Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(Cn3ccc4cc(F)ccc43)cc2)CC1
InChiKey
ZTFXALROPRRCAV-UHFFFAOYSA-N
Route Signature
2b8b8fbe93e6a4cd10fd91e8c571409e2a86f3e32da99f90de43db3ddeaa2717
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ed58035257019414599e9b02",
"signature": "2b8b8fbe93e6a4cd10fd91e8c571409e2a86f3e32da99f90de43db3ddeaa2717",
"contentHash": "5976a7887649f6988c1bdab1561587e4b64ca0ddafc8d5523dbb05140503d8d9",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_260863e61a62ad33b3ecf7c6",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-02156",
"moleculeId": "sa_fe718d9cf452c0f1f81e5cfb",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(Cn3ccc4cc(F)ccc43)cc2)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_fe718d9cf452c0f1f81e5cfb",
"inchikey": "ZTFXALROPRRCAV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(Cn3ccc4cc(F)ccc43)cc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "6199",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_fe718d9cf452c0f1f81e5cfb",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fe718d9cf452c0f1f81e5cfb",
"inchikey": "ZTFXALROPRRCAV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(Cn3ccc4cc(F)ccc43)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(Cn3ccc4cc(F)ccc43)cc2)CC1",
"reactionStepId": "sa_e207a4a35de941c440779fbd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040229874A1;0342;204604\",\"rsmi\":\"CS(=O)(=O)O[CH2:18][c:17]1[cH:16][cH:15][c:14](-[c:13]2[c:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:35]3)[cH:34][cH:33][cH:32][cH:31]2)[cH:30][cH:29]1.[nH:19]1[cH:20][cH:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]12>CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccccc1.O.O=C(O)O.O=S(=O)(O)O.[Na+].[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][n:19]4[cH:20][cH:21][c:22]5[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]45)[cH:29][cH:30]3)[cH:31][cH:32][cH:33][cH:34]2)[CH2:35][CH2:36]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:18][c:17]1[cH:16][cH:15][c:14](-[c:13]2[c:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:35]3)[cH:34][cH:33][cH:32][cH:31]2)[cH:30][cH:29]1.[nH:19]1[cH:20][cH:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]12>CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccccc1.O.O=C(O)O.O=S(=O)(O)O.[Na+].[Na+].O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][n:19]4[cH:20][cH:21][c:22]5[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]45)[cH:29][cH:30]3)[cH:31][cH:32][cH:33][cH:34]2)[CH2:35][CH2:36]1\"}",
"reactionStep": {
"id": "sa_e207a4a35de941c440779fbd",
"reactionHash": "30b07dadc16d8cef72c363ac96c7d25d40d50080e177adfba02cb36ef56e5125"
},
"children": [
{
"id": "6200",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_91d9d6ac6daa35e946b401f2",
"parentId": "6199",
"isLeaf": false,
"molecule": {
"id": "sa_91d9d6ac6daa35e946b401f2",
"inchikey": "HMNWDKVIQXZOAF-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(COS(C)(=O)=O)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(COS(C)(=O)=O)cc2)CC1",
"reactionStepId": "sa_72e54d0a98ffd801f2b3259c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040229874A1;0339;204603\",\"rsmi\":\"Cl[S:20]([CH3:21])(=[O:22])=[O:23].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:24][cH:25]3)[cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][O:19][S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]3)[cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"Cl[S:20]([CH3:21])(=[O:22])=[O:23].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:24][cH:25]3)[cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][O:19][S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25]3)[cH:26][cH:27][cH:28][cH:29]2)[CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_72e54d0a98ffd801f2b3259c",
"reactionHash": "248b6f11e2f689d13689890806aa92744f6deddef0a3c66fe0f8e4420c1a2c36"
},
"children": [
{
"id": "6201",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "6200",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6202",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_3013605c837a21ef2c6bace0",
"parentId": "6200",
"isLeaf": false,
"molecule": {
"id": "sa_3013605c837a21ef2c6bace0",
"inchikey": "QUSSCMCGBOXWBW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(CO)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(CO)cc2)CC1",
"reactionStepId": "sa_c14d6e0c29529f6d8bd3fd9d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040229874A1;0333;204602\",\"rsmi\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]3)[cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]3)[cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]3)[cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]3)[cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_c14d6e0c29529f6d8bd3fd9d",
"reactionHash": "8e7a08d17329b995e9056031bec2de74880fdecba584e5084f1559bf1dc21c68"
},
"children": [
{
"id": "6203",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_14fd3651e5591e3d8df820d2",
"parentId": "6202",
"isLeaf": false,
"molecule": {
"id": "sa_14fd3651e5591e3d8df820d2",
"inchikey": "IVPNMOJQSWDRDY-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(C=O)cc2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2-c2ccc(C=O)cc2)CC1",
"reactionStepId": "sa_4bf9444b7ad317a76b5cb4c5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040229874A1;0328;204601\",\"rsmi\":\"Br[c:13]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH2:26]2)[cH:25][cH:24][cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1>O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]3)[cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH2:26]2)[cH:25][cH:24][cH:23][cH:22]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1>O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]3)[cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1\"}",
"reactionStep": {
"id": "sa_4bf9444b7ad317a76b5cb4c5",
"reactionHash": "028ca9e90ef7b3f561ff19956c3413d199296c076cb74406bc119abe10325a0d"
},
"children": [
{
"id": "6204",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_fa1143412aac2808dece64ba",
"parentId": "6203",
"isLeaf": false,
"molecule": {
"id": "sa_fa1143412aac2808dece64ba",
"inchikey": "QEKMJBDSLYRIKY-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2Br)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCN(c2ccccc2Br)CC1",
"reactionStepId": "sa_8455e2390a4a35dc79f6e8ae",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040229874A1;0322;204600\",\"rsmi\":\"Br[c:12]1[c:13]([Br:14])[cH:15][cH:16][cH:17][cH:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:19][CH2:20]1>CC(=O)O.CC(=O)O.CC(C)(C)O.Cc1ccccc1.O.[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13]([Br:14])[cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[c:13]([Br:14])[cH:15][cH:16][cH:17][cH:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:19][CH2:20]1>CC(=O)O.CC(=O)O.CC(C)(C)O.Cc1ccccc1.O.[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[c:13]([Br:14])[cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1\"}",
"reactionStep": {
"id": "sa_8455e2390a4a35dc79f6e8ae",
"reactionHash": "b194bfd527cdf4999c70e1f20bb88c3557abc709dc2d3aa69a24c02300fa4848"
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"children": [
{
"id": "6205",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_04c50a88932aa2c9d9b979b4",
"parentId": "6204",
"isLeaf": true,
"molecule": {
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"inchikey": "CWXPZXBSDSIRCS-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCNCC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "6206",
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"moleculeId": "sa_89d6d74076ce4c4222585ec0",
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"molecule": {
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"inchikey": "WQONPSCCEXUXTQ-UHFFFAOYSA-N",
"smiles": "Brc1ccccc1Br"
},
"smiles": "Brc1ccccc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "6207",
"routeId": "sa_ed58035257019414599e9b02",
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"molecule": {
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"inchikey": "VXWBQOJISHAKKM-UHFFFAOYSA-N",
"smiles": "O=Cc1ccc(B(O)O)cc1"
},
"smiles": "O=Cc1ccc(B(O)O)cc1",
"reactionStepId": null,
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}
]
}
]
}
]
},
{
"id": "6208",
"routeId": "sa_ed58035257019414599e9b02",
"moleculeId": "sa_070c5b10b6a69ad81dce97ba",
"parentId": "6199",
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"molecule": {
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"inchikey": "ODFFPRGJZRXNHZ-UHFFFAOYSA-N",
"smiles": "Fc1ccc2[nH]ccc2c1"
},
"smiles": "Fc1ccc2[nH]ccc2c1",
"reactionStepId": null,
"template": null,
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"children": []
}
]
}
}