Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C=CC(=O)N1CCC[C@@H](Nc2nc(Nc3ccc4c(c3)CCN(C3CC3)CC4)ncc2F)C1
InChiKey
AIPIUSQTVSXHDN-HXUWFJFHSA-N
Route Signature
7ecc85a90958414c9b6597a075a588c6d95257bd3ea96dbd1733b6afe0150c27
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7d786467d50a71c1ecff8c36",
"signature": "7ecc85a90958414c9b6597a075a588c6d95257bd3ea96dbd1733b6afe0150c27",
"contentHash": "fef5f1be2e28c8b614e302acae15c32749b24b730f89a4c1f140234f77354997",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_bd1d3fae33c2c16e44a06a23",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01979",
"moleculeId": "sa_15f9ccab2fab81aeafd0eebe",
"smiles": "C=CC(=O)N1CCC[C@@H](Nc2nc(Nc3ccc4c(c3)CCN(C3CC3)CC4)ncc2F)C1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_15f9ccab2fab81aeafd0eebe",
"inchikey": "AIPIUSQTVSXHDN-HXUWFJFHSA-N",
"smiles": "C=CC(=O)N1CCC[C@@H](Nc2nc(Nc3ccc4c(c3)CCN(C3CC3)CC4)ncc2F)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10551",
"routeId": "sa_7d786467d50a71c1ecff8c36",
"moleculeId": "sa_15f9ccab2fab81aeafd0eebe",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_15f9ccab2fab81aeafd0eebe",
"inchikey": "AIPIUSQTVSXHDN-HXUWFJFHSA-N",
"smiles": "C=CC(=O)N1CCC[C@@H](Nc2nc(Nc3ccc4c(c3)CCN(C3CC3)CC4)ncc2F)C1"
},
"smiles": "C=CC(=O)N1CCC[C@@H](Nc2nc(Nc3ccc4c(c3)CCN(C3CC3)CC4)ncc2F)C1",
"reactionStepId": "sa_9d94cbd8b8934c59a1d02dbb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159774A1;0897;1888649\",\"rsmi\":\"Cl[c:13]1[n:12][c:11]([NH:10][C@@H:9]2[CH2:8][CH2:7][CH2:6][N:5]([C:3]([CH:2]=[CH2:1])=[O:4])[CH2:33]2)[c:31]([F:32])[cH:30][n:29]1.[NH2:14][c:15]1[cH:16][c:17]2[c:18]([cH:19][cH:20]1)[CH2:21][CH2:22][N:23]([CH:24]1[CH2:25][CH2:26]1)[CH2:27][CH2:28]2>CCC(C)(C)O.CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd]>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[n:12][c:13]([NH:14][c:15]3[cH:16][c:17]4[c:18]([cH:19][cH:20]3)[CH2:21][CH2:22][N:23]([CH:24]3[CH2:25][CH2:26]3)[CH2:27][CH2:28]4)[n:29][cH:30][c:31]2[F:32])[CH2:33]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[n:12][c:11]([NH:10][C@@H:9]2[CH2:8][CH2:7][CH2:6][N:5]([C:3]([CH:2]=[CH2:1])=[O:4])[CH2:33]2)[c:31]([F:32])[cH:30][n:29]1.[NH2:14][c:15]1[cH:16][c:17]2[c:18]([cH:19][cH:20]1)[CH2:21][CH2:22][N:23]([CH:24]1[CH2:25][CH2:26]1)[CH2:27][CH2:28]2>CCC(C)(C)O.CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd]>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[n:12][c:13]([NH:14][c:15]3[cH:16][c:17]4[c:18]([cH:19][cH:20]3)[CH2:21][CH2:22][N:23]([CH:24]3[CH2:25][CH2:26]3)[CH2:27][CH2:28]4)[n:29][cH:30][c:31]2[F:32])[CH2:33]1\"}",
"reactionStep": {
"id": "sa_9d94cbd8b8934c59a1d02dbb",
"reactionHash": "15f6e936be02e713df49be4d5823dbcb62a44b78568988437d8f02c375dc8fc7"
},
"children": [
{
"id": "10552",
"routeId": "sa_7d786467d50a71c1ecff8c36",
"moleculeId": "sa_30df782ddd075062e9bf7a3a",
"parentId": "10551",
"isLeaf": false,
"molecule": {
"id": "sa_30df782ddd075062e9bf7a3a",
"inchikey": "PMTHCJJMIHAJTP-MRVPVSSYSA-N",
"smiles": "C=CC(=O)N1CCC[C@@H](Nc2nc(Cl)ncc2F)C1"
},
"smiles": "C=CC(=O)N1CCC[C@@H](Nc2nc(Cl)ncc2F)C1",
"reactionStepId": "sa_7b121ab1d5da1d272a0ca5a9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159774A1;0350;1888513\",\"rsmi\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[F:18])[CH2:19]1>ClCCl.O.O=C(O)O.[K+].[K+]>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[F:18])[CH2:19]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[F:18])[CH2:19]1>ClCCl.O.O=C(O)O.[K+].[K+]>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[F:18])[CH2:19]1\"}",
"reactionStep": {
"id": "sa_7b121ab1d5da1d272a0ca5a9",
"reactionHash": "7cb0d62e4e5eb9505dcecbd681d048647aafd29a64dc37004aeb66f8d6eeb59a"
},
"children": [
{
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"routeId": "sa_7d786467d50a71c1ecff8c36",
"moleculeId": "sa_0b4e45c0d9e46a5808f6bc17",
"parentId": "10552",
"isLeaf": true,
"molecule": {
"id": "sa_0b4e45c0d9e46a5808f6bc17",
"inchikey": "HFBMWMNUJJDEQZ-UHFFFAOYSA-N",
"smiles": "C=CC(=O)Cl"
},
"smiles": "C=CC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10554",
"routeId": "sa_7d786467d50a71c1ecff8c36",
"moleculeId": "sa_be274c10165eeef8ac83a602",
"parentId": "10552",
"isLeaf": false,
"molecule": {
"id": "sa_be274c10165eeef8ac83a602",
"inchikey": "YBYVEMXOALXDFS-ZCFIWIBFSA-N",
"smiles": "Fc1cnc(Cl)nc1N[C@@H]1CCCNC1"
},
"smiles": "Fc1cnc(Cl)nc1N[C@@H]1CCCNC1",
"reactionStepId": "sa_60239f2a9319964cf3f5dd8f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159774A1;0349;1888512\",\"rsmi\":\"CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:9][c:8]2[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]2)[CH2:15]1>ClCCl.O=C(O)C(F)(F)F>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][C@@H:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:9][c:8]2[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]2)[CH2:15]1>ClCCl.O=C(O)C(F)(F)F>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][C@@H:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1\"}",
"reactionStep": {
"id": "sa_60239f2a9319964cf3f5dd8f",
"reactionHash": "d44f82862de0f8511e1391456e255d846de74c84de32508e77cbced43194da23"
},
"children": [
{
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"routeId": "sa_7d786467d50a71c1ecff8c36",
"moleculeId": "sa_5bec0816db2d5bfbc3d657f2",
"parentId": "10554",
"isLeaf": false,
"molecule": {
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"inchikey": "NZXWJKQNVRGUJC-SECBINFHSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nc(Cl)ncc2F)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](Nc2nc(Cl)ncc2F)C1",
"reactionStepId": "sa_5a2485e6c23e57f933ddc942",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159774A1;0347;1888511\",\"rsmi\":\"Cl[c:14]1[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]1[F:21].[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]([NH2:13])[CH2:22]1>CCN(C(C)C)C(C)C.CN1CCCC1=O>[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]([NH:13][c:14]2[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]2[F:21])[CH2:22]1\"},\"mapped_reaction_smiles\":\"Cl[c:14]1[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]1[F:21].[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]([NH2:13])[CH2:22]1>CCN(C(C)C)C(C)C.CN1CCCC1=O>[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]([NH:13][c:14]2[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]2[F:21])[CH2:22]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_08e7e777703c4906eed98980",
"parentId": "10555",
"isLeaf": true,
"molecule": {
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"inchikey": "AKQXKEBCONUWCL-MRVPVSSYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](N)C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC[C@@H](N)C1",
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"metadata": null,
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{
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"molecule": {
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"inchikey": "WHPFEQUEHBULBW-UHFFFAOYSA-N",
"smiles": "Fc1cnc(Cl)nc1Cl"
},
"smiles": "Fc1cnc(Cl)nc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "10558",
"routeId": "sa_7d786467d50a71c1ecff8c36",
"moleculeId": "sa_15034eafc323346f2545c345",
"parentId": "10551",
"isLeaf": false,
"molecule": {
"id": "sa_15034eafc323346f2545c345",
"inchikey": "SOHNDBTVKBBZQE-UHFFFAOYSA-N",
"smiles": "Nc1ccc2c(c1)CCN(C1CC1)CC2"
},
"smiles": "Nc1ccc2c(c1)CCN(C1CC1)CC2",
"reactionStepId": "sa_9accf0c402c3ef22bf9806b0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160159774A1;0894;1888648\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:8][CH2:9][N:10]([CH:11]1[CH2:12][CH2:13]1)[CH2:14][CH2:15]2>CCO.O.Cl.[Fe].N>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:8][CH2:9][N:10]([CH:11]1[CH2:12][CH2:13]1)[CH2:14][CH2:15]2\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:8][CH2:9][N:10]([CH:11]1[CH2:12][CH2:13]1)[CH2:14][CH2:15]2>CCO.O.Cl.[Fe].N>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[CH2:8][CH2:9][N:10]([CH:11]1[CH2:12][CH2:13]1)[CH2:14][CH2:15]2\"}",
"reactionStep": {
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"moleculeId": "sa_6fcd9708b6f52b329ac2127e",
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"smiles": "O=[N+]([O-])c1ccc2c(c1)CCN(C1CC1)CC2"
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"reactionStepId": "sa_fd2c0f4867c2d4fc39fa01ac",
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"metadata": "{\"annotations\":{\"ID\":\"US20160159774A1;0891;1888647\",\"rsmi\":\"CCO[C:13]1(O[Si](C)(C)C)[CH2:14][CH2:15]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][cH:9]1)[CH2:10][CH2:11][NH:12][CH2:16][CH2:17]2>CC(=O)O.CO.O.BC#N.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][cH:9]1)[CH2:10][CH2:11][N:12]([CH:13]1[CH2:14][CH2:15]1)[CH2:16][CH2:17]2\"},\"mapped_reaction_smiles\":\"CCO[C:13]1(O[Si](C)(C)C)[CH2:14][CH2:15]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][cH:9]1)[CH2:10][CH2:11][NH:12][CH2:16][CH2:17]2>CC(=O)O.CO.O.BC#N.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][cH:9]1)[CH2:10][CH2:11][N:12]([CH:13]1[CH2:14][CH2:15]1)[CH2:16][CH2:17]2\"}",
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{
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"smiles": "O=[N+]([O-])c1ccc2c(c1)CCNCC2"
},
"smiles": "O=[N+]([O-])c1ccc2c(c1)CCNCC2",
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]
}
}