Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CNC(=O)c3[nH]cnc3Cl)c2F)c1
InChiKey
XNJGUANOIXQQLT-UHFFFAOYSA-N
Route Signature
4ec3aec1d52e01c5bab69d8793dd339c366ceb8c75e874318c00cc514b561f75
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_286d461a7b5d0df6935e47d2",
"signature": "4ec3aec1d52e01c5bab69d8793dd339c366ceb8c75e874318c00cc514b561f75",
"contentHash": "c70c62e028280a30253d5e1bac7bacdf10d653cea8382f9fff87c6e7a312024b",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_63097dfd981e4d9750c4c356",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00169",
"moleculeId": "sa_1ed856d1432e3d3fa06bbf96",
"smiles": "N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CNC(=O)c3[nH]cnc3Cl)c2F)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1ed856d1432e3d3fa06bbf96",
"inchikey": "XNJGUANOIXQQLT-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CNC(=O)c3[nH]cnc3Cl)c2F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12614",
"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_1ed856d1432e3d3fa06bbf96",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1ed856d1432e3d3fa06bbf96",
"inchikey": "XNJGUANOIXQQLT-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CNC(=O)c3[nH]cnc3Cl)c2F)c1"
},
"smiles": "N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CNC(=O)c3[nH]cnc3Cl)c2F)c1",
"reactionStepId": "sa_070bac1552ac0938972be549",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08304419B2;0981;1247773\",\"rsmi\":\"C[Si](C)(C)CCOC[n:22]1[c:17]([C:15](O)=[O:16])[c:18]([Cl:19])[n:20][cH:21]1.[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([Cl:9])[cH:10][cH:11][c:12]([CH2:13][NH2:14])[c:23]2[F:24])[c:25]([Cl:26])[c:27]([F:28])[cH:29]1>C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[PH](F)(F)(F)(F)F>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([Cl:9])[cH:10][cH:11][c:12]([CH2:13][NH:14][C:15](=[O:16])[c:17]3[c:18]([Cl:19])[n:20][cH:21][nH:22]3)[c:23]2[F:24])[c:25]([Cl:26])[c:27]([F:28])[cH:29]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)CCOC[n:22]1[c:17]([C:15](O)=[O:16])[c:18]([Cl:19])[n:20][cH:21]1.[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([Cl:9])[cH:10][cH:11][c:12]([CH2:13][NH2:14])[c:23]2[F:24])[c:25]([Cl:26])[c:27]([F:28])[cH:29]1>C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[PH](F)(F)(F)(F)F>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([Cl:9])[cH:10][cH:11][c:12]([CH2:13][NH:14][C:15](=[O:16])[c:17]3[c:18]([Cl:19])[n:20][cH:21][nH:22]3)[c:23]2[F:24])[c:25]([Cl:26])[c:27]([F:28])[cH:29]1\"}",
"reactionStep": {
"id": "sa_070bac1552ac0938972be549",
"reactionHash": "14b633f6f21928201510328be88a9b062b44ed425750e18720887c15573274a4"
},
"children": [
{
"id": "12615",
"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_ae5e3ff3dca92ad1cb07bbc5",
"parentId": "12614",
"isLeaf": false,
"molecule": {
"id": "sa_ae5e3ff3dca92ad1cb07bbc5",
"inchikey": "HAKFWWNVLXQNPY-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CN)c2F)c1"
},
"smiles": "N#Cc1cc(F)c(Cl)c(Oc2c(Cl)ccc(CN)c2F)c1",
"reactionStepId": "sa_1e4b710ff6b477a6f2b1c724",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08304419B2;0980;1247772\",\"rsmi\":\"Br[c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH2:11][NH2:12])[cH:13][cH:14][c:15]2[Cl:16])[c:17]([Cl:18])[c:19]([F:20])[cH:21]1.N#C[Zn][C:2]#[N:1]>CCCO.CN(C)C=O.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH2:11][NH2:12])[cH:13][cH:14][c:15]2[Cl:16])[c:17]([Cl:18])[c:19]([F:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"Br[c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH2:11][NH2:12])[cH:13][cH:14][c:15]2[Cl:16])[c:17]([Cl:18])[c:19]([F:20])[cH:21]1.N#C[Zn][C:2]#[N:1]>CCCO.CN(C)C=O.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH2:11][NH2:12])[cH:13][cH:14][c:15]2[Cl:16])[c:17]([Cl:18])[c:19]([F:20])[cH:21]1\"}",
"reactionStep": {
"id": "sa_1e4b710ff6b477a6f2b1c724",
"reactionHash": "fe2193a532138fdf5f3900ed8cf4dbcfd9c24b3a0ac21ea706ab9e0bc9cd7cb7"
},
"children": [
{
"id": "12616",
"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_d1368d4c4e62cf344c92689c",
"parentId": "12615",
"isLeaf": false,
"molecule": {
"id": "sa_d1368d4c4e62cf344c92689c",
"inchikey": "DGRSHCXMPDQVGC-UHFFFAOYSA-N",
"smiles": "NCc1ccc(Cl)c(Oc2cc(Br)cc(F)c2Cl)c1F"
},
"smiles": "NCc1ccc(Cl)c(Oc2cc(Br)cc(F)c2Cl)c1F",
"reactionStepId": "sa_c19826fe3840b11a8d2f5ce9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08304419B2;0977;1247770\",\"rsmi\":\"[N-]=[N+]=[N:1][CH2:2][c:3]1[c:4]([F:5])[c:6]([O:7][c:8]2[c:9]([Cl:10])[c:11]([F:12])[cH:13][c:14]([Br:15])[cH:16]2)[c:17]([Cl:18])[cH:19][cH:20]1>C1CCOC1.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[NH2:1][CH2:2][c:3]1[c:4]([F:5])[c:6]([O:7][c:8]2[c:9]([Cl:10])[c:11]([F:12])[cH:13][c:14]([Br:15])[cH:16]2)[c:17]([Cl:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:1][CH2:2][c:3]1[c:4]([F:5])[c:6]([O:7][c:8]2[c:9]([Cl:10])[c:11]([F:12])[cH:13][c:14]([Br:15])[cH:16]2)[c:17]([Cl:18])[cH:19][cH:20]1>C1CCOC1.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[NH2:1][CH2:2][c:3]1[c:4]([F:5])[c:6]([O:7][c:8]2[c:9]([Cl:10])[c:11]([F:12])[cH:13][c:14]([Br:15])[cH:16]2)[c:17]([Cl:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_c19826fe3840b11a8d2f5ce9",
"reactionHash": "4ef0ea23e7a8c386f04741c066dd6240da5a625386ff4026398bbaa0d5b8f86b"
},
"children": [
{
"id": "12617",
"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_b5bbe9bdf1ecd6c6678519b5",
"parentId": "12616",
"isLeaf": false,
"molecule": {
"id": "sa_b5bbe9bdf1ecd6c6678519b5",
"inchikey": "ITTMDOANRBMSHQ-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCc1ccc(Cl)c(Oc2cc(Br)cc(F)c2Cl)c1F"
},
"smiles": "[N-]=[N+]=NCc1ccc(Cl)c(Oc2cc(Br)cc(F)c2Cl)c1F",
"reactionStepId": "sa_740b80b524182f97f8d15d62",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08304419B2;0976;1247769\",\"rsmi\":\"Br[CH2:4][c:5]1[c:6]([F:7])[c:8]([O:9][c:10]2[c:11]([Cl:12])[c:13]([F:14])[cH:15][c:16]([Br:17])[cH:18]2)[c:19]([Cl:20])[cH:21][cH:22]1.[N-:1]=[N+:2]=[N-:3]>CCOC(C)=O.CS(C)=O.[Na+]>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[c:6]([F:7])[c:8]([O:9][c:10]2[c:11]([Cl:12])[c:13]([F:14])[cH:15][c:16]([Br:17])[cH:18]2)[c:19]([Cl:20])[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Br[CH2:4][c:5]1[c:6]([F:7])[c:8]([O:9][c:10]2[c:11]([Cl:12])[c:13]([F:14])[cH:15][c:16]([Br:17])[cH:18]2)[c:19]([Cl:20])[cH:21][cH:22]1.[N-:1]=[N+:2]=[N-:3]>CCOC(C)=O.CS(C)=O.[Na+]>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[c:6]([F:7])[c:8]([O:9][c:10]2[c:11]([Cl:12])[c:13]([F:14])[cH:15][c:16]([Br:17])[cH:18]2)[c:19]([Cl:20])[cH:21][cH:22]1\"}",
"reactionStep": {
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"reactionHash": "d0894f3e743e84b70a0f2dddad741a0be5cab5918d8ebfd23198969dc01aed51"
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"children": [
{
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"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "12617",
"isLeaf": true,
"molecule": {
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"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12619",
"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_e7808af56ffe5c4ecd48a5ad",
"parentId": "12617",
"isLeaf": false,
"molecule": {
"id": "sa_e7808af56ffe5c4ecd48a5ad",
"inchikey": "RULQKBBAMXCMGI-UHFFFAOYSA-N",
"smiles": "Fc1cc(Br)cc(Oc2c(Cl)ccc(CBr)c2F)c1Cl"
},
"smiles": "Fc1cc(Br)cc(Oc2c(Cl)ccc(CBr)c2F)c1Cl",
"reactionStepId": "sa_5b1530392f0580161f1fd605",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08304419B2;0975;1247768\",\"rsmi\":\"O=C1CCC(=O)N1[Br:16].[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([O:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]([CH3:15])[c:17]2[F:18])[c:19]1[Cl:20]>CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl>[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([O:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]([CH2:15][Br:16])[c:17]2[F:18])[c:19]1[Cl:20]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:16].[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([O:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]([CH3:15])[c:17]2[F:18])[c:19]1[Cl:20]>CC(C)(C#N)N=NC(C)(C)C#N.ClC(Cl)(Cl)Cl>[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([O:8][c:9]2[c:10]([Cl:11])[cH:12][cH:13][c:14]([CH2:15][Br:16])[c:17]2[F:18])[c:19]1[Cl:20]\"}",
"reactionStep": {
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"reactionHash": "7b649ff21b35061a16d78dfe08709582428715dd3415d6e8bb085ad44af0198f"
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"children": [
{
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"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_0bb02f5630ed0400fafa8ee2",
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"isLeaf": false,
"molecule": {
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"inchikey": "AUXUEBFJMBIKPG-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Cl)c(Oc2cc(Br)cc(F)c2Cl)c1F"
},
"smiles": "Cc1ccc(Cl)c(Oc2cc(Br)cc(F)c2Cl)c1F",
"reactionStepId": "sa_900792b9547f21d502eceb81",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08304419B2;0974;1247767\",\"rsmi\":\"F[c:7]1[c:8]([Cl:9])[c:10]([F:11])[cH:12][c:13]([Br:14])[cH:15]1.[CH3:1][c:2]1[c:3]([F:4])[c:5]([OH:6])[c:16]([Cl:17])[cH:18][cH:19]1>C1CCOC1.C1COCCOCCOCCOCCOCCO1.CC(C)(C)O.CS(C)=O.[K+]>[CH3:1][c:2]1[c:3]([F:4])[c:5]([O:6][c:7]2[c:8]([Cl:9])[c:10]([F:11])[cH:12][c:13]([Br:14])[cH:15]2)[c:16]([Cl:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"F[c:7]1[c:8]([Cl:9])[c:10]([F:11])[cH:12][c:13]([Br:14])[cH:15]1.[CH3:1][c:2]1[c:3]([F:4])[c:5]([OH:6])[c:16]([Cl:17])[cH:18][cH:19]1>C1CCOC1.C1COCCOCCOCCOCCOCCO1.CC(C)(C)O.CS(C)=O.[K+]>[CH3:1][c:2]1[c:3]([F:4])[c:5]([O:6][c:7]2[c:8]([Cl:9])[c:10]([F:11])[cH:12][c:13]([Br:14])[cH:15]2)[c:16]([Cl:17])[cH:18][cH:19]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"inchikey": "HCZRPIVKIPIGDM-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Cl)c(O)c1F"
},
"smiles": "Cc1ccc(Cl)c(O)c1F",
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},
{
"id": "12622",
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"molecule": {
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"inchikey": "SWELJVAWQMCJLG-UHFFFAOYSA-N",
"smiles": "Fc1cc(Br)cc(F)c1Cl"
},
"smiles": "Fc1cc(Br)cc(F)c1Cl",
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}
]
},
{
"id": "12623",
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"molecule": {
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"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
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}
]
}
]
}
]
},
{
"id": "12624",
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"moleculeId": "sa_5dd167b03df19e637a07c8d1",
"parentId": "12615",
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"molecule": {
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"inchikey": "VJHHEOJUJAQMPF-UHFFFAOYSA-N",
"smiles": "N#[C][Zn][C]#N"
},
"smiles": "N#[C][Zn][C]#N",
"reactionStepId": null,
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}
]
},
{
"id": "12625",
"routeId": "sa_286d461a7b5d0df6935e47d2",
"moleculeId": "sa_888235b7b2d241bd5313f796",
"parentId": "12614",
"isLeaf": true,
"molecule": {
"id": "sa_888235b7b2d241bd5313f796",
"inchikey": "NSZRCRJAYJQOIH-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)CCOCn1cnc(Cl)c1C(=O)O"
},
"smiles": "C[Si](C)(C)CCOCn1cnc(Cl)c1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}