Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCCc2c1nc(N1CCN(Cc3ncc(F)cc3F)CC1)[nH]c2=O
InChiKey
YDGPFYFZYCIASD-UHFFFAOYSA-N
Route Signature
1d1b68d67cfa8c8c3f6f0442909590af6f642dae4c2aaf9334f4c428634fcef7
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_fcbbfb0c83ff9317544d9daa",
"signature": "1d1b68d67cfa8c8c3f6f0442909590af6f642dae4c2aaf9334f4c428634fcef7",
"contentHash": "e8a94f70292d0cbaed47b87c6791372aaee386c0c5326b04eaa2753d28153f2e",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_948c733389996d51774f3bbb",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01920",
"moleculeId": "sa_4edaa4be9b88f6ab2fe14c88",
"smiles": "CN1CCCc2c1nc(N1CCN(Cc3ncc(F)cc3F)CC1)[nH]c2=O",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_4edaa4be9b88f6ab2fe14c88",
"inchikey": "YDGPFYFZYCIASD-UHFFFAOYSA-N",
"smiles": "CN1CCCc2c1nc(N1CCN(Cc3ncc(F)cc3F)CC1)[nH]c2=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10511",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_4edaa4be9b88f6ab2fe14c88",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4edaa4be9b88f6ab2fe14c88",
"inchikey": "YDGPFYFZYCIASD-UHFFFAOYSA-N",
"smiles": "CN1CCCc2c1nc(N1CCN(Cc3ncc(F)cc3F)CC1)[nH]c2=O"
},
"smiles": "CN1CCCc2c1nc(N1CCN(Cc3ncc(F)cc3F)CC1)[nH]c2=O",
"reactionStepId": "sa_8d6736c9358c3bccd91ecfde",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251348A1;0152;1927399\",\"rsmi\":\"Cl[CH2:14][c:15]1[n:16][cH:17][c:18]([F:19])[cH:20][c:21]1[F:22].[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[n:8][c:9]([N:10]1[CH2:11][CH2:12][NH:13][CH2:23][CH2:24]1)[nH:25][c:26]2=[O:27]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[n:8][c:9]([N:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]3[n:16][cH:17][c:18]([F:19])[cH:20][c:21]3[F:22])[CH2:23][CH2:24]1)[nH:25][c:26]2=[O:27]\"},\"mapped_reaction_smiles\":\"Cl[CH2:14][c:15]1[n:16][cH:17][c:18]([F:19])[cH:20][c:21]1[F:22].[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[n:8][c:9]([N:10]1[CH2:11][CH2:12][NH:13][CH2:23][CH2:24]1)[nH:25][c:26]2=[O:27]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[n:8][c:9]([N:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]3[n:16][cH:17][c:18]([F:19])[cH:20][c:21]3[F:22])[CH2:23][CH2:24]1)[nH:25][c:26]2=[O:27]\"}",
"reactionStep": {
"id": "sa_8d6736c9358c3bccd91ecfde",
"reactionHash": "2724014c737df05df8afd68d6f67b677e37ae7d5bc61965ab1577ad5180d0661"
},
"children": [
{
"id": "10512",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_dd5e256a9d84cadb3a1f47b3",
"parentId": "10511",
"isLeaf": false,
"molecule": {
"id": "sa_dd5e256a9d84cadb3a1f47b3",
"inchikey": "HCYQZKMKFBJSAD-UHFFFAOYSA-N",
"smiles": "CN1CCCc2c1nc(N1CCNCC1)[nH]c2=O"
},
"smiles": "CN1CCCc2c1nc(N1CCNCC1)[nH]c2=O",
"reactionStepId": "sa_5ee3ae2c02e73e8caa9d2067",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251348A1;0102;1927386\",\"rsmi\":\"CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][N:10]([c:9]2[n:8][c:7]3[c:6]([c:17](=[O:18])[nH:16]2)[CH2:5][CH2:4][CH2:3][N:2]3[CH3:1])[CH2:15][CH2:14]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[n:8][c:9]([N:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1)[nH:16][c:17]2=[O:18]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][N:10]([c:9]2[n:8][c:7]3[c:6]([c:17](=[O:18])[nH:16]2)[CH2:5][CH2:4][CH2:3][N:2]3[CH3:1])[CH2:15][CH2:14]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][c:6]2[c:7]1[n:8][c:9]([N:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1)[nH:16][c:17]2=[O:18]\"}",
"reactionStep": {
"id": "sa_5ee3ae2c02e73e8caa9d2067",
"reactionHash": "ac9532df94eb365883ba251ac01c9ddc457d7661ab21fa356134151f42042ae2"
},
"children": [
{
"id": "10513",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_257aee102ed52fcbd94b78cf",
"parentId": "10512",
"isLeaf": true,
"molecule": {
"id": "sa_257aee102ed52fcbd94b78cf",
"inchikey": "XMBFEUHAINDBIA-UHFFFAOYSA-N",
"smiles": "CN1CCCc2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)[nH]c2=O"
},
"smiles": "CN1CCCc2c1nc(N1CCN(C(=O)OC(C)(C)C)CC1)[nH]c2=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10514",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_a5f864d177218e9909100345",
"parentId": "10511",
"isLeaf": false,
"molecule": {
"id": "sa_a5f864d177218e9909100345",
"inchikey": "PNRQVTCCNSHPBG-UHFFFAOYSA-N",
"smiles": "Fc1cnc(CCl)c(F)c1"
},
"smiles": "Fc1cnc(CCl)c(F)c1",
"reactionStepId": "sa_eca14dd5634f9b27975c2544",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251348A1;0081;1927379\",\"rsmi\":\"ClC[Cl:7].O[CH2:6][c:5]1[n:4][cH:3][c:2]([F:1])[cH:10][c:8]1[F:9]>CN(C)C=O.O=C(O)O.O=S(Cl)Cl.[Na+]>[F:1][c:2]1[cH:3][n:4][c:5]([CH2:6][Cl:7])[c:8]([F:9])[cH:10]1\"},\"mapped_reaction_smiles\":\"ClC[Cl:7].O[CH2:6][c:5]1[n:4][cH:3][c:2]([F:1])[cH:10][c:8]1[F:9]>CN(C)C=O.O=C(O)O.O=S(Cl)Cl.[Na+]>[F:1][c:2]1[cH:3][n:4][c:5]([CH2:6][Cl:7])[c:8]([F:9])[cH:10]1\"}",
"reactionStep": {
"id": "sa_eca14dd5634f9b27975c2544",
"reactionHash": "0781b27112352a2d30c7a8c578dbc6bed3b9058534c3ca27a0b61991f3bf28f4"
},
"children": [
{
"id": "10515",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_75d59874e79286890ea1cd19",
"parentId": "10514",
"isLeaf": false,
"molecule": {
"id": "sa_75d59874e79286890ea1cd19",
"inchikey": "XYNXXKCNVYDIET-UHFFFAOYSA-N",
"smiles": "OCc1ncc(F)cc1F"
},
"smiles": "OCc1ncc(F)cc1F",
"reactionStepId": "sa_bbc4ba5e994887e50118e145",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251348A1;0079;1927378\",\"rsmi\":\"C[O:1][C:2](=O)[c:3]1[n:4][cH:5][c:6]([F:7])[cH:8][c:9]1[F:10]>C1CCOC1.B.[Li+]>[OH:1][CH2:2][c:3]1[n:4][cH:5][c:6]([F:7])[cH:8][c:9]1[F:10]\"},\"mapped_reaction_smiles\":\"C[O:1][C:2](=O)[c:3]1[n:4][cH:5][c:6]([F:7])[cH:8][c:9]1[F:10]>C1CCOC1.B.[Li+]>[OH:1][CH2:2][c:3]1[n:4][cH:5][c:6]([F:7])[cH:8][c:9]1[F:10]\"}",
"reactionStep": {
"id": "sa_bbc4ba5e994887e50118e145",
"reactionHash": "5faeaf2685d1f5eced859c49b8fda4e982b26e08f19404d19adcf1ccd5879148"
},
"children": [
{
"id": "10516",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_f9aa37b00ec22ad859f6e71f",
"parentId": "10515",
"isLeaf": false,
"molecule": {
"id": "sa_f9aa37b00ec22ad859f6e71f",
"inchikey": "IYJHSWYHTRMPJE-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ncc(F)cc1F"
},
"smiles": "COC(=O)c1ncc(F)cc1F",
"reactionStepId": "sa_d73c182ba5d1f9a5207f50d7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251348A1;0077;1927377\",\"rsmi\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12]>CCN=C=NCCCN(C)C.CN(C)c1ccncc1.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12]\"},\"mapped_reaction_smiles\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12]>CCN=C=NCCCN(C)C.CN(C)c1ccncc1.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12]\"}",
"reactionStep": {
"id": "sa_d73c182ba5d1f9a5207f50d7",
"reactionHash": "3ada67fa8ecf7c2396270aec3bf320c5704158133fe12c35aee73f9ffd60cf9f"
},
"children": [
{
"id": "10517",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "10516",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10518",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_f7cd027428f959c58f17318a",
"parentId": "10516",
"isLeaf": true,
"molecule": {
"id": "sa_f7cd027428f959c58f17318a",
"inchikey": "QKLXAJQKMIWFRC-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ncc(F)cc1F"
},
"smiles": "O=C(O)c1ncc(F)cc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10519",
"routeId": "sa_fcbbfb0c83ff9317544d9daa",
"moleculeId": "sa_dc8cb1645d1f4dafe3621d07",
"parentId": "10514",
"isLeaf": true,
"molecule": {
"id": "sa_dc8cb1645d1f4dafe3621d07",
"inchikey": "YMWUJEATGCHHMB-UHFFFAOYSA-N",
"smiles": "ClCCl"
},
"smiles": "ClCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}