Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1)Oc1ccccc1
InChiKey
DNFMENQLTVOPCU-UHFFFAOYSA-N
Route Signature
9805dcc20c7a58c9d48d73565f3082a9fd05e3439c3cfb1b8babe48811769246
Synthesis route with 9 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_beea32134a3f49042ed99287",
"signature": "9805dcc20c7a58c9d48d73565f3082a9fd05e3439c3cfb1b8babe48811769246",
"contentHash": "d856a262aa1e6f4f983e424fc727e1c257ab5785fe6028e32b453ba47169851b",
"length": 9,
"isConvergent": false
},
"target": {
"id": "sa_97c988e5223ba4e560d6f781",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n1-00038",
"moleculeId": "sa_6b8a3e93f79c081b8365b750",
"smiles": "O=C(NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1)Oc1ccccc1",
"routeLength": 9,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_6b8a3e93f79c081b8365b750",
"inchikey": "DNFMENQLTVOPCU-UHFFFAOYSA-N",
"smiles": "O=C(NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1)Oc1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "16958",
"routeId": "sa_beea32134a3f49042ed99287",
"moleculeId": "sa_6b8a3e93f79c081b8365b750",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6b8a3e93f79c081b8365b750",
"inchikey": "DNFMENQLTVOPCU-UHFFFAOYSA-N",
"smiles": "O=C(NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1)Oc1ccccc1"
},
"smiles": "O=C(NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1)Oc1ccccc1",
"reactionStepId": "sa_20696341330a01c4b515fb51",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160145251A1;0426;1881630\",\"rsmi\":\"Cl[C:2](=[O:1])[O:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.[NH2:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][N:18]([C:19](=[O:20])[c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][o:28]3)[cH:29][cH:30][cH:31]2)[CH2:32]1>CCN(CC)CC.ClCCl>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][N:18]([C:19](=[O:20])[c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][o:28]3)[cH:29][cH:30][cH:31]2)[CH2:32]1)[O:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[O:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.[NH2:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][N:18]([C:19](=[O:20])[c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][o:28]3)[cH:29][cH:30][cH:31]2)[CH2:32]1>CCN(CC)CC.ClCCl>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][N:18]([C:19](=[O:20])[c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][o:28]3)[cH:29][cH:30][cH:31]2)[CH2:32]1)[O:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1\"}",
"reactionStep": {
"id": "sa_20696341330a01c4b515fb51",
"reactionHash": "3fae585cdfc07c9028bfedab8b94ed96bd55cb4c4736dd29cd998f31828b6580"
},
"children": [
{
"id": "16959",
"routeId": "sa_beea32134a3f49042ed99287",
"moleculeId": "sa_c3f902b5f9863db0f23f1ee5",
"parentId": "16958",
"isLeaf": true,
"molecule": {
"id": "sa_c3f902b5f9863db0f23f1ee5",
"inchikey": "AHWALFGBDFAJAI-UHFFFAOYSA-N",
"smiles": "O=C(Cl)Oc1ccccc1"
},
"smiles": "O=C(Cl)Oc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16960",
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"moleculeId": "sa_10fa9245fb9297ae8d4b8084",
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"isLeaf": false,
"molecule": {
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"inchikey": "LGGQVLIGLBIOQZ-UHFFFAOYSA-N",
"smiles": "NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1"
},
"smiles": "NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1",
"reactionStepId": "sa_0a4ac4a212c6f74b41afa5af",
"template": null,
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"reactionStep": {
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"reactionHash": "bb4619d3785c848f1936a75708f2acc5fdb71720e538eb59406cd90c775e0d52"
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"children": [
{
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"isLeaf": false,
"molecule": {
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"inchikey": "UEOPYRIWDIBPJP-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1"
},
"smiles": "[N-]=[N+]=NC1CC(C(=O)Nc2ccc(Cl)cc2)CN(C(=O)c2cccc(-c3ccco3)c2)C1",
"reactionStepId": "sa_ee2563ea29dbc4d08e6be65d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160145251A1;0374;1881610\",\"rsmi\":\"O[C:19](=[O:20])[c:21]1[cH:22][c:23](-[c:24]2[cH:25][cH:26][cH:27][o:28]2)[cH:29][cH:30][cH:31]1.[N-:1]=[N+:2]=[N:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][NH:18][CH2:32]1>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl>[N-:1]=[N+:2]=[N:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][N:18]([C:19](=[O:20])[c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][o:28]3)[cH:29][cH:30][cH:31]2)[CH2:32]1\"},\"mapped_reaction_smiles\":\"O[C:19](=[O:20])[c:21]1[cH:22][c:23](-[c:24]2[cH:25][cH:26][cH:27][o:28]2)[cH:29][cH:30][cH:31]1.[N-:1]=[N+:2]=[N:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][NH:18][CH2:32]1>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl>[N-:1]=[N+:2]=[N:3][CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[CH2:17][N:18]([C:19](=[O:20])[c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][o:28]3)[cH:29][cH:30][cH:31]2)[CH2:32]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_2a6d1712d73a75a3324928d8",
"parentId": "16961",
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"molecule": {
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"smiles": "[N-]=[N+]=NC1CNCC(C(=O)Nc2ccc(Cl)cc2)C1"
},
"smiles": "[N-]=[N+]=NC1CNCC(C(=O)Nc2ccc(Cl)cc2)C1",
"reactionStepId": "sa_7b95aee578d8674a89884d04",
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"metadata": "{\"annotations\":{\"ID\":\"US20160145251A1;0372;1881609\",\"rsmi\":\"CC(C)(C)OC(=O)[N:6]1[CH2:5][CH:4]([N:3]=[N+:2]=[N-:1])[CH2:19][CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:7]1>ClCCl.O=C(O)C(F)(F)F>[N-:1]=[N+:2]=[N:3][CH:4]1[CH2:5][NH:6][CH2:7][CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:6]1[CH2:5][CH:4]([N:3]=[N+:2]=[N-:1])[CH2:19][CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:7]1>ClCCl.O=C(O)C(F)(F)F>[N-:1]=[N+:2]=[N:3][CH:4]1[CH2:5][NH:6][CH2:7][CH:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"smiles": "CC(C)(C)OC(=O)N1CC(N=[N+]=[N-])CC(C(=O)Nc2ccc(Cl)cc2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CC(N=[N+]=[N-])CC(C(=O)Nc2ccc(Cl)cc2)C1",
"reactionStepId": "sa_b439a4e11b841c7e0f70534a",
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"metadata": "{\"annotations\":{\"ID\":\"US20160145251A1;0370;1881608\",\"rsmi\":\"O[C:16]([CH:15]1[CH2:14][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26]1)=[O:17].[NH2:18][c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)c1ccncc1.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:14][CH:15]([C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[CH2:26]1\"},\"mapped_reaction_smiles\":\"O[C:16]([CH:15]1[CH2:14][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26]1)=[O:17].[NH2:18][c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)c1ccncc1.Cl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:14][CH:15]([C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[CH2:26]1\"}",
"reactionStep": {
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"molecule": {
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"metadata": "{\"annotations\":{\"ID\":\"US20160145251A1;0368;1881607\",\"rsmi\":\"C[O:18][C:16]([CH:15]1[CH2:14][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:19]1)=[O:17]>CCOC(C)=O.CO.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:14][CH:15]([C:16](=[O:17])[OH:18])[CH2:19]1\"},\"mapped_reaction_smiles\":\"C[O:18][C:16]([CH:15]1[CH2:14][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:19]1)=[O:17]>CCOC(C)=O.CO.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([N:11]=[N+:12]=[N-:13])[CH2:14][CH:15]([C:16](=[O:17])[OH:18])[CH2:19]1\"}",
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"metadata": "{\"annotations\":{\"ID\":\"US20160145251A1;0366;1881606\",\"rsmi\":\"CS(=O)(=O)O[CH:7]1[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:20][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:11]1.[N-:8]=[N+:9]=[N-:10]>CN(C)C=O.O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([N:8]=[N+:9]=[N-:10])[CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH:7]1[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:20][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:11]1.[N-:8]=[N+:9]=[N-:10]>CN(C)C=O.O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([N:8]=[N+:9]=[N-:10])[CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1\"}",
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