Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21
InChiKey
SIIDRJFOXQBPHL-UHFFFAOYSA-N
Route Signature
49f93ad14f92f6999e0e3a5f8ff61fe281e429d74334164d8a4c192d47b9d154
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_6dba39dd1b18f45392402e91",
"signature": "49f93ad14f92f6999e0e3a5f8ff61fe281e429d74334164d8a4c192d47b9d154",
"contentHash": "d8cb21fb7631d6c02120a628a5d92a21ef153063532c22c3427e6f87ae531a3d",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_842c21ee0f6b23d7a9695af0",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00365",
"moleculeId": "sa_f8a676846d3a1fdc7975d15f",
"smiles": "CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f8a676846d3a1fdc7975d15f",
"inchikey": "SIIDRJFOXQBPHL-UHFFFAOYSA-N",
"smiles": "CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4121",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_f8a676846d3a1fdc7975d15f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f8a676846d3a1fdc7975d15f",
"inchikey": "SIIDRJFOXQBPHL-UHFFFAOYSA-N",
"smiles": "CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21"
},
"smiles": "CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21",
"reactionStepId": "sa_3de00dd4a2ef4522837ea65d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140371216A1;0478;1627082\",\"rsmi\":\"O=[C:15]([NH:14][c:13]1[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]1[NH2:20])[CH:16]1[CH2:17][CH2:18][CH2:19]1>CO.O.[Na+].O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]2[c:13]1[n:14][c:15]([CH:16]1[CH2:17][CH2:18][CH2:19]1)[nH:20]2\"},\"mapped_reaction_smiles\":\"O=[C:15]([NH:14][c:13]1[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]1[NH2:20])[CH:16]1[CH2:17][CH2:18][CH2:19]1>CO.O.[Na+].O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]2[c:13]1[n:14][c:15]([CH:16]1[CH2:17][CH2:18][CH2:19]1)[nH:20]2\"}",
"reactionStep": {
"id": "sa_3de00dd4a2ef4522837ea65d",
"reactionHash": "76c90eb2d97fa052de2e6cbda999acf69a4ab29cbc0c1a734a5fabdfeb9abcf4"
},
"children": [
{
"id": "4122",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_82aa447b24fe3ad07cd579a4",
"parentId": "4121",
"isLeaf": false,
"molecule": {
"id": "sa_82aa447b24fe3ad07cd579a4",
"inchikey": "YVHLGDWGAJENFC-UHFFFAOYSA-N",
"smiles": "CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S"
},
"smiles": "CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S",
"reactionStepId": "sa_b5bdb3fcb41aeb4769dc5265",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140371216A1;0476;1627081\",\"rsmi\":\"O[C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([NH2:13])[c:14]1[NH2:15]>CCN(CC)CC.CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[PH](F)(F)(F)(F)F.O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([NH2:13])[c:14]1[NH:15][C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21]1\"},\"mapped_reaction_smiles\":\"O[C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([NH2:13])[c:14]1[NH2:15]>CCN(CC)CC.CN(C)C=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[PH](F)(F)(F)(F)F.O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([NH2:13])[c:14]1[NH:15][C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21]1\"}",
"reactionStep": {
"id": "sa_b5bdb3fcb41aeb4769dc5265",
"reactionHash": "29bec593a9839a30d588f49b2e1b672ef6da540cf4e53ef2c49601ddec0ba6f5"
},
"children": [
{
"id": "4123",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_8a7e8e2c64e7e839a516d633",
"parentId": "4122",
"isLeaf": false,
"molecule": {
"id": "sa_8a7e8e2c64e7e839a516d633",
"inchikey": "GXLAPRKFYDNTKJ-UHFFFAOYSA-N",
"smiles": "CCCCCn1c(N)c(N)c(=O)[nH]c1=S"
},
"smiles": "CCCCCn1c(N)c(N)c(=O)[nH]c1=S",
"reactionStepId": "sa_3688f4ba20ef74c248ab11ad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140371216A1;0357;1627048\",\"rsmi\":\"O=[N:13][c:12]1[c:10](=[O:11])[nH:9][c:7](=[S:8])[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:14]1[NH2:15]>CC(=O)O.N.O.O=S(O)S(=O)O.[Na+].[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([NH2:13])[c:14]1[NH2:15]\"},\"mapped_reaction_smiles\":\"O=[N:13][c:12]1[c:10](=[O:11])[nH:9][c:7](=[S:8])[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:14]1[NH2:15]>CC(=O)O.N.O.O=S(O)S(=O)O.[Na+].[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([NH2:13])[c:14]1[NH2:15]\"}",
"reactionStep": {
"id": "sa_3688f4ba20ef74c248ab11ad",
"reactionHash": "1cd47c6447d72576216001be07c2ab93af984dc4bd9e65f51db08cbeb9172f7f"
},
"children": [
{
"id": "4124",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_71a7b9e31392ab341fc0ad44",
"parentId": "4123",
"isLeaf": false,
"molecule": {
"id": "sa_71a7b9e31392ab341fc0ad44",
"inchikey": "GYARZEHFEOGKPV-UHFFFAOYSA-N",
"smiles": "CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S"
},
"smiles": "CCCCCn1c(N)c(N=O)c(=O)[nH]c1=S",
"reactionStepId": "sa_80ed48753adc9e906868927a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140371216A1;0355;1627047\",\"rsmi\":\"[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[cH:12][c:15]1[NH2:16].O[N:13]=[O:14]>CC(=O)O.O.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([N:13]=[O:14])[c:15]1[NH2:16]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[cH:12][c:15]1[NH2:16].O[N:13]=[O:14]>CC(=O)O.O.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]([N:13]=[O:14])[c:15]1[NH2:16]\"}",
"reactionStep": {
"id": "sa_80ed48753adc9e906868927a",
"reactionHash": "c27751110d780378bdf99764600df1ef981e5c43c2813d47ab7ed1d06b9ecdd4"
},
"children": [
{
"id": "4125",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_81c0446884d57a7253ff6b54",
"parentId": "4124",
"isLeaf": true,
"molecule": {
"id": "sa_81c0446884d57a7253ff6b54",
"inchikey": "IOVCWXUNBOPUCH-UHFFFAOYSA-N",
"smiles": "[O-]N=[OH+]"
},
"smiles": "O=NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4126",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_503b75efdb02dc2c2bd07d5d",
"parentId": "4124",
"isLeaf": false,
"molecule": {
"id": "sa_503b75efdb02dc2c2bd07d5d",
"inchikey": "YHQOTTWJGCDALU-UHFFFAOYSA-N",
"smiles": "CCCCCn1c(N)cc(=O)[nH]c1=S"
},
"smiles": "CCCCCn1c(N)cc(=O)[nH]c1=S",
"reactionStepId": "sa_76644fd5ab80f79a0aa0d2ae",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140371216A1;0353;1627046\",\"rsmi\":\"CCO[C:10](=[O:11])[CH2:12][C:13]#[N:14].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[S:8])[NH2:9]>CC(=O)O.CCO.CCO.O.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[cH:12][c:13]1[NH2:14]\"},\"mapped_reaction_smiles\":\"CCO[C:10](=[O:11])[CH2:12][C:13]#[N:14].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[S:8])[NH2:9]>CC(=O)O.CCO.CCO.O.[Na+]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[cH:12][c:13]1[NH2:14]\"}",
"reactionStep": {
"id": "sa_76644fd5ab80f79a0aa0d2ae",
"reactionHash": "f0176415bf564e4dc35cbd244125c075b187f2a262559e916c01365f57cab603"
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"children": [
{
"id": "4127",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_92545e53517dcd1bd25dfc04",
"parentId": "4126",
"isLeaf": false,
"molecule": {
"id": "sa_92545e53517dcd1bd25dfc04",
"inchikey": "KIYXXKTUEPCNLC-UHFFFAOYSA-N",
"smiles": "CCCCCNC(N)=S"
},
"smiles": "CCCCCNC(N)=S",
"reactionStepId": "sa_2ca5e0681677bfff5cc0aaec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140371216A1;0351;1627045\",\"rsmi\":\"[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]=[C:7]=[S:9].[NH3:8]>CO>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[S:9]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]=[C:7]=[S:9].[NH3:8]>CO>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:8])=[S:9]\"}",
"reactionStep": {
"id": "sa_2ca5e0681677bfff5cc0aaec",
"reactionHash": "108c24cad65181b15eeb9d758070c6f757d07fe09034215a436674c2bcce3627"
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"children": [
{
"id": "4128",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "4127",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4129",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_a06279a29126db4d11bc1a8f",
"parentId": "4127",
"isLeaf": true,
"molecule": {
"id": "sa_a06279a29126db4d11bc1a8f",
"inchikey": "SGHJUJBYMSVAJY-UHFFFAOYSA-N",
"smiles": "CCCCCN=C=S"
},
"smiles": "CCCCCN=C=S",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "4130",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_065e13191da7c2aa80ed8ce8",
"parentId": "4126",
"isLeaf": true,
"molecule": {
"id": "sa_065e13191da7c2aa80ed8ce8",
"inchikey": "ZIUSEGSNTOUIPT-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CC#N"
},
"smiles": "CCOC(=O)CC#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "4131",
"routeId": "sa_6dba39dd1b18f45392402e91",
"moleculeId": "sa_615ecb8505a1052c94b168a6",
"parentId": "4122",
"isLeaf": true,
"molecule": {
"id": "sa_615ecb8505a1052c94b168a6",
"inchikey": "TXWOGHSRPAYOML-UHFFFAOYSA-N",
"smiles": "O=C(O)C1CCC1"
},
"smiles": "O=C(O)C1CCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}