Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1nc(-c2ccc(OCCCC3CCN(c4nc(C(C)C)no4)CC3)cc2)no1
InChiKey
PAEFVQKIBAJRIH-UHFFFAOYSA-N
Route Signature
db99084a9fd34b3b9034d3d983aa75899d73301fe53fb79ca04aaaa284615584
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b4440b22be20f90f6e85484e",
"signature": "db99084a9fd34b3b9034d3d983aa75899d73301fe53fb79ca04aaaa284615584",
"contentHash": "31b54bf2219c7ec4b4b2597bd6018d7b177fa3c29cd7721f45db9d0572799ec0",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_2e54a18b569b56f93ede3eb8",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01909",
"moleculeId": "sa_904381b4cbd85cba29cee36b",
"smiles": "Cc1nc(-c2ccc(OCCCC3CCN(c4nc(C(C)C)no4)CC3)cc2)no1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_904381b4cbd85cba29cee36b",
"inchikey": "PAEFVQKIBAJRIH-UHFFFAOYSA-N",
"smiles": "Cc1nc(-c2ccc(OCCCC3CCN(c4nc(C(C)C)no4)CC3)cc2)no1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6077",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_904381b4cbd85cba29cee36b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_904381b4cbd85cba29cee36b",
"inchikey": "PAEFVQKIBAJRIH-UHFFFAOYSA-N",
"smiles": "Cc1nc(-c2ccc(OCCCC3CCN(c4nc(C(C)C)no4)CC3)cc2)no1"
},
"smiles": "Cc1nc(-c2ccc(OCCCC3CCN(c4nc(C(C)C)no4)CC3)cc2)no1",
"reactionStepId": "sa_d842027080ddc07bc23ff966",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110212939A1;0266;1098191\",\"rsmi\":\"CS(=O)(=O)O[CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([c:17]2[n:18][c:19]([CH:20]([CH3:21])[CH3:22])[n:23][o:24]2)[CH2:25][CH2:26]1.[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([OH:9])[cH:27][cH:28]2)[n:29][o:30]1>CS(C)=O.ClCCl.O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]3[CH2:14][CH2:15][N:16]([c:17]4[n:18][c:19]([CH:20]([CH3:21])[CH3:22])[n:23][o:24]4)[CH2:25][CH2:26]3)[cH:27][cH:28]2)[n:29][o:30]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([c:17]2[n:18][c:19]([CH:20]([CH3:21])[CH3:22])[n:23][o:24]2)[CH2:25][CH2:26]1.[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([OH:9])[cH:27][cH:28]2)[n:29][o:30]1>CS(C)=O.ClCCl.O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]3[CH2:14][CH2:15][N:16]([c:17]4[n:18][c:19]([CH:20]([CH3:21])[CH3:22])[n:23][o:24]4)[CH2:25][CH2:26]3)[cH:27][cH:28]2)[n:29][o:30]1\"}",
"reactionStep": {
"id": "sa_d842027080ddc07bc23ff966",
"reactionHash": "131b508745e41f4d605e7d016dda44de61ff8c0571cd3aa584c6e05e35b1a075"
},
"children": [
{
"id": "6078",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_effa18dd24961d35af397d58",
"parentId": "6077",
"isLeaf": true,
"molecule": {
"id": "sa_effa18dd24961d35af397d58",
"inchikey": "CUCWKDHLIRIVLB-UHFFFAOYSA-N",
"smiles": "Cc1nc(-c2ccc(O)cc2)no1"
},
"smiles": "Cc1nc(-c2ccc(O)cc2)no1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6079",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_8305f41df00ca648924c220d",
"parentId": "6077",
"isLeaf": false,
"molecule": {
"id": "sa_8305f41df00ca648924c220d",
"inchikey": "NFFKLWVQLYXZEL-UHFFFAOYSA-N",
"smiles": "CC(C)c1noc(N2CCC(CCCOS(C)(=O)=O)CC2)n1"
},
"smiles": "CC(C)c1noc(N2CCC(CCCOS(C)(=O)=O)CC2)n1",
"reactionStepId": "sa_81778d6ad191db064b781ddb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110212939A1;0168;1098150\",\"rsmi\":\"Cl[S:16]([CH3:17])(=[O:18])=[O:19].[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:20][CH2:21]2)[n:22]1>CCN(CC)CC.ClCCl>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][O:15][S:16]([CH3:17])(=[O:18])=[O:19])[CH2:20][CH2:21]2)[n:22]1\"},\"mapped_reaction_smiles\":\"Cl[S:16]([CH3:17])(=[O:18])=[O:19].[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:20][CH2:21]2)[n:22]1>CCN(CC)CC.ClCCl>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][O:15][S:16]([CH3:17])(=[O:18])=[O:19])[CH2:20][CH2:21]2)[n:22]1\"}",
"reactionStep": {
"id": "sa_81778d6ad191db064b781ddb",
"reactionHash": "b9fd28d703c6c49c9011eaea3135834c51dba5112b844ed308e2619de87c563d"
},
"children": [
{
"id": "6080",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_69af97d2bc36da0927104cb3",
"parentId": "6079",
"isLeaf": false,
"molecule": {
"id": "sa_69af97d2bc36da0927104cb3",
"inchikey": "LGMIMRBZBZTNJS-UHFFFAOYSA-N",
"smiles": "CC(C)c1noc(N2CCC(CCCO)CC2)n1"
},
"smiles": "CC(C)c1noc(N2CCC(CCCO)CC2)n1",
"reactionStepId": "sa_62248a8d87130062e60c3851",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110212939A1;0166;1098149\",\"rsmi\":\"N#[C:7][N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:16][CH2:17]1.[CH3:1][CH:2]([CH3:3])[C:4]([NH:5][OH:6])=[NH:18]>C1CCOC1.CCOC(C)=O.Cl.Cl.[Zn+2]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:16][CH2:17]2)[n:18]1\"},\"mapped_reaction_smiles\":\"N#[C:7][N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:16][CH2:17]1.[CH3:1][CH:2]([CH3:3])[C:4]([NH:5][OH:6])=[NH:18]>C1CCOC1.CCOC(C)=O.Cl.Cl.[Zn+2]>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][o:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:16][CH2:17]2)[n:18]1\"}",
"reactionStep": {
"id": "sa_62248a8d87130062e60c3851",
"reactionHash": "c3333ac57dbf02795ad97ea8b4ca1f8e3ca684305c29517643179eaffe739d79"
},
"children": [
{
"id": "6081",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_af59ede67cfeb372876c1558",
"parentId": "6080",
"isLeaf": false,
"molecule": {
"id": "sa_af59ede67cfeb372876c1558",
"inchikey": "COTUKDXBXNOPQC-UHFFFAOYSA-N",
"smiles": "N#CN1CCC(CCCO)CC1"
},
"smiles": "N#CN1CCC(CCCO)CC1",
"reactionStepId": "sa_6a70799fa1ad78f719c79111",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110212939A1;0164;1098148\",\"rsmi\":\"Br[C:2]#[N:1].[NH:3]1[CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:11][CH2:12]1>ClCCl.O.O=C(O)O.[Na+]>[N:1]#[C:2][N:3]1[CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"Br[C:2]#[N:1].[NH:3]1[CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:11][CH2:12]1>ClCCl.O.O=C(O)O.[Na+]>[N:1]#[C:2][N:3]1[CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:11][CH2:12]1\"}",
"reactionStep": {
"id": "sa_6a70799fa1ad78f719c79111",
"reactionHash": "ab00aef0b194eca49378bdca1e9d0a349f8fbe7873b1e1d224e47948fce21ed6"
},
"children": [
{
"id": "6082",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_30011d6f02d7317821269823",
"parentId": "6081",
"isLeaf": true,
"molecule": {
"id": "sa_30011d6f02d7317821269823",
"inchikey": "ATDGTVJJHBUTRL-UHFFFAOYSA-N",
"smiles": "N#CBr"
},
"smiles": "N#CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6083",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_da7902d606d17672a44b3983",
"parentId": "6081",
"isLeaf": true,
"molecule": {
"id": "sa_da7902d606d17672a44b3983",
"inchikey": "DBIMLJDSPUCGGY-UHFFFAOYSA-N",
"smiles": "OCCCC1CCNCC1"
},
"smiles": "OCCCC1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "6084",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_dafa198e7186dab148199a9c",
"parentId": "6080",
"isLeaf": true,
"molecule": {
"id": "sa_dafa198e7186dab148199a9c",
"inchikey": "JHRDEHLFNLLCQS-UHFFFAOYSA-N",
"smiles": "CC(C)C(N)=NO"
},
"smiles": "CC(C)C(=N)NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "6085",
"routeId": "sa_b4440b22be20f90f6e85484e",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "6079",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}