Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1
InChiKey
XUAPPHGPCDOSLF-UHFFFAOYSA-N
Route Signature
bf846c5add2a0d1c2bd5aa3ba384575c033692a106260e73974ae29f5a565742
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e06c9f0423e00986d7665c49",
"signature": "bf846c5add2a0d1c2bd5aa3ba384575c033692a106260e73974ae29f5a565742",
"contentHash": "482aed0e8b5c69ba4a87b8519ceb2866f7eda77bad38cfaf5877d4b1d38af56d",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_de7bf9c64b7d72ca984cee3c",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01630",
"moleculeId": "sa_2f615754295fcfb48cbfd48a",
"smiles": "CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_2f615754295fcfb48cbfd48a",
"inchikey": "XUAPPHGPCDOSLF-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5880",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_2f615754295fcfb48cbfd48a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2f615754295fcfb48cbfd48a",
"inchikey": "XUAPPHGPCDOSLF-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1"
},
"smiles": "CC(C)(C)[Si](Oc1cc(Br)cc(Nc2cccnc2)c1)(c1ccccc1)c1ccccc1",
"reactionStepId": "sa_ab614dd808ab9cc72a76d40e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090093479A1;0514;687972\",\"rsmi\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1.[OH:6][c:7]1[cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[cH:17][c:18]([Br:19])[cH:20]1>CN(C)C=O.COC(C)(C)C.[HH].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][c:7]1[cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[cH:17][c:18]([Br:19])[cH:20]1)([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1.[OH:6][c:7]1[cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[cH:17][c:18]([Br:19])[cH:20]1>CN(C)C=O.COC(C)(C)C.[HH].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][c:7]1[cH:8][c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[cH:17][c:18]([Br:19])[cH:20]1)([c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_ab614dd808ab9cc72a76d40e",
"reactionHash": "ef25872de60298a752891df6ef765c6e810461c00f5f29e50f7a116156d15097"
},
"children": [
{
"id": "5881",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_5d6c837ad4e1c7355e5371fc",
"parentId": "5880",
"isLeaf": false,
"molecule": {
"id": "sa_5d6c837ad4e1c7355e5371fc",
"inchikey": "BIWCALVVGGZONL-UHFFFAOYSA-N",
"smiles": "Oc1cc(Br)cc(Nc2cccnc2)c1"
},
"smiles": "Oc1cc(Br)cc(Nc2cccnc2)c1",
"reactionStepId": "sa_293546fde88acc462eeb6536",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090093479A1;0513;687971\",\"rsmi\":\"COc1ccc(C[O:1][c:2]2[cH:3][c:4]([Br:5])[cH:6][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][n:13][cH:14]3)[cH:15]2)cc1>CSc1ccccc1.O.O=C(O)C(F)(F)F>[OH:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15]1\"},\"mapped_reaction_smiles\":\"COc1ccc(C[O:1][c:2]2[cH:3][c:4]([Br:5])[cH:6][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][n:13][cH:14]3)[cH:15]2)cc1>CSc1ccccc1.O.O=C(O)C(F)(F)F>[OH:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[cH:15]1\"}",
"reactionStep": {
"id": "sa_293546fde88acc462eeb6536",
"reactionHash": "b08a2f8ca0bac9859828c508d32377b540d41921ac2875e2c9ea700e57e04166"
},
"children": [
{
"id": "5882",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_acb715273675190ca138557c",
"parentId": "5881",
"isLeaf": false,
"molecule": {
"id": "sa_acb715273675190ca138557c",
"inchikey": "VFMBQVGVHAXEKX-UHFFFAOYSA-N",
"smiles": "COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1"
},
"smiles": "COc1ccc(COc2cc(Br)cc(Nc3cccnc3)c2)cc1",
"reactionStepId": "sa_c1c1a47fc92672575f35da81",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090093479A1;0391;687947\",\"rsmi\":\"Br[c:14]1[cH:13][c:11]([Br:12])[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[cH:22]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>CC(C)(C)O.CCCCCCC.CCOC(C)=O.CCOC(C)=O.Cc1ccccc1.ClC(Cl)Cl.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.Cl.[Na+].[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][n:20][cH:21]3)[cH:22]2)[cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Br[c:14]1[cH:13][c:11]([Br:12])[cH:10][c:9]([O:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[cH:22]1.[NH2:15][c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>CC(C)(C)O.CCCCCCC.CCOC(C)=O.CCOC(C)=O.Cc1ccccc1.ClC(Cl)Cl.O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.Cl.[Na+].[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][n:20][cH:21]3)[cH:22]2)[cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_c1c1a47fc92672575f35da81",
"reactionHash": "b6fb19eb28b34fd6b6ddaaa51e0a2ee3ac1972c833b7bd1d5b6102288c62c316"
},
"children": [
{
"id": "5883",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_d570773337f26185d8c32b33",
"parentId": "5882",
"isLeaf": true,
"molecule": {
"id": "sa_d570773337f26185d8c32b33",
"inchikey": "CUYKNJBYIJFRCU-UHFFFAOYSA-N",
"smiles": "Nc1cccnc1"
},
"smiles": "Nc1cccnc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5884",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_843e08d9a810801835374822",
"parentId": "5882",
"isLeaf": false,
"molecule": {
"id": "sa_843e08d9a810801835374822",
"inchikey": "VGUGTIFUFUMFLE-UHFFFAOYSA-N",
"smiles": "COc1ccc(COc2cc(Br)cc(Br)c2)cc1"
},
"smiles": "COc1ccc(COc2cc(Br)cc(Br)c2)cc1",
"reactionStepId": "sa_9003cab0a3297b718e1f65c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090093479A1;0389;687945\",\"rsmi\":\"O=[N+]([O-])[c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:17][cH:18]1>CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C(=O)N(C)C.Br.[K+].O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[N+]([O-])[c:9]1[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:17][cH:18]1>CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C(=O)N(C)C.Br.[K+].O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([Br:15])[cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_9003cab0a3297b718e1f65c1",
"reactionHash": "d3dcc4a340d67ef5563c16bd2e5ddaecbe2e022fe1830eec6265d13227e4529a"
},
"children": [
{
"id": "5885",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_c45792f3c564974d80913b96",
"parentId": "5884",
"isLeaf": true,
"molecule": {
"id": "sa_c45792f3c564974d80913b96",
"inchikey": "MSHFRERJPWKJFX-UHFFFAOYSA-N",
"smiles": "COc1ccc(CO)cc1"
},
"smiles": "COc1ccc(CO)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5886",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_ae6c155fdd8c1da630a4eee6",
"parentId": "5884",
"isLeaf": false,
"molecule": {
"id": "sa_ae6c155fdd8c1da630a4eee6",
"inchikey": "ZWBHGBWABMAWOV-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Br)cc(Br)c1"
},
"smiles": "O=[N+]([O-])c1cc(Br)cc(Br)c1",
"reactionStepId": "sa_a1b3f79695c5e4ede629d049",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090093479A1;0387;687943\",\"rsmi\":\"N[c:8]1[c:6]([Br:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:11][c:9]1[Br:10]>CCO.O=NO.O=S(=O)(O)O.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9]([Br:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"N[c:8]1[c:6]([Br:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:11][c:9]1[Br:10]>CCO.O=NO.O=S(=O)(O)O.[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][c:9]([Br:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_a1b3f79695c5e4ede629d049",
"reactionHash": "b4e47f5c73fb0cda5295dbb038dbe3af9c5d3cb2fb830a46cd7b68ef56a44104"
},
"children": [
{
"id": "5887",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_fbab6a7c8c4aedd56068a941",
"parentId": "5886",
"isLeaf": true,
"molecule": {
"id": "sa_fbab6a7c8c4aedd56068a941",
"inchikey": "YMZIFDLWYUSZCC-UHFFFAOYSA-N",
"smiles": "Nc1c(Br)cc([N+](=O)[O-])cc1Br"
},
"smiles": "Nc1c(Br)cc([N+](=O)[O-])cc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "5888",
"routeId": "sa_e06c9f0423e00986d7665c49",
"moleculeId": "sa_1738688ce5ddb973d5d05c68",
"parentId": "5880",
"isLeaf": true,
"molecule": {
"id": "sa_1738688ce5ddb973d5d05c68",
"inchikey": "MHYGQXWCZAYSLJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1"
},
"smiles": "CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}