Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(C#CC(C)(C)C)c(F)c3)[nH]c2=O)c1
InChiKey
NQEQEGJGTIMTFM-UHFFFAOYSA-N
Route Signature
e128177b12323473432db61e22f2a61016c0f7cc9be45541cf5740178fb5be5e
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d5684d9e63e91ed235d15684",
"signature": "e128177b12323473432db61e22f2a61016c0f7cc9be45541cf5740178fb5be5e",
"contentHash": "7088807e2f72f89359b93d60c162c543f62e1832ab7a79446cad705828d6d667",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_63f5e1f0d9e2a0c3e67959fe",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01049",
"moleculeId": "sa_394cb0950cb9a62861eb85da",
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(C#CC(C)(C)C)c(F)c3)[nH]c2=O)c1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_394cb0950cb9a62861eb85da",
"inchikey": "NQEQEGJGTIMTFM-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(C#CC(C)(C)C)c(F)c3)[nH]c2=O)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9927",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_394cb0950cb9a62861eb85da",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_394cb0950cb9a62861eb85da",
"inchikey": "NQEQEGJGTIMTFM-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(C#CC(C)(C)C)c(F)c3)[nH]c2=O)c1"
},
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(C#CC(C)(C)C)c(F)c3)[nH]c2=O)c1",
"reactionStepId": "sa_68cb0b80c324db06bddf04c4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09439890B2;1132;1803861\",\"rsmi\":\"I[c:18]1[c:16]([F:17])[cH:15][c:14](-[c:13]2[n:12][n:11](-[c:10]3[cH:9][c:8]([CH2:7][NH:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[cH:33][cH:32][c:30]3[Cl:31])[c:28](=[O:29])[nH:27]2)[cH:26][cH:25]1.[CH:19]#[C:20][C:21]([CH3:22])([CH3:23])[CH3:24]>CCCC[N+](CCCC)(CCCC)CCCC.CS(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.F>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10](-[n:11]2[n:12][c:13](-[c:14]3[cH:15][c:16]([F:17])[c:18]([C:19]#[C:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]3)[nH:27][c:28]2=[O:29])[c:30]([Cl:31])[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"I[c:18]1[c:16]([F:17])[cH:15][c:14](-[c:13]2[n:12][n:11](-[c:10]3[cH:9][c:8]([CH2:7][NH:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[cH:33][cH:32][c:30]3[Cl:31])[c:28](=[O:29])[nH:27]2)[cH:26][cH:25]1.[CH:19]#[C:20][C:21]([CH3:22])([CH3:23])[CH3:24]>CCCC[N+](CCCC)(CCCC)CCCC.CS(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.F>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10](-[n:11]2[n:12][c:13](-[c:14]3[cH:15][c:16]([F:17])[c:18]([C:19]#[C:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]3)[nH:27][c:28]2=[O:29])[c:30]([Cl:31])[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_68cb0b80c324db06bddf04c4",
"reactionHash": "0fe367971c2495d129bce48657fcc7e49a77a0da93b263b477bef6ee9359d70e"
},
"children": [
{
"id": "9928",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_39263692e20ad625e368ab8b",
"parentId": "9927",
"isLeaf": false,
"molecule": {
"id": "sa_39263692e20ad625e368ab8b",
"inchikey": "ABWDDRPCFJQDQR-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(I)c(F)c3)[nH]c2=O)c1"
},
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(-n2nc(-c3ccc(I)c(F)c3)[nH]c2=O)c1",
"reactionStepId": "sa_830f807e1746e09080d7f4ea",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09439890B2;1131;1803860\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:12][NH:11][c:10]1[cH:9][c:8]([CH2:7][NH:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[cH:28][cH:27][c:25]1[Cl:26].O=[C:13]([c:14]1[cH:15][c:16]([F:17])[c:18]([I:19])[cH:20][cH:21]1)[N:22]=[C:23]=[O:24]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10](-[n:11]2[n:12][c:13](-[c:14]3[cH:15][c:16]([F:17])[c:18]([I:19])[cH:20][cH:21]3)[nH:22][c:23]2=[O:24])[c:25]([Cl:26])[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:12][NH:11][c:10]1[cH:9][c:8]([CH2:7][NH:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[cH:28][cH:27][c:25]1[Cl:26].O=[C:13]([c:14]1[cH:15][c:16]([F:17])[c:18]([I:19])[cH:20][cH:21]1)[N:22]=[C:23]=[O:24]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10](-[n:11]2[n:12][c:13](-[c:14]3[cH:15][c:16]([F:17])[c:18]([I:19])[cH:20][cH:21]3)[nH:22][c:23]2=[O:24])[c:25]([Cl:26])[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_830f807e1746e09080d7f4ea",
"reactionHash": "93bc6632777dcd7c1a13343d63f9924bb219d6d82456c9b689f7e531be03060c"
},
"children": [
{
"id": "9929",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_1be2d41798be746eea75ad2c",
"parentId": "9928",
"isLeaf": false,
"molecule": {
"id": "sa_1be2d41798be746eea75ad2c",
"inchikey": "DRURXXDJDCJTEK-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(NNC(=O)OC(C)(C)C)c1"
},
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(NNC(=O)OC(C)(C)C)c1",
"reactionStepId": "sa_9139b1d72c67f90f6739e093",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09439890B2;0769;1803706\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10]([NH:11][NH2:12])[c:20]([Cl:21])[cH:22][cH:23]1>CC#N.O.O=C(O)O.[Na+].[Na+]>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10]([NH:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([Cl:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10]([NH:11][NH2:12])[c:20]([Cl:21])[cH:22][cH:23]1>CC#N.O.O=C(O)O.[Na+].[Na+]>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10]([NH:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([Cl:21])[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_9139b1d72c67f90f6739e093",
"reactionHash": "c14bab8e63b1d99a0a7d23978381ca7970fce7b7275cbd8a31bcffbb295bbbdc"
},
"children": [
{
"id": "9930",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_7808a01b37c6fad5f981eacd",
"parentId": "9929",
"isLeaf": true,
"molecule": {
"id": "sa_7808a01b37c6fad5f981eacd",
"inchikey": "AVFCDDBPCILHDF-UHFFFAOYSA-N",
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(NN)c1"
},
"smiles": "CC(C)C(=O)NCc1ccc(Cl)c(NN)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9931",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "9929",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9932",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_a43828aa96464f573e91adb3",
"parentId": "9928",
"isLeaf": false,
"molecule": {
"id": "sa_a43828aa96464f573e91adb3",
"inchikey": "WRKQVXWQQJQIER-UHFFFAOYSA-N",
"smiles": "O=C=NC(=O)c1ccc(I)c(F)c1"
},
"smiles": "O=C=NC(=O)c1ccc(I)c(F)c1",
"reactionStepId": "sa_2ef8f605b4070483292121e2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09439890B2;0781;1803712\",\"rsmi\":\"O=C(Cl)[C:2](Cl)=[O:1].[NH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12][cH:13]1>ClCCCl>[O:1]=[C:2]=[N:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=C(Cl)[C:2](Cl)=[O:1].[NH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12][cH:13]1>ClCCCl>[O:1]=[C:2]=[N:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_2ef8f605b4070483292121e2",
"reactionHash": "18db8232524b415e374030932daf434533a696d5bee4e5c550ac79c09a170824"
},
"children": [
{
"id": "9933",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_83e7d4ec882b44062b48ca58",
"parentId": "9932",
"isLeaf": true,
"molecule": {
"id": "sa_83e7d4ec882b44062b48ca58",
"inchikey": "CTSLXHKWHWQRSH-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C(=O)Cl"
},
"smiles": "O=C(Cl)C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9934",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_585cc043a0a478ec55f0b417",
"parentId": "9932",
"isLeaf": false,
"molecule": {
"id": "sa_585cc043a0a478ec55f0b417",
"inchikey": "OSZKPQBHGLYYIZ-UHFFFAOYSA-N",
"smiles": "NC(=O)c1ccc(I)c(F)c1"
},
"smiles": "NC(=O)c1ccc(I)c(F)c1",
"reactionStepId": "sa_aa6d87fd1fdb672a91738676",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09439890B2;0780;1803711\",\"rsmi\":\"O[OH:3].[N:1]#[C:2][c:4]1[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][cH:11]1>CS(C)=O.O=C(O)O.[K+].[K+]>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O[OH:3].[N:1]#[C:2][c:4]1[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][cH:11]1>CS(C)=O.O=C(O)O.[K+].[K+]>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][cH:11]1\"}",
"reactionStep": {
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"reactionHash": "f4196ab37cbd94853cbba4c5d3c2a6c6de95130aa1343e0ae343a8e6a183eee1"
},
"children": [
{
"id": "9935",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_4dba68d938224067da688ab5",
"parentId": "9934",
"isLeaf": true,
"molecule": {
"id": "sa_4dba68d938224067da688ab5",
"inchikey": "MHAJPDPJQMAIIY-UHFFFAOYSA-N",
"smiles": "OO"
},
"smiles": "OO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9936",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_68862592e8f1744bfbbc2dd8",
"parentId": "9934",
"isLeaf": true,
"molecule": {
"id": "sa_68862592e8f1744bfbbc2dd8",
"inchikey": "NPKQMCCUPXZXFI-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(I)c(F)c1"
},
"smiles": "N#Cc1ccc(I)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "9937",
"routeId": "sa_d5684d9e63e91ed235d15684",
"moleculeId": "sa_e4ae78c928ea5a44c128fa17",
"parentId": "9927",
"isLeaf": true,
"molecule": {
"id": "sa_e4ae78c928ea5a44c128fa17",
"inchikey": "PPWNCLVNXGCGAF-UHFFFAOYSA-N",
"smiles": "C#CC(C)(C)C"
},
"smiles": "C#CC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}