Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)c2cc(C(C)C)nn12
InChiKey
FBOBBIQRVQOSMF-UHFFFAOYSA-N
Route Signature
c36a68ec4586c75356bacdc3e2de59b121719193c7f29e86be76af858d1fc622
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_bfde7d6c741a210d60014e47",
"signature": "c36a68ec4586c75356bacdc3e2de59b121719193c7f29e86be76af858d1fc622",
"contentHash": "85255c047837352e32a1471990aa8e67cba9492083d830cc28867a4ea4660355",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_eab21bbff5ab89b3b2df820b",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00250",
"moleculeId": "sa_4e04d76b2bacb5671bf0b63c",
"smiles": "COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)c2cc(C(C)C)nn12",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_4e04d76b2bacb5671bf0b63c",
"inchikey": "FBOBBIQRVQOSMF-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)c2cc(C(C)C)nn12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12927",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_4e04d76b2bacb5671bf0b63c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4e04d76b2bacb5671bf0b63c",
"inchikey": "FBOBBIQRVQOSMF-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)c2cc(C(C)C)nn12"
},
"smiles": "COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)c2cc(C(C)C)nn12",
"reactionStepId": "sa_3be409c61631e7edf5bf83db",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0379;846427\",\"rsmi\":\"O=[N+]([O-])c1ccc(O[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:25]3[c:18]2[cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[n:24]3)=[O:8])cc1.[NH2:9][c:10]1[c:11]([Cl:12])[cH:13][n:14][cH:15][c:16]1[Cl:17]>CN(C)C=O.Cl.[HH].N.[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[c:11]([Cl:12])[cH:13][n:14][cH:15][c:16]2[Cl:17])[c:18]2[cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[n:24][n:25]12\"},\"mapped_reaction_smiles\":\"O=[N+]([O-])c1ccc(O[C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:25]3[c:18]2[cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[n:24]3)=[O:8])cc1.[NH2:9][c:10]1[c:11]([Cl:12])[cH:13][n:14][cH:15][c:16]1[Cl:17]>CN(C)C=O.Cl.[HH].N.[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[c:11]([Cl:12])[cH:13][n:14][cH:15][c:16]2[Cl:17])[c:18]2[cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[n:24][n:25]12\"}",
"reactionStep": {
"id": "sa_3be409c61631e7edf5bf83db",
"reactionHash": "824a8058b69c8300b41033acac91ed4860d2b8cc08cd92b69a8a379662e54a72"
},
"children": [
{
"id": "12928",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_4adc93cbab3cc37279c6a2d6",
"parentId": "12927",
"isLeaf": true,
"molecule": {
"id": "sa_4adc93cbab3cc37279c6a2d6",
"inchikey": "ISIQAMHROGZHOV-UHFFFAOYSA-N",
"smiles": "N=c1c(Cl)c[nH]cc1Cl"
},
"smiles": "Nc1c(Cl)cncc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12929",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_476b1045c75a332d2ded12b9",
"parentId": "12927",
"isLeaf": false,
"molecule": {
"id": "sa_476b1045c75a332d2ded12b9",
"inchikey": "USQZZIXXZBBPGK-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)Oc2ccc([N+](=O)[O-])cc2)c2cc(C(C)C)nn12"
},
"smiles": "COc1ccc(C(=O)Oc2ccc([N+](=O)[O-])cc2)c2cc(C(C)C)nn12",
"reactionStepId": "sa_89d689fabd0bb57b222e3dd3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0376;846426\",\"rsmi\":\"O[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:19]2[cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[n:25][n:26]12>CCN=C=NCCCN(C)C.CN(C)c1ccccn1.Cl.ClCCl.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[c:19]2[cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[n:25][n:26]12\"},\"mapped_reaction_smiles\":\"O[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:19]2[cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[n:25][n:26]12>CCN=C=NCCCN(C)C.CN(C)c1ccccn1.Cl.ClCCl.O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[c:19]2[cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[n:25][n:26]12\"}",
"reactionStep": {
"id": "sa_89d689fabd0bb57b222e3dd3",
"reactionHash": "461003fe5e03521888bf246f12ac25626bd058b81a269340ecfa1052cfac7fef"
},
"children": [
{
"id": "12930",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_147b4db36ece2bc0cf54b265",
"parentId": "12929",
"isLeaf": true,
"molecule": {
"id": "sa_147b4db36ece2bc0cf54b265",
"inchikey": "BTJIUGUIPKRLHP-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(O)cc1"
},
"smiles": "O=[N+]([O-])c1ccc(O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12931",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_f6138c8625aa64f614a4f5ec",
"parentId": "12929",
"isLeaf": false,
"molecule": {
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"inchikey": "PPOLRTCKWXWFDN-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)O)c2cc(C(C)C)nn12"
},
"smiles": "COc1ccc(C(=O)O)c2cc(C(C)C)nn12",
"reactionStepId": "sa_3036724d780025422d4de774",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0373;846425\",\"rsmi\":\"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:10]2[cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[n:16][n:17]12.[OH2:9]>O.O=[N+]([O-])O.[Ag+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[n:16][n:17]12\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:10]2[cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[n:16][n:17]12.[OH2:9]>O.O=[N+]([O-])O.[Ag+].[Na+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[n:16][n:17]12\"}",
"reactionStep": {
"id": "sa_3036724d780025422d4de774",
"reactionHash": "9ea2e7830fcbf040fe48ffba1dfd4559f0d77e497a0703864bad255b4d11b880"
},
"children": [
{
"id": "12932",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_78c27ec79b64543b4ad4e43f",
"parentId": "12931",
"isLeaf": false,
"molecule": {
"id": "sa_78c27ec79b64543b4ad4e43f",
"inchikey": "RZTANVXXIDNRJY-UHFFFAOYSA-N",
"smiles": "COc1ccc(C=O)c2cc(C(C)C)nn12"
},
"smiles": "COc1ccc(C=O)c2cc(C(C)C)nn12",
"reactionStepId": "sa_dda2b6002b24b0188dc15c42",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0370;846424\",\"rsmi\":\"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[n:15][n:16]12>ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]2[cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[n:15][n:16]12\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[n:15][n:16]12>ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]2[cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[n:15][n:16]12\"}",
"reactionStep": {
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"reactionHash": "907a797ccc06fdec6841daaab7efebe6987b2394608821911817c3fd1a54fa27"
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"children": [
{
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"moleculeId": "sa_2639c203f7da52127f5da1ba",
"parentId": "12932",
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"molecule": {
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"inchikey": "OBMHJKUWMNDWSJ-UHFFFAOYSA-N",
"smiles": "COc1ccc(CO)c2cc(C(C)C)nn12"
},
"smiles": "COc1ccc(CO)c2cc(C(C)C)nn12",
"reactionStepId": "sa_cd83ce36797ba29e186ee048",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0367;846423\",\"rsmi\":\"O=C(O)[c:10]1[c:9]2[c:6]([CH2:7][OH:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[n:16]2[n:15][c:11]1[CH:12]([CH3:13])[CH3:14]>Clc1ccccc1Cl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[n:15][n:16]12\"},\"mapped_reaction_smiles\":\"O=C(O)[c:10]1[c:9]2[c:6]([CH2:7][OH:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[n:16]2[n:15][c:11]1[CH:12]([CH3:13])[CH3:14]>Clc1ccccc1Cl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[n:15][n:16]12\"}",
"reactionStep": {
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"children": [
{
"id": "12934",
"routeId": "sa_bfde7d6c741a210d60014e47",
"moleculeId": "sa_2066b13f18b58559b7fc1fae",
"parentId": "12933",
"isLeaf": false,
"molecule": {
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"inchikey": "AMNRXVURESTCRB-UHFFFAOYSA-N",
"smiles": "COc1ccc(CO)c2c(C(=O)O)c(C(C)C)nn12"
},
"smiles": "COc1ccc(CO)c2c(C(=O)O)c(C(C)C)nn12",
"reactionStepId": "sa_eb627cec095bfc73997b3d50",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0364;846422\",\"rsmi\":\"c1ccc(C[O:13][C:11]([c:10]2[c:9]3[c:6]([CH2:7][OH:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[n:19]3[n:18][c:14]2[CH:15]([CH3:16])[CH3:17])=[O:12])cc1>CCO.O.[K+].O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[c:10]([C:11](=[O:12])[OH:13])[c:14]([CH:15]([CH3:16])[CH3:17])[n:18][n:19]12\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:13][C:11]([c:10]2[c:9]3[c:6]([CH2:7][OH:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[n:19]3[n:18][c:14]2[CH:15]([CH3:16])[CH3:17])=[O:12])cc1>CCO.O.[K+].O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[c:10]([C:11](=[O:12])[OH:13])[c:14]([CH:15]([CH3:16])[CH3:17])[n:18][n:19]12\"}",
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"children": [
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"molecule": {
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"inchikey": "BCJWARBVQJVCCL-UHFFFAOYSA-N",
"smiles": "COc1ccc(CO)c2c(C(=O)OCc3ccccc3)c(C(C)C)nn12"
},
"smiles": "COc1ccc(CO)c2c(C(=O)OCc3ccccc3)c(C(C)C)nn12",
"reactionStepId": "sa_5b257d4a1c0b48ef3d9a2870",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100056791A1;0361;846421\",\"rsmi\":\"[C:10]([C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)#[C:21][CH:22]([CH3:23])[CH3:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][n+:26]1[NH2:25]>CN(C)C=O.Cc1cc(C)c(S(=O)(=O)O)c(C)c1.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[c:10]([C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]([CH:22]([CH3:23])[CH3:24])[n:25][n:26]12\"},\"mapped_reaction_smiles\":\"[C:10]([C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)#[C:21][CH:22]([CH3:23])[CH3:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][n+:26]1[NH2:25]>CN(C)C=O.Cc1cc(C)c(S(=O)(=O)O)c(C)c1.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]2[c:10]([C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]([CH:22]([CH3:23])[CH3:24])[n:25][n:26]12\"}",
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"children": [
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"molecule": {
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"smiles": "COc1ccc(CO)c[n+]1N"
},
"smiles": "COc1ccc(CO)c[n+]1N",
"reactionStepId": null,
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{
"id": "12937",
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"molecule": {
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"inchikey": "PEVBBGQSDWAZSW-UHFFFAOYSA-N",
"smiles": "CC(C)C#CC(=O)OCc1ccccc1"
},
"smiles": "CC(C)C#CC(=O)OCc1ccccc1",
"reactionStepId": null,
"template": null,
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}
]
}
]
}
]
}
]
},
{
"id": "12938",
"routeId": "sa_bfde7d6c741a210d60014e47",
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"molecule": {
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"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
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}
]
}
]
}
]
}
}