Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)Oc1ccc(C[C@H](NC(=O)c2ccc3c(N4CCN(C)CC4)nc(N)nc3c2)C(=O)N(C)C)cc1
InChiKey
AOLLKZPYTAQTKW-DEOSSOPVSA-N
Route Signature
d5bac69e288a9dc2be97681521260373ca7384deb06489e6303de59b2e96234f
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_0770447fe0eb435753835726",
"signature": "d5bac69e288a9dc2be97681521260373ca7384deb06489e6303de59b2e96234f",
"contentHash": "0da5573d93c29ef6f8190fabd3ad56763c8759b53f05543b295487ec1c842072",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_f5955abe60eb949ff0e8c77b",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00682",
"moleculeId": "sa_5125bca701edaf1c6259cfaf",
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)c2ccc3c(N4CCN(C)CC4)nc(N)nc3c2)C(=O)N(C)C)cc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5125bca701edaf1c6259cfaf",
"inchikey": "AOLLKZPYTAQTKW-DEOSSOPVSA-N",
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)c2ccc3c(N4CCN(C)CC4)nc(N)nc3c2)C(=O)N(C)C)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9662",
"routeId": "sa_0770447fe0eb435753835726",
"moleculeId": "sa_5125bca701edaf1c6259cfaf",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5125bca701edaf1c6259cfaf",
"inchikey": "AOLLKZPYTAQTKW-DEOSSOPVSA-N",
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)c2ccc3c(N4CCN(C)CC4)nc(N)nc3c2)C(=O)N(C)C)cc1"
},
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)c2ccc3c(N4CCN(C)CC4)nc(N)nc3c2)C(=O)N(C)C)cc1",
"reactionStepId": "sa_5c3b84e9a0f035ef78860761",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130296327A1;1043;1446389\",\"rsmi\":\"O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]2[c:18]([cH:19]1)[n:20][c:21]([NH2:22])[n:23][c:24]2[N:25]1[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]1.[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH2:11])[C:32](=[O:33])[N:34]([CH3:35])[CH3:36])[cH:37][cH:38]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[n:20][c:21]([NH2:22])[n:23][c:24]3[N:25]2[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]2)[C:32](=[O:33])[N:34]([CH3:35])[CH3:36])[cH:37][cH:38]1\"},\"mapped_reaction_smiles\":\"O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]2[c:18]([cH:19]1)[n:20][c:21]([NH2:22])[n:23][c:24]2[N:25]1[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]1.[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH2:11])[C:32](=[O:33])[N:34]([CH3:35])[CH3:36])[cH:37][cH:38]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[n:20][c:21]([NH2:22])[n:23][c:24]3[N:25]2[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]2)[C:32](=[O:33])[N:34]([CH3:35])[CH3:36])[cH:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_5c3b84e9a0f035ef78860761",
"reactionHash": "0d42ca0171d8adc3d5e8e4b30d779b5b0156a9d022a566aebaf7995b390695df"
},
"children": [
{
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"routeId": "sa_0770447fe0eb435753835726",
"moleculeId": "sa_d19ba483c61e79ea6e555385",
"parentId": "9662",
"isLeaf": false,
"molecule": {
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"inchikey": "QFVGDWJDMSUJSO-ZDUSSCGKSA-N",
"smiles": "CC(C)Oc1ccc(C[C@H](N)C(=O)N(C)C)cc1"
},
"smiles": "CC(C)Oc1ccc(C[C@H](N)C(=O)N(C)C)cc1",
"reactionStepId": "sa_8205fd7486175dbd778fcc57",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130296327A1;1042;1446388\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:11][C@@H:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:18][cH:17]1)[C:12](=[O:13])[N:14]([CH3:15])[CH3:16]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH2:11])[C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:11][C@@H:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:18][cH:17]1)[C:12](=[O:13])[N:14]([CH3:15])[CH3:16]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH2:11])[C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_8205fd7486175dbd778fcc57",
"reactionHash": "2d2459077241607fcb34dd593637c5ad0a361dad2e83115925388a9a4d16c8e6"
},
"children": [
{
"id": "9664",
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"moleculeId": "sa_8456e72e0f17594c43fb897f",
"parentId": "9663",
"isLeaf": false,
"molecule": {
"id": "sa_8456e72e0f17594c43fb897f",
"inchikey": "WWWLFAMMNRYEAM-INIZCTEOSA-N",
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)N(C)C)cc1"
},
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)N(C)C)cc1",
"reactionStepId": "sa_bfc24399e7f5db0feed947d4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130296327A1;1040;1446387\",\"rsmi\":\"O[C:19]([C@H:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:25][cH:24]1)[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:20].[NH:21]([CH3:22])[CH3:23]>C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[N:21]([CH3:22])[CH3:23])[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"O[C:19]([C@H:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:25][cH:24]1)[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:20].[NH:21]([CH3:22])[CH3:23]>C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[N:21]([CH3:22])[CH3:23])[cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_bfc24399e7f5db0feed947d4",
"reactionHash": "f1eea8aa3d3dcbd029decea25194755bfb413090ab5a30ba840614fc521c43aa"
},
"children": [
{
"id": "9665",
"routeId": "sa_0770447fe0eb435753835726",
"moleculeId": "sa_e2676e5c7c9d7a020ed1780e",
"parentId": "9664",
"isLeaf": true,
"molecule": {
"id": "sa_e2676e5c7c9d7a020ed1780e",
"inchikey": "ROSDSFDQCJNGOL-UHFFFAOYSA-N",
"smiles": "CNC"
},
"smiles": "CNC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9666",
"routeId": "sa_0770447fe0eb435753835726",
"moleculeId": "sa_859e333dcddedb2a499a4e50",
"parentId": "9664",
"isLeaf": false,
"molecule": {
"id": "sa_859e333dcddedb2a499a4e50",
"inchikey": "XEKGNAQORBPDEJ-AWEZNQCLSA-N",
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)O)cc1"
},
"smiles": "CC(C)Oc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)O)cc1",
"reactionStepId": "sa_61cc15a58e4096f129b734ee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130296327A1;1038;1446386\",\"rsmi\":\"C[O:21][C:19]([C@H:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:23][cH:22]1)[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:20]>CO.O.[Li+].O>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[OH:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"C[O:21][C:19]([C@H:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:23][cH:22]1)[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:20]>CO.O.[Li+].O>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[OH:21])[cH:22][cH:23]1\"}",
"reactionStep": {
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"reactionHash": "2b35581a0e9fd22780d744590660fa5f7b974d25941b1fe8d5d219f3ffc6274f"
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"children": [
{
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"moleculeId": "sa_911842f01def2f03000e3aaf",
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"isLeaf": false,
"molecule": {
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"inchikey": "AHIJVAOXFJEFGI-HNNXBMFYSA-N",
"smiles": "COC(=O)[C@H](Cc1ccc(OC(C)C)cc1)NC(=O)OC(C)(C)C"
},
"smiles": "COC(=O)[C@H](Cc1ccc(OC(C)C)cc1)NC(=O)OC(C)(C)C",
"reactionStepId": "sa_e980b3f2a59efbe2df13371d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130296327A1;1024;1446380\",\"rsmi\":\"I[CH:12]([CH3:13])[CH3:14].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]\"},\"mapped_reaction_smiles\":\"I[CH:12]([CH3:13])[CH3:14].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1)[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24]\"}",
"reactionStep": {
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"molecule": {
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"inchikey": "FMKOJHQHASLBPH-UHFFFAOYSA-N",
"smiles": "CC(C)I"
},
"smiles": "CC(C)I",
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{
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"smiles": "COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C"
},
"smiles": "COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C",
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}
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}
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},
{
"id": "9670",
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"moleculeId": "sa_54c3ba6a96188e4156bb2f8e",
"parentId": "9662",
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"molecule": {
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"smiles": "CN1CCN(c2nc(N)nc3cc(C(=O)O)ccc23)CC1"
},
"smiles": "CN1CCN(c2nc(N)nc3cc(C(=O)O)ccc23)CC1",
"reactionStepId": "sa_3aa8aa39e396ea4d2469ffaf",
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},
"smiles": "COC(=O)c1ccc2c(N3CCN(C)CC3)nc(N)nc2c1",
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}
]
}
]
}
}