Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)c1ccc(-c2ccc(C3CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1
InChiKey
AEONNZZSCMEECP-IZBOIQIVSA-N
Route Signature
fed06023a4283a91b5afaa4e5a2984f275f6983ead2bf8503fdb422b22885cb1
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_2916ac4f87ee2d21effd26bc",
"signature": "fed06023a4283a91b5afaa4e5a2984f275f6983ead2bf8503fdb422b22885cb1",
"contentHash": "2b9c045775eee49c29844f56abe131255d687a91f573007644c30dba9b898f88",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_0e119bc0fe5b6c8f630fc14e",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-09501",
"moleculeId": "sa_8318303887a342d7fb113cc9",
"smiles": "CNC(=O)c1ccc(-c2ccc(C3CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_8318303887a342d7fb113cc9",
"inchikey": "AEONNZZSCMEECP-IZBOIQIVSA-N",
"smiles": "CNC(=O)c1ccc(-c2ccc(C3CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "8975",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_8318303887a342d7fb113cc9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_8318303887a342d7fb113cc9",
"inchikey": "AEONNZZSCMEECP-IZBOIQIVSA-N",
"smiles": "CNC(=O)c1ccc(-c2ccc(C3CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1"
},
"smiles": "CNC(=O)c1ccc(-c2ccc(C3CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1",
"reactionStepId": "sa_6d85ced6e609131844a9450e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070208001A1;0499;491558\",\"rsmi\":\"[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([C:14]3=[CH:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]4[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1>CO.[Pd]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([CH:14]3[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]4[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([C:14]3=[CH:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]4[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1>CO.[Pd]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([CH:14]3[CH2:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]4[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_6d85ced6e609131844a9450e",
"reactionHash": "c1dc737de081faf01f3c705f417617e218966dc026b9147e6d937c5bbfd8ba29"
},
"children": [
{
"id": "8976",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_0e86250005140c2510416489",
"parentId": "8975",
"isLeaf": false,
"molecule": {
"id": "sa_0e86250005140c2510416489",
"inchikey": "SFHIKHKUNINKGT-WINZOAQQSA-N",
"smiles": "CNC(=O)c1ccc(-c2ccc(C3=CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1"
},
"smiles": "CNC(=O)c1ccc(-c2ccc(C3=CCC(C(=O)N[C@H]4CC[C@@H](O)CC4)CC3)c(C)c2)cc1",
"reactionStepId": "sa_703eaa2f061ad49d2a793acf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070208001A1;0496;491556\",\"rsmi\":\"Br[c:9]1[cH:10][c:11]([CH3:12])[c:13]([C:14]2=[CH:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]3[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1.OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:33][cH:32]1>C1COCCO1.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([C:14]3=[CH:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]4[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:10][c:11]([CH3:12])[c:13]([C:14]2=[CH:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]3[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1.OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:33][cH:32]1>C1COCCO1.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([CH3:12])[c:13]([C:14]3=[CH:15][CH2:16][CH:17]([C:18](=[O:19])[NH:20][C@H:21]4[CH2:22][CH2:23][C@@H:24]([OH:25])[CH2:26][CH2:27]4)[CH2:28][CH2:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_703eaa2f061ad49d2a793acf",
"reactionHash": "c3e5500a07d913b884714a4b6e940b7796ef2ef8f8a66bb65a217765f71b405c"
},
"children": [
{
"id": "8977",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_10c1b45ed3885d256a995b50",
"parentId": "8976",
"isLeaf": true,
"molecule": {
"id": "sa_10c1b45ed3885d256a995b50",
"inchikey": "UWKSYZHFTGONHY-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1ccc(B(O)O)cc1"
},
"smiles": "CNC(=O)c1ccc(B(O)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8978",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_cd4e8e5112b68c8cace0fa5f",
"parentId": "8976",
"isLeaf": false,
"molecule": {
"id": "sa_cd4e8e5112b68c8cace0fa5f",
"inchikey": "WXWOTCVEDJDIJV-ZNXRZULTSA-N",
"smiles": "Cc1cc(Br)ccc1C1=CCC(C(=O)N[C@H]2CC[C@@H](O)CC2)CC1"
},
"smiles": "Cc1cc(Br)ccc1C1=CCC(C(=O)N[C@H]2CC[C@@H](O)CC2)CC1",
"reactionStepId": "sa_c855094e9a82582b7538175b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070208001A1;0488;491553\",\"rsmi\":\"O[C:4]1([c:3]2[c:2]([CH3:1])[cH:24][c:22]([Br:23])[cH:21][cH:20]2)[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[NH:10][C@H:11]2[CH2:12][CH2:13][C@@H:14]([OH:15])[CH2:16][CH2:17]2)[CH2:18][CH2:19]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][CH:7]([C:8](=[O:9])[NH:10][C@H:11]3[CH2:12][CH2:13][C@@H:14]([OH:15])[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21][c:22]([Br:23])[cH:24]1\"},\"mapped_reaction_smiles\":\"O[C:4]1([c:3]2[c:2]([CH3:1])[cH:24][c:22]([Br:23])[cH:21][cH:20]2)[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[NH:10][C@H:11]2[CH2:12][CH2:13][C@@H:14]([OH:15])[CH2:16][CH2:17]2)[CH2:18][CH2:19]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][CH:7]([C:8](=[O:9])[NH:10][C@H:11]3[CH2:12][CH2:13][C@@H:14]([OH:15])[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21][c:22]([Br:23])[cH:24]1\"}",
"reactionStep": {
"id": "sa_c855094e9a82582b7538175b",
"reactionHash": "b6fa03a37b94086b9f33f87847c2d744b6bad71607f5524ac265336c54fcb76c"
},
"children": [
{
"id": "8979",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_5dc65fd3605f9d0c38dd3a06",
"parentId": "8978",
"isLeaf": false,
"molecule": {
"id": "sa_5dc65fd3605f9d0c38dd3a06",
"inchikey": "PXJQNBLIHNNZBB-TUDZEASDSA-N",
"smiles": "Cc1cc(Br)ccc1C1(O)CCC(C(=O)N[C@H]2CC[C@@H](O)CC2)CC1"
},
"smiles": "Cc1cc(Br)ccc1C1(O)CCC(C(=O)N[C@H]2CC[C@@H](O)CC2)CC1",
"reactionStepId": "sa_510efd802ab743833218ce93",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070208001A1;0486;491552\",\"rsmi\":\"O[C:9]([CH:8]1[CH2:7][CH2:6][C:4]([c:3]2[c:2]([CH3:1])[cH:25][c:23]([Br:24])[cH:22][cH:21]2)([OH:5])[CH2:20][CH2:19]1)=[O:10].[NH2:11][C@H:12]1[CH2:13][CH2:14][C@@H:15]([OH:16])[CH2:17][CH2:18]1>CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CN1CCOCC1.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][c:2]1[c:3]([C:4]2([OH:5])[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([OH:16])[CH2:17][CH2:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22][c:23]([Br:24])[cH:25]1\"},\"mapped_reaction_smiles\":\"O[C:9]([CH:8]1[CH2:7][CH2:6][C:4]([c:3]2[c:2]([CH3:1])[cH:25][c:23]([Br:24])[cH:22][cH:21]2)([OH:5])[CH2:20][CH2:19]1)=[O:10].[NH2:11][C@H:12]1[CH2:13][CH2:14][C@@H:15]([OH:16])[CH2:17][CH2:18]1>CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CN1CCOCC1.Cl.F[PH](F)(F)(F)(F)F>[CH3:1][c:2]1[c:3]([C:4]2([OH:5])[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([OH:16])[CH2:17][CH2:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22][c:23]([Br:24])[cH:25]1\"}",
"reactionStep": {
"id": "sa_510efd802ab743833218ce93",
"reactionHash": "6a64f235fcc157113fe6010d29d9e3db203eba4b558820e7a777f93e62ded980"
},
"children": [
{
"id": "8980",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_4137887f268cb55ce991f4f5",
"parentId": "8979",
"isLeaf": true,
"molecule": {
"id": "sa_4137887f268cb55ce991f4f5",
"inchikey": "IMLXLGZJLAOKJN-OLQVQODUSA-N",
"smiles": "N[C@H]1CC[C@@H](O)CC1"
},
"smiles": "N[C@H]1CC[C@@H](O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8981",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_ad9181601baaa4a00a889a6e",
"parentId": "8979",
"isLeaf": false,
"molecule": {
"id": "sa_ad9181601baaa4a00a889a6e",
"inchikey": "WNFMFZXVWUKWJV-UHFFFAOYSA-N",
"smiles": "Cc1cc(Br)ccc1C1(O)CCC(C(=O)O)CC1"
},
"smiles": "Cc1cc(Br)ccc1C1(O)CCC(C(=O)O)CC1",
"reactionStepId": "sa_053ef2408b504c821a5c9828",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070208001A1;0484;491551\",\"rsmi\":\"CC[O:11][C:9]([CH:8]1[CH2:7][CH2:6][C:4]([c:3]2[c:2]([CH3:1])[cH:18][c:16]([Br:17])[cH:15][cH:14]2)([OH:5])[CH2:13][CH2:12]1)=[O:10]>CO.O.O.[Li+].O>[CH3:1][c:2]1[c:3]([C:4]2([OH:5])[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH2:13]2)[cH:14][cH:15][c:16]([Br:17])[cH:18]1\"},\"mapped_reaction_smiles\":\"CC[O:11][C:9]([CH:8]1[CH2:7][CH2:6][C:4]([c:3]2[c:2]([CH3:1])[cH:18][c:16]([Br:17])[cH:15][cH:14]2)([OH:5])[CH2:13][CH2:12]1)=[O:10]>CO.O.O.[Li+].O>[CH3:1][c:2]1[c:3]([C:4]2([OH:5])[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH2:13]2)[cH:14][cH:15][c:16]([Br:17])[cH:18]1\"}",
"reactionStep": {
"id": "sa_053ef2408b504c821a5c9828",
"reactionHash": "fcbac8d52b0ffdac667a238c763a0f0e27277fa19c4a91c03b92eac62be7d755"
},
"children": [
{
"id": "8982",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_d2ef6ea24cbd3f8f5e14a8a6",
"parentId": "8981",
"isLeaf": false,
"molecule": {
"id": "sa_d2ef6ea24cbd3f8f5e14a8a6",
"inchikey": "JZUZLIABMGCZGW-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCC(O)(c2ccc(Br)cc2C)CC1"
},
"smiles": "CCOC(=O)C1CCC(O)(c2ccc(Br)cc2C)CC1",
"reactionStepId": "sa_e87afb7a5b25c8221caec9f8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070208001A1;0482;491550\",\"rsmi\":\"I[c:11]1[c:12]([CH3:13])[cH:14][c:15]([Br:16])[cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[CH2:19][CH2:20]1>C1CCOC1.CC(C)[Mg]Br>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9]([OH:10])([c:11]2[c:12]([CH3:13])[cH:14][c:15]([Br:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"I[c:11]1[c:12]([CH3:13])[cH:14][c:15]([Br:16])[cH:17][cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[CH2:19][CH2:20]1>C1CCOC1.CC(C)[Mg]Br>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9]([OH:10])([c:11]2[c:12]([CH3:13])[cH:14][c:15]([Br:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1\"}",
"reactionStep": {
"id": "sa_e87afb7a5b25c8221caec9f8",
"reactionHash": "ae24d9b9295c18becb73b348d077f64c62f9bb1de55bed1926d0a989c8d8863a"
},
"children": [
{
"id": "8983",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_b58aa14a82999c2943cc78b1",
"parentId": "8982",
"isLeaf": true,
"molecule": {
"id": "sa_b58aa14a82999c2943cc78b1",
"inchikey": "GHTUADBHTFHMNI-UHFFFAOYSA-N",
"smiles": "Cc1cc(Br)ccc1I"
},
"smiles": "Cc1cc(Br)ccc1I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8984",
"routeId": "sa_2916ac4f87ee2d21effd26bc",
"moleculeId": "sa_f570bbe35c9787d7cf1cc093",
"parentId": "8982",
"isLeaf": true,
"molecule": {
"id": "sa_f570bbe35c9787d7cf1cc093",
"inchikey": "ZXYAWONOWHSQRU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1CCC(=O)CC1"
},
"smiles": "CCOC(=O)C1CCC(=O)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
]
}
}