Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc2c(cc1Br)N1C(=NNC(=O)C1C)CO2
InChiKey
ZKPQKLPYOFRZHU-UHFFFAOYSA-N
Route Signature
8f55ff9e332c1d9d7567c8d8b18a6b4633464ee88f5dd7d0f5fdb23f5fba5b78
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_59099c806a6eba3a8bda6c72",
"signature": "8f55ff9e332c1d9d7567c8d8b18a6b4633464ee88f5dd7d0f5fdb23f5fba5b78",
"contentHash": "efc655979da0869bebd0e7a4cb91c26e7bd8967304cdb819e5e5be897803143c",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_9a59e529772e1020a19abcde",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01504",
"moleculeId": "sa_c1c14bc860ac3ce5ff5f3220",
"smiles": "Cc1cc2c(cc1Br)N1C(=NNC(=O)C1C)CO2",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c1c14bc860ac3ce5ff5f3220",
"inchikey": "ZKPQKLPYOFRZHU-UHFFFAOYSA-N",
"smiles": "Cc1cc2c(cc1Br)N1C(=NNC(=O)C1C)CO2"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5672",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_c1c14bc860ac3ce5ff5f3220",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c1c14bc860ac3ce5ff5f3220",
"inchikey": "ZKPQKLPYOFRZHU-UHFFFAOYSA-N",
"smiles": "Cc1cc2c(cc1Br)N1C(=NNC(=O)C1C)CO2"
},
"smiles": "Cc1cc2c(cc1Br)N1C(=NNC(=O)C1C)CO2",
"reactionStepId": "sa_34563ed48c652ef715e86824",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206663A1;1724;1554492\",\"rsmi\":\"CCO[C:14](=[O:15])[CH:16]([CH3:17])[N:18]1[c:6]2[cH:5][c:3]([Br:4])[c:2]([CH3:1])[cH:8][c:7]2[O:9][CH2:10][C:11]1=S.[NH2:12][NH2:13]>CCO.O>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C:11]1=[N:12][NH:13][C:14](=[O:15])[CH:16]([CH3:17])[N:18]21\"},\"mapped_reaction_smiles\":\"CCO[C:14](=[O:15])[CH:16]([CH3:17])[N:18]1[c:6]2[cH:5][c:3]([Br:4])[c:2]([CH3:1])[cH:8][c:7]2[O:9][CH2:10][C:11]1=S.[NH2:12][NH2:13]>CCO.O>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C:11]1=[N:12][NH:13][C:14](=[O:15])[CH:16]([CH3:17])[N:18]21\"}",
"reactionStep": {
"id": "sa_34563ed48c652ef715e86824",
"reactionHash": "2163c556620c3d245649d8778d88dfbdd8de7c695821fd2f3ecd964e9a3bc14a"
},
"children": [
{
"id": "5673",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "5672",
"isLeaf": true,
"molecule": {
"id": "sa_681b90bfe3789a310096845b",
"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5674",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_9a81d9962011f9c2251b2e95",
"parentId": "5672",
"isLeaf": false,
"molecule": {
"id": "sa_9a81d9962011f9c2251b2e95",
"inchikey": "YSSKZFYUAJFPIW-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)N1C(=S)COc2cc(C)c(Br)cc21"
},
"smiles": "CCOC(=O)C(C)N1C(=S)COc2cc(C)c(Br)cc21",
"reactionStepId": "sa_352bdacae271618eca1720b3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206663A1;1722;1554491\",\"rsmi\":\"COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:10])S2)cc1.O=[C:9]1[N:8]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[c:14]2[c:13]([cH:20][c:18]([CH3:19])[c:16]([Br:17])[cH:15]2)[O:12][CH2:11]1>Cc1ccccc1.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[S:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][c:16]([Br:17])[c:18]([CH3:19])[cH:20]2\"},\"mapped_reaction_smiles\":\"COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:10])S2)cc1.O=[C:9]1[N:8]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[c:14]2[c:13]([cH:20][c:18]([CH3:19])[c:16]([Br:17])[cH:15]2)[O:12][CH2:11]1>Cc1ccccc1.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[S:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][c:16]([Br:17])[c:18]([CH3:19])[cH:20]2\"}",
"reactionStep": {
"id": "sa_352bdacae271618eca1720b3",
"reactionHash": "0a33fc2a6bd5f4c024b0abd17f252c99c99706fd49cabf2ecb3516643d23f09a"
},
"children": [
{
"id": "5675",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_fec89fa580d2d7c82276231c",
"parentId": "5674",
"isLeaf": true,
"molecule": {
"id": "sa_fec89fa580d2d7c82276231c",
"inchikey": "CFHGBZLNZZVTAY-UHFFFAOYSA-N",
"smiles": "COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1"
},
"smiles": "COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5676",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_182ea37026a9a7f9c5dadefa",
"parentId": "5674",
"isLeaf": false,
"molecule": {
"id": "sa_182ea37026a9a7f9c5dadefa",
"inchikey": "GIUJSRZLRLLGJL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)N1C(=O)COc2cc(C)c(Br)cc21"
},
"smiles": "CCOC(=O)C(C)N1C(=O)COc2cc(C)c(Br)cc21",
"reactionStepId": "sa_be4c66df5d876d850c214e8b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206663A1;1720;1554490\",\"rsmi\":\"O=C1CCC(=O)N1[Br:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][cH:16][c:18]([CH3:19])[cH:20]2>ClCCl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][c:16]([Br:17])[c:18]([CH3:19])[cH:20]2\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:17].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][cH:16][c:18]([CH3:19])[cH:20]2>ClCCl>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][c:16]([Br:17])[c:18]([CH3:19])[cH:20]2\"}",
"reactionStep": {
"id": "sa_be4c66df5d876d850c214e8b",
"reactionHash": "fb86c554e2e742a341d9db5e8bcd7b72d7228569f3479287400ccf880300acb5"
},
"children": [
{
"id": "5677",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_eed1832fb247e9c4275f64aa",
"parentId": "5676",
"isLeaf": false,
"molecule": {
"id": "sa_eed1832fb247e9c4275f64aa",
"inchikey": "FPVNYFLTTGFLIY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)N1C(=O)COc2cc(C)ccc21"
},
"smiles": "CCOC(=O)C(C)N1C(=O)COc2cc(C)ccc21",
"reactionStepId": "sa_545c86b2da46aa3a2264693b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206663A1;1718;1554489\",\"rsmi\":\"Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[NH:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19]2>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19]2\"},\"mapped_reaction_smiles\":\"Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[NH:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19]2>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][O:12][c:13]2[c:14]1[cH:15][cH:16][c:17]([CH3:18])[cH:19]2\"}",
"reactionStep": {
"id": "sa_545c86b2da46aa3a2264693b",
"reactionHash": "487ca57bfe8cab9721611c30fc27eac73f97f68d773a3e3278fb04f12cdf0412"
},
"children": [
{
"id": "5678",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_0edea11fc36bbfc57a5e83c2",
"parentId": "5677",
"isLeaf": true,
"molecule": {
"id": "sa_0edea11fc36bbfc57a5e83c2",
"inchikey": "ARFLASKVLJTEJD-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)Br"
},
"smiles": "CCOC(=O)C(C)Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5679",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_03b76dc10d886fafb0d9c8b8",
"parentId": "5677",
"isLeaf": false,
"molecule": {
"id": "sa_03b76dc10d886fafb0d9c8b8",
"inchikey": "XFJYLKINYUFREU-UHFFFAOYSA-N",
"smiles": "Cc1ccc2c(c1)OCC(O)=N2"
},
"smiles": "Cc1ccc2c(c1)OCC(=O)N2",
"reactionStepId": "sa_5a57e5d9635c14638543d245",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140206663A1;1716;1554488\",\"rsmi\":\"Cl[C:9](=[O:10])[CH2:11]Cl.[CH3:1][c:2]1[cH:3][c:4]([OH:12])[c:5]([NH2:8])[cH:6][cH:7]1>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.Br.[K+].[K+]>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[NH:8][C:9](=[O:10])[CH2:11][O:12]2\"},\"mapped_reaction_smiles\":\"Cl[C:9](=[O:10])[CH2:11]Cl.[CH3:1][c:2]1[cH:3][c:4]([OH:12])[c:5]([NH2:8])[cH:6][cH:7]1>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.Br.[K+].[K+]>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[NH:8][C:9](=[O:10])[CH2:11][O:12]2\"}",
"reactionStep": {
"id": "sa_5a57e5d9635c14638543d245",
"reactionHash": "44397046b5bfe75d2725403151693846c4b3ee0d742e262f3d93e25ea1c6bdc9"
},
"children": [
{
"id": "5680",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_371ad5a5ef04866af810abdd",
"parentId": "5679",
"isLeaf": true,
"molecule": {
"id": "sa_371ad5a5ef04866af810abdd",
"inchikey": "HCPJEHJGFKWRFM-UHFFFAOYSA-N",
"smiles": "Cc1ccc(N)c(O)c1"
},
"smiles": "Cc1ccc(N)c(O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5681",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_9bcb79a40efded362b9313ac",
"parentId": "5679",
"isLeaf": true,
"molecule": {
"id": "sa_9bcb79a40efded362b9313ac",
"inchikey": "VGCXGMAHQTYDJK-UHFFFAOYSA-N",
"smiles": "O=C(Cl)CCl"
},
"smiles": "O=C(Cl)CCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "5682",
"routeId": "sa_59099c806a6eba3a8bda6c72",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "5676",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}