Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)C(=O)c1cc(Oc2ccc(OC)cc2)c(Cl)cc1F
InChiKey
DPFZVXXWEPIMFG-UHFFFAOYSA-N
Route Signature
2a8f45d37e4b629b5f76ca7f745dac8e862ae5d83b2271ad7524a1763a376186
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ecee6fbf9c0624b1b64d0bda",
"signature": "2a8f45d37e4b629b5f76ca7f745dac8e862ae5d83b2271ad7524a1763a376186",
"contentHash": "e084a0c06dbeb1cffe8268e30115dcfbccf49abebe4ba5fca11800e9aefc9a98",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_7781a928ab46c74443e06648",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00478",
"moleculeId": "sa_158ecb4d212fdd4b039c0cf4",
"smiles": "CCOC(=O)C(=O)c1cc(Oc2ccc(OC)cc2)c(Cl)cc1F",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_158ecb4d212fdd4b039c0cf4",
"inchikey": "DPFZVXXWEPIMFG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)c1cc(Oc2ccc(OC)cc2)c(Cl)cc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13345",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_158ecb4d212fdd4b039c0cf4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_158ecb4d212fdd4b039c0cf4",
"inchikey": "DPFZVXXWEPIMFG-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)c1cc(Oc2ccc(OC)cc2)c(Cl)cc1F"
},
"smiles": "CCOC(=O)C(=O)c1cc(Oc2ccc(OC)cc2)c(Cl)cc1F",
"reactionStepId": "sa_ebb51a8f75ec40dc6282bc79",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024110A1;0815;1828931\",\"rsmi\":\"Br[c:8]1[c:9]([F:10])[cH:11][c:12]([Cl:13])[c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]2)[cH:24]1.CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>C1CCOC1.CC(C)[Mg]Cl.Cl.N>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[c:9]([F:10])[cH:11][c:12]([Cl:13])[c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]2)[cH:24]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[c:9]([F:10])[cH:11][c:12]([Cl:13])[c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]2)[cH:24]1.CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>C1CCOC1.CC(C)[Mg]Cl.Cl.N>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[c:9]([F:10])[cH:11][c:12]([Cl:13])[c:14]([O:15][c:16]2[cH:17][cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]2)[cH:24]1\"}",
"reactionStep": {
"id": "sa_ebb51a8f75ec40dc6282bc79",
"reactionHash": "eea4d9d30f47d17fb621f6ff038cd51428c7c0805de66efe05090725a8512df7"
},
"children": [
{
"id": "13346",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_ab0a3cf4ca71164a04c8f94b",
"parentId": "13345",
"isLeaf": true,
"molecule": {
"id": "sa_ab0a3cf4ca71164a04c8f94b",
"inchikey": "WYACBZDAHNBPPB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)OCC"
},
"smiles": "CCOC(=O)C(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13347",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_6c62edec37092505a06d0d00",
"parentId": "13345",
"isLeaf": false,
"molecule": {
"id": "sa_6c62edec37092505a06d0d00",
"inchikey": "XTEYDYWRVNGJOE-UHFFFAOYSA-N",
"smiles": "COc1ccc(Oc2cc(Br)c(F)cc2Cl)cc1"
},
"smiles": "COc1ccc(Oc2cc(Br)c(F)cc2Cl)cc1",
"reactionStepId": "sa_0927616c6e6cd3c389033369",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024110A1;0813;1828930\",\"rsmi\":\"N[c:15]1[c:8]([O:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14]1.[Cu][Cl:16]>CC#N.CC(C)CCON=O.Cl.Cl[Cu]Cl.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14][c:15]2[Cl:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"N[c:15]1[c:8]([O:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14]1.[Cu][Cl:16]>CC#N.CC(C)CCON=O.Cl.Cl[Cu]Cl.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14][c:15]2[Cl:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_0927616c6e6cd3c389033369",
"reactionHash": "89b415f9e8af9be1de90563122fa4e9b9465431b702a35807b050bba55504be8"
},
"children": [
{
"id": "13348",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_0055ad5f77494b47d5daab68",
"parentId": "13347",
"isLeaf": false,
"molecule": {
"id": "sa_0055ad5f77494b47d5daab68",
"inchikey": "KQYDTRFAOGSVNB-UHFFFAOYSA-N",
"smiles": "COc1ccc(Oc2cc(Br)c(F)cc2N)cc1"
},
"smiles": "COc1ccc(Oc2cc(Br)c(F)cc2N)cc1",
"reactionStepId": "sa_dfc138c85171da150c397e19",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024110A1;0812;1828929\",\"rsmi\":\"O=[N+:10]([O-])[c:9]1[c:8]([O:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[cH:16][c:14]([Br:15])[c:12]([F:13])[cH:11]1>CC(=O)O.CCOC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[c:9]([NH2:10])[cH:11][c:12]([F:13])[c:14]([Br:15])[cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:10]([O-])[c:9]1[c:8]([O:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[cH:16][c:14]([Br:15])[c:12]([F:13])[cH:11]1>CC(=O)O.CCOC(C)=O.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[c:9]([NH2:10])[cH:11][c:12]([F:13])[c:14]([Br:15])[cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_dfc138c85171da150c397e19",
"reactionHash": "001b5df0ef5d45dcd84234630d2fc01304cf2a460af9caa7e069b8d13a542a0a"
},
"children": [
{
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"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_46cb3eff9e38711ec76839c5",
"parentId": "13348",
"isLeaf": false,
"molecule": {
"id": "sa_46cb3eff9e38711ec76839c5",
"inchikey": "NGKVXOIJRSAXEW-UHFFFAOYSA-N",
"smiles": "COc1ccc(Oc2cc(Br)c(F)cc2[N+](=O)[O-])cc1"
},
"smiles": "COc1ccc(Oc2cc(Br)c(F)cc2[N+](=O)[O-])cc1",
"reactionStepId": "sa_7fec19fcbc4e9b8ec229c212",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024110A1;0811;1828928\",\"rsmi\":\"F[c:8]1[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:19][cH:20]1>C1CCOC1.[HH].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14][c:15]2[N+:16](=[O:17])[O-:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"F[c:8]1[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:19][cH:20]1>C1CCOC1.[HH].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:10]([Br:11])[c:12]([F:13])[cH:14][c:15]2[N+:16](=[O:17])[O-:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_7fec19fcbc4e9b8ec229c212",
"reactionHash": "476185f7691317fc4e9ffe13326c49355894138cf48412c8cb8dea89cdde3d20"
},
"children": [
{
"id": "13350",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_47c96751fa2be296b1b7b689",
"parentId": "13349",
"isLeaf": false,
"molecule": {
"id": "sa_47c96751fa2be296b1b7b689",
"inchikey": "GJFYMYJYPARISZ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(F)c(Br)cc1F"
},
"smiles": "O=[N+]([O-])c1cc(F)c(Br)cc1F",
"reactionStepId": "sa_99046d879b1ee5034093ec1b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024110A1;0810;1828927\",\"rsmi\":\"O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][c:6]([F:7])[c:8]([Br:9])[cH:10][c:11]1[F:12]>CC(Cl)Cl.O=S(=O)(O)O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([Br:9])[cH:10][c:11]1[F:12]\"},\"mapped_reaction_smiles\":\"O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][c:6]([F:7])[c:8]([Br:9])[cH:10][c:11]1[F:12]>CC(Cl)Cl.O=S(=O)(O)O>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([Br:9])[cH:10][c:11]1[F:12]\"}",
"reactionStep": {
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"children": [
{
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"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "13350",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "13352",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_aa0de8573b12ab81aedf7c2f",
"parentId": "13350",
"isLeaf": true,
"molecule": {
"id": "sa_aa0de8573b12ab81aedf7c2f",
"inchikey": "XCRCSPKQEDMVBO-UHFFFAOYSA-N",
"smiles": "Fc1ccc(F)c(Br)c1"
},
"smiles": "Fc1ccc(F)c(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13353",
"routeId": "sa_ecee6fbf9c0624b1b64d0bda",
"moleculeId": "sa_9043c2f932cd11332648454f",
"parentId": "13349",
"isLeaf": true,
"molecule": {
"id": "sa_9043c2f932cd11332648454f",
"inchikey": "NWVVVBRKAWDGAB-UHFFFAOYSA-N",
"smiles": "COc1ccc(O)cc1"
},
"smiles": "COc1ccc(O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "13354",
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"moleculeId": "sa_7169758091a67777042f7bf7",
"parentId": "13347",
"isLeaf": true,
"molecule": {
"id": "sa_7169758091a67777042f7bf7",
"inchikey": "OXBLHERUFWYNTN-UHFFFAOYSA-M",
"smiles": "[Cl][Cu]"
},
"smiles": "[Cl][Cu]",
"reactionStepId": null,
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}
]
}
]
}
}