Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1)C(C)C
InChiKey
OWXJFLBDZFOAIE-UHFFFAOYSA-N
Route Signature
f5956e91ffec1170f50b6d4352ab9e50069780da0eb0e90a91e160fea6c1ccae
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_b29783ade27d4c95645d987f",
"signature": "f5956e91ffec1170f50b6d4352ab9e50069780da0eb0e90a91e160fea6c1ccae",
"contentHash": "7e54d3ae4b5750e38d392807aec9098c4bb47e0342f22600525ccf3eb3e9c3b5",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_9efe95c6419c5567bc09e1ed",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01912",
"moleculeId": "sa_b8bad246507bed3d9a139a7a",
"smiles": "COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1)C(C)C",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_b8bad246507bed3d9a139a7a",
"inchikey": "OWXJFLBDZFOAIE-UHFFFAOYSA-N",
"smiles": "COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1)C(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10502",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_b8bad246507bed3d9a139a7a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b8bad246507bed3d9a139a7a",
"inchikey": "OWXJFLBDZFOAIE-UHFFFAOYSA-N",
"smiles": "COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1)C(C)C"
},
"smiles": "COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c1)C(C)C",
"reactionStepId": "sa_daeca3f9c273b4c5bbb6444a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140249074A1;2865;1575889\",\"rsmi\":\"CC1(C)OB([B:26]2[O:27][C:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[O:34]2)OC1(C)C.Cl[c:25]1[cH:24][cH:23][c:22](-[c:21]2[cH:20][cH:19][cH:18][c:17]([NH:16][C:14]([CH:13]3[N:9]([C:7]([CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:38]([CH3:39])[CH3:40])=[O:8])[CH2:10][CH2:11][CH2:12]3)=[O:15])[cH:37]2)[cH:36][cH:35]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1COCCO1.CC(=O)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.[K+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH:6]([C:7](=[O:8])[N:9]1[CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([B:26]3[O:27][C:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[O:34]3)[cH:35][cH:36]2)[cH:37]1)[CH:38]([CH3:39])[CH3:40]\"},\"mapped_reaction_smiles\":\"CC1(C)OB([B:26]2[O:27][C:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[O:34]2)OC1(C)C.Cl[c:25]1[cH:24][cH:23][c:22](-[c:21]2[cH:20][cH:19][cH:18][c:17]([NH:16][C:14]([CH:13]3[N:9]([C:7]([CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:38]([CH3:39])[CH3:40])=[O:8])[CH2:10][CH2:11][CH2:12]3)=[O:15])[cH:37]2)[cH:36][cH:35]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1COCCO1.CC(=O)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.[K+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH:6]([C:7](=[O:8])[N:9]1[CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([B:26]3[O:27][C:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[O:34]3)[cH:35][cH:36]2)[cH:37]1)[CH:38]([CH3:39])[CH3:40]\"}",
"reactionStep": {
"id": "sa_daeca3f9c273b4c5bbb6444a",
"reactionHash": "7359bedaecf517259889730dd1df672f2b88fd0247a51773bdc29ebbfefaafae"
},
"children": [
{
"id": "10503",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "10502",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10504",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_64feebb9638c4b0cacfee071",
"parentId": "10502",
"isLeaf": false,
"molecule": {
"id": "sa_64feebb9638c4b0cacfee071",
"inchikey": "MICCOBRNBSPAJN-UHFFFAOYSA-N",
"smiles": "COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(Cl)cc2)c1)C(C)C"
},
"smiles": "COC(=O)NC(C(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(Cl)cc2)c1)C(C)C",
"reactionStepId": "sa_a3e7148c7bf93156d525db6a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140249074A1;2864;1575888\",\"rsmi\":\"CC(C)(C)OC(=O)[N:9]1[CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29]1.O[C:7]([CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:30]([CH3:31])[CH3:32])=[O:8]>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.CO.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH:6]([C:7](=[O:8])[N:9]1[CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29]1)[CH:30]([CH3:31])[CH3:32]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:9]1[CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29]1.O[C:7]([CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:30]([CH3:31])[CH3:32])=[O:8]>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.CO.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH:6]([C:7](=[O:8])[N:9]1[CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[cH:29]1)[CH:30]([CH3:31])[CH3:32]\"}",
"reactionStep": {
"id": "sa_a3e7148c7bf93156d525db6a",
"reactionHash": "4f366d598a89103eb817e93b7a6bb2bfbcd3f64875519d94400740c00c83ed79"
},
"children": [
{
"id": "10505",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_f10e83914f651ce115f4f33f",
"parentId": "10504",
"isLeaf": false,
"molecule": {
"id": "sa_f10e83914f651ce115f4f33f",
"inchikey": "CEFVHPDFGLDQKU-UHFFFAOYSA-N",
"smiles": "COC(O)=NC(C(=O)O)C(C)C"
},
"smiles": "COC(=O)NC(C(=O)O)C(C)C",
"reactionStepId": "sa_775591313a1bc752f0b1e4d5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140249074A1;3470;1576057\",\"rsmi\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][C@H:6]([C:7](=[O:8])[OH:9])[CH:10]([CH3:11])[CH3:12]>O=C(O)O.[Na+].[Na+].[Na+].O>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH:6]([C:7](=[O:8])[OH:9])[CH:10]([CH3:11])[CH3:12]\"},\"mapped_reaction_smiles\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][C@H:6]([C:7](=[O:8])[OH:9])[CH:10]([CH3:11])[CH3:12]>O=C(O)O.[Na+].[Na+].[Na+].O>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH:6]([C:7](=[O:8])[OH:9])[CH:10]([CH3:11])[CH3:12]\"}",
"reactionStep": {
"id": "sa_775591313a1bc752f0b1e4d5",
"reactionHash": "a9bf63745e89cd4a98f2615e5069243bcb8d9b4ab9a17e17f5817082e7a6e300"
},
"children": [
{
"id": "10506",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_d70780e0e95fb563c08c49ac",
"parentId": "10505",
"isLeaf": true,
"molecule": {
"id": "sa_d70780e0e95fb563c08c49ac",
"inchikey": "KZSNJWFQEVHDMF-BYPYZUCNSA-N",
"smiles": "CC(C)[C@H](N)C(=O)O"
},
"smiles": "CC(C)[C@H](N)C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10507",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_786c6159be77bb31e43bff8a",
"parentId": "10505",
"isLeaf": true,
"molecule": {
"id": "sa_786c6159be77bb31e43bff8a",
"inchikey": "XMJHPCRAQCTCFT-UHFFFAOYSA-N",
"smiles": "COC(=O)Cl"
},
"smiles": "COC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10508",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_d55f864b3db670a3140aa7e9",
"parentId": "10504",
"isLeaf": false,
"molecule": {
"id": "sa_d55f864b3db670a3140aa7e9",
"inchikey": "HGHYECYJSOASPC-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(Cl)cc2)c1"
},
"smiles": "CC(C)(C)OC(=O)N1CCCC1C(=O)Nc1cccc(-c2ccc(Cl)cc2)c1",
"reactionStepId": "sa_8ed593164b07a86ba42ba587",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140249074A1;2863;1575887\",\"rsmi\":\"O[C:13]([CH:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1)=[O:14].[NH2:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[cH:28]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[C:13](=[O:14])[NH:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[cH:28]1\"},\"mapped_reaction_smiles\":\"O[C:13]([CH:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1)=[O:14].[NH2:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[cH:28]1>CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[C:13](=[O:14])[NH:15][c:16]1[cH:17][cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[cH:28]1\"}",
"reactionStep": {
"id": "sa_8ed593164b07a86ba42ba587",
"reactionHash": "64c326d0bd67b58560d0334a6b038555349b5b1c3f76494de30b01555ec87672"
},
"children": [
{
"id": "10509",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_bd9d0320715cd817bf1c10df",
"parentId": "10508",
"isLeaf": true,
"molecule": {
"id": "sa_bd9d0320715cd817bf1c10df",
"inchikey": "VUCKHKAVIGEKGO-UHFFFAOYSA-N",
"smiles": "Nc1cccc(-c2ccc(Cl)cc2)c1"
},
"smiles": "Nc1cccc(-c2ccc(Cl)cc2)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10510",
"routeId": "sa_b29783ade27d4c95645d987f",
"moleculeId": "sa_07e022ebd640662e8decf015",
"parentId": "10508",
"isLeaf": true,
"molecule": {
"id": "sa_07e022ebd640662e8decf015",
"inchikey": "ZQEBQGAAWMOMAI-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCCC1C(=O)O"
},
"smiles": "CC(C)(C)OC(=O)N1CCCC1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}