Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOCc1cc2cnc(Nc3ccc(N4CCCCC4)cn3)nc2n(C2CCCC2)c1=O
InChiKey
ZIEODHVYCDIFIB-UHFFFAOYSA-N
Route Signature
0921c8a565d4d35ccc04e6d4d1cdadcb71953986ea89cf9438c4ab6d4906e4ef
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_490d9c154501dff90295718a",
"signature": "0921c8a565d4d35ccc04e6d4d1cdadcb71953986ea89cf9438c4ab6d4906e4ef",
"contentHash": "3861db770ca31c8caa0d160c752144f25ad552be2b152a7bcfab3ceaa481bdb3",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_1dc79150f3578618da1c50d4",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05113",
"moleculeId": "sa_2ce1c8433d967ec57430436f",
"smiles": "CCOCc1cc2cnc(Nc3ccc(N4CCCCC4)cn3)nc2n(C2CCCC2)c1=O",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_2ce1c8433d967ec57430436f",
"inchikey": "ZIEODHVYCDIFIB-UHFFFAOYSA-N",
"smiles": "CCOCc1cc2cnc(Nc3ccc(N4CCCCC4)cn3)nc2n(C2CCCC2)c1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "2712",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_2ce1c8433d967ec57430436f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2ce1c8433d967ec57430436f",
"inchikey": "ZIEODHVYCDIFIB-UHFFFAOYSA-N",
"smiles": "CCOCc1cc2cnc(Nc3ccc(N4CCCCC4)cn3)nc2n(C2CCCC2)c1=O"
},
"smiles": "CCOCc1cc2cnc(Nc3ccc(N4CCCCC4)cn3)nc2n(C2CCCC2)c1=O",
"reactionStepId": "sa_75b2305f6718f76495172944",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07208489B2;0542;781765\",\"rsmi\":\"CS(=O)[c:10]1[n:9][c:8]2[c:7]([cH:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[c:32](=[O:33])[n:26]2[CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[cH:25][n:24]1.[NH2:11][c:12]1[cH:13][cH:14][c:15]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[cH:22][n:23]1>Cc1ccccc1>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]4)[cH:22][n:23]3)[n:24][cH:25]2)[n:26]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[c:32]1=[O:33]\"},\"mapped_reaction_smiles\":\"CS(=O)[c:10]1[n:9][c:8]2[c:7]([cH:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[c:32](=[O:33])[n:26]2[CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[cH:25][n:24]1.[NH2:11][c:12]1[cH:13][cH:14][c:15]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[cH:22][n:23]1>Cc1ccccc1>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]4)[cH:22][n:23]3)[n:24][cH:25]2)[n:26]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[c:32]1=[O:33]\"}",
"reactionStep": {
"id": "sa_75b2305f6718f76495172944",
"reactionHash": "03603ebd4f896d62837000bb7dc9712d6cd318003c2a933fc4259ca7b829771c"
},
"children": [
{
"id": "2713",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_cbdd5784d397bd4bf1fb59fb",
"parentId": "2712",
"isLeaf": false,
"molecule": {
"id": "sa_cbdd5784d397bd4bf1fb59fb",
"inchikey": "MJJZVJBSTHNOIV-UHFFFAOYSA-N",
"smiles": "CCOCc1cc2cnc(S(C)=O)nc2n(C2CCCC2)c1=O"
},
"smiles": "CCOCc1cc2cnc(S(C)=O)nc2n(C2CCCC2)c1=O",
"reactionStepId": "sa_e4a56c9a4168ceeaa40d0f04",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07208489B2;0532;781755\",\"rsmi\":\"O=S(c1ccccc1)(N1OC1c1ccccc1)=[O:13].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([S:11][CH3:12])[n:14][cH:15]2)[n:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:22]1=[O:23]>ClCCl>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([S:11]([CH3:12])=[O:13])[n:14][cH:15]2)[n:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:22]1=[O:23]\"},\"mapped_reaction_smiles\":\"O=S(c1ccccc1)(N1OC1c1ccccc1)=[O:13].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([S:11][CH3:12])[n:14][cH:15]2)[n:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:22]1=[O:23]>ClCCl>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([S:11]([CH3:12])=[O:13])[n:14][cH:15]2)[n:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:22]1=[O:23]\"}",
"reactionStep": {
"id": "sa_e4a56c9a4168ceeaa40d0f04",
"reactionHash": "4b813abba43539d544ac9ff946ec000b4eb0748043e089a9c7b49f52e5c28608"
},
"children": [
{
"id": "2714",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_5d2cd2ab3df343abffd341ba",
"parentId": "2713",
"isLeaf": true,
"molecule": {
"id": "sa_5d2cd2ab3df343abffd341ba",
"inchikey": "MKHGVMIXRPGHOO-UHFFFAOYSA-N",
"smiles": "O=S(=O)(c1ccccc1)N1OC1c1ccccc1"
},
"smiles": "O=S(=O)(c1ccccc1)N1OC1c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2715",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_e5476de81b4732367363e2fe",
"parentId": "2713",
"isLeaf": false,
"molecule": {
"id": "sa_e5476de81b4732367363e2fe",
"inchikey": "OIGCTULMBOHHNE-UHFFFAOYSA-N",
"smiles": "CCOCc1cc2cnc(SC)nc2n(C2CCCC2)c1=O"
},
"smiles": "CCOCc1cc2cnc(SC)nc2n(C2CCCC2)c1=O",
"reactionStepId": "sa_035aaf54586348b3a354e091",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07208489B2;0531;781754\",\"rsmi\":\"CCO[C:21]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])=[O:22].O=[CH:6][c:7]1[c:8]([NH:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[n:9][c:10]([S:11][CH3:12])[n:13][cH:14]1>C1CCOC1.CCOC(C)=O.C[Si](C)(C)N[Si](C)(C)C.O.[Li+]>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([S:11][CH3:12])[n:13][cH:14]2)[n:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[c:21]1=[O:22]\"},\"mapped_reaction_smiles\":\"CCO[C:21]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])=[O:22].O=[CH:6][c:7]1[c:8]([NH:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[n:9][c:10]([S:11][CH3:12])[n:13][cH:14]1>C1CCOC1.CCOC(C)=O.C[Si](C)(C)N[Si](C)(C)C.O.[Li+]>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][c:7]2[c:8]([n:9][c:10]([S:11][CH3:12])[n:13][cH:14]2)[n:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[c:21]1=[O:22]\"}",
"reactionStep": {
"id": "sa_035aaf54586348b3a354e091",
"reactionHash": "4cac57062279e89074134a97387a592c4befd7f1db53a1c577f250f6c638a561"
},
"children": [
{
"id": "2716",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_068515783c5abdbbe03e039e",
"parentId": "2715",
"isLeaf": true,
"molecule": {
"id": "sa_068515783c5abdbbe03e039e",
"inchikey": "BHXIWUJLHYHGSJ-UHFFFAOYSA-N",
"smiles": "CCOCCC(=O)OCC"
},
"smiles": "CCOCCC(=O)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2717",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_ce267568c0663e8d0fa579e1",
"parentId": "2715",
"isLeaf": true,
"molecule": {
"id": "sa_ce267568c0663e8d0fa579e1",
"inchikey": "QKRVSWPBAOCWHY-UHFFFAOYSA-N",
"smiles": "CSc1ncc(C=O)c(NC2CCCC2)n1"
},
"smiles": "CSc1ncc(C=O)c(NC2CCCC2)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "2718",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_d0b4254741e2eea7c64ee814",
"parentId": "2712",
"isLeaf": false,
"molecule": {
"id": "sa_d0b4254741e2eea7c64ee814",
"inchikey": "NEUQZUUDMLYGQM-UHFFFAOYSA-N",
"smiles": "Nc1ccc(N2CCCCC2)cn1"
},
"smiles": "Nc1ccc(N2CCCCC2)cn1",
"reactionStepId": "sa_a5b94574d1730380044b90fc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07208489B2;0520;781744\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][n:13]1>C1CCOC1.[Ni]>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][n:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][n:13]1>C1CCOC1.[Ni]>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][n:13]1\"}",
"reactionStep": {
"id": "sa_a5b94574d1730380044b90fc",
"reactionHash": "69a7dad9a9e9d78ab9bafbede6db843e3c74753c18aa899611b8e88234737e27"
},
"children": [
{
"id": "2719",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_69b6905d936837a81dca81f4",
"parentId": "2718",
"isLeaf": false,
"molecule": {
"id": "sa_69b6905d936837a81dca81f4",
"inchikey": "YWBNHAYIHYUOHN-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cn1"
},
"smiles": "O=[N+]([O-])c1ccc(N2CCCCC2)cn1",
"reactionStepId": "sa_ee22819f17c2058a5924d60e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07208489B2;0519;781743\",\"rsmi\":\"Br[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[n:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.CS(C)=O.O=C(O)O.I.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][n:15]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[n:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.CS(C)=O.O=C(O)O.I.[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][n:15]1\"}",
"reactionStep": {
"id": "sa_ee22819f17c2058a5924d60e",
"reactionHash": "038c1f112dc66d824a0f7070f2256f841b9104524b65969def590053ec89db0e"
},
"children": [
{
"id": "2720",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_34d3d65ad37c90ce30aa5a69",
"parentId": "2719",
"isLeaf": true,
"molecule": {
"id": "sa_34d3d65ad37c90ce30aa5a69",
"inchikey": "ATXXLNCPVSUCNK-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(Br)cn1"
},
"smiles": "O=[N+]([O-])c1ccc(Br)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2721",
"routeId": "sa_490d9c154501dff90295718a",
"moleculeId": "sa_60b03dbd902de8f42159b182",
"parentId": "2719",
"isLeaf": true,
"molecule": {
"id": "sa_60b03dbd902de8f42159b182",
"inchikey": "NQRYJNQNLNOLGT-UHFFFAOYSA-N",
"smiles": "C1CCNCC1"
},
"smiles": "C1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}