Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)[Si](C)(C)OCCN(C#N)c1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1
InChiKey
FFBDIEFSDMDGPZ-UHFFFAOYSA-N
Route Signature
bf90215bddc35ccefcd23fc6bf320e875f7d67fe33c7258d5c3539ab3a9ace33
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a62b3b917712d9f067f50adb",
"signature": "bf90215bddc35ccefcd23fc6bf320e875f7d67fe33c7258d5c3539ab3a9ace33",
"contentHash": "b46c37effb29e5342ac7dead7183111daaba9041b25cd613c1ab5f7c615d4dfc",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_3d042567ba20a6b42e4d75ba",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00853",
"moleculeId": "sa_70caac4bb5a391eeb5ab8e9d",
"smiles": "CC(C)(C)[Si](C)(C)OCCN(C#N)c1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_70caac4bb5a391eeb5ab8e9d",
"inchikey": "FFBDIEFSDMDGPZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCN(C#N)c1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1226",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_70caac4bb5a391eeb5ab8e9d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_70caac4bb5a391eeb5ab8e9d",
"inchikey": "FFBDIEFSDMDGPZ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCN(C#N)c1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCN(C#N)c1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1",
"reactionStepId": "sa_c92d9232f00edf05812e2626",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100004292A1;0751;818690\",\"rsmi\":\"Br[C:12]#[N:13].[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]2[n:22][cH:23][cH:24][n:25][c:26]2[NH:27][C:28](=[O:29])[c:30]2[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37][cH:38]1>O=C(O)O.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]([C:12]#[N:13])[c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]2[n:22][cH:23][cH:24][n:25][c:26]2[NH:27][C:28](=[O:29])[c:30]2[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37][cH:38]1\"},\"mapped_reaction_smiles\":\"Br[C:12]#[N:13].[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]2[n:22][cH:23][cH:24][n:25][c:26]2[NH:27][C:28](=[O:29])[c:30]2[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37][cH:38]1>O=C(O)O.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][N:11]([C:12]#[N:13])[c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]2[n:22][cH:23][cH:24][n:25][c:26]2[NH:27][C:28](=[O:29])[c:30]2[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]2)[cH:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_c92d9232f00edf05812e2626",
"reactionHash": "0f5725e5326b884b5514e46488f7eb03f075692b30c31f6b5a4fe72feed375ab"
},
"children": [
{
"id": "1227",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_30011d6f02d7317821269823",
"parentId": "1226",
"isLeaf": true,
"molecule": {
"id": "sa_30011d6f02d7317821269823",
"inchikey": "ATDGTVJJHBUTRL-UHFFFAOYSA-N",
"smiles": "N#CBr"
},
"smiles": "N#CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1228",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_ce9e37e2175bbf5d95d57f91",
"parentId": "1226",
"isLeaf": false,
"molecule": {
"id": "sa_ce9e37e2175bbf5d95d57f91",
"inchikey": "DOVSWGGGNORYPV-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccc(NC(=O)c2nccnc2NC(=O)c2ccc(Cl)cc2)cc1",
"reactionStepId": "sa_85dfdfb010b66524bc170d79",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100004292A1;0746;818689\",\"rsmi\":\"O[C:17](=[O:18])[c:19]1[n:20][cH:21][cH:22][n:23][c:24]1[NH:25][C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]1.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([NH2:16])[cH:35][cH:36]1>CC(C)(C)C(=O)Cl.CCN(CC)CC.CN(C)C=O>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[n:20][cH:21][cH:22][n:23][c:24]2[NH:25][C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]2)[cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"O[C:17](=[O:18])[c:19]1[n:20][cH:21][cH:22][n:23][c:24]1[NH:25][C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]1.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([NH2:16])[cH:35][cH:36]1>CC(C)(C)C(=O)Cl.CCN(CC)CC.CN(C)C=O>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[c:19]2[n:20][cH:21][cH:22][n:23][c:24]2[NH:25][C:26](=[O:27])[c:28]2[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]2)[cH:35][cH:36]1\"}",
"reactionStep": {
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"reactionHash": "2fed6379a2b34a0ef03a9a59655cb58b09873530a85052a76bf770b4c63053c1"
},
"children": [
{
"id": "1229",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_68c659b35e18f84799860632",
"parentId": "1228",
"isLeaf": false,
"molecule": {
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"inchikey": "MIGKVCZDGYFEPA-UHFFFAOYSA-N",
"smiles": "O=C(Nc1nccnc1C(=O)O)c1ccc(Cl)cc1"
},
"smiles": "O=C(Nc1nccnc1C(=O)O)c1ccc(Cl)cc1",
"reactionStepId": "sa_9bb713a6304feed5d7630fc7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100004292A1;0376;818647\",\"rsmi\":\"C[O:3][C:2](=[O:1])[c:4]1[n:5][cH:6][cH:7][n:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][cH:7][n:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[c:4]1[n:5][cH:6][cH:7][n:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][cH:7][n:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_9bb713a6304feed5d7630fc7",
"reactionHash": "9d41402042dec41e02b4bf8d0824200225fa77897b9face8084a6469ad93ee73"
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"children": [
{
"id": "1230",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_73ec4a69d138d82b18b765c1",
"parentId": "1229",
"isLeaf": false,
"molecule": {
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"inchikey": "MHCAAXPAAYXUBC-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nccnc1NC(=O)c1ccc(Cl)cc1"
},
"smiles": "COC(=O)c1nccnc1NC(=O)c1ccc(Cl)cc1",
"reactionStepId": "sa_0e0f1d94b15f44e5933c657b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100004292A1;0371;818646\",\"rsmi\":\"Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[NH2:11]>CC#N.CCOCC>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[NH2:11]>CC#N.CCOCC>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1\"}",
"reactionStep": {
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"children": [
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"parentId": "1230",
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"molecule": {
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"inchikey": "INCSQLZZXBPATR-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nccnc1N"
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"smiles": "COC(=O)c1nccnc1N",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "1232",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_421581d2a7104afc8fcc7471",
"parentId": "1230",
"isLeaf": true,
"molecule": {
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"inchikey": "RKIDDEGICSMIJA-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1ccc(Cl)cc1"
},
"smiles": "O=C(Cl)c1ccc(Cl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
},
{
"id": "1233",
"routeId": "sa_a62b3b917712d9f067f50adb",
"moleculeId": "sa_af4fdb26737130e58d82c9d4",
"parentId": "1228",
"isLeaf": false,
"molecule": {
"id": "sa_af4fdb26737130e58d82c9d4",
"inchikey": "XMSCZGPGMCTZSR-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccc(N)cc1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccc(N)cc1",
"reactionStepId": "sa_90d5c446879eaea57c5227c0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100004292A1;0235;818627\",\"rsmi\":\"O=[N+:16]([O-])[c:15]1[cH:14][cH:13][c:12]([NH:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:18][cH:17]1>CCO.[H][H].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([NH2:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:16]([O-])[c:15]1[cH:14][cH:13][c:12]([NH:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:18][cH:17]1>CCO.[H][H].[Pd]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([NH2:16])[cH:17][cH:18]1\"}",
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"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccc([N+](=O)[O-])cc1"
},
"smiles": "CC(C)(C)[Si](C)(C)OCCNc1ccc([N+](=O)[O-])cc1",
"reactionStepId": "sa_6cd9ba7d6fba1fd9de8fa3a0",
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"metadata": "{\"annotations\":{\"ID\":\"US20100004292A1;0229;818626\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>CN(C)C=O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>CN(C)C=O.c1c[nH]cn1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1\"}",
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"smiles": "CC(C)(C)[Si](C)(C)Cl"
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{
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"smiles": "O=[N+]([O-])c1ccc(NCCO)cc1"
},
"smiles": "O=[N+]([O-])c1ccc(NCCO)cc1",
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}
]
}
]
}
]
}
]
}
}