Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCC(O)CN1CCC[C@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1
InChiKey
ONYPOSKICCXRSL-LSLKUGRBSA-N
Route Signature
00c1974c326d844756eefa856fd78a440f42486027c229f10806f3c7f7ce1804
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_659a0b503fe378e12d723421",
"signature": "00c1974c326d844756eefa856fd78a440f42486027c229f10806f3c7f7ce1804",
"contentHash": "58b734f16f5e7de0ddbfd6ae815c5e605bbf106165e85190489fbfc5ba433221",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_57ea527638fd1a2696e2921a",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-04930",
"moleculeId": "sa_75dce21a668830b2d28af068",
"smiles": "COCC(O)CN1CCC[C@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_75dce21a668830b2d28af068",
"inchikey": "ONYPOSKICCXRSL-LSLKUGRBSA-N",
"smiles": "COCC(O)CN1CCC[C@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15596",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_75dce21a668830b2d28af068",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_75dce21a668830b2d28af068",
"inchikey": "ONYPOSKICCXRSL-LSLKUGRBSA-N",
"smiles": "COCC(O)CN1CCC[C@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1"
},
"smiles": "COCC(O)CN1CCC[C@H](Nc2nc(-c3c[nH]c4ncc(Cl)cc34)ncc2F)C1",
"reactionStepId": "sa_3435e052ed4115d791d91960",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09345708B2;1256;1763297\",\"rsmi\":\"Cc1ccc(S(=O)(=O)[n:18]2[cH:17][c:16](-[c:15]3[n:14][c:13]([NH:12][C@H:11]4[CH2:10][CH2:9][CH2:8][N:7]([CH2:6][CH:4]([CH2:3][O:2][CH3:1])[OH:5])[CH2:30]4)[c:28]([F:29])[cH:27][n:26]3)[c:25]3[c:19]2[n:20][cH:21][c:22]([Cl:23])[cH:24]3)cc1>C1CCOC1.O.[Li+].O>[CH3:1][O:2][CH2:3][CH:4]([OH:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]([NH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][nH:18][c:19]4[n:20][cH:21][c:22]([Cl:23])[cH:24][c:25]34)[n:26][cH:27][c:28]2[F:29])[CH2:30]1\"},\"mapped_reaction_smiles\":\"Cc1ccc(S(=O)(=O)[n:18]2[cH:17][c:16](-[c:15]3[n:14][c:13]([NH:12][C@H:11]4[CH2:10][CH2:9][CH2:8][N:7]([CH2:6][CH:4]([CH2:3][O:2][CH3:1])[OH:5])[CH2:30]4)[c:28]([F:29])[cH:27][n:26]3)[c:25]3[c:19]2[n:20][cH:21][c:22]([Cl:23])[cH:24]3)cc1>C1CCOC1.O.[Li+].O>[CH3:1][O:2][CH2:3][CH:4]([OH:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]([NH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][nH:18][c:19]4[n:20][cH:21][c:22]([Cl:23])[cH:24][c:25]34)[n:26][cH:27][c:28]2[F:29])[CH2:30]1\"}",
"reactionStep": {
"id": "sa_3435e052ed4115d791d91960",
"reactionHash": "86141fe79e4e7dacc8d0c896114d987b9f71f80c794714e1ce6c44580aa753a1"
},
"children": [
{
"id": "15597",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_2489ff5e23ce95d050d11c03",
"parentId": "15596",
"isLeaf": false,
"molecule": {
"id": "sa_2489ff5e23ce95d050d11c03",
"inchikey": "VASRNFMLZMPZGA-XJDOXCRVSA-N",
"smiles": "COCC(O)CN1CCC[C@H](Nc2nc(-c3cn(S(=O)(=O)c4ccc(C)cc4)c4ncc(Cl)cc34)ncc2F)C1"
},
"smiles": "COCC(O)CN1CCC[C@H](Nc2nc(-c3cn(S(=O)(=O)c4ccc(C)cc4)c4ncc(Cl)cc34)ncc2F)C1",
"reactionStepId": "sa_0892486a0e68c27a833801cf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09345708B2;1253;1763296\",\"rsmi\":\"[CH3:1][O:2][CH2:3][CH:4]1[O:5][CH2:6]1.[NH:7]1[CH2:8][CH2:9][CH2:10][C@H:11]([NH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][n:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[c:29]4[n:30][cH:31][c:32]([Cl:33])[cH:34][c:35]34)[n:36][cH:37][c:38]2[F:39])[CH2:40]1>CCO>[CH3:1][O:2][CH2:3][CH:4]([OH:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]([NH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][n:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[c:29]4[n:30][cH:31][c:32]([Cl:33])[cH:34][c:35]34)[n:36][cH:37][c:38]2[F:39])[CH2:40]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][CH2:3][CH:4]1[O:5][CH2:6]1.[NH:7]1[CH2:8][CH2:9][CH2:10][C@H:11]([NH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][n:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[c:29]4[n:30][cH:31][c:32]([Cl:33])[cH:34][c:35]34)[n:36][cH:37][c:38]2[F:39])[CH2:40]1>CCO>[CH3:1][O:2][CH2:3][CH:4]([OH:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]([NH:12][c:13]2[n:14][c:15](-[c:16]3[cH:17][n:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[c:29]4[n:30][cH:31][c:32]([Cl:33])[cH:34][c:35]34)[n:36][cH:37][c:38]2[F:39])[CH2:40]1\"}",
"reactionStep": {
"id": "sa_0892486a0e68c27a833801cf",
"reactionHash": "4a79c4daf01b03f04f22ab5b7e2d78af3d09ac3661ecdcd3772f60976280e748"
},
"children": [
{
"id": "15598",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_53b70e33e6925e9dcfaeb590",
"parentId": "15597",
"isLeaf": true,
"molecule": {
"id": "sa_53b70e33e6925e9dcfaeb590",
"inchikey": "LKMJVFRMDSNFRT-UHFFFAOYSA-N",
"smiles": "COCC1CO1"
},
"smiles": "COCC1CO1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15599",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_de5a74b29fe5748157a5d12b",
"parentId": "15597",
"isLeaf": false,
"molecule": {
"id": "sa_de5a74b29fe5748157a5d12b",
"inchikey": "LPVCBPZCYHLMGL-INIZCTEOSA-N",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(N[C@H]4CCCNC4)n3)c3cc(Cl)cnc32)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(N[C@H]4CCCNC4)n3)c3cc(Cl)cnc32)cc1",
"reactionStepId": "sa_f3d1a57196e7ced8357569e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09345708B2;1251;1763295\",\"rsmi\":\"CC(C)(C)OC(=O)[N:23]1[CH2:22][CH2:21][CH2:20][C@H:19]([NH:18][c:17]2[c:15]([F:16])[cH:14][n:13][c:12](-[c:11]3[cH:10][n:9]([S:6]([c:5]4[cH:4][cH:3][c:2]([CH3:1])[cH:34][cH:33]4)(=[O:7])=[O:8])[c:32]4[c:26]3[cH:27][c:28]([Cl:29])[cH:30][n:31]4)[n:25]2)[CH2:24]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11](-[c:12]3[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]4[CH2:20][CH2:21][CH2:22][NH:23][CH2:24]4)[n:25]3)[c:26]3[cH:27][c:28]([Cl:29])[cH:30][n:31][c:32]23)[cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:23]1[CH2:22][CH2:21][CH2:20][C@H:19]([NH:18][c:17]2[c:15]([F:16])[cH:14][n:13][c:12](-[c:11]3[cH:10][n:9]([S:6]([c:5]4[cH:4][cH:3][c:2]([CH3:1])[cH:34][cH:33]4)(=[O:7])=[O:8])[c:32]4[c:26]3[cH:27][c:28]([Cl:29])[cH:30][n:31]4)[n:25]2)[CH2:24]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11](-[c:12]3[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]4[CH2:20][CH2:21][CH2:22][NH:23][CH2:24]4)[n:25]3)[c:26]3[cH:27][c:28]([Cl:29])[cH:30][n:31][c:32]23)[cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_f3d1a57196e7ced8357569e3",
"reactionHash": "7e23077c49f31498ecab50914cf701fe23f88d92e7498562e3de0d9cc9636aab"
},
"children": [
{
"id": "15600",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_2d49cf9ed433115fe1a785e1",
"parentId": "15599",
"isLeaf": false,
"molecule": {
"id": "sa_2d49cf9ed433115fe1a785e1",
"inchikey": "OWCNXWBYDSJNEG-IBGZPJMESA-N",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(N[C@H]4CCCN(C(=O)OC(C)(C)C)C4)n3)c3cc(Cl)cnc32)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(N[C@H]4CCCN(C(=O)OC(C)(C)C)C4)n3)c3cc(Cl)cnc32)cc1",
"reactionStepId": "sa_2dee65a9be1116686817dc44",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09345708B2;1249;1763294\",\"rsmi\":\"CS(=O)(=O)[c:17]1[c:15]([F:16])[cH:14][n:13][c:12](-[c:11]2[cH:10][n:9]([S:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:41][cH:40]3)(=[O:7])=[O:8])[c:39]3[c:33]2[cH:34][c:35]([Cl:36])[cH:37][n:38]3)[n:32]1.[NH2:18][C@H:19]1[CH2:20][CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31]1>CCN(C(C)C)C(C)C.CN(C)C=O.Cl.N>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11](-[c:12]3[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]4[CH2:20][CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31]4)[n:32]3)[c:33]3[cH:34][c:35]([Cl:36])[cH:37][n:38][c:39]23)[cH:40][cH:41]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)[c:17]1[c:15]([F:16])[cH:14][n:13][c:12](-[c:11]2[cH:10][n:9]([S:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:41][cH:40]3)(=[O:7])=[O:8])[c:39]3[c:33]2[cH:34][c:35]([Cl:36])[cH:37][n:38]3)[n:32]1.[NH2:18][C@H:19]1[CH2:20][CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31]1>CCN(C(C)C)C(C)C.CN(C)C=O.Cl.N>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11](-[c:12]3[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]4[CH2:20][CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31]4)[n:32]3)[c:33]3[cH:34][c:35]([Cl:36])[cH:37][n:38][c:39]23)[cH:40][cH:41]1\"}",
"reactionStep": {
"id": "sa_2dee65a9be1116686817dc44",
"reactionHash": "733625d62cd99c83cd1ad8f028ce3d5c701075c8622ea906fbfe1b3b36f2e4b2"
},
"children": [
{
"id": "15601",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_299a0a7eb8237ace8169474c",
"parentId": "15600",
"isLeaf": true,
"molecule": {
"id": "sa_299a0a7eb8237ace8169474c",
"inchikey": "AKQXKEBCONUWCL-QMMMGPOBSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC[C@H](N)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@H](N)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15602",
"routeId": "sa_659a0b503fe378e12d723421",
"moleculeId": "sa_9965f39b994fca76b35b42ad",
"parentId": "15600",
"isLeaf": true,
"molecule": {
"id": "sa_9965f39b994fca76b35b42ad",
"inchikey": "QEZIPSHURZXRKN-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(S(C)(=O)=O)n3)c3cc(Cl)cnc32)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(S(C)(=O)=O)n3)c3cc(Cl)cnc32)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}