Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1
InChiKey
YQGMTFYBYOYNMH-UHFFFAOYSA-N
Route Signature
4e746a491ee6298b0b6acf46343d4102a511a259f1aa4182c81084c1f078f60f
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_69cc1086e46b8cb88cb8f1b8",
"signature": "4e746a491ee6298b0b6acf46343d4102a511a259f1aa4182c81084c1f078f60f",
"contentHash": "13a8bf2d5ef805342f93ac1289ce021d5c1be19f1099819e36e40142e8eff97d",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_d5d03b2e707a76eebf8b76bf",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-03705",
"moleculeId": "sa_76f51797f799c91fa354948c",
"smiles": "CC(=O)Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_76f51797f799c91fa354948c",
"inchikey": "YQGMTFYBYOYNMH-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "7010",
"routeId": "sa_69cc1086e46b8cb88cb8f1b8",
"moleculeId": "sa_76f51797f799c91fa354948c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_76f51797f799c91fa354948c",
"inchikey": "YQGMTFYBYOYNMH-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1"
},
"smiles": "CC(=O)Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1",
"reactionStepId": "sa_64dd9e68406e463975e241a5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100261732A1;0304;957414\",\"rsmi\":\"Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][c:14]3[n:15][nH:16][c:17](=[O:18])[n:19]3[CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30][cH:31]1>c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][c:14]3[n:15][nH:16][c:17](=[O:18])[n:19]3[CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][c:14]3[n:15][nH:16][c:17](=[O:18])[n:19]3[CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30][cH:31]1>c1ccncc1>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][c:14]3[n:15][nH:16][c:17](=[O:18])[n:19]3[CH2:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_64dd9e68406e463975e241a5",
"reactionHash": "9771b239be5b6d697335e0893f6ccd69072968ccd767f156c21ada1e1cd28662"
},
"children": [
{
"id": "7011",
"routeId": "sa_69cc1086e46b8cb88cb8f1b8",
"moleculeId": "sa_9c845b56012760c50fbc6149",
"parentId": "7010",
"isLeaf": false,
"molecule": {
"id": "sa_9c845b56012760c50fbc6149",
"inchikey": "AQMYREDPLLIPCM-UHFFFAOYSA-N",
"smiles": "Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1"
},
"smiles": "Nc1cccc(N2CCN(CCc3n[nH]c(=O)n3CC3CCCCC3)CC2)c1",
"reactionStepId": "sa_24c751e415806fcabefd6ab1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100261732A1;0175;957403\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]3[n:14][nH:15][c:16](=[O:17])[n:18]3[CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:26][CH2:27]2)[cH:28]1>CO.[Pd]>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]3[n:14][nH:15][c:16](=[O:17])[n:18]3[CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:26][CH2:27]2)[cH:28]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]3[n:14][nH:15][c:16](=[O:17])[n:18]3[CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:26][CH2:27]2)[cH:28]1>CO.[Pd]>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][c:13]3[n:14][nH:15][c:16](=[O:17])[n:18]3[CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:26][CH2:27]2)[cH:28]1\"}",
"reactionStep": {
"id": "sa_24c751e415806fcabefd6ab1",
"reactionHash": "cb3ab08729665f1312dd05021d4d9c19898cc0663f366148035882061004a70a"
},
"children": [
{
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"routeId": "sa_69cc1086e46b8cb88cb8f1b8",
"moleculeId": "sa_24340d3ac95db65e74bc9ba7",
"parentId": "7011",
"isLeaf": false,
"molecule": {
"id": "sa_24340d3ac95db65e74bc9ba7",
"inchikey": "MYMSARGMVCVHIC-UHFFFAOYSA-N",
"smiles": "O=c1[nH]nc(CCN2CCN(c3cccc([N+](=O)[O-])c3)CC2)n1CC1CCCCC1"
},
"smiles": "O=c1[nH]nc(CCN2CCN(c3cccc([N+](=O)[O-])c3)CC2)n1CC1CCCCC1",
"reactionStepId": "sa_617ade1d603aec458efd9c3c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100261732A1;0172;957402\",\"rsmi\":\"O=[C:5]([NH:4][NH:3][C:2](=[O:1])[NH:23][CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>Cl.[Na+].O>[O:1]=[c:2]1[nH:3][n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[n:23]1[CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1\"},\"mapped_reaction_smiles\":\"O=[C:5]([NH:4][NH:3][C:2](=[O:1])[NH:23][CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>Cl.[Na+].O>[O:1]=[c:2]1[nH:3][n:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[n:23]1[CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1\"}",
"reactionStep": {
"id": "sa_617ade1d603aec458efd9c3c",
"reactionHash": "9f912711a87d6c9f3f1baa8129d08a62caca6cc9833f2e1f28e9e2d1eb948548"
},
"children": [
{
"id": "7013",
"routeId": "sa_69cc1086e46b8cb88cb8f1b8",
"moleculeId": "sa_498ce2e2f2686be4a1829b32",
"parentId": "7012",
"isLeaf": false,
"molecule": {
"id": "sa_498ce2e2f2686be4a1829b32",
"inchikey": "QVYHBOQVXGUELX-UHFFFAOYSA-N",
"smiles": "O=C(CCN1CCN(c2cccc([N+](=O)[O-])c2)CC1)NNC(=O)NCC1CCCCC1"
},
"smiles": "O=C(CCN1CCN(c2cccc([N+](=O)[O-])c2)CC1)NNC(=O)NCC1CCCCC1",
"reactionStepId": "sa_a7ea4b903490a16f4b94255f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100261732A1;0169;957401\",\"rsmi\":\"[C:22](=[O:23])=[N:24][CH2:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1.[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[NH:20][NH2:21]>Cc1ccccc1>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[NH:20][NH:21][C:22](=[O:23])[NH:24][CH2:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"[C:22](=[O:23])=[N:24][CH2:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1.[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[NH:20][NH2:21]>Cc1ccccc1>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[NH:20][NH:21][C:22](=[O:23])[NH:24][CH2:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1\"}",
"reactionStep": {
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"reactionHash": "69a7a2be7840234e5c123a41e6e845e68d34918119af0ce4da1a59c560ed1694"
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"children": [
{
"id": "7014",
"routeId": "sa_69cc1086e46b8cb88cb8f1b8",
"moleculeId": "sa_c1c90c680ca38c54b9ae2f0a",
"parentId": "7013",
"isLeaf": true,
"molecule": {
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"inchikey": "DUDXQIXWPJMPRQ-UHFFFAOYSA-N",
"smiles": "O=C=NCC1CCCCC1"
},
"smiles": "O=C=NCC1CCCCC1",
"reactionStepId": null,
"template": null,
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{
"id": "7015",
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"parentId": "7013",
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"molecule": {
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"inchikey": "WIVWDZOBBFHYSR-UHFFFAOYSA-N",
"smiles": "NNC(=O)CCN1CCN(c2cccc([N+](=O)[O-])c2)CC1"
},
"smiles": "NNC(=O)CCN1CCN(c2cccc([N+](=O)[O-])c2)CC1",
"reactionStepId": "sa_d60dc419ef134bbe0ee5d4da",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100261732A1;0166;957400\",\"rsmi\":\"CCO[C:3](=[O:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1.[NH2:1][NH2:2]>CCO.O>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1\"},\"mapped_reaction_smiles\":\"CCO[C:3](=[O:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1.[NH2:1][NH2:2]>CCO.O>[NH2:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1\"}",
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"children": [
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"smiles": "CCOC(=O)CCN1CCN(c2cccc([N+](=O)[O-])c2)CC1"
},
"smiles": "CCOC(=O)CCN1CCN(c2cccc([N+](=O)[O-])c2)CC1",
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"metadata": "{\"annotations\":{\"ID\":\"US20100261732A1;0163;957399\",\"rsmi\":\"Br[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>CC#N.Cl.O=C(O)O.I.[K+].[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"Br[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>CC#N.Cl.O=C(O)O.I.[K+].[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1\"}",
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"smiles": "CCOC(=O)CCBr"
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"smiles": "CCOC(=O)CCBr",
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{
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"smiles": "O=[N+]([O-])c1cccc(N2CCNCC2)c1",
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{
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"smiles": "NN"
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}
]
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}
]
},
{
"id": "7020",
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"parentId": "7010",
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"molecule": {
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"smiles": "CC(=O)Cl"
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"smiles": "CC(=O)Cl",
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}
]
}
}