Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C([C@@H]1CCCN(c2ccc3nc(C4(c5cccnc5)CC4)[nH]c3n2)C1)N1CCCC1
InChiKey
FEKUNHHIZBHAIU-QGZVFWFLSA-N
Route Signature
517ca58cb4c264ca42f9a1353287bde049cadfd9c21b3a295b9ab9645b9e2c6e
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_1fb10758d661e57efb228927",
"signature": "517ca58cb4c264ca42f9a1353287bde049cadfd9c21b3a295b9ab9645b9e2c6e",
"contentHash": "8af681401765f21d54e35773e1642268fb66c0dd57141ffd5ae197a6e30e0b30",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_ddc76f8409773695b5e4bf12",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00804",
"moleculeId": "sa_76e34f10263857904127a98d",
"smiles": "O=C([C@@H]1CCCN(c2ccc3nc(C4(c5cccnc5)CC4)[nH]c3n2)C1)N1CCCC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_76e34f10263857904127a98d",
"inchikey": "FEKUNHHIZBHAIU-QGZVFWFLSA-N",
"smiles": "O=C([C@@H]1CCCN(c2ccc3nc(C4(c5cccnc5)CC4)[nH]c3n2)C1)N1CCCC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13801",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_76e34f10263857904127a98d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_76e34f10263857904127a98d",
"inchikey": "FEKUNHHIZBHAIU-QGZVFWFLSA-N",
"smiles": "O=C([C@@H]1CCCN(c2ccc3nc(C4(c5cccnc5)CC4)[nH]c3n2)C1)N1CCCC1"
},
"smiles": "O=C([C@@H]1CCCN(c2ccc3nc(C4(c5cccnc5)CC4)[nH]c3n2)C1)N1CCCC1",
"reactionStepId": "sa_02c3de140bb79cb7bb967d94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150087585A1;0445;1669317\",\"rsmi\":\"O=[C:13]([NH:12][c:11]1[cH:10][cH:9][c:8]([N:7]2[CH2:6][CH2:5][CH2:4][C@@H:3]([C:2](=[O:1])[N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:26]2)[n:25][c:24]1[NH2:23])[C:14]1([c:15]2[cH:16][cH:17][cH:18][n:19][cH:20]2)[CH2:21][CH2:22]1>CC(C)CO.CO.CO.[Na+]>[O:1]=[C:2]([C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]3[n:12][c:13]([C:14]4([c:15]5[cH:16][cH:17][cH:18][n:19][cH:20]5)[CH2:21][CH2:22]4)[nH:23][c:24]3[n:25]2)[CH2:26]1)[N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1\"},\"mapped_reaction_smiles\":\"O=[C:13]([NH:12][c:11]1[cH:10][cH:9][c:8]([N:7]2[CH2:6][CH2:5][CH2:4][C@@H:3]([C:2](=[O:1])[N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:26]2)[n:25][c:24]1[NH2:23])[C:14]1([c:15]2[cH:16][cH:17][cH:18][n:19][cH:20]2)[CH2:21][CH2:22]1>CC(C)CO.CO.CO.[Na+]>[O:1]=[C:2]([C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]3[n:12][c:13]([C:14]4([c:15]5[cH:16][cH:17][cH:18][n:19][cH:20]5)[CH2:21][CH2:22]4)[nH:23][c:24]3[n:25]2)[CH2:26]1)[N:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1\"}",
"reactionStep": {
"id": "sa_02c3de140bb79cb7bb967d94",
"reactionHash": "cadb9a7abadce83b35ca144d5aea8c504ebdb0981b42bfaaa6392e923cc89705"
},
"children": [
{
"id": "13802",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_fb50389860b65820890f7cd0",
"parentId": "13801",
"isLeaf": false,
"molecule": {
"id": "sa_fb50389860b65820890f7cd0",
"inchikey": "CQGNALBWPPSVBH-QGZVFWFLSA-N",
"smiles": "Nc1nc(N2CCC[C@@H](C(=O)N3CCCC3)C2)ccc1NC(=O)C1(c2cccnc2)CC1"
},
"smiles": "Nc1nc(N2CCC[C@@H](C(=O)N3CCCC3)C2)ccc1NC(=O)C1(c2cccnc2)CC1",
"reactionStepId": "sa_d2b6a6113c60ba522a90d4e2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150087585A1;0444;1669316\",\"rsmi\":\"O[C:22](=[O:23])[C:24]1([c:25]2[cH:26][cH:27][cH:28][n:29][cH:30]2)[CH2:31][CH2:32]1.[NH2:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][C@@H:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17]2)[cH:18][cH:19][c:20]1[NH2:21]>CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CN1CCOCC1.Cl.Cl.F[PH](F)(F)(F)(F)F>[NH2:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][C@@H:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17]2)[cH:18][cH:19][c:20]1[NH:21][C:22](=[O:23])[C:24]1([c:25]2[cH:26][cH:27][cH:28][n:29][cH:30]2)[CH2:31][CH2:32]1\"},\"mapped_reaction_smiles\":\"O[C:22](=[O:23])[C:24]1([c:25]2[cH:26][cH:27][cH:28][n:29][cH:30]2)[CH2:31][CH2:32]1.[NH2:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][C@@H:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17]2)[cH:18][cH:19][c:20]1[NH2:21]>CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CN1CCOCC1.Cl.Cl.F[PH](F)(F)(F)(F)F>[NH2:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][C@@H:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17]2)[cH:18][cH:19][c:20]1[NH:21][C:22](=[O:23])[C:24]1([c:25]2[cH:26][cH:27][cH:28][n:29][cH:30]2)[CH2:31][CH2:32]1\"}",
"reactionStep": {
"id": "sa_d2b6a6113c60ba522a90d4e2",
"reactionHash": "b62a9c570899d736adf3e0c8e26b79e70368bd5f53879f22d4aae4097195fbf0"
},
"children": [
{
"id": "13803",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_a1911b7f5442d2d639a5db2f",
"parentId": "13802",
"isLeaf": true,
"molecule": {
"id": "sa_a1911b7f5442d2d639a5db2f",
"inchikey": "HYEMICHUSHXQTM-UHFFFAOYSA-N",
"smiles": "O=C(O)C1(c2cccnc2)CC1"
},
"smiles": "O=C(O)C1(c2cccnc2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13804",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_ae27eae300d86b45c61bc449",
"parentId": "13802",
"isLeaf": false,
"molecule": {
"id": "sa_ae27eae300d86b45c61bc449",
"inchikey": "VIBVCSCSEMUUIO-LLVKDONJSA-N",
"smiles": "Nc1ccc(N2CCC[C@@H](C(=O)N3CCCC3)C2)nc1N"
},
"smiles": "Nc1ccc(N2CCC[C@@H](C(=O)N3CCCC3)C2)nc1N",
"reactionStepId": "sa_2352507a982b1d85cba24362",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150087585A1;0244;1669169\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[c:3]([NH2:4])[n:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:19]2)[cH:20][cH:21]1>CCO.[H][H].[Pd]>[NH2:1][c:2]1[c:3]([NH2:4])[n:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[c:3]([NH2:4])[n:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:19]2)[cH:20][cH:21]1>CCO.[H][H].[Pd]>[NH2:1][c:2]1[c:3]([NH2:4])[n:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_2352507a982b1d85cba24362",
"reactionHash": "2b9a48b4ca4bf49fd7d27d42c9c7d878e2510e54883714cd0877580f3073e8de"
},
"children": [
{
"id": "13805",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_e592fc5a7219865080dc4b0e",
"parentId": "13804",
"isLeaf": false,
"molecule": {
"id": "sa_e592fc5a7219865080dc4b0e",
"inchikey": "SLWPKGZOBHTHEY-LLVKDONJSA-N",
"smiles": "Nc1nc(N2CCC[C@@H](C(=O)N3CCCC3)C2)ccc1[N+](=O)[O-]"
},
"smiles": "Nc1nc(N2CCC[C@@H](C(=O)N3CCCC3)C2)ccc1[N+](=O)[O-]",
"reactionStepId": "sa_0175b62fe8ae9fe69cccfb99",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150087585A1;0242;1669167\",\"rsmi\":\"Cl[c:9]1[cH:8][cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([NH2:1])[n:23]1.[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22]1>CC#N.CCN(CC)CC.Cl>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][C@@H:14]([C:15](=[O:16])[N:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:22]2)[n:23]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[cH:8][cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([NH2:1])[n:23]1.[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22]1>CC#N.CCN(CC)CC.Cl>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH2:13][C@@H:14]([C:15](=[O:16])[N:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:22]2)[n:23]1\"}",
"reactionStep": {
"id": "sa_0175b62fe8ae9fe69cccfb99",
"reactionHash": "e8600acfde429c126de2e1cdf17e4b598b534ed274ab48789610fd9121996a52"
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"children": [
{
"id": "13806",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_069233949cbe790a8fa90d53",
"parentId": "13805",
"isLeaf": false,
"molecule": {
"id": "sa_069233949cbe790a8fa90d53",
"inchikey": "AMOUVOLDCHVMBJ-SECBINFHSA-N",
"smiles": "O=C([C@@H]1CCCNC1)N1CCCC1"
},
"smiles": "O=C([C@@H]1CCCNC1)N1CCCC1",
"reactionStepId": "sa_7e6269ef8bb971bb32ed8e0d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150087585A1;0396;1669295\",\"rsmi\":\"CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:2](=[O:1])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8]1>C1COCCO1.CO.Cl>[O:1]=[C:2]([C@@H:3]1[CH2:4][CH2:5][CH2:6][NH:7][CH2:8]1)[N:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:2](=[O:1])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8]1>C1COCCO1.CO.Cl>[O:1]=[C:2]([C@@H:3]1[CH2:4][CH2:5][CH2:6][NH:7][CH2:8]1)[N:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1\"}",
"reactionStep": {
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"reactionHash": "458fd55db85070830c44492866a9ccf1325788831af7fc5b1828be6947b21d21"
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"children": [
{
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"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_93dbdfcf5cdeba4e105e7cc4",
"parentId": "13806",
"isLeaf": false,
"molecule": {
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"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](C(=O)N2CCCC2)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](C(=O)N2CCCC2)C1",
"reactionStepId": "sa_a6aaceadcf75b382f0ed2727",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150087585A1;0240;1669165\",\"rsmi\":\"O[C:13]([C@@H:12]1[CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20]1)=[O:14].[NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1>C1CCOC1.O=C(n1ccnc1)n1ccnc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13](=[O:14])[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20]1\"},\"mapped_reaction_smiles\":\"O[C:13]([C@@H:12]1[CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20]1)=[O:14].[NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1>C1CCOC1.O=C(n1ccnc1)n1ccnc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13](=[O:14])[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:20]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_015ed24be958c9cd9ba41906",
"parentId": "13807",
"isLeaf": true,
"molecule": {
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"inchikey": "NXILIHONWRXHFA-MRVPVSSYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](C(=O)O)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](C(=O)O)C1",
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{
"id": "13809",
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"molecule": {
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"inchikey": "RWRDLPDLKQPQOW-UHFFFAOYSA-N",
"smiles": "C1CCNC1"
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"smiles": "C1CCNC1",
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}
]
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]
},
{
"id": "13810",
"routeId": "sa_1fb10758d661e57efb228927",
"moleculeId": "sa_c2333972b1bca1d858b0feda",
"parentId": "13805",
"isLeaf": true,
"molecule": {
"id": "sa_c2333972b1bca1d858b0feda",
"inchikey": "WERABQRUGJIMKQ-UHFFFAOYSA-N",
"smiles": "Nc1nc(Cl)ccc1[N+](=O)[O-]"
},
"smiles": "Nc1nc(Cl)ccc1[N+](=O)[O-]",
"reactionStepId": null,
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"children": []
}
]
}
]
}
]
}
]
}
}