Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2F)CC1
InChiKey
XNOZAJIYVNYLEI-UHFFFAOYSA-N
Route Signature
cfa1eb5933d66fb62e76cd6c66544f47742afdaed9385734248e1f1e52bfdffb
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e78c73a2906b7b6d184fdaa1",
"signature": "cfa1eb5933d66fb62e76cd6c66544f47742afdaed9385734248e1f1e52bfdffb",
"contentHash": "22ef90a48b9b7a665c648107f53b5059b34d85c1417789c946b31a079de9ecf8",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_0014b16267bfe9afdcb25e10",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-08366",
"moleculeId": "sa_6f3858f542b0721bcc0ec142",
"smiles": "CN1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2F)CC1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_6f3858f542b0721bcc0ec142",
"inchikey": "XNOZAJIYVNYLEI-UHFFFAOYSA-N",
"smiles": "CN1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2F)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "3132",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_6f3858f542b0721bcc0ec142",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6f3858f542b0721bcc0ec142",
"inchikey": "XNOZAJIYVNYLEI-UHFFFAOYSA-N",
"smiles": "CN1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2F)CC1"
},
"smiles": "CN1CCOCC1COC(=O)N1CCN(c2ccc(F)cc2F)CC1",
"reactionStepId": "sa_d4163a7ea7e6c470cd460d6c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181967A1;0299;737175\",\"rsmi\":\"O=[N+]([O-])c1ccc(O[C:10](=[O:11])[N:12]2[CH2:13][CH2:14][N:15]([c:16]3[c:17]([F:18])[cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)cc1.[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][OH:9]>C1CCOC1.[HH].[Na+]>[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][O:9][C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]([c:16]2[c:17]([F:18])[cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"O=[N+]([O-])c1ccc(O[C:10](=[O:11])[N:12]2[CH2:13][CH2:14][N:15]([c:16]3[c:17]([F:18])[cH:19][c:20]([F:21])[cH:22][cH:23]3)[CH2:24][CH2:25]2)cc1.[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][OH:9]>C1CCOC1.[HH].[Na+]>[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][O:9][C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]([c:16]2[c:17]([F:18])[cH:19][c:20]([F:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_d4163a7ea7e6c470cd460d6c",
"reactionHash": "34d317b029b13e0ae0109e1b69093bba772e0d4a0ef3f0567d997629f45c7cba"
},
"children": [
{
"id": "3133",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_20df3d8a5dea969cce4df353",
"parentId": "3132",
"isLeaf": false,
"molecule": {
"id": "sa_20df3d8a5dea969cce4df353",
"inchikey": "IJPSKCLYVSRGSK-UHFFFAOYSA-N",
"smiles": "O=C(Oc1ccc([N+](=O)[O-])cc1)N1CCN(c2ccc(F)cc2F)CC1"
},
"smiles": "O=C(Oc1ccc([N+](=O)[O-])cc1)N1CCN(c2ccc(F)cc2F)CC1",
"reactionStepId": "sa_e70c174b88ad53a7e76d35e0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181967A1;0188;737139\",\"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[c:18]([F:19])[cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]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[c:18]([F:19])[cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]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[c:18]([F:19])[cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]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[c:18]([F:19])[cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_e70c174b88ad53a7e76d35e0",
"reactionHash": "ea7cab8286131eb0474aa1d80238ab4a416059e45bf3e3c2b7a7d96e8387263f"
},
"children": [
{
"id": "3134",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_b644991127977a815e5d41cb",
"parentId": "3133",
"isLeaf": true,
"molecule": {
"id": "sa_b644991127977a815e5d41cb",
"inchikey": "CMCSPBOWEYUGHB-UHFFFAOYSA-N",
"smiles": "Fc1ccc(N2CCNCC2)c(F)c1"
},
"smiles": "Fc1ccc(N2CCNCC2)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3135",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_3863ce290d49123db29a5643",
"parentId": "3133",
"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,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3136",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_5f21e26d1a67305fa597b6c4",
"parentId": "3132",
"isLeaf": false,
"molecule": {
"id": "sa_5f21e26d1a67305fa597b6c4",
"inchikey": "WXGKNIRSXCAEEP-UHFFFAOYSA-N",
"smiles": "CN1CCOCC1CO"
},
"smiles": "CN1CCOCC1CO",
"reactionStepId": "sa_f36bd880ae389bb214303291",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090181967A1;0288;737169\",\"rsmi\":\"CC(C)(C)O[C:1](=O)[N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][OH:9]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][OH:9]\"},\"mapped_reaction_smiles\":\"CC(C)(C)O[C:1](=O)[N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][OH:9]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][CH:7]1[CH2:8][OH:9]\"}",
"reactionStep": {
"id": "sa_f36bd880ae389bb214303291",
"reactionHash": "46b8a6ff920c09b3f58b43959408941d58b39463c79d08a3bc5f781abb2a5ad8"
},
"children": [
{
"id": "3137",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_35c0a921eeb7a738438892fb",
"parentId": "3136",
"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\":\"US20090181967A1;0175;737133\",\"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": "3138",
"routeId": "sa_e78c73a2906b7b6d184fdaa1",
"moleculeId": "sa_454b0383b9d3b90386f3315d",
"parentId": "3137",
"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": []
}
]
}
]
}
]
}
}