Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(OCCCc2c(C(=O)NS(=O)(=O)c3ccccc3)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl
InChiKey
UTWBMMYEJOHBAI-UHFFFAOYSA-N
Route Signature
f8b89849b31ad2e5b3588a097bc2f322590a0e311bd9fa555193769afe8c9c3d
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_483f9f46deb69608ce812f17",
"signature": "f8b89849b31ad2e5b3588a097bc2f322590a0e311bd9fa555193769afe8c9c3d",
"contentHash": "aef4b542c5d36167e98ced1eac7c59d9db45dd06b8e0b5719b2f6b4dfeaed6e7",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_098788bd5ed45af3e94a2c58",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-06286",
"moleculeId": "sa_29b98b2772ed5af04f5817d4",
"smiles": "Cc1cc(OCCCc2c(C(=O)NS(=O)(=O)c3ccccc3)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_29b98b2772ed5af04f5817d4",
"inchikey": "UTWBMMYEJOHBAI-UHFFFAOYSA-N",
"smiles": "Cc1cc(OCCCc2c(C(=O)NS(=O)(=O)c3ccccc3)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15892",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_29b98b2772ed5af04f5817d4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_29b98b2772ed5af04f5817d4",
"inchikey": "UTWBMMYEJOHBAI-UHFFFAOYSA-N",
"smiles": "Cc1cc(OCCCc2c(C(=O)NS(=O)(=O)c3ccccc3)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl"
},
"smiles": "Cc1cc(OCCCc2c(C(=O)NS(=O)(=O)c3ccccc3)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl",
"reactionStepId": "sa_f685939ec16622cb1d0eb348",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150336925A1;1140;1790949\",\"rsmi\":\"O[C:11]([c:10]1[c:9]([CH2:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][c:2]([CH3:1])[c:38]([Cl:39])[c:36]([CH3:37])[cH:35]2)[c:34]2[c:24]([nH:23]1)[c:25](-[c:26]1[cH:27][cH:28][cH:29][o:30]1)[cH:31][cH:32][cH:33]2)=[O:12].[NH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>CC#N.CC#N.CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl.O>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][c:9]2[c:10]([C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[nH:23][c:24]3[c:25](-[c:26]4[cH:27][cH:28][cH:29][o:30]4)[cH:31][cH:32][cH:33][c:34]23)[cH:35][c:36]([CH3:37])[c:38]1[Cl:39]\"},\"mapped_reaction_smiles\":\"O[C:11]([c:10]1[c:9]([CH2:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][c:2]([CH3:1])[c:38]([Cl:39])[c:36]([CH3:37])[cH:35]2)[c:34]2[c:24]([nH:23]1)[c:25](-[c:26]1[cH:27][cH:28][cH:29][o:30]1)[cH:31][cH:32][cH:33]2)=[O:12].[NH2:13][S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>CC#N.CC#N.CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl.O>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][c:9]2[c:10]([C:11](=[O:12])[NH:13][S:14](=[O:15])(=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[nH:23][c:24]3[c:25](-[c:26]4[cH:27][cH:28][cH:29][o:30]4)[cH:31][cH:32][cH:33][c:34]23)[cH:35][c:36]([CH3:37])[c:38]1[Cl:39]\"}",
"reactionStep": {
"id": "sa_f685939ec16622cb1d0eb348",
"reactionHash": "4b119dceef3c936f7859fc83247d478f0be1c7f902a5b0b43874aa2e74998cd6"
},
"children": [
{
"id": "15893",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_0db796974552cb2e3fe16437",
"parentId": "15892",
"isLeaf": false,
"molecule": {
"id": "sa_0db796974552cb2e3fe16437",
"inchikey": "BTALEACIFCUVCA-UHFFFAOYSA-N",
"smiles": "Cc1cc(OCCCc2c(C(=O)O)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl"
},
"smiles": "Cc1cc(OCCCc2c(C(=O)O)[nH]c3c(-c4ccco4)cccc23)cc(C)c1Cl",
"reactionStepId": "sa_30a3b360d10ca353fcc07d3e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150336925A1;1139;1790948\",\"rsmi\":\"CC[O:13][C:11]([c:10]1[c:9]([CH2:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][c:2]([CH3:1])[c:29]([Cl:30])[c:27]([CH3:28])[cH:26]2)[c:25]2[c:15]([nH:14]1)[c:16](-[c:17]1[cH:18][cH:19][cH:20][o:21]1)[cH:22][cH:23][cH:24]2)=[O:12]>C1CCOC1.CC#N.CC#N.CCO.O.[Li+].O>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][c:9]2[c:10]([C:11](=[O:12])[OH:13])[nH:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][o:21]4)[cH:22][cH:23][cH:24][c:25]23)[cH:26][c:27]([CH3:28])[c:29]1[Cl:30]\"},\"mapped_reaction_smiles\":\"CC[O:13][C:11]([c:10]1[c:9]([CH2:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][c:2]([CH3:1])[c:29]([Cl:30])[c:27]([CH3:28])[cH:26]2)[c:25]2[c:15]([nH:14]1)[c:16](-[c:17]1[cH:18][cH:19][cH:20][o:21]1)[cH:22][cH:23][cH:24]2)=[O:12]>C1CCOC1.CC#N.CC#N.CCO.O.[Li+].O>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][c:9]2[c:10]([C:11](=[O:12])[OH:13])[nH:14][c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][o:21]4)[cH:22][cH:23][cH:24][c:25]23)[cH:26][c:27]([CH3:28])[c:29]1[Cl:30]\"}",
"reactionStep": {
"id": "sa_30a3b360d10ca353fcc07d3e",
"reactionHash": "085635f12cf94066f97f4129819804fc2ad48ca92a47d8621ba32043e64856c0"
},
"children": [
{
"id": "15894",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_d9dc4d0b64970e5e29710c09",
"parentId": "15893",
"isLeaf": false,
"molecule": {
"id": "sa_d9dc4d0b64970e5e29710c09",
"inchikey": "QWVFFZHVQCQZOT-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1[nH]c2c(-c3ccco3)cccc2c1CCCOc1cc(C)c(Cl)c(C)c1"
},
"smiles": "CCOC(=O)c1[nH]c2c(-c3ccco3)cccc2c1CCCOc1cc(C)c(Cl)c(C)c1",
"reactionStepId": "sa_3452898f2fc630d43a75f10b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150336925A1;1138;1790947\",\"rsmi\":\"Br[c:25]1[cH:24][cH:23][cH:22][c:21]2[c:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]3[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]3)[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:32][c:31]21.OB(O)[c:26]1[cH:27][cH:28][cH:29][o:30]1>CCO.COCCOC.[Cs+].F.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][o:30]3)[c:31]2[nH:32]1\"},\"mapped_reaction_smiles\":\"Br[c:25]1[cH:24][cH:23][cH:22][c:21]2[c:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]3[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]3)[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:32][c:31]21.OB(O)[c:26]1[cH:27][cH:28][cH:29][o:30]1>CCO.COCCOC.[Cs+].F.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][o:30]3)[c:31]2[nH:32]1\"}",
"reactionStep": {
"id": "sa_3452898f2fc630d43a75f10b",
"reactionHash": "9da4b023640e92175538ea9ddfb29a119b2880275c5409394e0aa3943b979ed6"
},
"children": [
{
"id": "15895",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_8ea08cc0222a01cefaca250c",
"parentId": "15894",
"isLeaf": true,
"molecule": {
"id": "sa_8ea08cc0222a01cefaca250c",
"inchikey": "PZJSZBJLOWMDRG-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccco1"
},
"smiles": "OB(O)c1ccco1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15896",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_8560cd0501a36f2575826411",
"parentId": "15894",
"isLeaf": false,
"molecule": {
"id": "sa_8560cd0501a36f2575826411",
"inchikey": "XEWOOWJVJRKXSX-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1[nH]c2c(Br)cccc2c1CCCOc1cc(C)c(Cl)c(C)c1"
},
"smiles": "CCOC(=O)c1[nH]c2c(Br)cccc2c1CCCOc1cc(C)c(Cl)c(C)c1",
"reactionStepId": "sa_9ea6cf4a4ad3d61da6b061e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150336925A1;1128;1790945\",\"rsmi\":\"O[c:12]1[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][CH2:10][OH:11])[c:21]2[cH:22][cH:23][cH:24][c:25]([Br:26])[c:27]2[nH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25]([Br:26])[c:27]2[nH:28]1\"},\"mapped_reaction_smiles\":\"O[c:12]1[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][CH2:10][OH:11])[c:21]2[cH:22][cH:23][cH:24][c:25]([Br:26])[c:27]2[nH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][c:14]([CH3:15])[c:16]([Cl:17])[c:18]([CH3:19])[cH:20]2)[c:21]2[cH:22][cH:23][cH:24][c:25]([Br:26])[c:27]2[nH:28]1\"}",
"reactionStep": {
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"reactionHash": "84abc2ab3b3e36417315bbad936e9e9ac653903de2bd8619495e1937cf57f057"
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"children": [
{
"id": "15897",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_589d94817dee88ae0c9f20bd",
"parentId": "15896",
"isLeaf": true,
"molecule": {
"id": "sa_589d94817dee88ae0c9f20bd",
"inchikey": "OSDLLIBGSJNGJE-UHFFFAOYSA-N",
"smiles": "Cc1cc(O)cc(C)c1Cl"
},
"smiles": "Cc1cc(O)cc(C)c1Cl",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "15898",
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"molecule": {
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"inchikey": "XKFBQKVPNUAJDF-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1[nH]c2c(Br)cccc2c1CCCO"
},
"smiles": "CCOC(=O)c1[nH]c2c(Br)cccc2c1CCCO",
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}
]
}
]
}
]
},
{
"id": "15899",
"routeId": "sa_483f9f46deb69608ce812f17",
"moleculeId": "sa_6e662650c0764352f4e132aa",
"parentId": "15892",
"isLeaf": true,
"molecule": {
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"inchikey": "KHBQMWCZKVMBLN-UHFFFAOYSA-N",
"smiles": "NS(=O)(=O)c1ccccc1"
},
"smiles": "NS(=O)(=O)c1ccccc1",
"reactionStepId": null,
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"metadata": null,
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"children": []
}
]
}
}