Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@H]1C(=O)NC[C@@H]1C(=O)Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1
InChiKey
HKQCVLMFGGWDCL-DYVFJYSZSA-N
Route Signature
7eb54b8ab9b1ec820d0d3bb6568faf4ec1f1b6b8e52d3a22b4e63cb41a3f5c68
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_de4e0b22440afc9315e34504",
"signature": "7eb54b8ab9b1ec820d0d3bb6568faf4ec1f1b6b8e52d3a22b4e63cb41a3f5c68",
"contentHash": "7f28e85364115c68253b4796b56a5c14c52babd9b7163ab6b3ec08092e175469",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_d01ecbaa0ad92f2e2a6cb8a1",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-03028",
"moleculeId": "sa_d5b2700d0da36f6a1dc6305c",
"smiles": "C[C@H]1C(=O)NC[C@@H]1C(=O)Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d5b2700d0da36f6a1dc6305c",
"inchikey": "HKQCVLMFGGWDCL-DYVFJYSZSA-N",
"smiles": "C[C@H]1C(=O)NC[C@@H]1C(=O)Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10956",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_d5b2700d0da36f6a1dc6305c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d5b2700d0da36f6a1dc6305c",
"inchikey": "HKQCVLMFGGWDCL-DYVFJYSZSA-N",
"smiles": "C[C@H]1C(=O)NC[C@@H]1C(=O)Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1"
},
"smiles": "C[C@H]1C(=O)NC[C@@H]1C(=O)Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1",
"reactionStepId": "sa_1e0f51e859cd9d87d015002b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150183763A1;0717;1715556\",\"rsmi\":\"O[C:8]([C@@H:7]1[C@@H:2]([CH3:1])[C:3](=[O:4])[NH:5][CH2:6]1)=[O:9].[NH2:10][c:11]1[n:12][n:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29][cH:30][cH:31]2)[cH:32]1>CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21>[CH3:1][C@H:2]1[C:3](=[O:4])[NH:5][CH2:6][C@@H:7]1[C:8](=[O:9])[NH:10][c:11]1[n:12][n:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29][cH:30][cH:31]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"O[C:8]([C@@H:7]1[C@@H:2]([CH3:1])[C:3](=[O:4])[NH:5][CH2:6]1)=[O:9].[NH2:10][c:11]1[n:12][n:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29][cH:30][cH:31]2)[cH:32]1>CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21>[CH3:1][C@H:2]1[C:3](=[O:4])[NH:5][CH2:6][C@@H:7]1[C:8](=[O:9])[NH:10][c:11]1[n:12][n:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29][cH:30][cH:31]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_1e0f51e859cd9d87d015002b",
"reactionHash": "681f3a649d3543143296d6dc1c2cfde8c7a1c054801bd5091ed649e7f6a6b38b"
},
"children": [
{
"id": "10957",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_0e4c461d81846d575f6bd03f",
"parentId": "10956",
"isLeaf": false,
"molecule": {
"id": "sa_0e4c461d81846d575f6bd03f",
"inchikey": "JHOVNMQPIDWADE-UHFFFAOYSA-N",
"smiles": "Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1"
},
"smiles": "Nc1cc(-c2cccc(OC(F)(F)F)c2)n(-c2ccccc2)n1",
"reactionStepId": "sa_464e64e779df895ce73d2a26",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150183763A1;0714;1715555\",\"rsmi\":\"I[c:11]1[n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:3][c:2]([NH2:1])[cH:23]1.OB(O)[c:12]1[cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)O.CC(=O)O.COCCOC.O=C(O)O.O=C(O)O.[Na+].[Na+].[Na+].[Pd+2]>[NH2:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11](-[c:12]2[cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22]2)[cH:23]1\"},\"mapped_reaction_smiles\":\"I[c:11]1[n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:3][c:2]([NH2:1])[cH:23]1.OB(O)[c:12]1[cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)O.CC(=O)O.COCCOC.O=C(O)O.O=C(O)O.[Na+].[Na+].[Na+].[Pd+2]>[NH2:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11](-[c:12]2[cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21][cH:22]2)[cH:23]1\"}",
"reactionStep": {
"id": "sa_464e64e779df895ce73d2a26",
"reactionHash": "18a13fe03645d1a773c95e85f2c70464f843be4e2af50b68dfb373b844d46912"
},
"children": [
{
"id": "10958",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_b472a6baac5f8892eee2c0c5",
"parentId": "10957",
"isLeaf": false,
"molecule": {
"id": "sa_b472a6baac5f8892eee2c0c5",
"inchikey": "DDMHKKCOMUSKRE-UHFFFAOYSA-N",
"smiles": "Nc1cc(I)n(-c2ccccc2)n1"
},
"smiles": "Nc1cc(I)n(-c2ccccc2)n1",
"reactionStepId": "sa_138070ed2e5c2141b8bbcc79",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150183763A1;0711;1715554\",\"rsmi\":\"Cc1ccc(C)[n:1]1-[c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([I:12])[cH:13]1>CCN(CC)CC.CCO.O.Cl.NO>[NH2:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([I:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"Cc1ccc(C)[n:1]1-[c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([I:12])[cH:13]1>CCN(CC)CC.CCO.O.Cl.NO>[NH2:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([I:12])[cH:13]1\"}",
"reactionStep": {
"id": "sa_138070ed2e5c2141b8bbcc79",
"reactionHash": "3a0833a4eb39a01667daa42d76c642ec172beb1abdb7309dfb13b2cddb286235"
},
"children": [
{
"id": "10959",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_8ffb23593264907e7568cfcc",
"parentId": "10958",
"isLeaf": false,
"molecule": {
"id": "sa_8ffb23593264907e7568cfcc",
"inchikey": "OGRDYJYNFFDNJA-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C)n1-c1cc(I)n(-c2ccccc2)n1"
},
"smiles": "Cc1ccc(C)n1-c1cc(I)n(-c2ccccc2)n1",
"reactionStepId": "sa_e9f07044062b051bbcc42fa0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150183763A1;0708;1715553\",\"rsmi\":\"I[I:18].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:19]1>C1CCOC1.O.O=S(O)O.[Li]CCCC.[Na+]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([I:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"I[I:18].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:19]1>C1CCOC1.O.O=S(O)O.[Li]CCCC.[Na+]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([I:18])[cH:19]1\"}",
"reactionStep": {
"id": "sa_e9f07044062b051bbcc42fa0",
"reactionHash": "0b4cc6a7ec01fbb1893ba237c98b99ecd96bf180a2594d5a677de0314176c4fc"
},
"children": [
{
"id": "10960",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_d9b8fd92b0cc1ed1551c5e82",
"parentId": "10959",
"isLeaf": false,
"molecule": {
"id": "sa_d9b8fd92b0cc1ed1551c5e82",
"inchikey": "AXERCXZFJKVWEZ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C)n1-c1ccn(-c2ccccc2)n1"
},
"smiles": "Cc1ccc(C)n1-c1ccn(-c2ccccc2)n1",
"reactionStepId": "sa_a2cf9187df38b8a180cf580e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150183763A1;0705;1715552\",\"rsmi\":\"O=[C:2]([CH3:1])[CH2:3][CH2:4][C:5](=O)[CH3:6].[NH2:7][c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>CC(=O)O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[C:2]([CH3:1])[CH2:3][CH2:4][C:5](=O)[CH3:6].[NH2:7][c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>CC(=O)O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[n:7]1-[c:8]1[n:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_a2cf9187df38b8a180cf580e",
"reactionHash": "58fec6d3c886a044af556699b99ef28b65caecd834b1fc48690f6b911e0b2ec3"
},
"children": [
{
"id": "10961",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_b3b333af71e7097427cef3a3",
"parentId": "10960",
"isLeaf": true,
"molecule": {
"id": "sa_b3b333af71e7097427cef3a3",
"inchikey": "BQQFSUKXGGGGLV-UHFFFAOYSA-N",
"smiles": "Nc1ccn(-c2ccccc2)n1"
},
"smiles": "Nc1ccn(-c2ccccc2)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10962",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_49458ddbe3fb90e1e95d8e58",
"parentId": "10960",
"isLeaf": true,
"molecule": {
"id": "sa_49458ddbe3fb90e1e95d8e58",
"inchikey": "OJVAMHKKJGICOG-UHFFFAOYSA-N",
"smiles": "CC(=O)CCC(C)=O"
},
"smiles": "CC(=O)CCC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10963",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_bc6c113460696c6012e3bdf5",
"parentId": "10959",
"isLeaf": true,
"molecule": {
"id": "sa_bc6c113460696c6012e3bdf5",
"inchikey": "PNDPGZBMCMUPRI-UHFFFAOYSA-N",
"smiles": "II"
},
"smiles": "II",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "10964",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_eb565db57e227dc8868eb5e9",
"parentId": "10957",
"isLeaf": true,
"molecule": {
"id": "sa_eb565db57e227dc8868eb5e9",
"inchikey": "UWDFWVLAHRQSKK-UHFFFAOYSA-N",
"smiles": "OB(O)c1cccc(OC(F)(F)F)c1"
},
"smiles": "OB(O)c1cccc(OC(F)(F)F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10965",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_69bfb555783cae97c7fdcce1",
"parentId": "10956",
"isLeaf": false,
"molecule": {
"id": "sa_69bfb555783cae97c7fdcce1",
"inchikey": "RTGUJFWBQLNZDR-DMTCNVIQSA-N",
"smiles": "C[C@H]1C(=O)NC[C@@H]1C(=O)O"
},
"smiles": "C[C@H]1C(=O)NC[C@@H]1C(=O)O",
"reactionStepId": "sa_89e32dca741d9cede115887d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150183763A1;0696;1715550\",\"rsmi\":\"COc1ccc(C[N:5]2[C:3](=[O:4])[C@H:2]([CH3:1])[C@@H:7]([C:8](=[O:9])[OH:10])[CH2:6]2)c(OC)c1>COc1ccccc1.O=C(O)C(F)(F)F>[CH3:1][C@H:2]1[C:3](=[O:4])[NH:5][CH2:6][C@@H:7]1[C:8](=[O:9])[OH:10]\"},\"mapped_reaction_smiles\":\"COc1ccc(C[N:5]2[C:3](=[O:4])[C@H:2]([CH3:1])[C@@H:7]([C:8](=[O:9])[OH:10])[CH2:6]2)c(OC)c1>COc1ccccc1.O=C(O)C(F)(F)F>[CH3:1][C@H:2]1[C:3](=[O:4])[NH:5][CH2:6][C@@H:7]1[C:8](=[O:9])[OH:10]\"}",
"reactionStep": {
"id": "sa_89e32dca741d9cede115887d",
"reactionHash": "ad91c55765152c67d81f578f9dc88af62c5539b357e79b8ba7d53fe94891c3c9"
},
"children": [
{
"id": "10966",
"routeId": "sa_de4e0b22440afc9315e34504",
"moleculeId": "sa_297a001fb5eb57ed17c2f7c6",
"parentId": "10965",
"isLeaf": true,
"molecule": {
"id": "sa_297a001fb5eb57ed17c2f7c6",
"inchikey": "RLYAPKHVGSBBJN-SKDRFNHKSA-N",
"smiles": "COc1ccc(CN2C[C@H](C(=O)O)[C@@H](C)C2=O)c(OC)c1"
},
"smiles": "COc1ccc(CN2C[C@H](C(=O)O)[C@@H](C)C2=O)c(OC)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}