Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccncc1N1CCc2[nH]c3ccc(F)cc3c2C1=O
InChiKey
ORCBHPRQSKOSRD-UHFFFAOYSA-N
Route Signature
691f105d1260539e43ea3dee66659c17d6d057ccd51e78037339fc8af9be25ec
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_34259264ba96892dd0543880",
"signature": "691f105d1260539e43ea3dee66659c17d6d057ccd51e78037339fc8af9be25ec",
"contentHash": "363051b17bf44ebd51c6759500e4b40824c5390e751126a67d6c9d92e5fc3b34",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_99977a81222d38e8ac97bc94",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01507",
"moleculeId": "sa_a7d7890bac7962c2a8a0d543",
"smiles": "Cc1ccncc1N1CCc2[nH]c3ccc(F)cc3c2C1=O",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a7d7890bac7962c2a8a0d543",
"inchikey": "ORCBHPRQSKOSRD-UHFFFAOYSA-N",
"smiles": "Cc1ccncc1N1CCc2[nH]c3ccc(F)cc3c2C1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5692",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_a7d7890bac7962c2a8a0d543",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a7d7890bac7962c2a8a0d543",
"inchikey": "ORCBHPRQSKOSRD-UHFFFAOYSA-N",
"smiles": "Cc1ccncc1N1CCc2[nH]c3ccc(F)cc3c2C1=O"
},
"smiles": "Cc1ccncc1N1CCc2[nH]c3ccc(F)cc3c2C1=O",
"reactionStepId": "sa_ee9cdb2f260c8bcd99c4103e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08946260B2;0935;1574135\",\"rsmi\":\"O=S(=O)(c1ccccc1)[n:18]1[c:7]2[c:8]([c:11]3[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17]3)[C:9](=[O:10])[N:4]([c:3]1[c:2]([CH3:1])[cH:22][cH:21][n:20][cH:19]1)[CH2:5][CH2:6]2>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CO.ClCCl.F>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][c:7]3[c:8]([c:11]4[c:12]([cH:13][cH:14][c:15]([F:16])[cH:17]4)[nH:18]3)[C:9]2=[O:10])[cH:19][n:20][cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(c1ccccc1)[n:18]1[c:7]2[c:8]([c:11]3[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17]3)[C:9](=[O:10])[N:4]([c:3]1[c:2]([CH3:1])[cH:22][cH:21][n:20][cH:19]1)[CH2:5][CH2:6]2>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CO.ClCCl.F>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][c:7]3[c:8]([c:11]4[c:12]([cH:13][cH:14][c:15]([F:16])[cH:17]4)[nH:18]3)[C:9]2=[O:10])[cH:19][n:20][cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_ee9cdb2f260c8bcd99c4103e",
"reactionHash": "80d95e3a470dfd6fdb9fd6042ffdb4217d0d393cd21db0b87479bf9db0da3002"
},
"children": [
{
"id": "5693",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_65d292153a89ace915ee24c6",
"parentId": "5692",
"isLeaf": false,
"molecule": {
"id": "sa_65d292153a89ace915ee24c6",
"inchikey": "QFQZCIYXIJZAEG-UHFFFAOYSA-N",
"smiles": "Cc1ccncc1N1CCc2c(c3cc(F)ccc3n2S(=O)(=O)c2ccccc2)C1=O"
},
"smiles": "Cc1ccncc1N1CCc2c(c3cc(F)ccc3n2S(=O)(=O)c2ccccc2)C1=O",
"reactionStepId": "sa_30b20eecf75b40893c19b2f0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08946260B2;0934;1574134\",\"rsmi\":\"I[c:3]1[c:2]([CH3:1])[cH:31][cH:30][n:29][cH:28]1.[NH:4]1[CH2:5][CH2:6][c:7]2[c:8]([c:11]3[c:12]([cH:13][cH:14][c:15]([F:16])[cH:17]3)[n:18]2[S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[C:9]1=[O:10]>C1COCCO1.I[Cu]I.O=P(O)(O)O.[K+].[K+].[K+]>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][c:7]3[c:8]([c:11]4[c:12]([cH:13][cH:14][c:15]([F:16])[cH:17]4)[n:18]3[S:19](=[O:20])(=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[C:9]2=[O:10])[cH:28][n:29][cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"I[c:3]1[c:2]([CH3:1])[cH:31][cH:30][n:29][cH:28]1.[NH:4]1[CH2:5][CH2:6][c:7]2[c:8]([c:11]3[c:12]([cH:13][cH:14][c:15]([F:16])[cH:17]3)[n:18]2[S:19](=[O:20])(=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[C:9]1=[O:10]>C1COCCO1.I[Cu]I.O=P(O)(O)O.[K+].[K+].[K+]>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][c:7]3[c:8]([c:11]4[c:12]([cH:13][cH:14][c:15]([F:16])[cH:17]4)[n:18]3[S:19](=[O:20])(=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[C:9]2=[O:10])[cH:28][n:29][cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_30b20eecf75b40893c19b2f0",
"reactionHash": "4fbe31bc748d2abdd92483643102c1f67797d50f3b60f4560fa45197f87fd2cd"
},
"children": [
{
"id": "5694",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_ac0204db6055cd1a01dcc233",
"parentId": "5693",
"isLeaf": false,
"molecule": {
"id": "sa_ac0204db6055cd1a01dcc233",
"inchikey": "QQOXPCKEFMWMMQ-UHFFFAOYSA-N",
"smiles": "O=C1NCCc2c1c1cc(F)ccc1n2S(=O)(=O)c1ccccc1"
},
"smiles": "O=C1NCCc2c1c1cc(F)ccc1n2S(=O)(=O)c1ccccc1",
"reactionStepId": "sa_f0780f4e5ecb9d8f962c3eac",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08946260B2;0931;1574133\",\"rsmi\":\"Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[c:9]([cH:10][cH:11][c:12]([F:13])[cH:14]1)[nH:15]2>CN(C)C=O.CO.ClCCl.[HH].[Na+]>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[c:9]([cH:10][cH:11][c:12]([F:13])[cH:14]1)[n:15]2[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[c:9]([cH:10][cH:11][c:12]([F:13])[cH:14]1)[nH:15]2>CN(C)C=O.CO.ClCCl.[HH].[Na+]>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[c:9]([cH:10][cH:11][c:12]([F:13])[cH:14]1)[n:15]2[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_f0780f4e5ecb9d8f962c3eac",
"reactionHash": "eb1787adf07c1f32d42fbf6a091e01028d271045ab2a401cb5c288810d75fdc9"
},
"children": [
{
"id": "5695",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_2e449791516bfe12bcac6036",
"parentId": "5694",
"isLeaf": true,
"molecule": {
"id": "sa_2e449791516bfe12bcac6036",
"inchikey": "CSKNSYBAZOQPLR-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccccc1"
},
"smiles": "O=S(=O)(Cl)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5696",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_f3c0c3e303f4cde1d328e2ea",
"parentId": "5694",
"isLeaf": false,
"molecule": {
"id": "sa_f3c0c3e303f4cde1d328e2ea",
"inchikey": "MRAOJMZEBWCXOA-UHFFFAOYSA-N",
"smiles": "O=C1NCCc2[nH]c3ccc(F)cc3c21"
},
"smiles": "O=C1NCCc2[nH]c3ccc(F)cc3c21",
"reactionStepId": "sa_7a763394f0aa21ea68b8b0de",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08946260B2;0922;1574131\",\"rsmi\":\"[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([NH:15][c:9]2[cH:8][cH:14][c:12]([F:13])[cH:11][cH:10]2)=[CH:7]1>CC(=O)O.CC(=O)O.CC(=O)O.CC(=O)O.CN(C)C=O.CO.ClCCl.[Cu+2].[Pd+2]>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[c:9]([cH:10][cH:11][c:12]([F:13])[cH:14]1)[nH:15]2\"},\"mapped_reaction_smiles\":\"[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][C:6]([NH:15][c:9]2[cH:8][cH:14][c:12]([F:13])[cH:11][cH:10]2)=[CH:7]1>CC(=O)O.CC(=O)O.CC(=O)O.CC(=O)O.CN(C)C=O.CO.ClCCl.[Cu+2].[Pd+2]>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]1[c:8]1[c:9]([cH:10][cH:11][c:12]([F:13])[cH:14]1)[nH:15]2\"}",
"reactionStep": {
"id": "sa_7a763394f0aa21ea68b8b0de",
"reactionHash": "fae5b684ac5883bdafd35cd032f213007f6f7feb4c13a4cba732953f0f96c2ad"
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"children": [
{
"id": "5697",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_130b06f3c97b4f977af0d108",
"parentId": "5696",
"isLeaf": false,
"molecule": {
"id": "sa_130b06f3c97b4f977af0d108",
"inchikey": "ZZHCWEFJHUMCOE-UHFFFAOYSA-N",
"smiles": "O=C1C=C(Nc2ccc(F)cc2)CCN1"
},
"smiles": "O=C1C=C(Nc2ccc(F)cc2)CCN1",
"reactionStepId": "sa_61c0a4c35c5013db6ab6707d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08946260B2;0920;1574130\",\"rsmi\":\"O=[C:4]1[CH2:3][C:2](=[O:1])[NH:15][CH2:14][CH2:13]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>CCOCC.CO.ClCCl>[O:1]=[C:2]1[CH:3]=[C:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1\"},\"mapped_reaction_smiles\":\"O=[C:4]1[CH2:3][C:2](=[O:1])[NH:15][CH2:14][CH2:13]1.[NH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>CCOCC.CO.ClCCl>[O:1]=[C:2]1[CH:3]=[C:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1\"}",
"reactionStep": {
"id": "sa_61c0a4c35c5013db6ab6707d",
"reactionHash": "03ba40f1860fe46f5c6147bff1dcbb77972cac55c0bbae0a55297cce0ca5a5c0"
},
"children": [
{
"id": "5698",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_a513f184ba08b4e72aa488b9",
"parentId": "5697",
"isLeaf": true,
"molecule": {
"id": "sa_a513f184ba08b4e72aa488b9",
"inchikey": "KRZCOLNOCZKSDF-UHFFFAOYSA-N",
"smiles": "Nc1ccc(F)cc1"
},
"smiles": "Nc1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5699",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_ab39d55d151e09273ac91fab",
"parentId": "5697",
"isLeaf": true,
"molecule": {
"id": "sa_ab39d55d151e09273ac91fab",
"inchikey": "RDNZDMDLRIQQAX-UHFFFAOYSA-N",
"smiles": "O=C1CCN=C(O)C1"
},
"smiles": "O=C1CCNC(=O)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "5700",
"routeId": "sa_34259264ba96892dd0543880",
"moleculeId": "sa_1e75efa97580b2848d624bac",
"parentId": "5693",
"isLeaf": true,
"molecule": {
"id": "sa_1e75efa97580b2848d624bac",
"inchikey": "SMXBHXFTAWZFAU-UHFFFAOYSA-N",
"smiles": "Cc1ccncc1I"
},
"smiles": "Cc1ccncc1I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}