Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccc(NC(=O)c2cc(CNS(=O)(=O)C3CC3)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1
InChiKey
HDKROJJLUDYIJJ-UHFFFAOYSA-N
Route Signature
c6e7fb65ad01ed8aba7ebed3047c74b5ed57ff193fe92ddbba482003471efb15
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_955f955f67cc9e8f3bc130f4",
"signature": "c6e7fb65ad01ed8aba7ebed3047c74b5ed57ff193fe92ddbba482003471efb15",
"contentHash": "04259967f867e608946917058033215477c8cc1db65b727c7af728dafc65b464",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_bc6f99762b5a887ad6a9042f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01940",
"moleculeId": "sa_a7214036d985bdeaf2161b03",
"smiles": "COc1ccc(NC(=O)c2cc(CNS(=O)(=O)C3CC3)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_a7214036d985bdeaf2161b03",
"inchikey": "HDKROJJLUDYIJJ-UHFFFAOYSA-N",
"smiles": "COc1ccc(NC(=O)c2cc(CNS(=O)(=O)C3CC3)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10520",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_a7214036d985bdeaf2161b03",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a7214036d985bdeaf2161b03",
"inchikey": "HDKROJJLUDYIJJ-UHFFFAOYSA-N",
"smiles": "COc1ccc(NC(=O)c2cc(CNS(=O)(=O)C3CC3)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1"
},
"smiles": "COc1ccc(NC(=O)c2cc(CNS(=O)(=O)C3CC3)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1",
"reactionStepId": "sa_d0993e8442c0f0bc2f63ff59",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110263556A1;0552;1118944\",\"rsmi\":\"Cl[S:28](=[O:29])(=[O:30])[CH:31]1[CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:34]2)[cH:35][cH:36]1>CC#N.c1ccncc1>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][S:28](=[O:29])(=[O:30])[CH:31]3[CH2:32][CH2:33]3)[cH:34]2)[cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"Cl[S:28](=[O:29])(=[O:30])[CH:31]1[CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:34]2)[cH:35][cH:36]1>CC#N.c1ccncc1>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][S:28](=[O:29])(=[O:30])[CH:31]3[CH2:32][CH2:33]3)[cH:34]2)[cH:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_d0993e8442c0f0bc2f63ff59",
"reactionHash": "77793bc12d6a59bcb0afd55a8260cfafc5b628b52793d889fadf6c4b297bdc06"
},
"children": [
{
"id": "10521",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_9932dfbed53ad5824dda517e",
"parentId": "10520",
"isLeaf": false,
"molecule": {
"id": "sa_9932dfbed53ad5824dda517e",
"inchikey": "HCDMYOLZXUHINU-UHFFFAOYSA-N",
"smiles": "COc1ccc(NC(=O)c2cc(CN)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1"
},
"smiles": "COc1ccc(NC(=O)c2cc(CN)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1",
"reactionStepId": "sa_f18668143ccd96cab861b46f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110263556A1;0542;1118941\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:27][CH2:26][c:25]1[cH:24][cH:23][c:21]([Cl:22])[c:20]([C:18]([NH:17][c:16]2[cH:15][c:4]([C:5](=[O:6])[NH:7][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]3)[c:3]([O:2][CH3:1])[cH:30][cH:29]2)=[O:19])[cH:28]1>C1COCCO1>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:27][CH2:26][c:25]1[cH:24][cH:23][c:21]([Cl:22])[c:20]([C:18]([NH:17][c:16]2[cH:15][c:4]([C:5](=[O:6])[NH:7][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]3)[c:3]([O:2][CH3:1])[cH:30][cH:29]2)=[O:19])[cH:28]1>C1COCCO1>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_f18668143ccd96cab861b46f",
"reactionHash": "8616bb2ad510dc159a7f7ee2610a2123b1f84ea6640b162cb6d34caf89fe00c0"
},
"children": [
{
"id": "10522",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_abc7a759fb20db08eb749a91",
"parentId": "10521",
"isLeaf": false,
"molecule": {
"id": "sa_abc7a759fb20db08eb749a91",
"inchikey": "UITWKVWZBNXJIA-UHFFFAOYSA-N",
"smiles": "COc1ccc(NC(=O)c2cc(CNC(=O)OC(C)(C)C)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1"
},
"smiles": "COc1ccc(NC(=O)c2cc(CNC(=O)OC(C)(C)C)ccc2Cl)cc1C(=O)Nc1ccc(Br)cc1",
"reactionStepId": "sa_9810f379254bdf41e479922a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110263556A1;0541;1118940\",\"rsmi\":\"O[C:18](=[O:19])[c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1.[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH2:17])[cH:36][cH:37]1>CCO.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[B-](F)(F)F>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]2)[cH:36][cH:37]1\"},\"mapped_reaction_smiles\":\"O[C:18](=[O:19])[c:20]1[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]1.[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH2:17])[cH:36][cH:37]1>CCO.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[B-](F)(F)F>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]2[c:21]([Cl:22])[cH:23][cH:24][c:25]([CH2:26][NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:35]2)[cH:36][cH:37]1\"}",
"reactionStep": {
"id": "sa_9810f379254bdf41e479922a",
"reactionHash": "23d3fd92327ae675782ebe16d57f81cb6f109526d9360dd78be7cd87492b5c68"
},
"children": [
{
"id": "10523",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_8226236e136ef26e3aeb0a89",
"parentId": "10522",
"isLeaf": false,
"molecule": {
"id": "sa_8226236e136ef26e3aeb0a89",
"inchikey": "FKULUOQYTJAVOW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCc1ccc(Cl)c(C(=O)O)c1"
},
"smiles": "CC(C)(C)OC(=O)NCc1ccc(Cl)c(C(=O)O)c1",
"reactionStepId": "sa_26c27aace169c8137ad341fe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110263556A1;0540;1118939\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]([Cl:17])[cH:18][cH:19]1>C1CCOC1.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]([Cl:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]([Cl:17])[cH:18][cH:19]1>C1CCOC1.[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]([Cl:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_26c27aace169c8137ad341fe",
"reactionHash": "b3070891258ea0a455be606c27d1ef5d4cdd59bf2c95365045ff0af305e30cf1"
},
"children": [
{
"id": "10524",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "10523",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10525",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_33b391c0c6e4032ea32f4a04",
"parentId": "10523",
"isLeaf": true,
"molecule": {
"id": "sa_33b391c0c6e4032ea32f4a04",
"inchikey": "YFQKOOJYQYRSTI-UHFFFAOYSA-N",
"smiles": "NCc1ccc(Cl)c(C(=O)O)c1"
},
"smiles": "NCc1ccc(Cl)c(C(=O)O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10526",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_aa628335d7f7ebef387e0d36",
"parentId": "10522",
"isLeaf": false,
"molecule": {
"id": "sa_aa628335d7f7ebef387e0d36",
"inchikey": "HMOZECDTYVOMSA-UHFFFAOYSA-N",
"smiles": "COc1ccc(N)cc1C(=O)Nc1ccc(Br)cc1"
},
"smiles": "COc1ccc(N)cc1C(=O)Nc1ccc(Br)cc1",
"reactionStepId": "sa_827ceec34feb7be76f9c314a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110263556A1;0499;1118928\",\"rsmi\":\"O=[N+:17]([O-])[c:16]1[cH:15][c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[c:3]([O:2][CH3:1])[cH:19][cH:18]1>C1CCOC1.[Ni]>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH2:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"O=[N+:17]([O-])[c:16]1[cH:15][c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[c:3]([O:2][CH3:1])[cH:19][cH:18]1>C1CCOC1.[Ni]>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[cH:15][c:16]([NH2:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_827ceec34feb7be76f9c314a",
"reactionHash": "e4c0a4e96d8bbb1c7ce6ef44e33b7c5ff9a2f1dac1a2d978e880e597e651beab"
},
"children": [
{
"id": "10527",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_68eee35a4caf42eb7cff71d2",
"parentId": "10526",
"isLeaf": true,
"molecule": {
"id": "sa_68eee35a4caf42eb7cff71d2",
"inchikey": "YQDBYDHXBJIYDV-UHFFFAOYSA-N",
"smiles": "COc1ccc([N+](=O)[O-])cc1C(=O)Nc1ccc(Br)cc1"
},
"smiles": "COc1ccc([N+](=O)[O-])cc1C(=O)Nc1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "10528",
"routeId": "sa_955f955f67cc9e8f3bc130f4",
"moleculeId": "sa_2765c7c5491f0cd94fe6d445",
"parentId": "10520",
"isLeaf": true,
"molecule": {
"id": "sa_2765c7c5491f0cd94fe6d445",
"inchikey": "PFWWSGFPICCWGU-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)C1CC1"
},
"smiles": "O=S(=O)(Cl)C1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}