Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(-c2ccc(C)o2)cc1Cl
InChiKey
IVITYWXJLJXMDX-IYBDPMFKSA-N
Route Signature
e45fb5c9c9ac98dfdaae0e48f43d5d2690afb57295b89d5ce54a895e5b7f7ecb
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_f3a0695aeac9b8865ac17729",
"signature": "e45fb5c9c9ac98dfdaae0e48f43d5d2690afb57295b89d5ce54a895e5b7f7ecb",
"contentHash": "28463e1c872c519d699bb3e8dfe9a01db0795e6a6580d43f4adbe55e65059b14",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_9b7f437c3fed357762110c32",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-05458",
"moleculeId": "sa_77575882ab4136a221512292",
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(-c2ccc(C)o2)cc1Cl",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_77575882ab4136a221512292",
"inchikey": "IVITYWXJLJXMDX-IYBDPMFKSA-N",
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(-c2ccc(C)o2)cc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "7696",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_77575882ab4136a221512292",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_77575882ab4136a221512292",
"inchikey": "IVITYWXJLJXMDX-IYBDPMFKSA-N",
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(-c2ccc(C)o2)cc1Cl"
},
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(-c2ccc(C)o2)cc1Cl",
"reactionStepId": "sa_94f9a9e3ee869f66b356eb9a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07381728B2;0736;840187\",\"rsmi\":\"Br[c:13]1[cH:12][c:10]([Cl:11])[c:9]([S:6]([NH:5][c:4]2[c:3]([O:2][CH3:1])[cH:33][cH:32][c:23]([N:24]3[CH2:25][C@H:26]([CH3:27])[NH:28][C@H:29]([CH3:30])[CH2:31]3)[cH:22]2)(=[O:7])=[O:8])[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([CH3:18])[o:19]1>CC(C)(C)O.COCCOC.O.[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[c:10]([Cl:11])[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([CH3:18])[o:19]3)[cH:20][cH:21]2)[cH:22][c:23]([N:24]2[CH2:25][C@H:26]([CH3:27])[NH:28][C@H:29]([CH3:30])[CH2:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[cH:12][c:10]([Cl:11])[c:9]([S:6]([NH:5][c:4]2[c:3]([O:2][CH3:1])[cH:33][cH:32][c:23]([N:24]3[CH2:25][C@H:26]([CH3:27])[NH:28][C@H:29]([CH3:30])[CH2:31]3)[cH:22]2)(=[O:7])=[O:8])[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([CH3:18])[o:19]1>CC(C)(C)O.COCCOC.O.[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[c:10]([Cl:11])[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([CH3:18])[o:19]3)[cH:20][cH:21]2)[cH:22][c:23]([N:24]2[CH2:25][C@H:26]([CH3:27])[NH:28][C@H:29]([CH3:30])[CH2:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_94f9a9e3ee869f66b356eb9a",
"reactionHash": "7de8e701fbfca1096fffa894e6ef7496c48334bfb400901b8773ff2fcf60a2be"
},
"children": [
{
"id": "7697",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_8a91914dcce073c2e52fbac8",
"parentId": "7696",
"isLeaf": false,
"molecule": {
"id": "sa_8a91914dcce073c2e52fbac8",
"inchikey": "BDAQLMBXLLVVGN-BETUJISGSA-N",
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(Br)cc1Cl"
},
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1NS(=O)(=O)c1ccc(Br)cc1Cl",
"reactionStepId": "sa_882d20cfc2d7b4b7b3dfabf1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07381728B2;0621;840154\",\"rsmi\":\"Cl[S:6](=[O:7])(=[O:8])[c:9]1[c:10]([Cl:11])[cH:12][c:13]([Br:14])[cH:15][cH:16]1.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:17][c:18]([N:19]2[CH2:20][C@H:21]([CH3:22])[NH:23][C@H:24]([CH3:25])[CH2:26]2)[cH:27][cH:28]1>CN1CCOCC1.ClCCl>[CH3:1][O:2][c:3]1[c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[c:10]([Cl:11])[cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][c:18]([N:19]2[CH2:20][C@H:21]([CH3:22])[NH:23][C@H:24]([CH3:25])[CH2:26]2)[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"Cl[S:6](=[O:7])(=[O:8])[c:9]1[c:10]([Cl:11])[cH:12][c:13]([Br:14])[cH:15][cH:16]1.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:17][c:18]([N:19]2[CH2:20][C@H:21]([CH3:22])[NH:23][C@H:24]([CH3:25])[CH2:26]2)[cH:27][cH:28]1>CN1CCOCC1.ClCCl>[CH3:1][O:2][c:3]1[c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[c:10]([Cl:11])[cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][c:18]([N:19]2[CH2:20][C@H:21]([CH3:22])[NH:23][C@H:24]([CH3:25])[CH2:26]2)[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_882d20cfc2d7b4b7b3dfabf1",
"reactionHash": "8afea6a5edc6adee81e04bf12573244f33dd7a2b2736048468c17668afcb7e80"
},
"children": [
{
"id": "7698",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_3181a5656c79891a4006c48d",
"parentId": "7697",
"isLeaf": true,
"molecule": {
"id": "sa_3181a5656c79891a4006c48d",
"inchikey": "OECYEHWJPRPCOH-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccc(Br)cc1Cl"
},
"smiles": "O=S(=O)(Cl)c1ccc(Br)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7699",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_146eb444f6a6f4bb7ff43459",
"parentId": "7697",
"isLeaf": false,
"molecule": {
"id": "sa_146eb444f6a6f4bb7ff43459",
"inchikey": "SIZILKHACPJUJH-AOOOYVTPSA-N",
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1N"
},
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1N",
"reactionStepId": "sa_fd44d8844ad9bfbc112ce4ba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07381728B2;0500;840115\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([O:2][CH3:1])[cH:17][cH:16][c:7]([N:8]2[CH2:9][C@H:10]([CH3:11])[NH:12][C@H:13]([CH3:14])[CH2:15]2)[cH:6]1>CCO.[Pd]>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N:8]2[CH2:9][C@H:10]([CH3:11])[NH:12][C@H:13]([CH3:14])[CH2:15]2)[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([O:2][CH3:1])[cH:17][cH:16][c:7]([N:8]2[CH2:9][C@H:10]([CH3:11])[NH:12][C@H:13]([CH3:14])[CH2:15]2)[cH:6]1>CCO.[Pd]>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N:8]2[CH2:9][C@H:10]([CH3:11])[NH:12][C@H:13]([CH3:14])[CH2:15]2)[cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_fd44d8844ad9bfbc112ce4ba",
"reactionHash": "da6bffc75af534c0a48da3affa714553d575cbcf1d076d22cfb3c13d963ed2cf"
},
"children": [
{
"id": "7700",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_fd6fa0678bde8cfefd466cec",
"parentId": "7699",
"isLeaf": false,
"molecule": {
"id": "sa_fd6fa0678bde8cfefd466cec",
"inchikey": "WWODBTHXAOGIAU-AOOOYVTPSA-N",
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-]"
},
"smiles": "COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-]",
"reactionStepId": "sa_56c251045bceec3c6f3c1e63",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07381728B2;0498;840114\",\"rsmi\":\"Br[c:9]1[cH:8][c:4]([N+:5](=[O:6])[O-:7])[c:3]([O:2][CH3:1])[cH:19][cH:18]1.[NH:10]1[CH2:11][C@@H:12]([CH3:13])[NH:14][C@@H:15]([CH3:16])[CH2:17]1>C1COCCO1.CC(=O)O.CC(=O)O.O=C(O)O.[Cs+].[Cs+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([N:10]2[CH2:11][C@H:12]([CH3:13])[NH:14][C@H:15]([CH3:16])[CH2:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][c:4]([N+:5](=[O:6])[O-:7])[c:3]([O:2][CH3:1])[cH:19][cH:18]1.[NH:10]1[CH2:11][C@@H:12]([CH3:13])[NH:14][C@@H:15]([CH3:16])[CH2:17]1>C1COCCO1.CC(=O)O.CC(=O)O.O=C(O)O.[Cs+].[Cs+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([N:10]2[CH2:11][C@H:12]([CH3:13])[NH:14][C@H:15]([CH3:16])[CH2:17]2)[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_56c251045bceec3c6f3c1e63",
"reactionHash": "a7a6d0dce8f4429f2b5f0e5f608766bd436fdd488f4fa5ac51e0a560c789d1d4"
},
"children": [
{
"id": "7701",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_a380e3aae47a9322cd3f1ed7",
"parentId": "7700",
"isLeaf": true,
"molecule": {
"id": "sa_a380e3aae47a9322cd3f1ed7",
"inchikey": "IFNWESYYDINUHV-OLQVQODUSA-N",
"smiles": "C[C@@H]1CNC[C@H](C)N1"
},
"smiles": "C[C@@H]1CNC[C@H](C)N1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "7702",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_4dc3460e4a1f84e4a9e5823f",
"parentId": "7700",
"isLeaf": true,
"molecule": {
"id": "sa_4dc3460e4a1f84e4a9e5823f",
"inchikey": "ORBHQHXVVMZIDP-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)cc1[N+](=O)[O-]"
},
"smiles": "COc1ccc(Br)cc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "7703",
"routeId": "sa_f3a0695aeac9b8865ac17729",
"moleculeId": "sa_e07d25180bc9b746028b8005",
"parentId": "7696",
"isLeaf": true,
"molecule": {
"id": "sa_e07d25180bc9b746028b8005",
"inchikey": "LMJIDBVSSSPRII-UHFFFAOYSA-N",
"smiles": "Cc1ccc(B(O)O)o1"
},
"smiles": "Cc1ccc(B(O)O)o1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}