Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(N3CCC(O)C3)cc21
InChiKey
GXEOWOARTLHHKG-UHFFFAOYSA-N
Route Signature
615720a2560a2dc883e8260847368adc334297d7d263d6045b53ecff847bf825
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_59a20b16b73ec70596d23945",
"signature": "615720a2560a2dc883e8260847368adc334297d7d263d6045b53ecff847bf825",
"contentHash": "8837a083ccb9a9ee7b0d272665b19628eacf11170592f885b17d5326ab30f03c",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_a35f2038d260e231f2670a35",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02633",
"moleculeId": "sa_e6470fa2444e9e1693fe8a36",
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(N3CCC(O)C3)cc21",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_e6470fa2444e9e1693fe8a36",
"inchikey": "GXEOWOARTLHHKG-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(N3CCC(O)C3)cc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10807",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_e6470fa2444e9e1693fe8a36",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e6470fa2444e9e1693fe8a36",
"inchikey": "GXEOWOARTLHHKG-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(N3CCC(O)C3)cc21"
},
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(N3CCC(O)C3)cc21",
"reactionStepId": "sa_936ba4b832db37338297fc00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309210A1;0482;1597734\",\"rsmi\":\"Br[c:32]1[cH:31][cH:30][c:29]2[c:11]([C:12](=[O:13])[NH:14][c:15]3[cH:16][n:17]([CH2:18][c:19]4[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]4)[n:27][cH:28]3)[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:40]2[cH:39]1.[NH:33]1[CH2:34][CH2:35][CH:36]([OH:37])[CH2:38]1>CC(C)(C)O.CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C(O)O.[Cs+].[Cs+]>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][n:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28]2)[c:29]2[cH:30][cH:31][c:32]([N:33]3[CH2:34][CH2:35][CH:36]([OH:37])[CH2:38]3)[cH:39][c:40]12\"},\"mapped_reaction_smiles\":\"Br[c:32]1[cH:31][cH:30][c:29]2[c:11]([C:12](=[O:13])[NH:14][c:15]3[cH:16][n:17]([CH2:18][c:19]4[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]4)[n:27][cH:28]3)[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:40]2[cH:39]1.[NH:33]1[CH2:34][CH2:35][CH:36]([OH:37])[CH2:38]1>CC(C)(C)O.CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C(O)O.[Cs+].[Cs+]>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][n:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28]2)[c:29]2[cH:30][cH:31][c:32]([N:33]3[CH2:34][CH2:35][CH:36]([OH:37])[CH2:38]3)[cH:39][c:40]12\"}",
"reactionStep": {
"id": "sa_936ba4b832db37338297fc00",
"reactionHash": "4cda70b75ba0f4b0fb1470c57624e0f614161de139c04707c9011670e990d077"
},
"children": [
{
"id": "10808",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_da9451c32ade5b0a49e479f0",
"parentId": "10807",
"isLeaf": false,
"molecule": {
"id": "sa_da9451c32ade5b0a49e479f0",
"inchikey": "DUFGJDPAECOKOD-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(Br)cc21"
},
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)Nc2cnn(Cc3cccc(C#N)c3)c2)c2ccc(Br)cc21",
"reactionStepId": "sa_42254df34ac21b315c52bbfb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309210A1;0254;1597695\",\"rsmi\":\"O[C:12]([c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:35]2[c:29]1[cH:30][cH:31][c:32]([Br:33])[cH:34]2)=[O:13].[NH2:14][c:15]1[cH:16][n:17]([CH2:18][c:19]2[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]2)[n:27][cH:28]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][n:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28]2)[c:29]2[cH:30][cH:31][c:32]([Br:33])[cH:34][c:35]12\"},\"mapped_reaction_smiles\":\"O[C:12]([c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:35]2[c:29]1[cH:30][cH:31][c:32]([Br:33])[cH:34]2)=[O:13].[NH2:14][c:15]1[cH:16][n:17]([CH2:18][c:19]2[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]2)[n:27][cH:28]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][n:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25][cH:26]3)[n:27][cH:28]2)[c:29]2[cH:30][cH:31][c:32]([Br:33])[cH:34][c:35]12\"}",
"reactionStep": {
"id": "sa_42254df34ac21b315c52bbfb",
"reactionHash": "5c9bc9492ff23076c87759a7c1bd6dfcce312223e8a40a889658296f4c424b96"
},
"children": [
{
"id": "10809",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_f8c0c6eae76d05e52e864ecd",
"parentId": "10808",
"isLeaf": false,
"molecule": {
"id": "sa_f8c0c6eae76d05e52e864ecd",
"inchikey": "BRYKUVLJGRHSQI-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)O)c2ccc(Br)cc21"
},
"smiles": "C[Si](C)(C)CCOCn1nc(C(=O)O)c2ccc(Br)cc21",
"reactionStepId": "sa_66d6196d51bb765677ef3fce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309210A1;0238;1597687\",\"rsmi\":\"C[O:14][C:12]([c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:21]2[c:15]1[cH:16][cH:17][c:18]([Br:19])[cH:20]2)=[O:13]>C1CCOC1.CCOC(C)=O.Cl.O.[Li+].O>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][c:11]([C:12](=[O:13])[OH:14])[c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]12\"},\"mapped_reaction_smiles\":\"C[O:14][C:12]([c:11]1[n:10][n:9]([CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[c:21]2[c:15]1[cH:16][cH:17][c:18]([Br:19])[cH:20]2)=[O:13]>C1CCOC1.CCOC(C)=O.Cl.O.[Li+].O>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][c:11]([C:12](=[O:13])[OH:14])[c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][c:21]12\"}",
"reactionStep": {
"id": "sa_66d6196d51bb765677ef3fce",
"reactionHash": "8b44962186ec3cf0c5e285734d0e194af07b5c981bffbf698d7e1739bd9671f7"
},
"children": [
{
"id": "10810",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_dbb380161d75ebc9abf298e5",
"parentId": "10809",
"isLeaf": true,
"molecule": {
"id": "sa_dbb380161d75ebc9abf298e5",
"inchikey": "BUGQTJTXPKBJBA-UHFFFAOYSA-N",
"smiles": "COC(=O)c1nn(COCC[Si](C)(C)C)c2cc(Br)ccc12"
},
"smiles": "COC(=O)c1nn(COCC[Si](C)(C)C)c2cc(Br)ccc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10811",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_dee8d98fd23f835e981b7a7d",
"parentId": "10808",
"isLeaf": false,
"molecule": {
"id": "sa_dee8d98fd23f835e981b7a7d",
"inchikey": "DSBXCIXDUULTMD-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(Cn2cc(N)cn2)c1"
},
"smiles": "N#Cc1cccc(Cn2cc(N)cn2)c1",
"reactionStepId": "sa_0960cd836d29afca118b1bbf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309210A1;0252;1597694\",\"rsmi\":\"O=[N+:10]([O-])[c:9]1[cH:8][n:7]([CH2:6][c:5]2[cH:4][c:3]([C:2]#[N:1])[cH:15][cH:14][cH:13]2)[n:12][cH:11]1>CCO.CCOC(C)=O.O.Cl.[Fe].N>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][n:7]2[cH:8][c:9]([NH2:10])[cH:11][n:12]2)[cH:13][cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:10]([O-])[c:9]1[cH:8][n:7]([CH2:6][c:5]2[cH:4][c:3]([C:2]#[N:1])[cH:15][cH:14][cH:13]2)[n:12][cH:11]1>CCO.CCOC(C)=O.O.Cl.[Fe].N>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][n:7]2[cH:8][c:9]([NH2:10])[cH:11][n:12]2)[cH:13][cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_0960cd836d29afca118b1bbf",
"reactionHash": "2c9df3ce0fe51f0361a46379925702a5473a79117a9422b3b531ec0c9deb98ec"
},
"children": [
{
"id": "10812",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_3630cdce9f7defeb199603a4",
"parentId": "10811",
"isLeaf": false,
"molecule": {
"id": "sa_3630cdce9f7defeb199603a4",
"inchikey": "GDRDZXJSBMVENL-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(Cn2cc([N+](=O)[O-])cn2)c1"
},
"smiles": "N#Cc1cccc(Cn2cc([N+](=O)[O-])cn2)c1",
"reactionStepId": "sa_8c55c282acfbea5a73820623",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309210A1;0250;1597693\",\"rsmi\":\"Br[CH2:6][c:5]1[cH:4][c:3]([C:2]#[N:1])[cH:17][cH:16][cH:15]1.[nH:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][n:14]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][n:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][n:14]2)[cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"Br[CH2:6][c:5]1[cH:4][c:3]([C:2]#[N:1])[cH:17][cH:16][cH:15]1.[nH:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][n:14]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][n:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][n:14]2)[cH:15][cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_8c55c282acfbea5a73820623",
"reactionHash": "c184a3f808fa2a7888a56958e709becd3e04ccf2204f48e1dc4bb4b49e132fdb"
},
"children": [
{
"id": "10813",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_7e2124afd264e450b670b7b9",
"parentId": "10812",
"isLeaf": true,
"molecule": {
"id": "sa_7e2124afd264e450b670b7b9",
"inchikey": "CVKOOKPNCVYHNY-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(CBr)c1"
},
"smiles": "N#Cc1cccc(CBr)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10814",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_f213c836485a16207ffe20c5",
"parentId": "10812",
"isLeaf": true,
"molecule": {
"id": "sa_f213c836485a16207ffe20c5",
"inchikey": "XORHNJQEWQGXCN-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cn[nH]c1"
},
"smiles": "O=[N+]([O-])c1cn[nH]c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "10815",
"routeId": "sa_59a20b16b73ec70596d23945",
"moleculeId": "sa_ea090c03f700fd5cfada6118",
"parentId": "10807",
"isLeaf": true,
"molecule": {
"id": "sa_ea090c03f700fd5cfada6118",
"inchikey": "JHHZLHWJQPUNKB-UHFFFAOYSA-N",
"smiles": "OC1CCNC1"
},
"smiles": "OC1CCNC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}