Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCCN(CCCC)C(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1
InChiKey
VRUBQEICLABHEB-UHFFFAOYSA-N
Route Signature
3ddfaacf112e64e43113a2a8e3e7b076ebc793af028a4d7080aebe10f6dfdb82
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_730633da33c597f90b478e75",
"signature": "3ddfaacf112e64e43113a2a8e3e7b076ebc793af028a4d7080aebe10f6dfdb82",
"contentHash": "fe9ec9d09311a5030022fca929f0d45954c4b2ebf3458f2216d683820ecc8d59",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_4def125799fa96844eae9a03",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01165",
"moleculeId": "sa_0d43ab5d0db8ff4ee1131b56",
"smiles": "CCCCN(CCCC)C(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_0d43ab5d0db8ff4ee1131b56",
"inchikey": "VRUBQEICLABHEB-UHFFFAOYSA-N",
"smiles": "CCCCN(CCCC)C(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5290",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_0d43ab5d0db8ff4ee1131b56",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0d43ab5d0db8ff4ee1131b56",
"inchikey": "VRUBQEICLABHEB-UHFFFAOYSA-N",
"smiles": "CCCCN(CCCC)C(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1"
},
"smiles": "CCCCN(CCCC)C(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1",
"reactionStepId": "sa_257fe7bad76e01bc636722a7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130165426A1;0388;1385135\",\"rsmi\":\"O[C:10](=[O:11])[c:12]1[cH:13][c:14]2[c:15]([cH:16][n:17]1)[n:18][c:19]([NH:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]1)[n:29]2[CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1.[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH3:9]>CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[C:10](=[O:11])[c:12]1[cH:13][c:14]2[c:15]([cH:16][n:17]1)[n:18][c:19]([NH:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]1)[n:29]2[CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1\"},\"mapped_reaction_smiles\":\"O[C:10](=[O:11])[c:12]1[cH:13][c:14]2[c:15]([cH:16][n:17]1)[n:18][c:19]([NH:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]1)[n:29]2[CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1.[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH3:9]>CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[C:10](=[O:11])[c:12]1[cH:13][c:14]2[c:15]([cH:16][n:17]1)[n:18][c:19]([NH:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]1)[n:29]2[CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1\"}",
"reactionStep": {
"id": "sa_257fe7bad76e01bc636722a7",
"reactionHash": "1fd4703af9fb7090a3d3c097513f9eb1d009fd6a2977ad09c775153154ad1835"
},
"children": [
{
"id": "5291",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_8345b79d27b2cbb12928e685",
"parentId": "5290",
"isLeaf": false,
"molecule": {
"id": "sa_8345b79d27b2cbb12928e685",
"inchikey": "GTXGECUICLRETD-UHFFFAOYSA-N",
"smiles": "COc1ccc(Nc2nc3cnc(C(=O)O)cc3n2CCCN2CCCCC2)cc1"
},
"smiles": "COc1ccc(Nc2nc3cnc(C(=O)O)cc3n2CCCN2CCCCC2)cc1",
"reactionStepId": "sa_a0210cea3e295fc1591dd44e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130165426A1;0386;1385134\",\"rsmi\":\"CC[O:16][C:14]([c:13]1[cH:12][c:11]2[c:10]([n:9][c:8]([NH:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]3)[n:19]2[CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:18][n:17]1)=[O:15]>Cl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]3[c:11]([cH:12][c:13]([C:14](=[O:15])[OH:16])[n:17][cH:18]3)[n:19]2[CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CC[O:16][C:14]([c:13]1[cH:12][c:11]2[c:10]([n:9][c:8]([NH:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]3)[n:19]2[CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:18][n:17]1)=[O:15]>Cl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]3[c:11]([cH:12][c:13]([C:14](=[O:15])[OH:16])[n:17][cH:18]3)[n:19]2[CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_a0210cea3e295fc1591dd44e",
"reactionHash": "2e377e990a00f173ae5d4f78b5aa3a453e81d7afed2ed714bb2a30686734ebf7"
},
"children": [
{
"id": "5292",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_24d2053c07247b731a2c54a2",
"parentId": "5291",
"isLeaf": false,
"molecule": {
"id": "sa_24d2053c07247b731a2c54a2",
"inchikey": "DINNSRWYOZZCQU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1"
},
"smiles": "CCOC(=O)c1cc2c(cn1)nc(Nc1ccc(OC)cc1)n2CCCN1CCCCC1",
"reactionStepId": "sa_164cb162a6e4a049a0740eec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130165426A1;0384;1385133\",\"rsmi\":\"Cl[CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][n:11]1)[n:12][c:13]([NH:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[nH:23]2>CCOC(C)=O.CN(C)C=O.Cl.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][n:11]1)[n:12][c:13]([NH:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[n:23]2[CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][n:11]1)[n:12][c:13]([NH:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[nH:23]2>CCOC(C)=O.CN(C)C=O.Cl.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][n:11]1)[n:12][c:13]([NH:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[n:23]2[CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1\"}",
"reactionStep": {
"id": "sa_164cb162a6e4a049a0740eec",
"reactionHash": "4c15a51ec862e58de71c2790193980f6c4ecadc8d72b1c059c0649afe10b8f68"
},
"children": [
{
"id": "5293",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_71b1d8ec83f443124d48f6d5",
"parentId": "5292",
"isLeaf": true,
"molecule": {
"id": "sa_71b1d8ec83f443124d48f6d5",
"inchikey": "HDDNBUNZJIQDBQ-UHFFFAOYSA-N",
"smiles": "ClCCCN1CCCCC1"
},
"smiles": "ClCCCN1CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5294",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_8d54a9d14e05e8ba9200bf64",
"parentId": "5292",
"isLeaf": false,
"molecule": {
"id": "sa_8d54a9d14e05e8ba9200bf64",
"inchikey": "RJQJYISSEVBQLQ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc2[nH]c(Nc3ccc(OC)cc3)nc2cn1"
},
"smiles": "CCOC(=O)c1cc2[nH]c(Nc3ccc(OC)cc3)nc2cn1",
"reactionStepId": "sa_59783bc18b6edac35c5de0e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130165426A1;0382;1385132\",\"rsmi\":\"S=[C:13]=[N:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:23])[c:9]([NH2:12])[cH:10][n:11]1>C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.CCOC(C)=O.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][n:11]1)[n:12][c:13]([NH:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[nH:23]2\"},\"mapped_reaction_smiles\":\"S=[C:13]=[N:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:23])[c:9]([NH2:12])[cH:10][n:11]1>C(=NC1CCCCC1)=NC1CCCCC1.C1CCOC1.CCOC(C)=O.Cl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][n:11]1)[n:12][c:13]([NH:14][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1)[nH:23]2\"}",
"reactionStep": {
"id": "sa_59783bc18b6edac35c5de0e8",
"reactionHash": "4821ca5d209f67d9ad18dd1c3ac06f954105b1ce6674e4df398782c5de13fc36"
},
"children": [
{
"id": "5295",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_66c704ab49835e7d980eecf5",
"parentId": "5294",
"isLeaf": true,
"molecule": {
"id": "sa_66c704ab49835e7d980eecf5",
"inchikey": "VRPQCVLBOZOYCG-UHFFFAOYSA-N",
"smiles": "COc1ccc(N=C=S)cc1"
},
"smiles": "COc1ccc(N=C=S)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5296",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_e93d5bc67119b16bfac7af35",
"parentId": "5294",
"isLeaf": false,
"molecule": {
"id": "sa_e93d5bc67119b16bfac7af35",
"inchikey": "XFGYUNVIMSXNNA-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(N)c(N)cn1"
},
"smiles": "CCOC(=O)c1cc(N)c(N)cn1",
"reactionStepId": "sa_f48d5db246693d58a4e4a0da",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130165426A1;0380;1385131\",\"rsmi\":\"O=[N+:10]([O-])[c:9]1[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:13][c:11]1[NH2:12]>CC(C)O.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([NH2:10])[c:11]([NH2:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:10]([O-])[c:9]1[cH:8][n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:13][c:11]1[NH2:12]>CC(C)O.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][c:9]([NH2:10])[c:11]([NH2:12])[cH:13]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_701533e9421dbfc164b75904",
"parentId": "5296",
"isLeaf": true,
"molecule": {
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"inchikey": "PGSAVGAWCWMKJF-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(N)c([N+](=O)[O-])cn1"
},
"smiles": "CCOC(=O)c1cc(N)c([N+](=O)[O-])cn1",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
},
{
"id": "5298",
"routeId": "sa_730633da33c597f90b478e75",
"moleculeId": "sa_8e9224cf7238fbcebbf74e2a",
"parentId": "5290",
"isLeaf": true,
"molecule": {
"id": "sa_8e9224cf7238fbcebbf74e2a",
"inchikey": "JQVDAXLFBXTEQA-UHFFFAOYSA-N",
"smiles": "CCCCNCCCC"
},
"smiles": "CCCCNCCCC",
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"metadata": null,
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"children": []
}
]
}
}