Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)N(CC(=O)NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1)S(=O)(=O)c1ccc(F)cc1
InChiKey
USAKNJFJFIOYMS-UHFFFAOYSA-N
Route Signature
e003d8ef5d7a3b074216caba9a27477ed347443268611638a92496ee542dad71
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f31d0ac32f10b19a1b5007dd",
"signature": "e003d8ef5d7a3b074216caba9a27477ed347443268611638a92496ee542dad71",
"contentHash": "1e8dbe448a56eb573f4dbe064baf2dc52d323c2a7a43a4c698127088c7464688",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_b4f8d6542a947537f7fc4698",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01381",
"moleculeId": "sa_66f55dcf945991ac904fc0b6",
"smiles": "CC(C)N(CC(=O)NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1)S(=O)(=O)c1ccc(F)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_66f55dcf945991ac904fc0b6",
"inchikey": "USAKNJFJFIOYMS-UHFFFAOYSA-N",
"smiles": "CC(C)N(CC(=O)NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1)S(=O)(=O)c1ccc(F)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10117",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_66f55dcf945991ac904fc0b6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_66f55dcf945991ac904fc0b6",
"inchikey": "USAKNJFJFIOYMS-UHFFFAOYSA-N",
"smiles": "CC(C)N(CC(=O)NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "CC(C)N(CC(=O)NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_f33946d0233696b8c5cd579a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150197509A1;0583;1722737\",\"rsmi\":\"O[C:6]([CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1)=[O:7].[NH2:8][CH2:9][c:10]1[n:11][cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[n:23][cH:24]2)[cH:25]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[n:11][cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[n:23][cH:24]2)[cH:25]1)[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"O[C:6]([CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1)=[O:7].[NH2:8][CH2:9][c:10]1[n:11][cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[n:23][cH:24]2)[cH:25]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[n:11][cH:12][n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[n:23][cH:24]2)[cH:25]1)[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_f33946d0233696b8c5cd579a",
"reactionHash": "fc578a72ba7bf2f65f02c87df519c9f9cf230db5af52234d3dbebd10e6acf2e8"
},
"children": [
{
"id": "10118",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_612ec3126844f631c6eb2ba9",
"parentId": "10117",
"isLeaf": false,
"molecule": {
"id": "sa_612ec3126844f631c6eb2ba9",
"inchikey": "GUVJJZHGUBAILY-UHFFFAOYSA-N",
"smiles": "NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1"
},
"smiles": "NCc1cc(-c2ccc(C(F)(F)F)nc2)ncn1",
"reactionStepId": "sa_71376e8c1e632803f5d56867",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150197509A1;0582;1722736\",\"rsmi\":\"[N:1]#[C:2][c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1>CCO.[H][H].[Pd]>[NH2:1][CH2:2][c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"[N:1]#[C:2][c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1>CCO.[H][H].[Pd]>[NH2:1][CH2:2][c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_71376e8c1e632803f5d56867",
"reactionHash": "d80093688827487b2e148886a88b9f0ee442ae377dd11d87f89829ee7f4e27b8"
},
"children": [
{
"id": "10119",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_4ee37942f9887c1aac419546",
"parentId": "10118",
"isLeaf": false,
"molecule": {
"id": "sa_4ee37942f9887c1aac419546",
"inchikey": "DJVNFLRRQADOHZ-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(-c2ccc(C(F)(F)F)nc2)ncn1"
},
"smiles": "N#Cc1cc(-c2ccc(C(F)(F)F)nc2)ncn1",
"reactionStepId": "sa_4900f4b5c8ecd6e964690f3c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150197509A1;0581;1722735\",\"rsmi\":\"Cl[c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1.[N:1]#[CH:2]>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.CCN(CC)CC.CCOCC>[N:1]#[C:2][c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"Cl[c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1.[N:1]#[CH:2]>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.CCN(CC)CC.CCOCC>[N:1]#[C:2][c:3]1[n:4][cH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][cH:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_4900f4b5c8ecd6e964690f3c",
"reactionHash": "366d6f941077ea309aa7199c0b98bbe39ea64d3cbadf6ab1bef29342c2c60338"
},
"children": [
{
"id": "10120",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "10119",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10121",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_b76b533e5cad57b52f3f51fb",
"parentId": "10119",
"isLeaf": true,
"molecule": {
"id": "sa_b76b533e5cad57b52f3f51fb",
"inchikey": "UUVHCYYYFHRZOS-UHFFFAOYSA-N",
"smiles": "FC(F)(F)c1ccc(-c2cc(Cl)ncn2)cn1"
},
"smiles": "FC(F)(F)c1ccc(-c2cc(Cl)ncn2)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10122",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_8704915d8d4da806332afaa6",
"parentId": "10117",
"isLeaf": false,
"molecule": {
"id": "sa_8704915d8d4da806332afaa6",
"inchikey": "PPZCMLQRAJNTOP-UHFFFAOYSA-N",
"smiles": "CC(C)N(CC(=O)O)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "CC(C)N(CC(=O)O)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_ae9ce0e8af6f0496a2fcb2d8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150197509A1;0635;1722772\",\"rsmi\":\"C[O:8][C:6]([CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)=[O:7]>C1CCOC1.O.[Li+].O>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6](=[O:7])[OH:8])[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"C[O:8][C:6]([CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)=[O:7]>C1CCOC1.O.[Li+].O>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6](=[O:7])[OH:8])[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_ae9ce0e8af6f0496a2fcb2d8",
"reactionHash": "f61406fd136e4d2f386040cf07fd54a23afa318744b3565c5748baf074f369b7"
},
"children": [
{
"id": "10123",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_3a21e20570da86c662d6a32f",
"parentId": "10122",
"isLeaf": false,
"molecule": {
"id": "sa_3a21e20570da86c662d6a32f",
"inchikey": "GCCPEGVEWFUGIS-UHFFFAOYSA-N",
"smiles": "COC(=O)CN(C(C)C)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "COC(=O)CN(C(C)C)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_ca13cf47ceab705fa5c7cdf7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150197509A1;0634;1722771\",\"rsmi\":\"Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:7]([CH3:8])[CH3:9]>CCN(C(C)C)C(C)C.CN(C)c1ccncc1.ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([CH:7]([CH3:8])[CH3:9])[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:7]([CH3:8])[CH3:9]>CCN(C(C)C)C(C)C.CN(C)c1ccncc1.ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]([CH:7]([CH3:8])[CH3:9])[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_ca13cf47ceab705fa5c7cdf7",
"reactionHash": "b5c548e530de73c91ceb0474a2632e92ecbb01bf3b352519bbdd70639395bd39"
},
"children": [
{
"id": "10124",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_fc86336e1b262adfba88e57f",
"parentId": "10123",
"isLeaf": true,
"molecule": {
"id": "sa_fc86336e1b262adfba88e57f",
"inchikey": "BFXHJFKKRGVUMU-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccc(F)cc1"
},
"smiles": "O=S(=O)(Cl)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10125",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_248b08de60343279513f463d",
"parentId": "10123",
"isLeaf": false,
"molecule": {
"id": "sa_248b08de60343279513f463d",
"inchikey": "JFDSZJZAEPWYJL-UHFFFAOYSA-N",
"smiles": "COC(=O)CNC(C)C"
},
"smiles": "COC(=O)CNC(C)C",
"reactionStepId": "sa_9f0551493ecaeae2897ee0b3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150197509A1;0633;1722770\",\"rsmi\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][CH:7]([CH3:8])[CH3:9]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:7]([CH3:8])[CH3:9]\"},\"mapped_reaction_smiles\":\"Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][CH:7]([CH3:8])[CH3:9]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][CH:7]([CH3:8])[CH3:9]\"}",
"reactionStep": {
"id": "sa_9f0551493ecaeae2897ee0b3",
"reactionHash": "22ef0e265f4cb45eff8ebe02ac7ff44f2a580d34afc71732f172ab096f9bb29a"
},
"children": [
{
"id": "10126",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_2e72c1c53065e4af6ee24789",
"parentId": "10125",
"isLeaf": true,
"molecule": {
"id": "sa_2e72c1c53065e4af6ee24789",
"inchikey": "JJWLVOIRVHMVIS-UHFFFAOYSA-N",
"smiles": "CC(C)N"
},
"smiles": "CC(C)N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10127",
"routeId": "sa_f31d0ac32f10b19a1b5007dd",
"moleculeId": "sa_d6971278542e932ae568b29f",
"parentId": "10125",
"isLeaf": true,
"molecule": {
"id": "sa_d6971278542e932ae568b29f",
"inchikey": "YDCHPLOFQATIDS-UHFFFAOYSA-N",
"smiles": "COC(=O)CBr"
},
"smiles": "COC(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}