Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(c1ccc(OCC(=O)O)c(-c2cccc(C(F)(F)F)c2)c1)N(C)S(=O)(=O)c1ccc(F)cc1
InChiKey
XKNQWAKZLILMRD-UHFFFAOYSA-N
Route Signature
4d5b54c0960cc01a073092f8e8494caa49eb820f5b60fe360a3606d3aa32833a
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d02d361489cd16833f77fc76",
"signature": "4d5b54c0960cc01a073092f8e8494caa49eb820f5b60fe360a3606d3aa32833a",
"contentHash": "e8bc1873b7a1c626cb050bfad19295e943fca992de6132c5bf953702d07c5a3a",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_e25600b51bf6993dbce78c89",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01301",
"moleculeId": "sa_a8fd4ebbf5758a1c9059405d",
"smiles": "CC(c1ccc(OCC(=O)O)c(-c2cccc(C(F)(F)F)c2)c1)N(C)S(=O)(=O)c1ccc(F)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_a8fd4ebbf5758a1c9059405d",
"inchikey": "XKNQWAKZLILMRD-UHFFFAOYSA-N",
"smiles": "CC(c1ccc(OCC(=O)O)c(-c2cccc(C(F)(F)F)c2)c1)N(C)S(=O)(=O)c1ccc(F)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5438",
"routeId": "sa_d02d361489cd16833f77fc76",
"moleculeId": "sa_a8fd4ebbf5758a1c9059405d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_a8fd4ebbf5758a1c9059405d",
"inchikey": "XKNQWAKZLILMRD-UHFFFAOYSA-N",
"smiles": "CC(c1ccc(OCC(=O)O)c(-c2cccc(C(F)(F)F)c2)c1)N(C)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "CC(c1ccc(OCC(=O)O)c(-c2cccc(C(F)(F)F)c2)c1)N(C)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_40f40506cb476935b42ba659",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0298;1358894\",\"rsmi\":\"C[O:21][C:19]([CH2:18][O:17][c:16]1[c:5](-[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]2)[cH:4][c:3]([CH:2]([CH3:1])[N:24]([CH3:25])[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]2)[cH:23][cH:22]1)=[O:20]>CO.O.[Li+].O>[CH3:1][CH:2]([c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[OH:21])[cH:22][cH:23]1)[N:24]([CH3:25])[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"C[O:21][C:19]([CH2:18][O:17][c:16]1[c:5](-[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]2)[cH:4][c:3]([CH:2]([CH3:1])[N:24]([CH3:25])[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]2)[cH:23][cH:22]1)=[O:20]>CO.O.[Li+].O>[CH3:1][CH:2]([c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[OH:21])[cH:22][cH:23]1)[N:24]([CH3:25])[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_40f40506cb476935b42ba659",
"reactionHash": "a7888ca52b20a793f1e0cc5552c644b33a46c18adbab79e83c6372b81cf2f7bb"
},
"children": [
{
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"routeId": "sa_d02d361489cd16833f77fc76",
"moleculeId": "sa_f7466a6326570e084f722ab5",
"parentId": "5438",
"isLeaf": false,
"molecule": {
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"inchikey": "GDUAEKTXSWXRMV-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1ccc(C(C)N(C)S(=O)(=O)c2ccc(F)cc2)cc1-c1cccc(C(F)(F)F)c1"
},
"smiles": "COC(=O)COc1ccc(C(C)N(C)S(=O)(=O)c2ccc(F)cc2)cc1-c1cccc(C(F)(F)F)c1",
"reactionStepId": "sa_cf0b00c830cc3e7fd156879e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0296;1358893\",\"rsmi\":\"Cl[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([CH:21]([CH3:22])[NH:23][CH3:24])[cH:35][cH:36]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([CH:21]([CH3:22])[N:23]([CH3:24])[S:25](=[O:26])(=[O:27])[c:28]2[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]2)[cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"Cl[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([CH:21]([CH3:22])[NH:23][CH3:24])[cH:35][cH:36]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([CH:21]([CH3:22])[N:23]([CH3:24])[S:25](=[O:26])(=[O:27])[c:28]2[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]2)[cH:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_cf0b00c830cc3e7fd156879e",
"reactionHash": "a9c8f07a5bd3cac66adbc2615deaf0a01abf55a4204b69064250768f7922b601"
},
"children": [
{
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"moleculeId": "sa_fc86336e1b262adfba88e57f",
"parentId": "5439",
"isLeaf": true,
"molecule": {
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"inchikey": "BFXHJFKKRGVUMU-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccc(F)cc1"
},
"smiles": "O=S(=O)(Cl)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
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},
{
"id": "5441",
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"moleculeId": "sa_7980e93ced1cb4aca95c4605",
"parentId": "5439",
"isLeaf": false,
"molecule": {
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"inchikey": "WQPXCWXLDFQNEC-UHFFFAOYSA-N",
"smiles": "CNC(C)c1ccc(OCC(=O)OC)c(-c2cccc(C(F)(F)F)c2)c1"
},
"smiles": "CNC(C)c1ccc(OCC(=O)OC)c(-c2cccc(C(F)(F)F)c2)c1",
"reactionStepId": "sa_e681a0eb5b965b8dd2825b15",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0294;1358892\",\"rsmi\":\"O=[C:3]([CH3:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][CH3:24])[cH:25][cH:26]1.[CH3:1][NH2:2]>CCOC(C)=O.CO.Cl.BC#N.[Na+]>[CH3:1][NH:2][CH:3]([CH3:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][CH3:24])[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O=[C:3]([CH3:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][CH3:24])[cH:25][cH:26]1.[CH3:1][NH2:2]>CCOC(C)=O.CO.Cl.BC#N.[Na+]>[CH3:1][NH:2][CH:3]([CH3:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][CH3:24])[cH:25][cH:26]1\"}",
"reactionStep": {
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"reactionHash": "c881a89049ee538d43bd1046e58b74aaddccb36555362d0c2ab94db36435d60f"
},
"children": [
{
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"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "5441",
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"molecule": {
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"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
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},
{
"id": "5443",
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"moleculeId": "sa_ef6eb8b0092b2962934351f6",
"parentId": "5441",
"isLeaf": false,
"molecule": {
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"inchikey": "NYDVOKVHGDJGKO-UHFFFAOYSA-N",
"smiles": "COC(=O)COc1ccc(C(C)=O)cc1-c1cccc(C(F)(F)F)c1"
},
"smiles": "COC(=O)COc1ccc(C(C)=O)cc1-c1cccc(C(F)(F)F)c1",
"reactionStepId": "sa_1f6664a9d92bade0ab91a224",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0292;1358891\",\"rsmi\":\"Br[c:8]1[c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:25][cH:24][c:20]([C:21]([CH3:22])=[O:23])[cH:19]1.OB(O)[c:9]1[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]1>CC(C)(C)O.CCOC(C)=O.O.O=C(O)O.[K+].[K+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([C:21]([CH3:22])=[O:23])[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:25][cH:24][c:20]([C:21]([CH3:22])=[O:23])[cH:19]1.OB(O)[c:9]1[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]1>CC(C)(C)O.CCOC(C)=O.O.O=C(O)O.[K+].[K+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17][cH:18]2)[cH:19][c:20]([C:21]([CH3:22])=[O:23])[cH:24][cH:25]1\"}",
"reactionStep": {
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},
"smiles": "COC(=O)COc1ccc(C(C)=O)cc1Br",
"reactionStepId": "sa_6258f928977402045f6028fd",
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"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0290;1358890\",\"rsmi\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[c:8]([Br:9])[cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8]([Br:9])[cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[c:8]([Br:9])[cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[c:8]([Br:9])[cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16]1\"}",
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{
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{
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"smiles": "COC(=O)CBr"
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{
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},
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}
]
}
]
}
}