Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4C)c4cc(F)ccc43)cn12
InChiKey
XFNMNLDXIQSHBL-FCHUYYIVSA-N
Route Signature
6fd847a3ac0986deac8421a84125d6f7b04c51b704a0f1773265295be1ea0414
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_29d2202d0a623f2457b72e52",
"signature": "6fd847a3ac0986deac8421a84125d6f7b04c51b704a0f1773265295be1ea0414",
"contentHash": "eb93777e526097770c5f2c391a7bb0407326081c29cf484f9da5fcd21913ef25",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_1957d2193d4fc98a521c1843",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01430",
"moleculeId": "sa_129c4b655cca418167dabc40",
"smiles": "CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4C)c4cc(F)ccc43)cn12",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_129c4b655cca418167dabc40",
"inchikey": "XFNMNLDXIQSHBL-FCHUYYIVSA-N",
"smiles": "CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4C)c4cc(F)ccc43)cn12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10181",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_129c4b655cca418167dabc40",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_129c4b655cca418167dabc40",
"inchikey": "XFNMNLDXIQSHBL-FCHUYYIVSA-N",
"smiles": "CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4C)c4cc(F)ccc43)cn12"
},
"smiles": "CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4C)c4cc(F)ccc43)cn12",
"reactionStepId": "sa_0347ebe5e73c050836c9cf7d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140343055A1;0506;1614182\",\"rsmi\":\"ClC(Cl)(Cl)CO[C:17](=[O:18])[NH:19][c:20]1[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][n:28]1[CH3:29].[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][C@@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[c:30]4[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]43)[cH:37][n:38]12>C1COCCO1.CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][C@@H:12]3[CH2:13][CH2:14][C@H:15]([NH:16][C:17](=[O:18])[NH:19][c:20]4[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][n:28]4[CH3:29])[c:30]4[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]43)[cH:37][n:38]12\"},\"mapped_reaction_smiles\":\"ClC(Cl)(Cl)CO[C:17](=[O:18])[NH:19][c:20]1[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][n:28]1[CH3:29].[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][C@@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[c:30]4[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]43)[cH:37][n:38]12>C1COCCO1.CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][C@@H:12]3[CH2:13][CH2:14][C@H:15]([NH:16][C:17](=[O:18])[NH:19][c:20]4[cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][n:28]4[CH3:29])[c:30]4[cH:31][c:32]([F:33])[cH:34][cH:35][c:36]43)[cH:37][n:38]12\"}",
"reactionStep": {
"id": "sa_0347ebe5e73c050836c9cf7d",
"reactionHash": "3f234b990c6724495edda6f3f3e63bbb20833f4d2bbf14b320264efcc6b65522"
},
"children": [
{
"id": "10182",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_e1582666802fd88c7d89e87c",
"parentId": "10181",
"isLeaf": false,
"molecule": {
"id": "sa_e1582666802fd88c7d89e87c",
"inchikey": "QARUGXGAJOKFDK-DLBZAZTESA-N",
"smiles": "CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](N)c4cc(F)ccc43)cn12"
},
"smiles": "CC(C)c1nnc2ccc(O[C@@H]3CC[C@H](N)c4cc(F)ccc43)cn12",
"reactionStepId": "sa_846f1b59553dbfdc1c231074",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140343055A1;0505;1614181\",\"rsmi\":\"F[c:10]1[cH:9][cH:8][c:7]2[n:6][n:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:25]2[cH:24]1.[OH:11][C@@H:12]1[CH2:13][CH2:14][C@H:15]([NH2:16])[c:17]2[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]21>CN(C)C=O.[HH].[Na+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][C@@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[c:17]4[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]43)[cH:24][n:25]12\"},\"mapped_reaction_smiles\":\"F[c:10]1[cH:9][cH:8][c:7]2[n:6][n:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:25]2[cH:24]1.[OH:11][C@@H:12]1[CH2:13][CH2:14][C@H:15]([NH2:16])[c:17]2[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]21>CN(C)C=O.[HH].[Na+]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([O:11][C@@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[c:17]4[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]43)[cH:24][n:25]12\"}",
"reactionStep": {
"id": "sa_846f1b59553dbfdc1c231074",
"reactionHash": "d76d0aafcbac0854c1c445cb40f7af3f568f67992c2fe789d7564a849d4bdbe6"
},
"children": [
{
"id": "10183",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_cb643b6bb59e18a104860626",
"parentId": "10182",
"isLeaf": false,
"molecule": {
"id": "sa_cb643b6bb59e18a104860626",
"inchikey": "BRUIUUVNLUYGSY-UHFFFAOYSA-N",
"smiles": "CC(C)c1nnc2ccc(F)cn12"
},
"smiles": "CC(C)c1nnc2ccc(F)cn12",
"reactionStepId": "sa_b3a925cf3f0ae6d14eaa4737",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140343055A1;0401;1614148\",\"rsmi\":\"O=[C:4]([CH:2]([CH3:1])[CH3:3])[NH:5][NH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][n:13]1>C1CCOC1.CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][n:13]12\"},\"mapped_reaction_smiles\":\"O=[C:4]([CH:2]([CH3:1])[CH3:3])[NH:5][NH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][n:13]1>C1CCOC1.CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][n:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][n:13]12\"}",
"reactionStep": {
"id": "sa_b3a925cf3f0ae6d14eaa4737",
"reactionHash": "9cd020fc63a1b167c64df8b2e63610d32e7bb26d8446fcf9fc7909bfa7e54aff"
},
"children": [
{
"id": "10184",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_68b80660ea5c51b6d8c066c6",
"parentId": "10183",
"isLeaf": false,
"molecule": {
"id": "sa_68b80660ea5c51b6d8c066c6",
"inchikey": "XMCKSPOUUZAXSZ-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)NNc1ccc(F)cn1"
},
"smiles": "CC(C)C(=O)NNc1ccc(F)cn1",
"reactionStepId": "sa_e49fc3c283f073af2b5d4066",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140343055A1;0399;1614147\",\"rsmi\":\"O[C:4]([CH:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][NH:7][c:8]1[n:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>CCOCC.ClCCCl.ClCCl.O.O=C(O)O.On1nnc2ccccc21.[Na+]>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][NH:7][c:8]1[n:9][cH:10][c:11]([F:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[C:4]([CH:2]([CH3:1])[CH3:3])=[O:5].[NH2:6][NH:7][c:8]1[n:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>CCOCC.ClCCCl.ClCCl.O.O=C(O)O.On1nnc2ccccc21.[Na+]>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][NH:7][c:8]1[n:9][cH:10][c:11]([F:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_e49fc3c283f073af2b5d4066",
"reactionHash": "9f8c6d6bfeaa0147228a638d65372233966ec11eae86f45bca074fc0cc1658b1"
},
"children": [
{
"id": "10185",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_3dc550641fd224a8a0bdcfc8",
"parentId": "10184",
"isLeaf": true,
"molecule": {
"id": "sa_3dc550641fd224a8a0bdcfc8",
"inchikey": "KQNPFQTWMSNSAP-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)O"
},
"smiles": "CC(C)C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10186",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_e3601c6e14cbeaf03a11cb6d",
"parentId": "10184",
"isLeaf": true,
"molecule": {
"id": "sa_e3601c6e14cbeaf03a11cb6d",
"inchikey": "XGEZFYOWXLYYNM-UHFFFAOYSA-N",
"smiles": "NNc1ccc(F)cn1"
},
"smiles": "NNc1ccc(F)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10187",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_88b8159d7434342a24358be2",
"parentId": "10182",
"isLeaf": false,
"molecule": {
"id": "sa_88b8159d7434342a24358be2",
"inchikey": "RUKJQRYDQWRZMS-VHSXEESVSA-N",
"smiles": "N[C@H]1CC[C@@H](O)c2ccc(F)cc21"
},
"smiles": "N[C@H]1CC[C@@H](O)c2ccc(F)cc21",
"reactionStepId": "sa_b470448981eac07903290e29",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140343055A1;0503;1614180\",\"rsmi\":\"O=C(C(F)(F)F)[NH:1][C@H:2]1[CH2:3][CH2:4][C@@H:5]([OH:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]21>CO.O.[Na+].O>[NH2:1][C@H:2]1[CH2:3][CH2:4][C@@H:5]([OH:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]21\"},\"mapped_reaction_smiles\":\"O=C(C(F)(F)F)[NH:1][C@H:2]1[CH2:3][CH2:4][C@@H:5]([OH:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]21>CO.O.[Na+].O>[NH2:1][C@H:2]1[CH2:3][CH2:4][C@@H:5]([OH:6])[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]21\"}",
"reactionStep": {
"id": "sa_b470448981eac07903290e29",
"reactionHash": "762b89251945ea96ee48aabb8ceb63a09e35b2028f5ea05bf737ed00efb980b7"
},
"children": [
{
"id": "10188",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_50bd96c72df1f4281bf08870",
"parentId": "10187",
"isLeaf": true,
"molecule": {
"id": "sa_50bd96c72df1f4281bf08870",
"inchikey": "IAVJGJFUPVFGMZ-VHSXEESVSA-N",
"smiles": "O=C(N[C@H]1CC[C@@H](O)c2ccc(F)cc21)C(F)(F)F"
},
"smiles": "O=C(N[C@H]1CC[C@@H](O)c2ccc(F)cc21)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10189",
"routeId": "sa_29d2202d0a623f2457b72e52",
"moleculeId": "sa_e64e4fca1bde3bd42dc78d21",
"parentId": "10181",
"isLeaf": true,
"molecule": {
"id": "sa_e64e4fca1bde3bd42dc78d21",
"inchikey": "XNZFWEHRBNJAGI-UHFFFAOYSA-N",
"smiles": "Cn1nc(C(C)(C)C)cc1NC(=O)OCC(Cl)(Cl)Cl"
},
"smiles": "Cn1nc(C(C)(C)C)cc1NC(=O)OCC(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}