Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C=Cc1cc(Nc2ncc(Cl)c(Nc3cc(Br)ccc3N(C)S(C)(=O)=O)n2)ccc1N1CCN(C)CC1
InChiKey
YRQOUCUKJFAXOY-UHFFFAOYSA-N
Route Signature
6b0955974a82dd219a4d6f8b07c04dfbc1b7bc682781c2a6fd801847c8a54d76
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f7804dbcb5b633a632ff922f",
"signature": "6b0955974a82dd219a4d6f8b07c04dfbc1b7bc682781c2a6fd801847c8a54d76",
"contentHash": "b8a985c3940b89a21de72a8d9fa6b3cc82732741515cc93aeab8dcbd8593330b",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_70eca05e21e6ffe96b63510d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05777",
"moleculeId": "sa_d10f6ee94c043fee2597c64d",
"smiles": "C=Cc1cc(Nc2ncc(Cl)c(Nc3cc(Br)ccc3N(C)S(C)(=O)=O)n2)ccc1N1CCN(C)CC1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d10f6ee94c043fee2597c64d",
"inchikey": "YRQOUCUKJFAXOY-UHFFFAOYSA-N",
"smiles": "C=Cc1cc(Nc2ncc(Cl)c(Nc3cc(Br)ccc3N(C)S(C)(=O)=O)n2)ccc1N1CCN(C)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11474",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_d10f6ee94c043fee2597c64d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d10f6ee94c043fee2597c64d",
"inchikey": "YRQOUCUKJFAXOY-UHFFFAOYSA-N",
"smiles": "C=Cc1cc(Nc2ncc(Cl)c(Nc3cc(Br)ccc3N(C)S(C)(=O)=O)n2)ccc1N1CCN(C)CC1"
},
"smiles": "C=Cc1cc(Nc2ncc(Cl)c(Nc3cc(Br)ccc3N(C)S(C)(=O)=O)n2)ccc1N1CCN(C)CC1",
"reactionStepId": "sa_55a70237a4cd4d444ba389f7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031351A1;0183;1479505\",\"rsmi\":\"Cl[c:16]1[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]2[c:24]([N:25]([CH3:26])[S:27]([CH3:28])(=[O:29])=[O:30])[cH:31][cH:32][c:33]([Br:34])[cH:35]2)[n:36]1.[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([NH2:15])[cH:37]1>COCCO.CS(=O)(=O)O>[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]3[c:24]([N:25]([CH3:26])[S:27]([CH3:28])(=[O:29])=[O:30])[cH:31][cH:32][c:33]([Br:34])[cH:35]3)[n:36]2)[cH:37]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]2[c:24]([N:25]([CH3:26])[S:27]([CH3:28])(=[O:29])=[O:30])[cH:31][cH:32][c:33]([Br:34])[cH:35]2)[n:36]1.[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([NH2:15])[cH:37]1>COCCO.CS(=O)(=O)O>[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([Cl:20])[c:21]([NH:22][c:23]3[c:24]([N:25]([CH3:26])[S:27]([CH3:28])(=[O:29])=[O:30])[cH:31][cH:32][c:33]([Br:34])[cH:35]3)[n:36]2)[cH:37]1\"}",
"reactionStep": {
"id": "sa_55a70237a4cd4d444ba389f7",
"reactionHash": "365f12a55d6019d326e7ff4292bc8ec4118503b16b0d9ffc127e9e7b355e10f2"
},
"children": [
{
"id": "11475",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_3108876bee3fa19e6d7b1977",
"parentId": "11474",
"isLeaf": false,
"molecule": {
"id": "sa_3108876bee3fa19e6d7b1977",
"inchikey": "SVNGNYQEBCYIBV-UHFFFAOYSA-N",
"smiles": "C=Cc1cc(N)ccc1N1CCN(C)CC1"
},
"smiles": "C=Cc1cc(N)ccc1N1CCN(C)CC1",
"reactionStepId": "sa_936478c826f5baaf1c6b1103",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031351A1;0182;1479504\",\"rsmi\":\"O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[c:3]([CH:2]=[CH2:1])[cH:16]1>C1CCOC1.CC(=O)O.[Fe]>[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([NH2:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[c:3]([CH:2]=[CH2:1])[cH:16]1>C1CCOC1.CC(=O)O.[Fe]>[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([NH2:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_936478c826f5baaf1c6b1103",
"reactionHash": "6ad664bdb74e16982b6fa5d0ea5a1284d1d55cb4345ca5d3d1f81b1a2253b16e"
},
"children": [
{
"id": "11476",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_97364dad7d320835fc6e1fd3",
"parentId": "11475",
"isLeaf": false,
"molecule": {
"id": "sa_97364dad7d320835fc6e1fd3",
"inchikey": "AZGHMYVINCUZRP-UHFFFAOYSA-N",
"smiles": "C=Cc1cc([N+](=O)[O-])ccc1N1CCN(C)CC1"
},
"smiles": "C=Cc1cc([N+](=O)[O-])ccc1N1CCN(C)CC1",
"reactionStepId": "sa_aa33fb9b21797c7444d1e252",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031351A1;0181;1479503\",\"rsmi\":\"Br[c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1.CCCCOB(OCCCC)[CH:2]=[CH2:1]>COCCOC.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1\"},\"mapped_reaction_smiles\":\"Br[c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1.CCCCOB(OCCCC)[CH:2]=[CH2:1]>COCCOC.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH2:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]2)[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1\"}",
"reactionStep": {
"id": "sa_aa33fb9b21797c7444d1e252",
"reactionHash": "b1ae18a21a06f2f3488184a3c2fb30b9ccee4534c6b1e6344139f63393eeac6f"
},
"children": [
{
"id": "11477",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_0fef4a856454c45f0e1559c4",
"parentId": "11476",
"isLeaf": true,
"molecule": {
"id": "sa_0fef4a856454c45f0e1559c4",
"inchikey": "JQKJEPJLCSCBGW-UHFFFAOYSA-N",
"smiles": "C=CB(OCCCC)OCCCC"
},
"smiles": "C=CB(OCCCC)OCCCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11478",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_5b021b2c036dfcfbdaaff2be",
"parentId": "11476",
"isLeaf": true,
"molecule": {
"id": "sa_5b021b2c036dfcfbdaaff2be",
"inchikey": "WDTGICOJIRJONX-UHFFFAOYSA-N",
"smiles": "CN1CCN(c2ccc([N+](=O)[O-])cc2Br)CC1"
},
"smiles": "CN1CCN(c2ccc([N+](=O)[O-])cc2Br)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "11479",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_5db3145f58d9d4a211311b11",
"parentId": "11474",
"isLeaf": false,
"molecule": {
"id": "sa_5db3145f58d9d4a211311b11",
"inchikey": "UGJBTKNJBBUOAQ-UHFFFAOYSA-N",
"smiles": "CN(c1ccc(Br)cc1Nc1nc(Cl)ncc1Cl)S(C)(=O)=O"
},
"smiles": "CN(c1ccc(Br)cc1Nc1nc(Cl)ncc1Cl)S(C)(=O)=O",
"reactionStepId": "sa_d00a590e6ec09d9f695c6edc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031351A1;0179;1479502\",\"rsmi\":\"Cl[c:6]1[n:7][c:8]([Cl:9])[n:10][cH:11][c:12]1[Cl:13].[CH3:1][N:2]([c:3]1[c:4]([NH2:5])[cH:14][c:15]([Br:16])[cH:17][cH:18]1)[S:19]([CH3:20])(=[O:21])=[O:22]>CCN(C(C)C)C(C)C.CN1CCCC1=O>[CH3:1][N:2]([c:3]1[c:4]([NH:5][c:6]2[n:7][c:8]([Cl:9])[n:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]([Br:16])[cH:17][cH:18]1)[S:19]([CH3:20])(=[O:21])=[O:22]\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][c:8]([Cl:9])[n:10][cH:11][c:12]1[Cl:13].[CH3:1][N:2]([c:3]1[c:4]([NH2:5])[cH:14][c:15]([Br:16])[cH:17][cH:18]1)[S:19]([CH3:20])(=[O:21])=[O:22]>CCN(C(C)C)C(C)C.CN1CCCC1=O>[CH3:1][N:2]([c:3]1[c:4]([NH:5][c:6]2[n:7][c:8]([Cl:9])[n:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]([Br:16])[cH:17][cH:18]1)[S:19]([CH3:20])(=[O:21])=[O:22]\"}",
"reactionStep": {
"id": "sa_d00a590e6ec09d9f695c6edc",
"reactionHash": "a2f87d809a2b83f9cee705b02d67b52a839fa4b3fe9ea3fcb32dc6d6373ec481"
},
"children": [
{
"id": "11480",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_fde86ac4eaa353047ff34d33",
"parentId": "11479",
"isLeaf": true,
"molecule": {
"id": "sa_fde86ac4eaa353047ff34d33",
"inchikey": "GIKMWFAAEIACRF-UHFFFAOYSA-N",
"smiles": "Clc1ncc(Cl)c(Cl)n1"
},
"smiles": "Clc1ncc(Cl)c(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11481",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_5205a8171042c0d5aacb69f0",
"parentId": "11479",
"isLeaf": false,
"molecule": {
"id": "sa_5205a8171042c0d5aacb69f0",
"inchikey": "UFHONEUSCSVWJH-UHFFFAOYSA-N",
"smiles": "CN(c1ccc(Br)cc1N)S(C)(=O)=O"
},
"smiles": "CN(c1ccc(Br)cc1N)S(C)(=O)=O",
"reactionStepId": "sa_c2ed931cd366bdd010b56d17",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031351A1;0178;1479501\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([N:2]([CH3:1])[S:11]([CH3:12])(=[O:13])=[O:14])[cH:10][cH:9][c:7]([Br:8])[cH:6]1>C1CCOC1.CC(=O)O.[Fe]>[CH3:1][N:2]([c:3]1[c:4]([NH2:5])[cH:6][c:7]([Br:8])[cH:9][cH:10]1)[S:11]([CH3:12])(=[O:13])=[O:14]\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([N:2]([CH3:1])[S:11]([CH3:12])(=[O:13])=[O:14])[cH:10][cH:9][c:7]([Br:8])[cH:6]1>C1CCOC1.CC(=O)O.[Fe]>[CH3:1][N:2]([c:3]1[c:4]([NH2:5])[cH:6][c:7]([Br:8])[cH:9][cH:10]1)[S:11]([CH3:12])(=[O:13])=[O:14]\"}",
"reactionStep": {
"id": "sa_c2ed931cd366bdd010b56d17",
"reactionHash": "7c724d11a875961739503ecd919d820dbf4c96a542ff5dbac946f42c5ca453f7"
},
"children": [
{
"id": "11482",
"routeId": "sa_f7804dbcb5b633a632ff922f",
"moleculeId": "sa_98c4d726c18defb0f56d3266",
"parentId": "11481",
"isLeaf": true,
"molecule": {
"id": "sa_98c4d726c18defb0f56d3266",
"inchikey": "VPUAAVPUYCHXMP-UHFFFAOYSA-N",
"smiles": "CN(c1ccc(Br)cc1[N+](=O)[O-])S(C)(=O)=O"
},
"smiles": "CN(c1ccc(Br)cc1[N+](=O)[O-])S(C)(=O)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}