Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)CC(NC(=O)[C@@H]1CCCN(C(=O)CCC2CCN(C(=O)OC(C)(C)C)CC2)C1)c1cc(F)cc(Br)c1
InChiKey
KHCCTWSTHGEYDG-CGHJUBPDSA-N
Route Signature
00d2eedb1274993f8032f5ad2c524ea09e3a8716c35c769ae0f3ef97f65f2eac
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a1a5e1221a7cfcb04faf4c58",
"signature": "00d2eedb1274993f8032f5ad2c524ea09e3a8716c35c769ae0f3ef97f65f2eac",
"contentHash": "47d05750d1c20049cf565e4d3fc3923dc55ec9433d4a7be8ed1563cfcb838dc4",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_e6e667647d564902b108ca93",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02277",
"moleculeId": "sa_b55867d42d3702c227418090",
"smiles": "COC(=O)CC(NC(=O)[C@@H]1CCCN(C(=O)CCC2CCN(C(=O)OC(C)(C)C)CC2)C1)c1cc(F)cc(Br)c1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_b55867d42d3702c227418090",
"inchikey": "KHCCTWSTHGEYDG-CGHJUBPDSA-N",
"smiles": "COC(=O)CC(NC(=O)[C@@H]1CCCN(C(=O)CCC2CCN(C(=O)OC(C)(C)C)CC2)C1)c1cc(F)cc(Br)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10673",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_b55867d42d3702c227418090",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b55867d42d3702c227418090",
"inchikey": "KHCCTWSTHGEYDG-CGHJUBPDSA-N",
"smiles": "COC(=O)CC(NC(=O)[C@@H]1CCCN(C(=O)CCC2CCN(C(=O)OC(C)(C)C)CC2)C1)c1cc(F)cc(Br)c1"
},
"smiles": "COC(=O)CC(NC(=O)[C@@H]1CCCN(C(=O)CCC2CCN(C(=O)OC(C)(C)C)CC2)C1)c1cc(F)cc(Br)c1",
"reactionStepId": "sa_e9e89b7adbedad2680fb0474",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140314669A1;0949;1600033\",\"rsmi\":\"O=C1CCC(=O)N1O[C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)[CH2:32]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:33]1[cH:34][c:35]([Br:36])[cH:37][c:38]([F:39])[cH:40]1>CCN(CC)CC.CN(C)C=O.ClCCl.Cl.N>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH:7][C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)[CH2:32]1)[c:33]1[cH:34][c:35]([Br:36])[cH:37][c:38]([F:39])[cH:40]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1O[C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)[CH2:32]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:33]1[cH:34][c:35]([Br:36])[cH:37][c:38]([F:39])[cH:40]1>CCN(CC)CC.CN(C)C=O.ClCCl.Cl.N>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH:7][C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]2)[CH2:32]1)[c:33]1[cH:34][c:35]([Br:36])[cH:37][c:38]([F:39])[cH:40]1\"}",
"reactionStep": {
"id": "sa_e9e89b7adbedad2680fb0474",
"reactionHash": "4cc3016151d176ab6ec5c828d0bcccb15f9fcac3fd6f8e5b85d1f74ef22d51cb"
},
"children": [
{
"id": "10674",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_404d7ebfbbc16161220bd17a",
"parentId": "10673",
"isLeaf": false,
"molecule": {
"id": "sa_404d7ebfbbc16161220bd17a",
"inchikey": "MUAFAKRFKIXLJW-QGZVFWFLSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(CCC(=O)N2CCC[C@@H](C(=O)ON3C(=O)CCC3=O)C2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(CCC(=O)N2CCC[C@@H](C(=O)ON3C(=O)CCC3=O)C2)CC1",
"reactionStepId": "sa_348232622ea2c8495af8b612",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140314669A1;0732;1600003\",\"rsmi\":\"O[C:21]([C@@H:20]1[CH2:19][CH2:18][CH2:17][N:16]([C:14]([CH2:13][CH2:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]2)=[O:15])[CH2:31]1)=[O:22].[OH:23][N:24]1[C:25](=[O:26])[CH2:27][CH2:28][C:29]1=[O:30]>C(=NC1CCCCC1)=NC1CCCCC1.COCCOC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][C:14](=[O:15])[N:16]2[CH2:17][CH2:18][CH2:19][C@@H:20]([C:21](=[O:22])[O:23][N:24]3[C:25](=[O:26])[CH2:27][CH2:28][C:29]3=[O:30])[CH2:31]2)[CH2:32][CH2:33]1\"},\"mapped_reaction_smiles\":\"O[C:21]([C@@H:20]1[CH2:19][CH2:18][CH2:17][N:16]([C:14]([CH2:13][CH2:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]2)=[O:15])[CH2:31]1)=[O:22].[OH:23][N:24]1[C:25](=[O:26])[CH2:27][CH2:28][C:29]1=[O:30]>C(=NC1CCCCC1)=NC1CCCCC1.COCCOC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][C:14](=[O:15])[N:16]2[CH2:17][CH2:18][CH2:19][C@@H:20]([C:21](=[O:22])[O:23][N:24]3[C:25](=[O:26])[CH2:27][CH2:28][C:29]3=[O:30])[CH2:31]2)[CH2:32][CH2:33]1\"}",
"reactionStep": {
"id": "sa_348232622ea2c8495af8b612",
"reactionHash": "216f03e2414343a8230357c18adbb5a7851fc10242c189e3af3d579e8014d83e"
},
"children": [
{
"id": "10675",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_7115ff34a78af3f36581b332",
"parentId": "10674",
"isLeaf": true,
"molecule": {
"id": "sa_7115ff34a78af3f36581b332",
"inchikey": "NQTADLQHYWFPDB-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1O"
},
"smiles": "O=C1CCC(=O)N1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10676",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_fe9aa5798294d3723d2975f8",
"parentId": "10674",
"isLeaf": true,
"molecule": {
"id": "sa_fe9aa5798294d3723d2975f8",
"inchikey": "VSFRIVKRORDWLD-OAHLLOKOSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(CCC(=O)N2CCC[C@@H](C(=O)O)C2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(CCC(=O)N2CCC[C@@H](C(=O)O)C2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10677",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_82955cf436363a2a018f1b34",
"parentId": "10673",
"isLeaf": false,
"molecule": {
"id": "sa_82955cf436363a2a018f1b34",
"inchikey": "NNRXYZJZNNWFST-UHFFFAOYSA-N",
"smiles": "COC(=O)CC(N)c1cc(F)cc(Br)c1"
},
"smiles": "COC(=O)CC(N)c1cc(F)cc(Br)c1",
"reactionStepId": "sa_73e63e9b2f0e6c5c47909c77",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140314669A1;0944;1600032\",\"rsmi\":\"O[C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][c:13]([F:14])[cH:15]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][c:13]([F:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][c:13]([F:14])[cH:15]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH2:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][c:13]([F:14])[cH:15]1\"}",
"reactionStep": {
"id": "sa_73e63e9b2f0e6c5c47909c77",
"reactionHash": "2b89be772d6b4affb190b68f7279c07a50c1e46abaf293f2dbc9e4d89f739898"
},
"children": [
{
"id": "10678",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_54ed73db4fb4d60885ce91f9",
"parentId": "10677",
"isLeaf": false,
"molecule": {
"id": "sa_54ed73db4fb4d60885ce91f9",
"inchikey": "NLQSIYYNYUJEFN-UHFFFAOYSA-N",
"smiles": "NC(CC(=O)O)c1cc(F)cc(Br)c1"
},
"smiles": "NC(CC(=O)O)c1cc(F)cc(Br)c1",
"reactionStepId": "sa_351c460556a0150984646380",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140314669A1;0938;1600031\",\"rsmi\":\"O=C(O)[CH2:3][C:4](=[O:5])[OH:6].O=[CH:2][c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([F:13])[cH:14]1.[NH3:1]>CC(=O)O.CCO>[NH2:1][CH:2]([CH2:3][C:4](=[O:5])[OH:6])[c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([F:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"O=C(O)[CH2:3][C:4](=[O:5])[OH:6].O=[CH:2][c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([F:13])[cH:14]1.[NH3:1]>CC(=O)O.CCO>[NH2:1][CH:2]([CH2:3][C:4](=[O:5])[OH:6])[c:7]1[cH:8][c:9]([Br:10])[cH:11][c:12]([F:13])[cH:14]1\"}",
"reactionStep": {
"id": "sa_351c460556a0150984646380",
"reactionHash": "d2c21dd56702bfc75452877b28c4e7f5e2eadeef28da1f05a7f1e109d2d52716"
},
"children": [
{
"id": "10679",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_5da9e84d3893cc5b679ce4b5",
"parentId": "10678",
"isLeaf": true,
"molecule": {
"id": "sa_5da9e84d3893cc5b679ce4b5",
"inchikey": "MEFQRXHVMJPOKZ-UHFFFAOYSA-N",
"smiles": "O=Cc1cc(F)cc(Br)c1"
},
"smiles": "O=Cc1cc(F)cc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10680",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_4a1b0ed29ccb7ff1c5d04fc6",
"parentId": "10678",
"isLeaf": true,
"molecule": {
"id": "sa_4a1b0ed29ccb7ff1c5d04fc6",
"inchikey": "OFOBLEOULBTSOW-UHFFFAOYSA-N",
"smiles": "O=C(O)CC(=O)O"
},
"smiles": "O=C(O)CC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10681",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "10678",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10682",
"routeId": "sa_a1a5e1221a7cfcb04faf4c58",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "10677",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}