Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1
InChiKey
ISEBCFGSJIHLLZ-UHFFFAOYSA-N
Route Signature
c87d3790fc9dad866a15edfd939203061714e0ec6913c53e47ad9e4cd118bcfa
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_0bfa1daa0e390f20a5dcdd0f",
"signature": "c87d3790fc9dad866a15edfd939203061714e0ec6913c53e47ad9e4cd118bcfa",
"contentHash": "da3efac1465950d4751564813d0d664cb896fec7b8fb0527d0453f530dde87e4",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_f4123528933aebf15a75bd75",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00209",
"moleculeId": "sa_7f7a1a92f8bf32e1e2fbd324",
"smiles": "O=C(O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7f7a1a92f8bf32e1e2fbd324",
"inchikey": "ISEBCFGSJIHLLZ-UHFFFAOYSA-N",
"smiles": "O=C(O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9267",
"routeId": "sa_0bfa1daa0e390f20a5dcdd0f",
"moleculeId": "sa_7f7a1a92f8bf32e1e2fbd324",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7f7a1a92f8bf32e1e2fbd324",
"inchikey": "ISEBCFGSJIHLLZ-UHFFFAOYSA-N",
"smiles": "O=C(O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1"
},
"smiles": "O=C(O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1",
"reactionStepId": "sa_de323984c83db5392103cf7c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0126;1710738\",\"rsmi\":\"C[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][c:8]([O:9][CH:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][c:19]([F:20])[cH:21][cH:22][cH:23]4)[cH:24][c:25]32)[cH:26][cH:27][cH:28]1>C1CCOC1.[Li+].O>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][c:8]([O:9][CH:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][c:19]([F:20])[cH:21][cH:22][cH:23]4)[cH:24][c:25]32)[cH:26][cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][c:8]([O:9][CH:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][c:19]([F:20])[cH:21][cH:22][cH:23]4)[cH:24][c:25]32)[cH:26][cH:27][cH:28]1>C1CCOC1.[Li+].O>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][c:8]([O:9][CH:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][c:19]([F:20])[cH:21][cH:22][cH:23]4)[cH:24][c:25]32)[cH:26][cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_de323984c83db5392103cf7c",
"reactionHash": "16efd6e0358d69a727f4a76d262853d05684b3adda35679ae8115f6ded57f40f"
},
"children": [
{
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"routeId": "sa_0bfa1daa0e390f20a5dcdd0f",
"moleculeId": "sa_8f00ac148d44c89992e77d28",
"parentId": "9267",
"isLeaf": false,
"molecule": {
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"inchikey": "ITERUWZHSHOWBH-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1"
},
"smiles": "COC(=O)COc1cccc(OC2CCc3ccc(-c4cccc(F)c4)cc32)c1",
"reactionStepId": "sa_5196eb4bb0fc73e50b871582",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0124;1710737\",\"rsmi\":\"O[c:9]1[cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:29][cH:28][cH:27]1.[OH:10][CH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][c:20]([F:21])[cH:22][cH:23][cH:24]3)[cH:25][c:26]21>CC(C)OC(=O)N=NC(=O)OC(C)C.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([O:10][CH:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17](-[c:18]4[cH:19][c:20]([F:21])[cH:22][cH:23][cH:24]4)[cH:25][c:26]32)[cH:27][cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O[c:9]1[cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:29][cH:28][cH:27]1.[OH:10][CH:11]1[CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][c:20]([F:21])[cH:22][cH:23][cH:24]3)[cH:25][c:26]21>CC(C)OC(=O)N=NC(=O)OC(C)C.ClCCl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([O:10][CH:11]2[CH2:12][CH2:13][c:14]3[cH:15][cH:16][c:17](-[c:18]4[cH:19][c:20]([F:21])[cH:22][cH:23][cH:24]4)[cH:25][c:26]32)[cH:27][cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_5196eb4bb0fc73e50b871582",
"reactionHash": "1f8ee5832ce66aa7768ae55b24d43377249cdf79b6d56f486eb4dd5563b33017"
},
"children": [
{
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"routeId": "sa_0bfa1daa0e390f20a5dcdd0f",
"moleculeId": "sa_8d9b0c4e9ee28b18de9f87ec",
"parentId": "9268",
"isLeaf": false,
"molecule": {
"id": "sa_8d9b0c4e9ee28b18de9f87ec",
"inchikey": "SQRPEDUEGWFUKZ-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1cccc(O)c1"
},
"smiles": "COC(=O)COc1cccc(O)c1",
"reactionStepId": "sa_82b83542ad0d975ac82452ba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0120;1710735\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:10][c:9]1[cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12][cH:11]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:10][c:9]1[cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12][cH:11]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][cH:13]1\"}",
"reactionStep": {
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"reactionHash": "6ab78032e596ddba220390d089058b15aaf93f189ae1113157fbde4f2a9075ea"
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"children": [
{
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"routeId": "sa_0bfa1daa0e390f20a5dcdd0f",
"moleculeId": "sa_f37abeb09687c55b8f26c964",
"parentId": "9269",
"isLeaf": false,
"molecule": {
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"inchikey": "JMZSXRYBTZOSCT-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1cccc(O[Si](C)(C)C(C)(C)C)c1"
},
"smiles": "COC(=O)COc1cccc(O[Si](C)(C)C(C)(C)C)c1",
"reactionStepId": "sa_435940ec4ccfc4925c935fc9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0119;1710734\",\"rsmi\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19][cH:20]1>CN(C)C=O.[HH].[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19][cH:20]1>CN(C)C=O.[HH].[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19][cH:20]1\"}",
"reactionStep": {
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"reactionHash": "8279fcfa81f346cb78ae307f2dc0033652ec3fdbba1fa85e1bcd5417559b2200"
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"children": [
{
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"parentId": "9270",
"isLeaf": false,
"molecule": {
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"inchikey": "WNTUMICETVLAST-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Oc1cccc(O)c1"
},
"smiles": "CC(C)(C)[Si](C)(C)Oc1cccc(O)c1",
"reactionStepId": "sa_969ef62560ed58abc577c86e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0117;1710733\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([OH:14])[cH:15]1>CN(C)C=O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][cH:12][c:13]([OH:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([OH:14])[cH:15]1>CN(C)C=O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][cH:12][c:13]([OH:14])[cH:15]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "9271",
"isLeaf": true,
"molecule": {
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"inchikey": "BCNZYOJHNLTNEZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Cl"
},
"smiles": "CC(C)(C)[Si](C)(C)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
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{
"id": "9273",
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"moleculeId": "sa_18a59ac672d4024e96730d8a",
"parentId": "9271",
"isLeaf": true,
"molecule": {
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"inchikey": "GHMLBKRAJCXXBS-UHFFFAOYSA-N",
"smiles": "Oc1cccc(O)c1"
},
"smiles": "Oc1cccc(O)c1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "9274",
"routeId": "sa_0bfa1daa0e390f20a5dcdd0f",
"moleculeId": "sa_d6971278542e932ae568b29f",
"parentId": "9270",
"isLeaf": true,
"molecule": {
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"inchikey": "YDCHPLOFQATIDS-UHFFFAOYSA-N",
"smiles": "COC(=O)CBr"
},
"smiles": "COC(=O)CBr",
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}
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]
},
{
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"molecule": {
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"inchikey": "YKIVVSUPIKEAFF-UHFFFAOYSA-N",
"smiles": "OC1CCc2ccc(-c3cccc(F)c3)cc21"
},
"smiles": "OC1CCc2ccc(-c3cccc(F)c3)cc21",
"reactionStepId": "sa_4ee47fced35c5362858673b7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0122;1710736\",\"rsmi\":\"[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[cH:16][c:17]21>CO.[Na]>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[cH:16][c:17]21\"},\"mapped_reaction_smiles\":\"[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[cH:16][c:17]21>CO.[Na]>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[cH:16][c:17]21\"}",
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"molecule": {
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"smiles": "O=C1CCc2ccc(-c3cccc(F)c3)cc21"
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"smiles": "O=C1CCc2ccc(-c3cccc(F)c3)cc21",
"reactionStepId": "sa_27ab172bbd89100d4bdfbe5a",
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"metadata": "{\"annotations\":{\"ID\":\"US20150175567A1;0097;1710723\",\"rsmi\":\"Br[c:8]1[cH:7][cH:6][c:5]2[c:17]([cH:16]1)[C:2](=[O:1])[CH2:3][CH2:4]2.OB(O)[c:9]1[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]1>CCOC(C)=O.Cc1ccccc1.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[cH:16][c:17]21\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:7][cH:6][c:5]2[c:17]([cH:16]1)[C:2](=[O:1])[CH2:3][CH2:4]2.OB(O)[c:9]1[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]1>CCOC(C)=O.Cc1ccccc1.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][c:11]([F:12])[cH:13][cH:14][cH:15]3)[cH:16][c:17]21\"}",
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"molecule": {
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},
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{
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"molecule": {
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"smiles": "O=C1CCc2ccc(Br)cc21"
},
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}
]
}
]
}
]
}
]
}
}