Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(OCC1COCCN1)N1CCN(c2ccc(F)cc2)CC1
InChiKey
KLPAHFQIJHFKLX-UHFFFAOYSA-N
Route Signature
7354d7608df845715b5b5cb4b59a103b3bf3933ecefa9f2148208e81c223c25c
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_8d4a9709b8d2aec0c61f8b83",
"signature": "7354d7608df845715b5b5cb4b59a103b3bf3933ecefa9f2148208e81c223c25c",
"contentHash": "b5e88ab9c2dc9a0ce9eff36574f9db420d1220eb0872ea34064e33e9c092df8b",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_fe6008396515ef0c81ef1551",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-07183",
"moleculeId": "sa_6bb0d4ccc428e970715077bc",
"smiles": "O=C(OCC1COCCN1)N1CCN(c2ccc(F)cc2)CC1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_6bb0d4ccc428e970715077bc",
"inchikey": "KLPAHFQIJHFKLX-UHFFFAOYSA-N",
"smiles": "O=C(OCC1COCCN1)N1CCN(c2ccc(F)cc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "2966",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_6bb0d4ccc428e970715077bc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6bb0d4ccc428e970715077bc",
"inchikey": "KLPAHFQIJHFKLX-UHFFFAOYSA-N",
"smiles": "O=C(OCC1COCCN1)N1CCN(c2ccc(F)cc2)CC1"
},
"smiles": "O=C(OCC1COCCN1)N1CCN(c2ccc(F)cc2)CC1",
"reactionStepId": "sa_19927a3185eed3792e64fd7a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110059969A1;0306;1024358\",\"rsmi\":\"CC(C)(C)OC(=O)[N:10]1[CH:5]([CH2:4][O:3][C:2](=[O:1])[N:11]2[CH2:12][CH2:13][N:14]([c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[CH2:22][CH2:23]2)[CH2:6][O:7][CH2:8][CH2:9]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([O:3][CH2:4][CH:5]1[CH2:6][O:7][CH2:8][CH2:9][NH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:10]1[CH:5]([CH2:4][O:3][C:2](=[O:1])[N:11]2[CH2:12][CH2:13][N:14]([c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[CH2:22][CH2:23]2)[CH2:6][O:7][CH2:8][CH2:9]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([O:3][CH2:4][CH:5]1[CH2:6][O:7][CH2:8][CH2:9][NH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1\"}",
"reactionStep": {
"id": "sa_19927a3185eed3792e64fd7a",
"reactionHash": "4f330c09c656ac1c68753e32a9b3ac91fd60c99708eb1aac3058cb6fab3fb76d"
},
"children": [
{
"id": "2967",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_0cfd73aa0d2ea6e2322e068f",
"parentId": "2966",
"isLeaf": false,
"molecule": {
"id": "sa_0cfd73aa0d2ea6e2322e068f",
"inchikey": "LJTBKYQRDAFBFA-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2)CC1",
"reactionStepId": "sa_6cc636798e5eeba618413b34",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110059969A1;0305;1024357\",\"rsmi\":\"O=[N+]([O-])c1ccc(O[C:16](=[O:17])[N:18]2[CH2:19][CH2:20][N:21]([c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[CH2:29][CH2:30]2)cc1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:14][OH:15]>C1CCOC1.O=C(O)O.[HH].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:14][O:15][C:16](=[O:17])[N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1\"},\"mapped_reaction_smiles\":\"O=[N+]([O-])c1ccc(O[C:16](=[O:17])[N:18]2[CH2:19][CH2:20][N:21]([c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[CH2:29][CH2:30]2)cc1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:14][OH:15]>C1CCOC1.O=C(O)O.[HH].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:14][O:15][C:16](=[O:17])[N:18]1[CH2:19][CH2:20][N:21]([c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1\"}",
"reactionStep": {
"id": "sa_6cc636798e5eeba618413b34",
"reactionHash": "dad38b8b7988a821557c7e4577ddc866cdcb0aafa1b921761bc2f6da27b915fa"
},
"children": [
{
"id": "2968",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_35c0a921eeb7a738438892fb",
"parentId": "2967",
"isLeaf": false,
"molecule": {
"id": "sa_35c0a921eeb7a738438892fb",
"inchikey": "AIQSXVGBMCJQAG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCOCC1CO"
},
"smiles": "CC(C)(C)OC(=O)N1CCOCC1CO",
"reactionStepId": "sa_9a5f9283f3c6faa7a022f9b8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110059969A1;0204;1024326\",\"rsmi\":\"O=[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][O:11][CH2:12]1)[OH:15]>B.C1CCOC1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:14][OH:15]\"},\"mapped_reaction_smiles\":\"O=[C:14]([CH:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][O:11][CH2:12]1)[OH:15]>B.C1CCOC1.O.O=C(O)O.[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH2:14][OH:15]\"}",
"reactionStep": {
"id": "sa_9a5f9283f3c6faa7a022f9b8",
"reactionHash": "0ac374dccb84c9a74feec758b912df8fd260e6ba9f8335a81830b14d7246727a"
},
"children": [
{
"id": "2969",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_454b0383b9d3b90386f3315d",
"parentId": "2968",
"isLeaf": true,
"molecule": {
"id": "sa_454b0383b9d3b90386f3315d",
"inchikey": "KVXXEKIGMOEPSA-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCOCC1C(=O)O"
},
"smiles": "CC(C)(C)OC(=O)N1CCOCC1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "2970",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_ec7b2d5d4e423848bf1ab878",
"parentId": "2967",
"isLeaf": false,
"molecule": {
"id": "sa_ec7b2d5d4e423848bf1ab878",
"inchikey": "YYTKBRZTEVEWTK-UHFFFAOYSA-N",
"smiles": "O=C(Oc1ccc([N+](=O)[O-])cc1)N1CCN(c2ccc(F)cc2)CC1"
},
"smiles": "O=C(Oc1ccc([N+](=O)[O-])cc1)N1CCN(c2ccc(F)cc2)CC1",
"reactionStepId": "sa_03ba450023baf4458869c0cc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110059969A1;0202;1024325\",\"rsmi\":\"Cl[C:2](=[O:1])[O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1>C1CCOC1.CCN(CC)CC>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1>C1CCOC1.CCN(CC)CC>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
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"reactionHash": "b590cbb4a0ce47f86ecd6dad8221750506e256cc94fc3a46a56c16361f1d834a"
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"children": [
{
"id": "2971",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_6ac526bb46c0389a656c742b",
"parentId": "2970",
"isLeaf": true,
"molecule": {
"id": "sa_6ac526bb46c0389a656c742b",
"inchikey": "AVJKDKWRVSSJPK-UHFFFAOYSA-N",
"smiles": "Fc1ccc(N2CCNCC2)cc1"
},
"smiles": "Fc1ccc(N2CCNCC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2972",
"routeId": "sa_8d4a9709b8d2aec0c61f8b83",
"moleculeId": "sa_3863ce290d49123db29a5643",
"parentId": "2970",
"isLeaf": true,
"molecule": {
"id": "sa_3863ce290d49123db29a5643",
"inchikey": "NXLNNXIXOYSCMB-UHFFFAOYSA-N",
"smiles": "O=C(Cl)Oc1ccc([N+](=O)[O-])cc1"
},
"smiles": "O=C(Cl)Oc1ccc([N+](=O)[O-])cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}