Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)c1c[nH]c(C(=O)NCc2ccc(Cl)c(Oc3cc(Cl)cc(C#N)c3)c2F)c1Cl
InChiKey
SOXVDHSPYFKTRM-UHFFFAOYSA-N
Route Signature
4e66c99c5068afb47e5dda8b1f057c32b56fa4970ce7f8ecd597c6a23eb795b9
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_2aede9d57e1df48231efde2b",
"signature": "4e66c99c5068afb47e5dda8b1f057c32b56fa4970ce7f8ecd597c6a23eb795b9",
"contentHash": "c0976d61978d432c3afbef06960bb921720fe199069aee21054db8410e838ac8",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_8cdb3549bbacba06c864c55f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00954",
"moleculeId": "sa_03566785a88356d4050b5811",
"smiles": "CNC(=O)c1c[nH]c(C(=O)NCc2ccc(Cl)c(Oc3cc(Cl)cc(C#N)c3)c2F)c1Cl",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_03566785a88356d4050b5811",
"inchikey": "SOXVDHSPYFKTRM-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c[nH]c(C(=O)NCc2ccc(Cl)c(Oc3cc(Cl)cc(C#N)c3)c2F)c1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9811",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_03566785a88356d4050b5811",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_03566785a88356d4050b5811",
"inchikey": "SOXVDHSPYFKTRM-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c[nH]c(C(=O)NCc2ccc(Cl)c(Oc3cc(Cl)cc(C#N)c3)c2F)c1Cl"
},
"smiles": "CNC(=O)c1c[nH]c(C(=O)NCc2ccc(Cl)c(Oc3cc(Cl)cc(C#N)c3)c2F)c1Cl",
"reactionStepId": "sa_10dd54d24cf61a7bc7363a0d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100216746A1;1204;936071\",\"rsmi\":\"CO[C:9]([c:8]1[nH:7][cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:31]1[Cl:32])=[O:10].[NH2:11][CH2:12][c:13]1[c:14]([F:15])[c:16]([O:17][c:18]2[cH:19][c:20]([Cl:21])[cH:22][c:23]([C:24]#[N:25])[cH:26]2)[c:27]([Cl:28])[cH:29][cH:30]1>C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F.O.[Li+].O>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([C:9](=[O:10])[NH:11][CH2:12][c:13]2[c:14]([F:15])[c:16]([O:17][c:18]3[cH:19][c:20]([Cl:21])[cH:22][c:23]([C:24]#[N:25])[cH:26]3)[c:27]([Cl:28])[cH:29][cH:30]2)[c:31]1[Cl:32]\"},\"mapped_reaction_smiles\":\"CO[C:9]([c:8]1[nH:7][cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:31]1[Cl:32])=[O:10].[NH2:11][CH2:12][c:13]1[c:14]([F:15])[c:16]([O:17][c:18]2[cH:19][c:20]([Cl:21])[cH:22][c:23]([C:24]#[N:25])[cH:26]2)[c:27]([Cl:28])[cH:29][cH:30]1>C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F.O.[Li+].O>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([C:9](=[O:10])[NH:11][CH2:12][c:13]2[c:14]([F:15])[c:16]([O:17][c:18]3[cH:19][c:20]([Cl:21])[cH:22][c:23]([C:24]#[N:25])[cH:26]3)[c:27]([Cl:28])[cH:29][cH:30]2)[c:31]1[Cl:32]\"}",
"reactionStep": {
"id": "sa_10dd54d24cf61a7bc7363a0d",
"reactionHash": "9e56b5565a4166183b6336d9d0fbc7a7891af1f1ea3d40201679318b7f52e244"
},
"children": [
{
"id": "9812",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_9ba9feea209453910dc80aad",
"parentId": "9811",
"isLeaf": false,
"molecule": {
"id": "sa_9ba9feea209453910dc80aad",
"inchikey": "MTVQDSLJBBNYPP-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c[nH]c(C(=O)OC)c1Cl"
},
"smiles": "CNC(=O)c1c[nH]c(C(=O)OC)c1Cl",
"reactionStepId": "sa_c7a5267f5482c8d946cf4a66",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100216746A1;1203;936070\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[c:13]1[Cl:14].[CH3:1][NH2:2]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[c:13]1[Cl:14]\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[c:13]1[Cl:14].[CH3:1][NH2:2]>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[c:13]1[Cl:14]\"}",
"reactionStep": {
"id": "sa_c7a5267f5482c8d946cf4a66",
"reactionHash": "a84af3d13936a8b47cb14795a5b67d8304debd2b9d56f44f0211ac38cfaacc52"
},
"children": [
{
"id": "9813",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "9812",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9814",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_e2713c7f4f44d600ff9b375b",
"parentId": "9812",
"isLeaf": true,
"molecule": {
"id": "sa_e2713c7f4f44d600ff9b375b",
"inchikey": "QORKFPKYZXOBQY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1[nH]cc(C(=O)O)c1Cl"
},
"smiles": "COC(=O)c1[nH]cc(C(=O)O)c1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9815",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_6a397a0d6de98a6bf3637e07",
"parentId": "9811",
"isLeaf": false,
"molecule": {
"id": "sa_6a397a0d6de98a6bf3637e07",
"inchikey": "WCXOLXMRYQMCRI-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(Cl)cc(Oc2c(Cl)ccc(CN)c2F)c1"
},
"smiles": "N#Cc1cc(Cl)cc(Oc2c(Cl)ccc(CN)c2F)c1",
"reactionStepId": "sa_08ea0d63358cff4ce0917628",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100216746A1;0515;935822\",\"rsmi\":\"Br[CH2:11][c:10]1[c:8]([F:9])[c:7]([O:6][c:5]2[cH:4][c:3]([C:2]#[N:1])[cH:20][c:18]([Cl:19])[cH:17]2)[c:15]([Cl:16])[cH:14][cH:13]1.[NH3:12]>CO.ClCCl>[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])[cH:17][c:18]([Cl:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"Br[CH2:11][c:10]1[c:8]([F:9])[c:7]([O:6][c:5]2[cH:4][c:3]([C:2]#[N:1])[cH:20][c:18]([Cl:19])[cH:17]2)[c:15]([Cl:16])[cH:14][cH:13]1.[NH3:12]>CO.ClCCl>[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])[cH:17][c:18]([Cl:19])[cH:20]1\"}",
"reactionStep": {
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"reactionHash": "047998bbd4a9f091513133300e45a395e30302e73b34f6330b663173f178c430"
},
"children": [
{
"id": "9816",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_ef9ab4697bbaef1e7ac7a7fb",
"parentId": "9815",
"isLeaf": false,
"molecule": {
"id": "sa_ef9ab4697bbaef1e7ac7a7fb",
"inchikey": "GJJRWDOMQXGDBK-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(Cl)cc(Oc2c(Cl)ccc(CBr)c2F)c1"
},
"smiles": "N#Cc1cc(Cl)cc(Oc2c(Cl)ccc(CBr)c2F)c1",
"reactionStepId": "sa_6695cf56bbccad8a125a5673",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100216746A1;0513;935821\",\"rsmi\":\"O=C1CCC(=O)N1[Br:12].[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH3:11])[cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]([Cl:19])[cH:20]1>ClC(Cl)(Cl)Cl>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH2:11][Br:12])[cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]([Cl:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:12].[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH3:11])[cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]([Cl:19])[cH:20]1>ClC(Cl)(Cl)Cl>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][c:7]2[c:8]([F:9])[c:10]([CH2:11][Br:12])[cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]([Cl:19])[cH:20]1\"}",
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"children": [
{
"id": "9817",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "9816",
"isLeaf": true,
"molecule": {
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"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9818",
"routeId": "sa_2aede9d57e1df48231efde2b",
"moleculeId": "sa_167062d8993acf56d6781c6f",
"parentId": "9816",
"isLeaf": false,
"molecule": {
"id": "sa_167062d8993acf56d6781c6f",
"inchikey": "ZSWXSINGKZZWMW-UHFFFAOYSA-N",
"smiles": "Cc1ccc(Cl)c(Oc2cc(Cl)cc(C#N)c2)c1F"
},
"smiles": "Cc1ccc(Cl)c(Oc2cc(Cl)cc(C#N)c2)c1F",
"reactionStepId": "sa_bff1a927c1a2555d1d9ff2b4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100216746A1;0511;935820\",\"rsmi\":\"N[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:18]([F:19])[c:7]1[O:8][c:9]1[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([Cl:16])[cH:17]1.[ClH:6]>CC#N.CC(C)(C)ON=O.CCOC(C)=O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[c:7]([O:8][c:9]2[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([Cl:16])[cH:17]2)[c:18]1[F:19]\"},\"mapped_reaction_smiles\":\"N[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:18]([F:19])[c:7]1[O:8][c:9]1[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([Cl:16])[cH:17]1.[ClH:6]>CC#N.CC(C)(C)ON=O.CCOC(C)=O>[CH3:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[c:7]([O:8][c:9]2[cH:10][c:11]([C:12]#[N:13])[cH:14][c:15]([Cl:16])[cH:17]2)[c:18]1[F:19]\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_f00fe4bc04e21997e2ed2f5b",
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"molecule": {
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"smiles": "Cc1ccc(N)c(Oc2cc(Cl)cc(C#N)c2)c1F"
},
"smiles": "Cc1ccc(N)c(Oc2cc(Cl)cc(C#N)c2)c1F",
"reactionStepId": "sa_be5906d02e0f12df7ea0d731",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100216746A1;0509;935819\",\"rsmi\":\"O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:18]([F:19])[c:7]1[O:8][c:9]1[cH:10][c:11]([Cl:12])[cH:13][c:14]([C:15]#[N:16])[cH:17]1>C1CCOC1.CCOC(C)=O.O.O=S(O)S(=O)O.[Na+].[Na+]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:7]([O:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][c:14]([C:15]#[N:16])[cH:17]2)[c:18]1[F:19]\"},\"mapped_reaction_smiles\":\"O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:18]([F:19])[c:7]1[O:8][c:9]1[cH:10][c:11]([Cl:12])[cH:13][c:14]([C:15]#[N:16])[cH:17]1>C1CCOC1.CCOC(C)=O.O.O=S(O)S(=O)O.[Na+].[Na+]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:7]([O:8][c:9]2[cH:10][c:11]([Cl:12])[cH:13][c:14]([C:15]#[N:16])[cH:17]2)[c:18]1[F:19]\"}",
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"children": [
{
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"parentId": "9819",
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"molecule": {
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},
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},
{
"id": "9821",
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"molecule": {
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"smiles": "Cl"
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}
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]
},
{
"id": "9822",
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"molecule": {
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"smiles": "N"
},
"smiles": "N",
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}
]
}
]
}
}