Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)N1CCN(c2ccc(CCc3ccc(CN)cc3)nc2)CC1
InChiKey
ZPBNKBMFZZBZAT-UHFFFAOYSA-N
Route Signature
21b061a728627268feb02edca753663adbd0df5bb3cc61b02c8ad46140f6389a
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_24e954d7ff31f8c9d5592a09",
"signature": "21b061a728627268feb02edca753663adbd0df5bb3cc61b02c8ad46140f6389a",
"contentHash": "5375c8a438f4467460aa8fd55832956fa51a43c0940b752d6f8e210c7457be12",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_2838c123ba4a0a9e083260ab",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00357",
"moleculeId": "sa_252dd10451100b8a172ebad9",
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CN)cc3)nc2)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_252dd10451100b8a172ebad9",
"inchikey": "ZPBNKBMFZZBZAT-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CN)cc3)nc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13136",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_252dd10451100b8a172ebad9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_252dd10451100b8a172ebad9",
"inchikey": "ZPBNKBMFZZBZAT-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CN)cc3)nc2)CC1"
},
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CN)cc3)nc2)CC1",
"reactionStepId": "sa_b4e972158bc4eabc60040c2d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08999989B2;0650;1601035\",\"rsmi\":\"[N-]=[N+]=[N:19][CH2:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][CH2:12][c:11]2[n:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:25][CH2:24]3)[cH:23][cH:22]2)[cH:21][cH:20]1>C.CCOC(C)=O.CO.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][NH2:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:19][CH2:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][CH2:12][c:11]2[n:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:25][CH2:24]3)[cH:23][cH:22]2)[cH:21][cH:20]1>C.CCOC(C)=O.CO.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][NH2:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_b4e972158bc4eabc60040c2d",
"reactionHash": "a99ca876c943f1df2d20ee3f501cbe8b99699d399cab51005d3a4b08585f204f"
},
"children": [
{
"id": "13137",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_5bec799b4c6591ecb86aef56",
"parentId": "13136",
"isLeaf": false,
"molecule": {
"id": "sa_5bec799b4c6591ecb86aef56",
"inchikey": "SRNFCHHYUBFAHZ-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CN=[N+]=[N-])cc3)nc2)CC1"
},
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CN=[N+]=[N-])cc3)nc2)CC1",
"reactionStepId": "sa_0333ead24d19ff189c4b2dde",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08999989B2;0648;1601034\",\"rsmi\":\"Cl[CH2:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][CH2:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:27][CH2:26]3)[cH:25][n:24]2)[cH:23][cH:22]1.[N-:19]=[N+:20]=[N-:21]>CCOC(C)=O.CN(C)C=O.O=C(O)O.[Na+].[Na+].[Na+]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][N:19]=[N+:20]=[N-:21])[cH:22][cH:23]3)[n:24][cH:25]2)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][CH2:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:27][CH2:26]3)[cH:25][n:24]2)[cH:23][cH:22]1.[N-:19]=[N+:20]=[N-:21]>CCOC(C)=O.CN(C)C=O.O=C(O)O.[Na+].[Na+].[Na+]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][N:19]=[N+:20]=[N-:21])[cH:22][cH:23]3)[n:24][cH:25]2)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_0333ead24d19ff189c4b2dde",
"reactionHash": "b88b1aeae91ae5d66ef63d7754c76c3dae56e3b633f42b1657d4b6d4bc143708"
},
"children": [
{
"id": "13138",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_9ce3a581f6f344f6df66738e",
"parentId": "13137",
"isLeaf": false,
"molecule": {
"id": "sa_9ce3a581f6f344f6df66738e",
"inchikey": "HHMZSZOMWBRDIR-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CCl)cc3)nc2)CC1"
},
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CCl)cc3)nc2)CC1",
"reactionStepId": "sa_cd0bd6b2244d57fff2cbf2fb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08999989B2;0646;1601033\",\"rsmi\":\"ClC[Cl:19].O[CH2:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][CH2:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:25][CH2:24]3)[cH:23][n:22]2)[cH:21][cH:20]1>O=S(Cl)Cl>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][Cl:19])[cH:20][cH:21]3)[n:22][cH:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"ClC[Cl:19].O[CH2:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][CH2:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:25][CH2:24]3)[cH:23][n:22]2)[cH:21][cH:20]1>O=S(Cl)Cl>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][Cl:19])[cH:20][cH:21]3)[n:22][cH:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_cd0bd6b2244d57fff2cbf2fb",
"reactionHash": "b2155b676f4adee0f56540b37f57c667c9db731a7064ecce4c35a464388028ce"
},
"children": [
{
"id": "13139",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_85d38a8ca90453d40884ac43",
"parentId": "13138",
"isLeaf": false,
"molecule": {
"id": "sa_85d38a8ca90453d40884ac43",
"inchikey": "AQRILOWZXOAUAS-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CO)cc3)nc2)CC1"
},
"smiles": "CC(=O)N1CCN(c2ccc(CCc3ccc(CO)cc3)nc2)CC1",
"reactionStepId": "sa_002513f54cd97e1f587baa1d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08999989B2;0640;1601030\",\"rsmi\":\"CC(=O)OC(=O)[CH3:1].CC(C)(C)O[C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1>C1CCOC1.CCN(CC)CC.ClCCl.O=C(O)C(F)(F)F>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"CC(=O)OC(=O)[CH3:1].CC(C)(C)O[C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1>C1CCOC1.CCN(CC)CC.ClCCl.O=C(O)C(F)(F)F>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][n:10][c:11]([CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_002513f54cd97e1f587baa1d",
"reactionHash": "21c7a522601452348f955637c6318cbec349cf5b15a9f85268ef44389d4b4fd5"
},
"children": [
{
"id": "13140",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_a0a536e62b655e9684a22bb5",
"parentId": "13139",
"isLeaf": false,
"molecule": {
"id": "sa_a0a536e62b655e9684a22bb5",
"inchikey": "BDYKBXMARMPTSW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccc(CCc3ccc(CO)cc3)nc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccc(CCc3ccc(CO)cc3)nc2)CC1",
"reactionStepId": "sa_af1c9429cb7dfa9f1574e491",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08999989B2;0638;1601029\",\"rsmi\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]3[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]3)[n:26][cH:27]2)[CH2:28][CH2:29]1>C.CCOC(C)=O.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH2:16][CH2:17][c:18]3[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]3)[n:26][cH:27]2)[CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]3[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]3)[n:26][cH:27]2)[CH2:28][CH2:29]1>C.CCOC(C)=O.[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH2:16][CH2:17][c:18]3[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]3)[n:26][cH:27]2)[CH2:28][CH2:29]1\"}",
"reactionStep": {
"id": "sa_af1c9429cb7dfa9f1574e491",
"reactionHash": "57810399105d47dd78095ac7a49dc5467883f72c7304df54ce9e2b85306b8e49"
},
"children": [
{
"id": "13141",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_b3d55cad0748374b2dfe8558",
"parentId": "13140",
"isLeaf": false,
"molecule": {
"id": "sa_b3d55cad0748374b2dfe8558",
"inchikey": "DKIXSUXAZNLYOJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccc(C=Cc3ccc(CO)cc3)nc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccc(C=Cc3ccc(CO)cc3)nc2)CC1",
"reactionStepId": "sa_a31444b966d140c1bfed314e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08999989B2;0636;1601028\",\"rsmi\":\"O=[CH:16][c:15]1[cH:14][cH:13][c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:29][CH2:28]2)[cH:27][n:26]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:17][c:18]2[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]2)cc1>C1CCOC1.CC(C)(C)O.O.Cl.[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]3[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]3)[n:26][cH:27]2)[CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"O=[CH:16][c:15]1[cH:14][cH:13][c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:29][CH2:28]2)[cH:27][n:26]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:17][c:18]2[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]2)cc1>C1CCOC1.CC(C)(C)O.O.Cl.[K+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]3[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]3)[n:26][cH:27]2)[CH2:28][CH2:29]1\"}",
"reactionStep": {
"id": "sa_a31444b966d140c1bfed314e",
"reactionHash": "4235671b9f6a8bc65ff74df8eaac5fad0b0f920049d687f7f00381b6a7d4cab4"
},
"children": [
{
"id": "13142",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_c66f26fdada78cb6579341a9",
"parentId": "13141",
"isLeaf": true,
"molecule": {
"id": "sa_c66f26fdada78cb6579341a9",
"inchikey": "YFVCDHOUTSOCRI-UHFFFAOYSA-N",
"smiles": "OCc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1"
},
"smiles": "OCc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13143",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_8824bdcd392be9e8d5ff036b",
"parentId": "13141",
"isLeaf": true,
"molecule": {
"id": "sa_8824bdcd392be9e8d5ff036b",
"inchikey": "ZDLAEYGQLPLNTP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccc(C=O)nc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccc(C=O)nc2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13144",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "13139",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13145",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_dc8cb1645d1f4dafe3621d07",
"parentId": "13138",
"isLeaf": true,
"molecule": {
"id": "sa_dc8cb1645d1f4dafe3621d07",
"inchikey": "YMWUJEATGCHHMB-UHFFFAOYSA-N",
"smiles": "ClCCl"
},
"smiles": "ClCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13146",
"routeId": "sa_24e954d7ff31f8c9d5592a09",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "13137",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}