Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1
InChiKey
DGIVUBQEEGDBQM-UHFFFAOYSA-N
Route Signature
df56b07e7ad1ce2e37422bcf5380ae3e9a51e33f480d2cb2a0e9c5f80cda7146
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_20d608840cc2d965cd2f30a6",
"signature": "df56b07e7ad1ce2e37422bcf5380ae3e9a51e33f480d2cb2a0e9c5f80cda7146",
"contentHash": "868d9553372ef7973fc92888463a94c411b38cfb9a287984838bb01c6291a2af",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_8cb2ec1252cd63cae677d6af",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-02184",
"moleculeId": "sa_1a2838ea105f838df7c82924",
"smiles": "CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1a2838ea105f838df7c82924",
"inchikey": "DGIVUBQEEGDBQM-UHFFFAOYSA-N",
"smiles": "CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6217",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_1a2838ea105f838df7c82924",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1a2838ea105f838df7c82924",
"inchikey": "DGIVUBQEEGDBQM-UHFFFAOYSA-N",
"smiles": "CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1"
},
"smiles": "CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1",
"reactionStepId": "sa_1504fe6b88fe1586e1be39e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090208557A1;0172;750339\",\"rsmi\":\"CCO[CH:25]=[O:26].[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH3:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:27]([cH:28]2)[CH2:24][C:22](=[O:23])[NH:21]3)[cH:29][cH:30]1>CCO.CCO.Cl.[Na+]>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH3:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:27]([cH:28]2)[C:24](=[CH:25][OH:26])[C:22](=[O:23])[NH:21]3)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CCO[CH:25]=[O:26].[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH3:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:27]([cH:28]2)[CH2:24][C:22](=[O:23])[NH:21]3)[cH:29][cH:30]1>CCO.CCO.Cl.[Na+]>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH3:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:27]([cH:28]2)[C:24](=[CH:25][OH:26])[C:22](=[O:23])[NH:21]3)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_1504fe6b88fe1586e1be39e3",
"reactionHash": "a805cc49b58f5a737fe4f2ba64bdbc787e2a886e29ef11fbd9ed653433a9394f"
},
"children": [
{
"id": "6218",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_097e1db814269d674b54057e",
"parentId": "6217",
"isLeaf": false,
"molecule": {
"id": "sa_097e1db814269d674b54057e",
"inchikey": "HZSWNIOXFMFXID-UHFFFAOYSA-N",
"smiles": "CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)CC(=O)N3)cc1"
},
"smiles": "CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)CC(=O)N3)cc1",
"reactionStepId": "sa_8fda9688916517f1fd456798",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090208557A1;0171;750338\",\"rsmi\":\"O[C:9]([c:8]1[n:3]([CH2:2][CH3:1])[n:4][c:5]([CH3:6])[cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:25]([cH:26]2)[CH2:24][C:22](=[O:23])[NH:21]3)[cH:27][cH:28]1>C1CCOC1.O=S(Cl)Cl>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH3:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:25]([cH:26]2)[CH2:24][C:22](=[O:23])[NH:21]3)[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"O[C:9]([c:8]1[n:3]([CH2:2][CH3:1])[n:4][c:5]([CH3:6])[cH:7]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:25]([cH:26]2)[CH2:24][C:22](=[O:23])[NH:21]3)[cH:27][cH:28]1>C1CCOC1.O=S(Cl)Cl>[CH3:1][CH2:2][n:3]1[n:4][c:5]([CH3:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]3[c:25]([cH:26]2)[CH2:24][C:22](=[O:23])[NH:21]3)[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_8fda9688916517f1fd456798",
"reactionHash": "ef7eb26e36673edc19ad95245d42d23ab4e1afb93bb1df0423f32fe7030c2e02"
},
"children": [
{
"id": "6219",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_21106fad1efc6bccdc291cbd",
"parentId": "6218",
"isLeaf": false,
"molecule": {
"id": "sa_21106fad1efc6bccdc291cbd",
"inchikey": "RAOOQYQSMJUDKV-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Cc2ccc3c(c2)CC(=O)N3)cc1"
},
"smiles": "Nc1ccc(Cc2ccc3c(c2)CC(=O)N3)cc1",
"reactionStepId": "sa_d6c19b5ec8fe3249fa72c185",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090208557A1;0170;750337\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]3[c:15]([cH:16]2)[CH2:14][C:12](=[O:13])[NH:11]3)[cH:17][cH:18]1>CO.[Pd]>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]3[c:15]([cH:16]2)[CH2:14][C:12](=[O:13])[NH:11]3)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]3[c:15]([cH:16]2)[CH2:14][C:12](=[O:13])[NH:11]3)[cH:17][cH:18]1>CO.[Pd]>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]3[c:15]([cH:16]2)[CH2:14][C:12](=[O:13])[NH:11]3)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_d6c19b5ec8fe3249fa72c185",
"reactionHash": "cab4d119d53f0d5d2505168485a0eba3fefc06082c503fa4ad4c900758a3e607"
},
"children": [
{
"id": "6220",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_c36d9427c1f6bd121359445c",
"parentId": "6219",
"isLeaf": false,
"molecule": {
"id": "sa_c36d9427c1f6bd121359445c",
"inchikey": "JKMVMICPIZREFA-UHFFFAOYSA-N",
"smiles": "O=C1Cc2cc(Cc3ccc([N+](=O)[O-])cc3)ccc2N1"
},
"smiles": "O=C1Cc2cc(Cc3ccc([N+](=O)[O-])cc3)ccc2N1",
"reactionStepId": "sa_320a43e800dd31068f03329c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090208557A1;0169;750336\",\"rsmi\":\"O=[C:7]([c:6]1[cH:5][c:4]2[c:19]([cH:18][cH:17]1)[NH:20][C:2](=[O:1])[CH2:3]2)[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>O=C(O)C(F)(F)F.B.[Na+]>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([CH2:7][c:8]3[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]3)[cH:17][cH:18][c:19]2[NH:20]1\"},\"mapped_reaction_smiles\":\"O=[C:7]([c:6]1[cH:5][c:4]2[c:19]([cH:18][cH:17]1)[NH:20][C:2](=[O:1])[CH2:3]2)[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>O=C(O)C(F)(F)F.B.[Na+]>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([CH2:7][c:8]3[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]3)[cH:17][cH:18][c:19]2[NH:20]1\"}",
"reactionStep": {
"id": "sa_320a43e800dd31068f03329c",
"reactionHash": "8adb3339da5491dfafcbe57afd6f1a8b37132d618576a80d4c386c00163ba937"
},
"children": [
{
"id": "6221",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_ed459d6c7bc1485b3b724175",
"parentId": "6220",
"isLeaf": false,
"molecule": {
"id": "sa_ed459d6c7bc1485b3b724175",
"inchikey": "AMDJWMIYGKZLGA-UHFFFAOYSA-N",
"smiles": "O=C1Cc2cc(C(=O)c3ccc([N+](=O)[O-])cc3)ccc2N1"
},
"smiles": "O=C1Cc2cc(C(=O)c3ccc([N+](=O)[O-])cc3)ccc2N1",
"reactionStepId": "sa_216115be416698bf86517c5e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090208557A1;0154;750323\",\"rsmi\":\"Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1.[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:18][cH:19][c:20]2[NH:21]1>CN(C)C=O.Cl.O.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[c:9]3[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]3)[cH:18][cH:19][c:20]2[NH:21]1\"},\"mapped_reaction_smiles\":\"Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1.[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:18][cH:19][c:20]2[NH:21]1>CN(C)C=O.Cl.O.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[c:9]3[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]3)[cH:18][cH:19][c:20]2[NH:21]1\"}",
"reactionStep": {
"id": "sa_216115be416698bf86517c5e",
"reactionHash": "e76f3b60e16f116745af91fc7f82ab81cc430ea8e0def49e65b1fadb43b2fa68"
},
"children": [
{
"id": "6222",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_4a6865a174b5e4e0a4cbb8b8",
"parentId": "6221",
"isLeaf": true,
"molecule": {
"id": "sa_4a6865a174b5e4e0a4cbb8b8",
"inchikey": "JYGFTBXVXVMTGB-UHFFFAOYSA-N",
"smiles": "OC1=Nc2ccccc2C1"
},
"smiles": "O=C1Cc2ccccc2N1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6223",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_a9c9831d94f67e76c2c09138",
"parentId": "6221",
"isLeaf": true,
"molecule": {
"id": "sa_a9c9831d94f67e76c2c09138",
"inchikey": "SKDHHIUENRGTHK-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1ccc([N+](=O)[O-])cc1"
},
"smiles": "O=C(Cl)c1ccc([N+](=O)[O-])cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "6224",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_77311b060c7d84642a0f7d78",
"parentId": "6218",
"isLeaf": true,
"molecule": {
"id": "sa_77311b060c7d84642a0f7d78",
"inchikey": "VFMGOJUUTAPPDA-UHFFFAOYSA-N",
"smiles": "CCn1nc(C)cc1C(=O)O"
},
"smiles": "CCn1nc(C)cc1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "6225",
"routeId": "sa_20d608840cc2d965cd2f30a6",
"moleculeId": "sa_fe35c93b34b37939ff23116d",
"parentId": "6217",
"isLeaf": true,
"molecule": {
"id": "sa_fe35c93b34b37939ff23116d",
"inchikey": "WBJINCZRORDGAQ-UHFFFAOYSA-N",
"smiles": "CCOC=O"
},
"smiles": "CCOC=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}