Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2cnc(CC#N)cn2)cc1Cl
InChiKey
BPXLLUOTZHRROR-UHFFFAOYSA-N
Route Signature
f36c355e1a3417d917af06d4d95fa08698f4eaa4990521f83f97026020a3ff7f
Synthesis route with 8 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b1306814859fd7766bca1631",
"signature": "f36c355e1a3417d917af06d4d95fa08698f4eaa4990521f83f97026020a3ff7f",
"contentHash": "980065f5c0199ee8e9ac3fa66c4b7e926b0938abffe0241935a1a7484c213954",
"length": 8,
"isConvergent": false
},
"target": {
"id": "sa_4ad6018498c9ccc40f9e7dfd",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n1-00248",
"moleculeId": "sa_c9d1fa91f56a799eb1247407",
"smiles": "CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2cnc(CC#N)cn2)cc1Cl",
"routeLength": 8,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c9d1fa91f56a799eb1247407",
"inchikey": "BPXLLUOTZHRROR-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2cnc(CC#N)cn2)cc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17112",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_c9d1fa91f56a799eb1247407",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c9d1fa91f56a799eb1247407",
"inchikey": "BPXLLUOTZHRROR-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2cnc(CC#N)cn2)cc1Cl"
},
"smiles": "CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2cnc(CC#N)cn2)cc1Cl",
"reactionStepId": "sa_58250effaedb602c509b0c76",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0370;754075\",\"rsmi\":\"O[C:17]([CH:10]([c:9]1[cH:8][c:6]([Cl:7])[c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:30][cH:29]1)[CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:18].[NH2:19][c:20]1[n:21][cH:22][c:23]([CH2:24][C:25]#[N:26])[n:27][cH:28]1>CN(C)C=O.ClCCl.O.O=C(Cl)C(=O)Cl.c1ccncc1>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[c:6]([Cl:7])[cH:8][c:9]([CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[NH:19][c:20]2[n:21][cH:22][c:23]([CH2:24][C:25]#[N:26])[n:27][cH:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"O[C:17]([CH:10]([c:9]1[cH:8][c:6]([Cl:7])[c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:30][cH:29]1)[CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:18].[NH2:19][c:20]1[n:21][cH:22][c:23]([CH2:24][C:25]#[N:26])[n:27][cH:28]1>CN(C)C=O.ClCCl.O.O=C(Cl)C(=O)Cl.c1ccncc1>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[c:6]([Cl:7])[cH:8][c:9]([CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[NH:19][c:20]2[n:21][cH:22][c:23]([CH2:24][C:25]#[N:26])[n:27][cH:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_58250effaedb602c509b0c76",
"reactionHash": "3c8775f0573960f60880dedffb17f188b591470cf75c60f5d62b53b6e38f27cd"
},
"children": [
{
"id": "17113",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_8c04c65651277095aa415cd0",
"parentId": "17112",
"isLeaf": false,
"molecule": {
"id": "sa_8c04c65651277095aa415cd0",
"inchikey": "NVODVFUXRXQBQK-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)O)cc1Cl"
},
"smiles": "CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)O)cc1Cl",
"reactionStepId": "sa_bbb004cf820dc2bdb8685a25",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0352;754062\",\"rsmi\":\"[CH3:1][S:2][c:5]1[c:6]([Cl:7])[cH:8][c:9]([CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[OH:19])[cH:20][cH:21]1.[OH:3][OH:4]>C1CCOC1.O=CO.O=S(O)O.[Na+].[Na+]>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[c:6]([Cl:7])[cH:8][c:9]([CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[OH:19])[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"[CH3:1][S:2][c:5]1[c:6]([Cl:7])[cH:8][c:9]([CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[OH:19])[cH:20][cH:21]1.[OH:3][OH:4]>C1CCOC1.O=CO.O=S(O)O.[Na+].[Na+]>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[c:6]([Cl:7])[cH:8][c:9]([CH:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[OH:19])[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_bbb004cf820dc2bdb8685a25",
"reactionHash": "901677142c0722bde2b1529ed57c5eb218052a34ed618d3f91d4bc83e4808c40"
},
"children": [
{
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"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_4dba68d938224067da688ab5",
"parentId": "17113",
"isLeaf": true,
"molecule": {
"id": "sa_4dba68d938224067da688ab5",
"inchikey": "MHAJPDPJQMAIIY-UHFFFAOYSA-N",
"smiles": "OO"
},
"smiles": "OO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17115",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_f9e62c42d569aa60570f89ea",
"parentId": "17113",
"isLeaf": false,
"molecule": {
"id": "sa_f9e62c42d569aa60570f89ea",
"inchikey": "QQSUNHONYLAAGS-UHFFFAOYSA-N",
"smiles": "CSc1ccc(C(CC2CCCC2)C(=O)O)cc1Cl"
},
"smiles": "CSc1ccc(C(CC2CCCC2)C(=O)O)cc1Cl",
"reactionStepId": "sa_22da383738a415858576354d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0351;754061\",\"rsmi\":\"C[O:17][C:15]([CH:8]([c:7]1[cH:6][c:4]([Cl:5])[c:3]([S:2][CH3:1])[cH:19][cH:18]1)[CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:16]>CCO.O.[K+].O>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH:8]([CH2:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[C:15](=[O:16])[OH:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"C[O:17][C:15]([CH:8]([c:7]1[cH:6][c:4]([Cl:5])[c:3]([S:2][CH3:1])[cH:19][cH:18]1)[CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:16]>CCO.O.[K+].O>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH:8]([CH2:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[C:15](=[O:16])[OH:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_22da383738a415858576354d",
"reactionHash": "83022aea02af4d35e11f5f0bcf6ba993c3ca132255e6ea3692db17d535a4a960"
},
"children": [
{
"id": "17116",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_026baed2434a138eda248185",
"parentId": "17115",
"isLeaf": false,
"molecule": {
"id": "sa_026baed2434a138eda248185",
"inchikey": "PCAVNVCMJIVESZ-UHFFFAOYSA-N",
"smiles": "COC(=O)C(CC1CCCC1)c1ccc(SC)c(Cl)c1"
},
"smiles": "COC(=O)C(CC1CCCC1)c1ccc(SC)c(Cl)c1",
"reactionStepId": "sa_0179a25deee9c62377014e3c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0350;754060\",\"rsmi\":\"I[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:12]1[cH:13][c:14]([Cl:15])[c:16]([S:17][CH3:18])[cH:19][cH:20]1>C1CCOC1.CC(C)NC(C)C.CN1CCCN(C)C1=O.[Li]CCCC>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[cH:13][c:14]([Cl:15])[c:16]([S:17][CH3:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"I[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:12]1[cH:13][c:14]([Cl:15])[c:16]([S:17][CH3:18])[cH:19][cH:20]1>C1CCOC1.CC(C)NC(C)C.CN1CCCN(C)C1=O.[Li]CCCC>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[cH:13][c:14]([Cl:15])[c:16]([S:17][CH3:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_0179a25deee9c62377014e3c",
"reactionHash": "2506185475df2ba163c812964cb88084837a358b461610e592844370d3ae6823"
},
"children": [
{
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"moleculeId": "sa_87bae35c0a4c0ef2265278e0",
"parentId": "17116",
"isLeaf": true,
"molecule": {
"id": "sa_87bae35c0a4c0ef2265278e0",
"inchikey": "DUMSKQUKLVSSII-UHFFFAOYSA-N",
"smiles": "ICC1CCCC1"
},
"smiles": "ICC1CCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "17118",
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"moleculeId": "sa_93325b29e6b1e6d5c6e4edf8",
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"molecule": {
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"inchikey": "IJYMZQYIMMYFSA-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(SC)c(Cl)c1"
},
"smiles": "COC(=O)Cc1ccc(SC)c(Cl)c1",
"reactionStepId": "sa_b573065bc39b0f1cefe853b8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0349;754059\",\"rsmi\":\"O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([S:11][CH3:12])[cH:13][cH:14]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([S:11][CH3:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([S:11][CH3:12])[cH:13][cH:14]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([S:11][CH3:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_b573065bc39b0f1cefe853b8",
"reactionHash": "ca32a62687511d4f7ed6a27cf1777adf659cd8be978533a9f08b4dbbcf7dd04f"
},
"children": [
{
"id": "17119",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "17118",
"isLeaf": true,
"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "17120",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_5620a716f20130e61299afa2",
"parentId": "17118",
"isLeaf": false,
"molecule": {
"id": "sa_5620a716f20130e61299afa2",
"inchikey": "RUUPIFBYMDGMPN-UHFFFAOYSA-N",
"smiles": "CSc1ccc(CC(=O)O)cc1Cl"
},
"smiles": "CSc1ccc(CC(=O)O)cc1Cl",
"reactionStepId": "sa_01cfcdf136de4b77e34204d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0229;754005\",\"rsmi\":\"O=[C:8]([c:7]1[cH:6][c:4]([Cl:5])[c:3]([S:2][CH3:1])[cH:13][cH:12]1)[C:9](=[O:10])[OH:11]>Cl.NN.O.O.[K+].O>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=[C:8]([c:7]1[cH:6][c:4]([Cl:5])[c:3]([S:2][CH3:1])[cH:13][cH:12]1)[C:9](=[O:10])[OH:11]>Cl.NN.O.O.[K+].O>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[cH:12][cH:13]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_3e6bc64053ef0352b6f83e42",
"parentId": "17120",
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"molecule": {
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"inchikey": "MWEYYCKEPCNPQL-UHFFFAOYSA-N",
"smiles": "CSc1ccc(C(=O)C(=O)O)cc1Cl"
},
"smiles": "CSc1ccc(C(=O)C(=O)O)cc1Cl",
"reactionStepId": "sa_30ddbc03c30e3ecc33686436",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0228;754004\",\"rsmi\":\"C[O:12][C:10]([C:8]([c:7]1[cH:6][c:4]([Cl:5])[c:3]([S:2][CH3:1])[cH:14][cH:13]1)=[O:9])=[O:11]>Cc1ccccc1.Cl.[Na+].O>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([C:8](=[O:9])[C:10](=[O:11])[OH:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"C[O:12][C:10]([C:8]([c:7]1[cH:6][c:4]([Cl:5])[c:3]([S:2][CH3:1])[cH:14][cH:13]1)=[O:9])=[O:11]>Cc1ccccc1.Cl.[Na+].O>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([C:8](=[O:9])[C:10](=[O:11])[OH:12])[cH:13][cH:14]1\"}",
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"children": [
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},
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"metadata": "{\"annotations\":{\"ID\":\"US07132425B2;0227;754003\",\"rsmi\":\"Cl[C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6].[cH:7]1[cH:8][c:9]([Cl:10])[c:11]([S:12][CH3:13])[cH:14][cH:15]1>ClC(Cl)Cl.[Al+3].Cl.Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([Cl:10])[c:11]([S:12][CH3:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"Cl[C:5]([C:3]([O:2][CH3:1])=[O:4])=[O:6].[cH:7]1[cH:8][c:9]([Cl:10])[c:11]([S:12][CH3:13])[cH:14][cH:15]1>ClC(Cl)Cl.[Al+3].Cl.Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([Cl:10])[c:11]([S:12][CH3:13])[cH:14][cH:15]1\"}",
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"children": [
{
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"moleculeId": "sa_c5ea83dd4a61b04ac1df9f0b",
"parentId": "17122",
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"molecule": {
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"inchikey": "IHLDFHCSSCVPQW-UHFFFAOYSA-N",
"smiles": "CSc1ccccc1Cl"
},
"smiles": "CSc1ccccc1Cl",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "17124",
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"molecule": {
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"inchikey": "ZXUQEPZWVQIOJE-UHFFFAOYSA-N",
"smiles": "COC(=O)C(=O)Cl"
},
"smiles": "COC(=O)C(=O)Cl",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
}
]
}
]
}
]
},
{
"id": "17125",
"routeId": "sa_b1306814859fd7766bca1631",
"moleculeId": "sa_0541afb79d7d077921e360ab",
"parentId": "17112",
"isLeaf": true,
"molecule": {
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"inchikey": "PYJSFZXSSTXBBZ-UHFFFAOYSA-N",
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