Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(N2CCCC(CO)C2)cc1C(=O)Nc1c(C)ccc(C(=O)O)c1C
InChiKey
LGVRQIKHFHBPSK-UHFFFAOYSA-N
Route Signature
11085dd63d6775b2dd6f82242d487ada7a25b89a8412162c4c7f01f691c89774
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7fcf36d3794d501f2ae93639",
"signature": "11085dd63d6775b2dd6f82242d487ada7a25b89a8412162c4c7f01f691c89774",
"contentHash": "5688ff482ced86ef046a52446a0493991eb684b10103e8b18bebe916b6450b35",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_7e054a09fcd13f4380bc3f16",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00203",
"moleculeId": "sa_0803ec4a915dfcdf0f7776d6",
"smiles": "Cc1ccc(N2CCCC(CO)C2)cc1C(=O)Nc1c(C)ccc(C(=O)O)c1C",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_0803ec4a915dfcdf0f7776d6",
"inchikey": "LGVRQIKHFHBPSK-UHFFFAOYSA-N",
"smiles": "Cc1ccc(N2CCCC(CO)C2)cc1C(=O)Nc1c(C)ccc(C(=O)O)c1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9242",
"routeId": "sa_7fcf36d3794d501f2ae93639",
"moleculeId": "sa_0803ec4a915dfcdf0f7776d6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0803ec4a915dfcdf0f7776d6",
"inchikey": "LGVRQIKHFHBPSK-UHFFFAOYSA-N",
"smiles": "Cc1ccc(N2CCCC(CO)C2)cc1C(=O)Nc1c(C)ccc(C(=O)O)c1C"
},
"smiles": "Cc1ccc(N2CCCC(CO)C2)cc1C(=O)Nc1c(C)ccc(C(=O)O)c1C",
"reactionStepId": "sa_75b991f33b48ce66ea2a0a62",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140094491A1;0126;1510496\",\"rsmi\":\"C[O:15][C:13]([c:12]1[cH:11][cH:10][c:8]([CH3:9])[c:7]([NH:6][C:4]([c:3]2[c:2]([CH3:1])[cH:29][cH:28][c:19]([N:20]3[CH2:21][CH2:22][CH2:23][CH:24]([CH2:25][OH:26])[CH2:27]3)[cH:18]2)=[O:5])[c:16]1[CH3:17])=[O:14]>C1CCOC1.CO.[Na+].O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][c:7]2[c:8]([CH3:9])[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]2[CH3:17])[cH:18][c:19]([N:20]2[CH2:21][CH2:22][CH2:23][CH:24]([CH2:25][OH:26])[CH2:27]2)[cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"C[O:15][C:13]([c:12]1[cH:11][cH:10][c:8]([CH3:9])[c:7]([NH:6][C:4]([c:3]2[c:2]([CH3:1])[cH:29][cH:28][c:19]([N:20]3[CH2:21][CH2:22][CH2:23][CH:24]([CH2:25][OH:26])[CH2:27]3)[cH:18]2)=[O:5])[c:16]1[CH3:17])=[O:14]>C1CCOC1.CO.[Na+].O>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][c:7]2[c:8]([CH3:9])[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[c:16]2[CH3:17])[cH:18][c:19]([N:20]2[CH2:21][CH2:22][CH2:23][CH:24]([CH2:25][OH:26])[CH2:27]2)[cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_75b991f33b48ce66ea2a0a62",
"reactionHash": "26d07203cf4af8771c6a172d357d9cc94aabfe3030707781dca61d40c452bb76"
},
"children": [
{
"id": "9243",
"routeId": "sa_7fcf36d3794d501f2ae93639",
"moleculeId": "sa_cab6e747ecee5c96eb74fef8",
"parentId": "9242",
"isLeaf": false,
"molecule": {
"id": "sa_cab6e747ecee5c96eb74fef8",
"inchikey": "WITRDJAYJGTMMC-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C)c(NC(=O)c2cc(N3CCCC(CO)C3)ccc2C)c1C"
},
"smiles": "COC(=O)c1ccc(C)c(NC(=O)c2cc(N3CCCC(CO)C3)ccc2C)c1C",
"reactionStepId": "sa_b0787e994fc216cee345e6a3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140094491A1;0123;1510495\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:24][CH2:23][CH:22]1[CH2:21][CH2:20][CH2:19][N:18]([c:17]2[cH:16][cH:15][c:13]([CH3:14])[c:12]([C:10]([NH:9][c:8]3[c:6]([CH3:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29][c:27]3[CH3:28])=[O:11])[cH:26]2)[CH2:25]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[c:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][OH:24])[CH2:25]3)[cH:26]2)[c:27]([CH3:28])[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:24][CH2:23][CH:22]1[CH2:21][CH2:20][CH2:19][N:18]([c:17]2[cH:16][cH:15][c:13]([CH3:14])[c:12]([C:10]([NH:9][c:8]3[c:6]([CH3:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29][c:27]3[CH3:28])=[O:11])[cH:26]2)[CH2:25]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.F>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[c:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][OH:24])[CH2:25]3)[cH:26]2)[c:27]([CH3:28])[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_b0787e994fc216cee345e6a3",
"reactionHash": "2dba33c138e3d8ad6c2619ab03b0041da29c648b79afb14a3612640768e1af8a"
},
"children": [
{
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"routeId": "sa_7fcf36d3794d501f2ae93639",
"moleculeId": "sa_1685a9e87812449d1e25c322",
"parentId": "9243",
"isLeaf": false,
"molecule": {
"id": "sa_1685a9e87812449d1e25c322",
"inchikey": "PCJARQBUUGUZDA-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C)c(NC(=O)c2cc(N3CCCC(CO[Si](C)(C)C(C)(C)C)C3)ccc2C)c1C"
},
"smiles": "COC(=O)c1ccc(C)c(NC(=O)c2cc(N3CCCC(CO[Si](C)(C)C(C)(C)C)C3)ccc2C)c1C",
"reactionStepId": "sa_0c8776e241679ad07ddba9a7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140094491A1;0120;1510494\",\"rsmi\":\"Br[c:17]1[cH:16][cH:15][c:13]([CH3:14])[c:12]([C:10]([NH:9][c:8]2[c:6]([CH3:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:37][cH:36][c:34]2[CH3:35])=[O:11])[cH:33]1.[NH:18]1[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]1>C1COCCO1.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[c:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]3)[cH:33]2)[c:34]([CH3:35])[cH:36][cH:37]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[cH:16][cH:15][c:13]([CH3:14])[c:12]([C:10]([NH:9][c:8]2[c:6]([CH3:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:37][cH:36][c:34]2[CH3:35])=[O:11])[cH:33]1.[NH:18]1[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]1>C1COCCO1.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[c:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]3)[cH:33]2)[c:34]([CH3:35])[cH:36][cH:37]1\"}",
"reactionStep": {
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"reactionHash": "4b943bb96705b18dbba57ea3842728393e460fb5ad4b57f1b383c3bc7449fe58"
},
"children": [
{
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"moleculeId": "sa_50bbf63152a4cb860eb2a8d9",
"parentId": "9244",
"isLeaf": false,
"molecule": {
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"inchikey": "LGRNCIPHZAOULB-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCC1CCCNC1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCC1CCCNC1",
"reactionStepId": "sa_69e5172e70eb8efdcd1712e5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140094491A1;0090;1510485\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]1\"}",
"reactionStep": {
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"reactionHash": "ddbca66795825efc1d0ade36e25ec0a09a1465e6320050fcca18789efc631800"
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"children": [
{
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"moleculeId": "sa_1785e67b778eb91f7e04c15a",
"parentId": "9245",
"isLeaf": true,
"molecule": {
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"inchikey": "BCNZYOJHNLTNEZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Cl"
},
"smiles": "CC(C)(C)[Si](C)(C)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "9247",
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"moleculeId": "sa_c84de76e10379fd9aea3cd06",
"parentId": "9245",
"isLeaf": true,
"molecule": {
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"inchikey": "VUNPWIPIOOMCPT-UHFFFAOYSA-N",
"smiles": "OCC1CCCNC1"
},
"smiles": "OCC1CCCNC1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "9248",
"routeId": "sa_7fcf36d3794d501f2ae93639",
"moleculeId": "sa_31588424581a37123484048c",
"parentId": "9244",
"isLeaf": false,
"molecule": {
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"inchikey": "SSPQOLHQGAFWCA-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C)c(NC(=O)c2cc(Br)ccc2C)c1C"
},
"smiles": "COC(=O)c1ccc(C)c(NC(=O)c2cc(Br)ccc2C)c1C",
"reactionStepId": "sa_442ca82d422020959f5b6121",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140094491A1;0117;1510493\",\"rsmi\":\"O[C:10](=[O:11])[c:12]1[c:13]([CH3:14])[cH:15][cH:16][c:17]([Br:18])[cH:19]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH2:9])[c:20]([CH3:21])[cH:22][cH:23]1>CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[c:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]([Br:18])[cH:19]2)[c:20]([CH3:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O[C:10](=[O:11])[c:12]1[c:13]([CH3:14])[cH:15][cH:16][c:17]([Br:18])[cH:19]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH2:9])[c:20]([CH3:21])[cH:22][cH:23]1>CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[c:12]2[c:13]([CH3:14])[cH:15][cH:16][c:17]([Br:18])[cH:19]2)[c:20]([CH3:21])[cH:22][cH:23]1\"}",
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"isLeaf": true,
"molecule": {
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"inchikey": "SEENCYZQHCUTSB-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Br)cc1C(=O)O"
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{
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"metadata": "{\"annotations\":{\"ID\":\"US20140094491A1;0078;1510481\",\"rsmi\":\"O=[N+:9]([O-])[c:8]1[c:6]([CH3:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12][c:10]1[CH3:11]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH2:9])[c:10]([CH3:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:9]([O-])[c:8]1[c:6]([CH3:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12][c:10]1[CH3:11]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH2:9])[c:10]([CH3:11])[cH:12][cH:13]1\"}",
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},
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}
]
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]
}
]
}
]
}
]
}
}