Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1(C)CC(=C(c2ccc(/C=C/C(=O)O)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1
InChiKey
OMGMXYACDPFCEG-KPKJPENVSA-N
Route Signature
cda70b9debfd184a14fdc1b3c97eb8bbf180b13f74a596f98acb0a4647d5c9d4
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_f56d1fb650ebe59f13df9737",
"signature": "cda70b9debfd184a14fdc1b3c97eb8bbf180b13f74a596f98acb0a4647d5c9d4",
"contentHash": "63a433332789401b815bc6f3b581bad1a16906bcf86dcba1872cabe1afd51785",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_19b8a332128287ac3c94622b",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00368",
"moleculeId": "sa_e7cc0ab90342adf02cfca870",
"smiles": "CC1(C)CC(=C(c2ccc(/C=C/C(=O)O)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_e7cc0ab90342adf02cfca870",
"inchikey": "OMGMXYACDPFCEG-KPKJPENVSA-N",
"smiles": "CC1(C)CC(=C(c2ccc(/C=C/C(=O)O)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "4152",
"routeId": "sa_f56d1fb650ebe59f13df9737",
"moleculeId": "sa_e7cc0ab90342adf02cfca870",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e7cc0ab90342adf02cfca870",
"inchikey": "OMGMXYACDPFCEG-KPKJPENVSA-N",
"smiles": "CC1(C)CC(=C(c2ccc(/C=C/C(=O)O)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1"
},
"smiles": "CC1(C)CC(=C(c2ccc(/C=C/C(=O)O)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1",
"reactionStepId": "sa_a4823940150b4b9829103eeb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070213348A1;0409;495390\",\"rsmi\":\"CC[O:15][C:13](/[CH:12]=[CH:11]/[c:10]1[cH:9][cH:8][c:7]([C:6](=[C:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[CH2:30][C:27]([CH3:28])([CH3:29])[CH2:26]2)[c:18]2[cH:19][c:20]([F:21])[c:22]([OH:23])[cH:24][cH:25]2)[cH:17][cH:16]1)=[O:14]>C1CCOC1.CCO.Cl.[Na+].O>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[C:6]([c:7]2[cH:8][cH:9][c:10](/[CH:11]=[CH:12]/[C:13](=[O:14])[OH:15])[cH:16][cH:17]2)[c:18]2[cH:19][c:20]([F:21])[c:22]([OH:23])[cH:24][cH:25]2)[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]1\"},\"mapped_reaction_smiles\":\"CC[O:15][C:13](/[CH:12]=[CH:11]/[c:10]1[cH:9][cH:8][c:7]([C:6](=[C:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[CH2:30][C:27]([CH3:28])([CH3:29])[CH2:26]2)[c:18]2[cH:19][c:20]([F:21])[c:22]([OH:23])[cH:24][cH:25]2)[cH:17][cH:16]1)=[O:14]>C1CCOC1.CCO.Cl.[Na+].O>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[C:6]([c:7]2[cH:8][cH:9][c:10](/[CH:11]=[CH:12]/[C:13](=[O:14])[OH:15])[cH:16][cH:17]2)[c:18]2[cH:19][c:20]([F:21])[c:22]([OH:23])[cH:24][cH:25]2)[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]1\"}",
"reactionStep": {
"id": "sa_a4823940150b4b9829103eeb",
"reactionHash": "49b6296eb0d8dc2084c21058f5a5a79d02ece540dc7b16ba4053d87be11b5a00"
},
"children": [
{
"id": "4153",
"routeId": "sa_f56d1fb650ebe59f13df9737",
"moleculeId": "sa_6c7f37ab17b8047b10d663c6",
"parentId": "4152",
"isLeaf": false,
"molecule": {
"id": "sa_6c7f37ab17b8047b10d663c6",
"inchikey": "LDGDMXISAUCEFY-NTEUORMPSA-N",
"smiles": "CCOC(=O)/C=C/c1ccc(C(=C2CC(C)(C)CC(C)(C)C2)c2ccc(O)c(F)c2)cc1"
},
"smiles": "CCOC(=O)/C=C/c1ccc(C(=C2CC(C)(C)CC(C)(C)C2)c2ccc(O)c(F)c2)cc1",
"reactionStepId": "sa_8f2b954d5b51e86cbd90aab2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070213348A1;0408;495389\",\"rsmi\":\"Br[c:8]1[cH:9][cH:10][c:11]([C:12]([c:13]2[cH:14][c:15]([F:16])[c:17]([OH:18])[cH:19][cH:20]2)=[C:21]2[CH2:22][C:23]([CH3:24])([CH3:25])[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]2)[cH:31][cH:32]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([C:12]([c:13]2[cH:14][c:15]([F:16])[c:17]([OH:18])[cH:19][cH:20]2)=[C:21]2[CH2:22][C:23]([CH3:24])([CH3:25])[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]2)[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:9][cH:10][c:11]([C:12]([c:13]2[cH:14][c:15]([F:16])[c:17]([OH:18])[cH:19][cH:20]2)=[C:21]2[CH2:22][C:23]([CH3:24])([CH3:25])[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]2)[cH:31][cH:32]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([C:12]([c:13]2[cH:14][c:15]([F:16])[c:17]([OH:18])[cH:19][cH:20]2)=[C:21]2[CH2:22][C:23]([CH3:24])([CH3:25])[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]2)[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_8f2b954d5b51e86cbd90aab2",
"reactionHash": "7e7d6091365b6255bbc0e412637927f9ff5ad81b5a34f73a27a77f19e473bb1c"
},
"children": [
{
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"routeId": "sa_f56d1fb650ebe59f13df9737",
"moleculeId": "sa_167a1e4c9d83b5bfc1544756",
"parentId": "4153",
"isLeaf": true,
"molecule": {
"id": "sa_167a1e4c9d83b5bfc1544756",
"inchikey": "JIGUQPWFLRLWPJ-UHFFFAOYSA-N",
"smiles": "C=CC(=O)OCC"
},
"smiles": "C=CC(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4155",
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"moleculeId": "sa_ef1b5ba5b23d3b45035cac84",
"parentId": "4153",
"isLeaf": false,
"molecule": {
"id": "sa_ef1b5ba5b23d3b45035cac84",
"inchikey": "XUVJIFGMIUZMQK-UHFFFAOYSA-N",
"smiles": "CC1(C)CC(=C(c2ccc(Br)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1"
},
"smiles": "CC1(C)CC(=C(c2ccc(Br)cc2)c2ccc(O)c(F)c2)CC(C)(C)C1",
"reactionStepId": "sa_fb9d3ee85a10130fe1f010f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070213348A1;0407;495388\",\"rsmi\":\"O=[C:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[CH2:26][C:23]([CH3:24])([CH3:25])[CH2:22]1.O=[C:6]([c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[c:14]1[cH:15][c:16]([F:17])[c:18]([OH:19])[cH:20][cH:21]1>C1CCOC1.Cl[Ti](Cl)(Cl)Cl.O=C(O)O.[K+].[K+].[Zn]>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[C:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[c:14]2[cH:15][c:16]([F:17])[c:18]([OH:19])[cH:20][cH:21]2)[CH2:22][C:23]([CH3:24])([CH3:25])[CH2:26]1\"},\"mapped_reaction_smiles\":\"O=[C:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[CH2:26][C:23]([CH3:24])([CH3:25])[CH2:22]1.O=[C:6]([c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[c:14]1[cH:15][c:16]([F:17])[c:18]([OH:19])[cH:20][cH:21]1>C1CCOC1.Cl[Ti](Cl)(Cl)Cl.O=C(O)O.[K+].[K+].[Zn]>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[C:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[c:14]2[cH:15][c:16]([F:17])[c:18]([OH:19])[cH:20][cH:21]2)[CH2:22][C:23]([CH3:24])([CH3:25])[CH2:26]1\"}",
"reactionStep": {
"id": "sa_fb9d3ee85a10130fe1f010f3",
"reactionHash": "c54b612ae5363c2776ab1ac1f1630531ace7d6058d7c9e7f1d0f5fed78de3d40"
},
"children": [
{
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"routeId": "sa_f56d1fb650ebe59f13df9737",
"moleculeId": "sa_df842d811aeb2c02dfc57cc8",
"parentId": "4155",
"isLeaf": false,
"molecule": {
"id": "sa_df842d811aeb2c02dfc57cc8",
"inchikey": "HRQGKJVRJYEBPA-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(Br)cc1)c1ccc(O)c(F)c1"
},
"smiles": "O=C(c1ccc(Br)cc1)c1ccc(O)c(F)c1",
"reactionStepId": "sa_379fbec3e988c37672f2a09d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070213348A1;0331;495356\",\"rsmi\":\"C[O:15][c:14]1[c:12]([F:13])[cH:11][c:10]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]2)[cH:17][cH:16]1>O.[Al+3].Cl.Cl.Cl.c1ccccc1>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[c:10]1[cH:11][c:12]([F:13])[c:14]([OH:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"C[O:15][c:14]1[c:12]([F:13])[cH:11][c:10]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]2)[cH:17][cH:16]1>O.[Al+3].Cl.Cl.Cl.c1ccccc1>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[c:10]1[cH:11][c:12]([F:13])[c:14]([OH:15])[cH:16][cH:17]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_1c1c740503766ffb92ebd082",
"parentId": "4156",
"isLeaf": false,
"molecule": {
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"inchikey": "GHUMLKAJACJMCH-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)c2ccc(Br)cc2)cc1F"
},
"smiles": "COc1ccc(C(=O)c2ccc(Br)cc2)cc1F",
"reactionStepId": "sa_c519d716bf0596bc2ed3cdc3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070213348A1;0330;495355\",\"rsmi\":\"Br[c:7]1[cH:6][c:4]([F:5])[c:3]([O:2][CH3:1])[cH:18][cH:17]1.CON(C)[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>C1CCOC1.O.[Li]CCCC>[CH3:1][O:2][c:3]1[c:4]([F:5])[cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:6][c:4]([F:5])[c:3]([O:2][CH3:1])[cH:18][cH:17]1.CON(C)[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>C1CCOC1.O.[Li]CCCC>[CH3:1][O:2][c:3]1[c:4]([F:5])[cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1\"}",
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"smiles": "COc1ccc(Br)cc1F"
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{
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},
"smiles": "CON(C)C(=O)c1ccc(Br)cc1",
"reactionStepId": "sa_cf85ddec8a29d25c36801769",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070213348A1;0329;495354\",\"rsmi\":\"Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1.[CH3:1][O:2][NH:3][CH3:4]>Cl.ClCCl.c1ccncc1>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1.[CH3:1][O:2][NH:3][CH3:4]>Cl.ClCCl.c1ccncc1>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1\"}",
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{
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{
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}
]
}
]
}
]
}
}