Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)C1CCC(NC(=O)c2ccc(Oc3cc4c(cc3Cl)C(C(=O)O)CCO4)cc2)CC1
InChiKey
KCLHUHUYVJRBPK-UHFFFAOYSA-N
Route Signature
dd6b0fd9f218727c00636c7b14da48fdfee3d1fe811f4efdfd55daf3edb7fbe8
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_2778172ed2b4c729f44659c4",
"signature": "dd6b0fd9f218727c00636c7b14da48fdfee3d1fe811f4efdfd55daf3edb7fbe8",
"contentHash": "ad5b6faf00d03c2a05009c1dd643d348962fe51a4cf5de6214abe9832ff10296",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_6d181637264385c33be716dc",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-04936",
"moleculeId": "sa_c892a8bed9e29aa2ea230b8c",
"smiles": "CC(C)(C)C1CCC(NC(=O)c2ccc(Oc3cc4c(cc3Cl)C(C(=O)O)CCO4)cc2)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c892a8bed9e29aa2ea230b8c",
"inchikey": "KCLHUHUYVJRBPK-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C1CCC(NC(=O)c2ccc(Oc3cc4c(cc3Cl)C(C(=O)O)CCO4)cc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15603",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_c892a8bed9e29aa2ea230b8c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c892a8bed9e29aa2ea230b8c",
"inchikey": "KCLHUHUYVJRBPK-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C1CCC(NC(=O)c2ccc(Oc3cc4c(cc3Cl)C(C(=O)O)CCO4)cc2)CC1"
},
"smiles": "CC(C)(C)C1CCC(NC(=O)c2ccc(Oc3cc4c(cc3Cl)C(C(=O)O)CCO4)cc2)CC1",
"reactionStepId": "sa_91f9f02971d28b8b45fd6eb9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08716498B2;1107;1455809\",\"rsmi\":\"CC[O:30][C:28]([CH:27]1[c:21]2[cH:20][c:18]([Cl:19])[c:17]([O:16][c:15]3[cH:14][cH:13][c:12]([C:10]([NH:9][CH:8]4[CH2:7][CH2:6][CH:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:34][CH2:33]4)=[O:11])[cH:32][cH:31]3)[cH:23][c:22]2[O:24][CH2:25][CH2:26]1)=[O:29]>C1CCOC1.CO.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH2:7][CH:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[c:18]([Cl:19])[cH:20][c:21]4[c:22]([cH:23]3)[O:24][CH2:25][CH2:26][CH:27]4[C:28](=[O:29])[OH:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"CC[O:30][C:28]([CH:27]1[c:21]2[cH:20][c:18]([Cl:19])[c:17]([O:16][c:15]3[cH:14][cH:13][c:12]([C:10]([NH:9][CH:8]4[CH2:7][CH2:6][CH:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:34][CH2:33]4)=[O:11])[cH:32][cH:31]3)[cH:23][c:22]2[O:24][CH2:25][CH2:26]1)=[O:29]>C1CCOC1.CO.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH2:7][CH:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[c:18]([Cl:19])[cH:20][c:21]4[c:22]([cH:23]3)[O:24][CH2:25][CH2:26][CH:27]4[C:28](=[O:29])[OH:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_91f9f02971d28b8b45fd6eb9",
"reactionHash": "7de919c65995a4feeecc02e15ee264db5bfbace6623bca3c4f9454d864b1fe10"
},
"children": [
{
"id": "15604",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_b836f9ad3e48574e9544efcb",
"parentId": "15603",
"isLeaf": false,
"molecule": {
"id": "sa_b836f9ad3e48574e9544efcb",
"inchikey": "QMQSBDAYMYRCMM-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)NC4CCC(C(C)(C)C)CC4)cc3)c(Cl)cc21"
},
"smiles": "CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)NC4CCC(C(C)(C)C)CC4)cc3)c(Cl)cc21",
"reactionStepId": "sa_d08d96cc03a2778cf3054592",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08716498B2;1106;1455808\",\"rsmi\":\"O[C:18]([c:17]1[cH:16][cH:15][c:14]([O:13][c:12]2[cH:11][c:10]3[c:36]([cH:35][c:33]2[Cl:34])[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][O:9]3)[cH:32][cH:31]1)=[O:19].[NH2:20][CH:21]1[CH2:22][CH2:23][CH:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]1>CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.CN(C)c1ccncc1.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[NH:20][CH:21]4[CH2:22][CH2:23][CH:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]4)[cH:31][cH:32]3)[c:33]([Cl:34])[cH:35][c:36]21\"},\"mapped_reaction_smiles\":\"O[C:18]([c:17]1[cH:16][cH:15][c:14]([O:13][c:12]2[cH:11][c:10]3[c:36]([cH:35][c:33]2[Cl:34])[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][O:9]3)[cH:32][cH:31]1)=[O:19].[NH2:20][CH:21]1[CH2:22][CH2:23][CH:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]1>CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.CN(C)c1ccncc1.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[NH:20][CH:21]4[CH2:22][CH2:23][CH:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]4)[cH:31][cH:32]3)[c:33]([Cl:34])[cH:35][c:36]21\"}",
"reactionStep": {
"id": "sa_d08d96cc03a2778cf3054592",
"reactionHash": "1e3f8c45326e3f83cee3ea9f4f32ec5413a94ee383fe595694496959e5994499"
},
"children": [
{
"id": "15605",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_889976879846e045e9a6a48e",
"parentId": "15604",
"isLeaf": true,
"molecule": {
"id": "sa_889976879846e045e9a6a48e",
"inchikey": "BGNLXETYTAAURD-UHFFFAOYSA-N",
"smiles": "CC(C)(C)C1CCC(N)CC1"
},
"smiles": "CC(C)(C)C1CCC(N)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15606",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_99986464da4bb340726aeec5",
"parentId": "15604",
"isLeaf": false,
"molecule": {
"id": "sa_99986464da4bb340726aeec5",
"inchikey": "WREVNSQSYUJJKJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)O)cc3)c(Cl)cc21"
},
"smiles": "CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)O)cc3)c(Cl)cc21",
"reactionStepId": "sa_5cf49a4cc3d9f339c89c309e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08716498B2;0602;1455630\",\"rsmi\":\"CC(C)(C)[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([O:13][c:12]2[cH:11][c:10]3[c:26]([cH:25][c:23]2[Cl:24])[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][O:9]3)[cH:22][cH:21]1)=[O:19]>CCOC(C)=O.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]3)[c:23]([Cl:24])[cH:25][c:26]21\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([O:13][c:12]2[cH:11][c:10]3[c:26]([cH:25][c:23]2[Cl:24])[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][O:9]3)[cH:22][cH:21]1)=[O:19]>CCOC(C)=O.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]3)[c:23]([Cl:24])[cH:25][c:26]21\"}",
"reactionStep": {
"id": "sa_5cf49a4cc3d9f339c89c309e",
"reactionHash": "8833b2da2547991c92e2b64ab8e3e46daad236c95f7ee4eb2a8719a6cb2b8de2"
},
"children": [
{
"id": "15607",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_72b19276badcec95e67232c7",
"parentId": "15606",
"isLeaf": false,
"molecule": {
"id": "sa_72b19276badcec95e67232c7",
"inchikey": "LKHBRRLGUNKYKV-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)OC(C)(C)C)cc3)c(Cl)cc21"
},
"smiles": "CCOC(=O)C1CCOc2cc(Oc3ccc(C(=O)OC(C)(C)C)cc3)c(Cl)cc21",
"reactionStepId": "sa_9b145e76b8376a7a4dfac6b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08716498B2;0601;1455629\",\"rsmi\":\"Br[c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[c:27]([Cl:28])[cH:29][c:30]21>C.C1COCCO1.CCOC(C)=O.CN(C)CC(=O)O.Cl.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]3)[c:27]([Cl:28])[cH:29][c:30]21\"},\"mapped_reaction_smiles\":\"Br[c:14]1[cH:15][cH:16][c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[c:27]([Cl:28])[cH:29][c:30]21>C.C1COCCO1.CCOC(C)=O.CN(C)CC(=O)O.Cl.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]3)[c:27]([Cl:28])[cH:29][c:30]21\"}",
"reactionStep": {
"id": "sa_9b145e76b8376a7a4dfac6b2",
"reactionHash": "f4c444ef1d3160762773449f2993849d75f93a2b1d725d25850bc372132761e1"
},
"children": [
{
"id": "15608",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_5ed9c87044282787554536dd",
"parentId": "15607",
"isLeaf": true,
"molecule": {
"id": "sa_5ed9c87044282787554536dd",
"inchikey": "BFJJYXUCGYOXDM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)c1ccc(Br)cc1"
},
"smiles": "CC(C)(C)OC(=O)c1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15609",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_bf326f2f9b731d18bbab81f8",
"parentId": "15607",
"isLeaf": false,
"molecule": {
"id": "sa_bf326f2f9b731d18bbab81f8",
"inchikey": "RXVPHMIRHIHSOQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCOc2cc(O)c(Cl)cc21"
},
"smiles": "CCOC(=O)C1CCOc2cc(O)c(Cl)cc21",
"reactionStepId": "sa_b49d6d755ecc9fc9caacbd2f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08716498B2;0600;1455628\",\"rsmi\":\"O[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[c:14]([Cl:15])[cH:16][c:17]21.[CH3:1][CH2:2][OH:3]>CCOC(C)=O.O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[c:14]([Cl:15])[cH:16][c:17]21\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[c:14]([Cl:15])[cH:16][c:17]21.[CH3:1][CH2:2][OH:3]>CCOC(C)=O.O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][c:12]([OH:13])[c:14]([Cl:15])[cH:16][c:17]21\"}",
"reactionStep": {
"id": "sa_b49d6d755ecc9fc9caacbd2f",
"reactionHash": "d3dfb3ad34d866de74c70866bd01a0d020a7d1678c0a20f78e3fc1499f1a65e8"
},
"children": [
{
"id": "15610",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "15609",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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},
{
"id": "15611",
"routeId": "sa_2778172ed2b4c729f44659c4",
"moleculeId": "sa_c0e794673d41f8abf25bbef8",
"parentId": "15609",
"isLeaf": true,
"molecule": {
"id": "sa_c0e794673d41f8abf25bbef8",
"inchikey": "ZBWHVZZJKGPNDS-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CCOc2cc(O)c(Cl)cc21"
},
"smiles": "O=C(O)C1CCOc2cc(O)c(Cl)cc21",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
}
]
}
]
}
}