Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(O)c5ccccc5)ccc4o3)c(F)c2)C1
InChiKey
BBVCPOXXWYEPSH-UHFFFAOYSA-N
Route Signature
295295b5f6e3d8681eac48fd7a55c380ab7048b417e0e69f4f855a12b880d86e
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_6d1d51a823f784847d72c347",
"signature": "295295b5f6e3d8681eac48fd7a55c380ab7048b417e0e69f4f855a12b880d86e",
"contentHash": "5213f353db63f10c027bf4876b02485f238fc063c25e3112eae0f7c8afe91e1b",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_776ea037a1c7f0da54452fb0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-03519",
"moleculeId": "sa_3604dfb13164e122dcbbf08d",
"smiles": "COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(O)c5ccccc5)ccc4o3)c(F)c2)C1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_3604dfb13164e122dcbbf08d",
"inchikey": "BBVCPOXXWYEPSH-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(O)c5ccccc5)ccc4o3)c(F)c2)C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11035",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_3604dfb13164e122dcbbf08d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3604dfb13164e122dcbbf08d",
"inchikey": "BBVCPOXXWYEPSH-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(O)c5ccccc5)ccc4o3)c(F)c2)C1"
},
"smiles": "COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(O)c5ccccc5)ccc4o3)c(F)c2)C1",
"reactionStepId": "sa_22e40556860565a74c72f6eb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07919519B2;1009;1066375\",\"rsmi\":\"[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[cH:15][c:16]4[c:17]([cH:18][cH:19][c:20]([C:21](=[O:22])[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29]4)[o:30]3)[cH:31][cH:32]2)[CH2:33]1>C1CCOC1.CO.B.Cl.N.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[cH:15][c:16]4[c:17]([cH:18][cH:19][c:20]([CH:21]([OH:22])[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29]4)[o:30]3)[cH:31][cH:32]2)[CH2:33]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[cH:15][c:16]4[c:17]([cH:18][cH:19][c:20]([C:21](=[O:22])[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29]4)[o:30]3)[cH:31][cH:32]2)[CH2:33]1>C1CCOC1.CO.B.Cl.N.[Na+]>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[cH:15][c:16]4[c:17]([cH:18][cH:19][c:20]([CH:21]([OH:22])[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29]4)[o:30]3)[cH:31][cH:32]2)[CH2:33]1\"}",
"reactionStep": {
"id": "sa_22e40556860565a74c72f6eb",
"reactionHash": "23136d3a928c579da98451e279b45cac1acc65cef38cc8da85a18e3b24c76280"
},
"children": [
{
"id": "11036",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_dbf17fd6070c3ab4b2da8048",
"parentId": "11035",
"isLeaf": false,
"molecule": {
"id": "sa_dbf17fd6070c3ab4b2da8048",
"inchikey": "MTKYIWSHZKUEAJ-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(=O)c5ccccc5)ccc4o3)c(F)c2)C1"
},
"smiles": "COC(=O)C1CN(Cc2ccc(-c3cc4cc(C(=O)c5ccccc5)ccc4o3)c(F)c2)C1",
"reactionStepId": "sa_4d785fe1417b9ab9a9be8f1a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07919519B2;0999;1066374\",\"rsmi\":\"I[c:16]1[c:17]([OH:30])[cH:18][cH:19][c:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[CH:15])[cH:31][cH:32]2)[CH2:33]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[cH:15][c:16]4[c:17]([cH:18][cH:19][c:20]([C:21](=[O:22])[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29]4)[o:30]3)[cH:31][cH:32]2)[CH2:33]1\"},\"mapped_reaction_smiles\":\"I[c:16]1[c:17]([OH:30])[cH:18][cH:19][c:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[CH:15])[cH:31][cH:32]2)[CH2:33]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13](-[c:14]3[cH:15][c:16]4[c:17]([cH:18][cH:19][c:20]([C:21](=[O:22])[c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29]4)[o:30]3)[cH:31][cH:32]2)[CH2:33]1\"}",
"reactionStep": {
"id": "sa_4d785fe1417b9ab9a9be8f1a",
"reactionHash": "a74c264dfd018ad33c7b602867969391198eba97c357f099b1ca3cb13de23048"
},
"children": [
{
"id": "11037",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_29bf2a44c0bdf5aaf2da865c",
"parentId": "11036",
"isLeaf": false,
"molecule": {
"id": "sa_29bf2a44c0bdf5aaf2da865c",
"inchikey": "GIAVTQYCKZHWIJ-UHFFFAOYSA-N",
"smiles": "C#Cc1ccc(CN2CC(C(=O)OC)C2)cc1F"
},
"smiles": "C#Cc1ccc(CN2CC(C(=O)OC)C2)cc1F",
"reactionStepId": "sa_6c4d006e40ed6a1b6158c3cc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07919519B2;0866;1066327\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH:11]([C:12](=[O:13])[O:14][CH3:15])[CH2:16]2)[cH:17][cH:18]1>CN(C)C=O.CO.[Cs+].F>[CH:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH:11]([C:12](=[O:13])[O:14][CH3:15])[CH2:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH:11]([C:12](=[O:13])[O:14][CH3:15])[CH2:16]2)[cH:17][cH:18]1>CN(C)C=O.CO.[Cs+].F>[CH:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH:11]([C:12](=[O:13])[O:14][CH3:15])[CH2:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_6c4d006e40ed6a1b6158c3cc",
"reactionHash": "acdcbd9979312bbb8d29a4d068f9370c496eb6c0bde0eeda434a65ad8144edd9"
},
"children": [
{
"id": "11038",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_4fadac5eaac34d4bee1bacca",
"parentId": "11037",
"isLeaf": false,
"molecule": {
"id": "sa_4fadac5eaac34d4bee1bacca",
"inchikey": "ZPWLVLNBUFZYNS-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CN(Cc2ccc(C#C[Si](C)(C)C)c(F)c2)C1"
},
"smiles": "COC(=O)C1CN(Cc2ccc(C#C[Si](C)(C)C)c(F)c2)C1",
"reactionStepId": "sa_2c6a95ccd839c7ba696c26a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07919519B2;0864;1066326\",\"rsmi\":\"Br[c:13]1[c:11]([F:12])[cH:10][c:9]([CH2:8][N:7]2[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:22]2)[cH:21][cH:20]1.[CH:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19]>C1CCOC1.CCN(C(C)C)C(C)C.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]2)[CH2:22]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[c:11]([F:12])[cH:10][c:9]([CH2:8][N:7]2[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:22]2)[cH:21][cH:20]1.[CH:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19]>C1CCOC1.CCN(C(C)C)C(C)C.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]2)[CH2:22]1\"}",
"reactionStep": {
"id": "sa_2c6a95ccd839c7ba696c26a8",
"reactionHash": "4f1cc996dc751dc531134043fcb75215d9ab1f6290e51bfea4c1847f93537cac"
},
"children": [
{
"id": "11039",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "11038",
"isLeaf": true,
"molecule": {
"id": "sa_95a9277ba0d873f43bb42b7f",
"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11040",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_a8ef91ca679ca860c35e806d",
"parentId": "11038",
"isLeaf": true,
"molecule": {
"id": "sa_a8ef91ca679ca860c35e806d",
"inchikey": "NORYIKADRHSDGG-UHFFFAOYSA-N",
"smiles": "COC(=O)C1CN(Cc2ccc(Br)c(F)c2)C1"
},
"smiles": "COC(=O)C1CN(Cc2ccc(Br)c(F)c2)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "11041",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_c9cdecac332330f5eeed1cfd",
"parentId": "11036",
"isLeaf": false,
"molecule": {
"id": "sa_c9cdecac332330f5eeed1cfd",
"inchikey": "YKAHHNPIXNXHLX-UHFFFAOYSA-N",
"smiles": "O=C(c1ccccc1)c1ccc(O)c(I)c1"
},
"smiles": "O=C(c1ccccc1)c1ccc(O)c(I)c1",
"reactionStepId": "sa_e8149e0746f317bd31f704df",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07919519B2;0997;1066373\",\"rsmi\":\"I[I:12].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][c:13]([OH:14])[cH:15][cH:16]1>Cl.O.I.[K+].N.O>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][c:11]([I:12])[c:13]([OH:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"I[I:12].[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][c:13]([OH:14])[cH:15][cH:16]1>Cl.O.I.[K+].N.O>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][c:11]([I:12])[c:13]([OH:14])[cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_e8149e0746f317bd31f704df",
"reactionHash": "6cc8ecd73d44925f90e12ae81d61ae52c68c78747228caeec0ecd3e08e2cd9a1"
},
"children": [
{
"id": "11042",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_bbc028fb31fdca08e7b1d43c",
"parentId": "11041",
"isLeaf": true,
"molecule": {
"id": "sa_bbc028fb31fdca08e7b1d43c",
"inchikey": "NPFYZDNDJHZQKY-UHFFFAOYSA-N",
"smiles": "O=C(c1ccccc1)c1ccc(O)cc1"
},
"smiles": "O=C(c1ccccc1)c1ccc(O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11043",
"routeId": "sa_6d1d51a823f784847d72c347",
"moleculeId": "sa_bc6c113460696c6012e3bdf5",
"parentId": "11041",
"isLeaf": true,
"molecule": {
"id": "sa_bc6c113460696c6012e3bdf5",
"inchikey": "PNDPGZBMCMUPRI-UHFFFAOYSA-N",
"smiles": "II"
},
"smiles": "II",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}