0b698f8b1b6885d09b73492ebd",
"contentHash": "bf350b3d589724547ca220328af573524472c77187e7689967bca0baffbc0490",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_0ac6428b2a1a112458aaca16",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01712",
"moleculeId": "sa_d11b963fd2640a0f9be159f7",
"smiles": "CN(C[C@@H](CCN1CC(N2CCC(C(=O)N3CCC3)CC2)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d11b963fd2640a0f9be159f7",
"inchikey": "OFWACLABIZNOCB-HSZRJFAPSA-N",
"smiles": "CN(C[C@@H](CCN1CC(N2CCC(C(=O)N3CCC3)CC2)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10416",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_d11b963fd2640a0f9be159f7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d11b963fd2640a0f9be159f7",
"inchikey": "OFWACLABIZNOCB-HSZRJFAPSA-N",
"smiles": "CN(C[C@@H](CCN1CC(N2CCC(C(=O)N3CCC3)CC2)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1"
},
"smiles": "CN(C[C@@H](CCN1CC(N2CCC(C(=O)N3CCC3)CC2)C1)c1ccc(F)cc1)C(=O)c1cc(Br)cc(C(F)(F)F)c1",
"reactionStepId": "sa_2806512ca35b3821e3f57fb6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070270398A1;0049;519998\",\"rsmi\":\"O=[CH:6][CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:30](=[O:31])[c:32]1[cH:33][c:34]([Br:35])[cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1.[NH:7]1[CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][CH:13]([C:14](=[O:15])[N:16]3[CH2:17][CH2:18][CH2:19]3)[CH2:20][CH2:21]2)[CH2:22]1>CC(=O)OB(OC(C)=O)OC(C)=O.CCN(C(C)C)C(C)C.CO.ClCCl.[Na+]>[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][CH:13]([C:14](=[O:15])[N:16]3[CH2:17][CH2:18][CH2:19]3)[CH2:20][CH2:21]2)[CH2:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[C:30](=[O:31])[c:32]1[cH:33][c:34]([Br:35])[cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]1\"},\"mapped_reaction_smiles\":\"O=[CH:6][CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:30](=[O:31])[c:32]1[cH:33][c:34]([Br:35])[cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1.[NH:7]1[CH2:8][CH:9]([N:10]2[CH2:11][CH2:12][CH:13]([C:14](=[O:15])[N:16]3[CH2:17][CH2:18][CH2:19]3)[CH2:20][CH2:21]2)[CH2:22]1>CC(=O)OB(OC(C)=O)OC(C)=O.CCN(C(C)C)C(C)C.CO.ClCCl.[Na+]>[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][CH:13]([C:14](=[O:15])[N:16]3[CH2:17][CH2:18][CH2:19]3)[CH2:20][CH2:21]2)[CH2:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[C:30](=[O:31])[c:32]1[cH:33][c:34]([Br:35])[cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]1\"}",
"reactionStep": {
"id": "sa_2806512ca35b3821e3f57fb6",
"reactionHash": "8f58abce718764fde0cfe3523da9eca4de78bb5af7d136ad11798998c68a5f90"
},
"children": [
{
"id": "10417",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_84af3457feeec98abbf87e26",
"parentId": "10416",
"isLeaf": false,
"molecule": {
"id": "sa_84af3457feeec98abbf87e26",
"inchikey": "AATQMDRYCJBPMP-UHFFFAOYSA-N",
"smiles": "O=C(C1CCN(C2CNC2)CC1)N1CCC1"
},
"smiles": "O=C(C1CCN(C2CNC2)CC1)N1CCC1",
"reactionStepId": "sa_9b7dfdecc31ff0a0e3428a10",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070270398A1;0078;520007\",\"rsmi\":\"c1ccc(C(c2ccccc2)[N:9]2[CH2:8][CH:7]([N:6]3[CH2:5][CH2:4][CH:3]([C:2](=[O:1])[N:13]4[CH2:14][CH2:15][CH2:16]4)[CH2:12][CH2:11]3)[CH2:10]2)cc1>CCO.O=CO.N.O.O.[Pd+2]>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][NH:9][CH2:10]2)[CH2:11][CH2:12]1)[N:13]1[CH2:14][CH2:15][CH2:16]1\"},\"mapped_reaction_smiles\":\"c1ccc(C(c2ccccc2)[N:9]2[CH2:8][CH:7]([N:6]3[CH2:5][CH2:4][CH:3]([C:2](=[O:1])[N:13]4[CH2:14][CH2:15][CH2:16]4)[CH2:12][CH2:11]3)[CH2:10]2)cc1>CCO.O=CO.N.O.O.[Pd+2]>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][NH:9][CH2:10]2)[CH2:11][CH2:12]1)[N:13]1[CH2:14][CH2:15][CH2:16]1\"}",
"reactionStep": {
"id": "sa_9b7dfdecc31ff0a0e3428a10",
"reactionHash": "585f7ea2539326640c4041025df96a11e0e30ac2fea7f199e262f85bf6b95fb0"
},
"children": [
{
"id": "10418",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_80d57f3a935b2c0d335119fd",
"parentId": "10417",
"isLeaf": false,
"molecule": {
"id": "sa_80d57f3a935b2c0d335119fd",
"inchikey": "HPNCHLRKPTUFQG-UHFFFAOYSA-N",
"smiles": "O=C(C1CCN(C2CN(C(c3ccccc3)c3ccccc3)C2)CC1)N1CCC1"
},
"smiles": "O=C(C1CCN(C2CN(C(c3ccccc3)c3ccccc3)C2)CC1)N1CCC1",
"reactionStepId": "sa_3a1c535e092675b4ba72cc32",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070270398A1;0077;520006\",\"rsmi\":\"O=[C:7]1[CH2:8][N:9]([CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1.[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][NH:6][CH2:24][CH2:25]1)[N:26]1[CH2:27][CH2:28][CH2:29]1>CC(=O)O.CO>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][N:9]([CH:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[CH2:23]2)[CH2:24][CH2:25]1)[N:26]1[CH2:27][CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"O=[C:7]1[CH2:8][N:9]([CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1.[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][NH:6][CH2:24][CH2:25]1)[N:26]1[CH2:27][CH2:28][CH2:29]1>CC(=O)O.CO>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][N:9]([CH:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[CH2:23]2)[CH2:24][CH2:25]1)[N:26]1[CH2:27][CH2:28][CH2:29]1\"}",
"reactionStep": {
"id": "sa_3a1c535e092675b4ba72cc32",
"reactionHash": "e281433dd53f9d7d0f2a337552f394189337053a17e67ba560eb23f7b7336d4a"
},
"children": [
{
"id": "10419",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_af06f85da4614c85edde9d01",
"parentId": "10418",
"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": "10420",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_df561b3dcd01c77c998fbd81",
"parentId": "10418",
"isLeaf": false,
"molecule": {
"id": "sa_df561b3dcd01c77c998fbd81",
"inchikey": "MNHOGCGLTKEWMC-UHFFFAOYSA-N",
"smiles": "O=C(C1CCNCC1)N1CCC1"
},
"smiles": "O=C(C1CCNCC1)N1CCC1",
"reactionStepId": "sa_af74220c0059e3328d19a209",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070270398A1;0076;520005\",\"rsmi\":\"CC(C)(C)OC(=O)[N:6]1[CH2:5][CH2:4][CH:3]([C:2](=[O:1])[N:9]2[CH2:10][CH2:11][CH2:12]2)[CH2:8][CH2:7]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)[N:9]1[CH2:10][CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:6]1[CH2:5][CH2:4][CH:3]([C:2](=[O:1])[N:9]2[CH2:10][CH2:11][CH2:12]2)[CH2:8][CH2:7]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)[N:9]1[CH2:10][CH2:11][CH2:12]1\"}",
"reactionStep": {
"id": "sa_af74220c0059e3328d19a209",
"reactionHash": "97098e2d0137a5e58f48db0a15c1e9af8727d90cfd16b253e1397eff27876383"
},
"children": [
{
"id": "10421",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_05d5460dceb60e756edf59cd",
"parentId": "10420",
"isLeaf": false,
"molecule": {
"id": "sa_05d5460dceb60e756edf59cd",
"inchikey": "JGTDDPZXRFQITN-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(C(=O)N2CCC2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(C(=O)N2CCC2)CC1",
"reactionStepId": "sa_c9b93b6a50030e9d63883711",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070270398A1;0075;520004\",\"rsmi\":\"O[C:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:19][CH2:18]1)=[O:13].[NH:14]1[CH2:15][CH2:16][CH2:17]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.ClCCl.F[B-](F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][CH2:17]2)[CH2:18][CH2:19]1\"},\"mapped_reaction_smiles\":\"O[C:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:19][CH2:18]1)=[O:13].[NH:14]1[CH2:15][CH2:16][CH2:17]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.ClCCl.F[B-](F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][CH2:17]2)[CH2:18][CH2:19]1\"}",
"reactionStep": {
"id": "sa_c9b93b6a50030e9d63883711",
"reactionHash": "723c751ebed2eadff41906f9163f4bda3f9a36149aa1d6b20719e2f3aa059818"
},
"children": [
{
"id": "10422",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_3edf2a7ec025f1195f3401ef",
"parentId": "10421",
"isLeaf": true,
"molecule": {
"id": "sa_3edf2a7ec025f1195f3401ef",
"inchikey": "HONIICLYMWZJFZ-UHFFFAOYSA-N",
"smiles": "C1CNC1"
},
"smiles": "C1CNC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10423",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_dc27c9e8a13a89af1784a25f",
"parentId": "10421",
"isLeaf": true,
"molecule": {
"id": "sa_dc27c9e8a13a89af1784a25f",
"inchikey": "JWOHBPPVVDQMKB-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
},
{
"id": "10424",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_27771897b269e045b8efd523",
"parentId": "10416",
"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\":\"US20070270398A1;0073;520003\",\"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": {
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"reactionHash": "30943ef284c467dbc6c395bd403b7492d510799a6673a8515d8ef3b893b1b9d7"
},
"children": [
{
"id": "10425",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_42db6bd3dc142a44dd9502b9",
"parentId": "10424",
"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": "10426",
"routeId": "sa_b6c97c7a71399c779e89e55f",
"moleculeId": "sa_b09447f6ab7ffdf98f3195fb",
"parentId": "10424",
"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,
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"children": []
}
]
}
]
}
}