Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1OS(=O)(=O)C(F)(F)F
InChiKey
SIUNGUVCWPGDDB-UHFFFAOYSA-N
Route Signature
dedb70a34fb7e0a888d96e8aaf84853f696b5087452642583f62e06be51803ec
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b7dc6f62087e5a8363e25bd0",
"signature": "dedb70a34fb7e0a888d96e8aaf84853f696b5087452642583f62e06be51803ec",
"contentHash": "f163772183825090caabfecb1b6ffce6a89e578b9f5d8f5ce7d68779185255c3",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_dda285022f0f671f02b3c1a0",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00067",
"moleculeId": "sa_855ea52d5f3e87b5b7565829",
"smiles": "COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1OS(=O)(=O)C(F)(F)F",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_855ea52d5f3e87b5b7565829",
"inchikey": "SIUNGUVCWPGDDB-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1OS(=O)(=O)C(F)(F)F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "3417",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_855ea52d5f3e87b5b7565829",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_855ea52d5f3e87b5b7565829",
"inchikey": "SIUNGUVCWPGDDB-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1OS(=O)(=O)C(F)(F)F"
},
"smiles": "COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1OS(=O)(=O)C(F)(F)F",
"reactionStepId": "sa_60065427ae5de44a7e86e581",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150307451A1;1052;1777479\",\"rsmi\":\"O=S(=O)(N(c1ccccc1)[S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])C(F)(F)F.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:15]([Cl:16])[c:17]([CH3:18])[c:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]2)[cH:29]1>CN(C)C=O.Cl.[HH].[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[c:15]([Cl:16])[c:17]([CH3:18])[c:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]2)[cH:29]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(N(c1ccccc1)[S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])C(F)(F)F.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:15]([Cl:16])[c:17]([CH3:18])[c:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]2)[cH:29]1>CN(C)C=O.Cl.[HH].[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([O:7][S:8](=[O:9])(=[O:10])[C:11]([F:12])([F:13])[F:14])[c:15]([Cl:16])[c:17]([CH3:18])[c:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]2)[cH:29]1\"}",
"reactionStep": {
"id": "sa_60065427ae5de44a7e86e581",
"reactionHash": "8e52ab96434ebf568d6d88096e1f3cb50852eaca9403743f9bb5dc62036b8e35"
},
"children": [
{
"id": "3418",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_24bc5b50442cd9e5fcf68f54",
"parentId": "3417",
"isLeaf": true,
"molecule": {
"id": "sa_24bc5b50442cd9e5fcf68f54",
"inchikey": "DIOHEXPTUTVCNX-UHFFFAOYSA-N",
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3419",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_02857657aaddfe622d652cea",
"parentId": "3417",
"isLeaf": false,
"molecule": {
"id": "sa_02857657aaddfe622d652cea",
"inchikey": "TWDTUBUCUCRWQJ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1O"
},
"smiles": "COC(=O)c1cc(Cc2ccc(OC)cc2)c(C)c(Cl)c1O",
"reactionStepId": "sa_6b723fd9a5cd6bfea99c03ad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150307451A1;1050;1777478\",\"rsmi\":\"CC1(C)OB([c:12]2[c:10]([CH3:11])[c:8]([Cl:9])[c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22]2)OC1(C)C.Cl[CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1>CCOC(C)=O.COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:8]([Cl:9])[c:10]([CH3:11])[c:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]2)[cH:22]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:12]2[c:10]([CH3:11])[c:8]([Cl:9])[c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22]2)OC1(C)C.Cl[CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1>CCOC(C)=O.COCCOC.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:8]([Cl:9])[c:10]([CH3:11])[c:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]2)[cH:22]1\"}",
"reactionStep": {
"id": "sa_6b723fd9a5cd6bfea99c03ad",
"reactionHash": "24fc6c815bbb170d4da501f6d4a2305a6caaa189a50c9b32208a87e3046baa9f"
},
"children": [
{
"id": "3420",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_32414fe9877ead197e1bf13f",
"parentId": "3419",
"isLeaf": true,
"molecule": {
"id": "sa_32414fe9877ead197e1bf13f",
"inchikey": "MOHYOXXOKFQHDC-UHFFFAOYSA-N",
"smiles": "COc1ccc(CCl)cc1"
},
"smiles": "COc1ccc(CCl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3421",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_e7cabc5ebfac0688c3b7291d",
"parentId": "3419",
"isLeaf": false,
"molecule": {
"id": "sa_e7cabc5ebfac0688c3b7291d",
"inchikey": "RRPGORAUBLNECT-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)c(C)c(Cl)c1O"
},
"smiles": "COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)c(C)c(Cl)c1O",
"reactionStepId": "sa_325792537b4349d88cd76043",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150307451A1;1048;1777477\",\"rsmi\":\"Br[c:12]1[c:10]([CH3:11])[c:8]([Cl:9])[c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22]1.CC1(C)OB([B:13]2[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]2)OC1(C)C>CC(=O)O.CCOC(C)=O.Cc1ccccc1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:8]([Cl:9])[c:10]([CH3:11])[c:12]([B:13]2[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]2)[cH:22]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[c:10]([CH3:11])[c:8]([Cl:9])[c:6]([OH:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22]1.CC1(C)OB([B:13]2[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]2)OC1(C)C>CC(=O)O.CCOC(C)=O.Cc1ccccc1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:8]([Cl:9])[c:10]([CH3:11])[c:12]([B:13]2[O:14][C:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[O:21]2)[cH:22]1\"}",
"reactionStep": {
"id": "sa_325792537b4349d88cd76043",
"reactionHash": "2733e92967ecf3523a844e3b1f17c176a5654c2f80d5250cdb96a92e2ad31b79"
},
"children": [
{
"id": "3422",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "3421",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3423",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_cdbd3e9594e9a12550bee553",
"parentId": "3421",
"isLeaf": false,
"molecule": {
"id": "sa_cdbd3e9594e9a12550bee553",
"inchikey": "JGRJFHLKEAASFI-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)c(C)c(Cl)c1O"
},
"smiles": "COC(=O)c1cc(Br)c(C)c(Cl)c1O",
"reactionStepId": "sa_2a67b0c2fb120372d4eacbc1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150307451A1;1046;1777476\",\"rsmi\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:10]([CH3:11])[c:12]([Br:13])[cH:14]1>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:8]([Cl:9])[c:10]([CH3:11])[c:12]([Br:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Cl:9].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:10]([CH3:11])[c:12]([Br:13])[cH:14]1>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[c:8]([Cl:9])[c:10]([CH3:11])[c:12]([Br:13])[cH:14]1\"}",
"reactionStep": {
"id": "sa_2a67b0c2fb120372d4eacbc1",
"reactionHash": "07d1d8ec4aaeb4f7848b730d59915dfba54fe439113792f46bf82dc825cdc3e7"
},
"children": [
{
"id": "3424",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_012e7f6438bea15c19206e8b",
"parentId": "3423",
"isLeaf": false,
"molecule": {
"id": "sa_012e7f6438bea15c19206e8b",
"inchikey": "DEMKAVJRIYGNEQ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)c(C)cc1O"
},
"smiles": "COC(=O)c1cc(Br)c(C)cc1O",
"reactionStepId": "sa_7583ef8a5d288049bdfd2087",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150307451A1;0720;1777326\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH3:10])[c:11]([Br:12])[cH:13]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH3:10])[c:11]([Br:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH3:10])[c:11]([Br:12])[cH:13]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([OH:7])[cH:8][c:9]([CH3:10])[c:11]([Br:12])[cH:13]1\"}",
"reactionStep": {
"id": "sa_7583ef8a5d288049bdfd2087",
"reactionHash": "8f1795124f115f0973658c22831a4abe20a7d489bd547c4f45c08e39e214ac8a"
},
"children": [
{
"id": "3425",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_5ca50dbd8ffe1803fec8129a",
"parentId": "3424",
"isLeaf": false,
"molecule": {
"id": "sa_5ca50dbd8ffe1803fec8129a",
"inchikey": "IMEIVUHCRPYYIF-UHFFFAOYSA-N",
"smiles": "Cc1cc(O)c(C(=O)O)cc1Br"
},
"smiles": "Cc1cc(O)c(C(=O)O)cc1Br",
"reactionStepId": "sa_f2d295abd11a510f4b71c24e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150307451A1;0718;1777325\",\"rsmi\":\"Br[Br:12].[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[OH:9])[cH:10][cH:11]1>CC(=O)O.O>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[Br:12]\"},\"mapped_reaction_smiles\":\"Br[Br:12].[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[OH:9])[cH:10][cH:11]1>CC(=O)O.O>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[Br:12]\"}",
"reactionStep": {
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"reactionHash": "1ff23c26e635f6fc66c7aa8787507a603e5c33c8255dfaffbac3ce74031087d9"
},
"children": [
{
"id": "3426",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "3425",
"isLeaf": true,
"molecule": {
"id": "sa_24211e89e565c162ea935f73",
"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3427",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_145be07062de4bea112fa321",
"parentId": "3425",
"isLeaf": true,
"molecule": {
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"inchikey": "NJESAXZANHETJV-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(=O)O)c(O)c1"
},
"smiles": "Cc1ccc(C(=O)O)c(O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3428",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "3424",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3429",
"routeId": "sa_b7dc6f62087e5a8363e25bd0",
"moleculeId": "sa_a576f9b9a2caa305053d217d",
"parentId": "3423",
"isLeaf": true,
"molecule": {
"id": "sa_a576f9b9a2caa305053d217d",
"inchikey": "JRNVZBWKYDBUCA-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Cl"
},
"smiles": "O=C1CCC(=O)N1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}