Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1c(C2CCCCC2)cc2cc(N)ccc21
InChiKey
DKADOVUVXZNITD-UHFFFAOYSA-N
Route Signature
336146a3d428756c5b9f561ea0f5aa1bba34fba82c587c5acf81c924bf9d8ab4
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_0a22a5a5bbfa8f4b1a57f410",
"signature": "336146a3d428756c5b9f561ea0f5aa1bba34fba82c587c5acf81c924bf9d8ab4",
"contentHash": "0b47a4b16bdc16a0387c82f67b8b77de9fc0dc33af594ee6aeb61f16261b491e",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_4144fa46f125f42beb861090",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00345",
"moleculeId": "sa_7e612c72d59abc9e0d50a733",
"smiles": "CCn1c(C2CCCCC2)cc2cc(N)ccc21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7e612c72d59abc9e0d50a733",
"inchikey": "DKADOVUVXZNITD-UHFFFAOYSA-N",
"smiles": "CCn1c(C2CCCCC2)cc2cc(N)ccc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4097",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_7e612c72d59abc9e0d50a733",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7e612c72d59abc9e0d50a733",
"inchikey": "DKADOVUVXZNITD-UHFFFAOYSA-N",
"smiles": "CCn1c(C2CCCCC2)cc2cc(N)ccc21"
},
"smiles": "CCn1c(C2CCCCC2)cc2cc(N)ccc21",
"reactionStepId": "sa_181394eec5e6c5cf29064763",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158269A1;0182;1384420\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]2[n:3]([CH2:2][CH3:1])[c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[cH:11][c:10]2[cH:9]1>CCO.[Pd]>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][c:7]([NH2:8])[cH:9][c:10]2[cH:11][c:12]1[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]2[n:3]([CH2:2][CH3:1])[c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[cH:11][c:10]2[cH:9]1>CCO.[Pd]>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][c:7]([NH2:8])[cH:9][c:10]2[cH:11][c:12]1[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1\"}",
"reactionStep": {
"id": "sa_181394eec5e6c5cf29064763",
"reactionHash": "9289e35ca0dd67ab36f61f4ac1ed71da4a861a5d30b551c8a52406a76e05ab2e"
},
"children": [
{
"id": "4098",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_e4180a4502abd8fe464b8158",
"parentId": "4097",
"isLeaf": false,
"molecule": {
"id": "sa_e4180a4502abd8fe464b8158",
"inchikey": "KWRRMLVKMUUSOD-UHFFFAOYSA-N",
"smiles": "CCn1c(C2CCCCC2)cc2cc([N+](=O)[O-])ccc21"
},
"smiles": "CCn1c(C2CCCCC2)cc2cc([N+](=O)[O-])ccc21",
"reactionStepId": "sa_b7ad8f88653bf44a9e9472df",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158269A1;0180;1384419\",\"rsmi\":\"I[CH2:2][CH3:1].[nH:3]1[c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[cH:13][c:14]1[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>CN(C)C=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[cH:13][c:14]1[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"I[CH2:2][CH3:1].[nH:3]1[c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[cH:13][c:14]1[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>CN(C)C=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[cH:13][c:14]1[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1\"}",
"reactionStep": {
"id": "sa_b7ad8f88653bf44a9e9472df",
"reactionHash": "0d73e71b5a088e45ba6dbee9f28b0489a0843a57dd25262c6d5b5886b5743fe1"
},
"children": [
{
"id": "4099",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_01a8c578f81f45a8be948ed8",
"parentId": "4098",
"isLeaf": false,
"molecule": {
"id": "sa_01a8c578f81f45a8be948ed8",
"inchikey": "CEZBRURXBKQSAJ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc2[nH]c(C3CCCCC3)cc2c1"
},
"smiles": "O=[N+]([O-])c1ccc2[nH]c(C3CCCCC3)cc2c1",
"reactionStepId": "sa_a075b06c23f16eb5b34e8d8b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158269A1;0178;1384418\",\"rsmi\":\"CS(=O)(=O)[n:8]1[c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][c:17]2[cH:16][c:9]1[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.O.F>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][c:17]2[cH:18]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)[n:8]1[c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:18][c:17]2[cH:16][c:9]1[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.O.F>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][c:17]2[cH:18]1\"}",
"reactionStep": {
"id": "sa_a075b06c23f16eb5b34e8d8b",
"reactionHash": "29bceafbfe32ca674b118d0d477428027b90ff09eff292489345b8e09fa43f44"
},
"children": [
{
"id": "4100",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_a2d51bd10f41b4ded0276900",
"parentId": "4099",
"isLeaf": false,
"molecule": {
"id": "sa_a2d51bd10f41b4ded0276900",
"inchikey": "ZHAUVKNYECDONZ-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)n1c(C2CCCCC2)cc2cc([N+](=O)[O-])ccc21"
},
"smiles": "CS(=O)(=O)n1c(C2CCCCC2)cc2cc([N+](=O)[O-])ccc21",
"reactionStepId": "sa_5fdedaf3c47b7c58d313ece0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158269A1;0176;1384417\",\"rsmi\":\"I[c:14]1[c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1.[CH:15]#[C:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][S:2](=[O:3])(=[O:4])[n:5]1[c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]2[cH:15][c:16]1[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"I[c:14]1[c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1.[CH:15]#[C:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][S:2](=[O:3])(=[O:4])[n:5]1[c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]2[cH:15][c:16]1[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1\"}",
"reactionStep": {
"id": "sa_5fdedaf3c47b7c58d313ece0",
"reactionHash": "f8287e56b485b61812a401d59b43eb7d60994381545fa1a7ea06c8d059a69aaf"
},
"children": [
{
"id": "4101",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_0e7f464680cfa282239ea733",
"parentId": "4100",
"isLeaf": false,
"molecule": {
"id": "sa_0e7f464680cfa282239ea733",
"inchikey": "BXRLNVJONDVTMW-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1I"
},
"smiles": "CS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1I",
"reactionStepId": "sa_b68496bc9ea281355fb38875",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158269A1;0174;1384416\",\"rsmi\":\"CS(=O)(=O)[N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1>CCO.O.[Li+].O>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)[N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1>CCO.O.[Li+].O>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "d3e7c3860e45807d4b1408a62c3d2b813aeea77999781bf2d96a70f11cead320"
},
"children": [
{
"id": "4102",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_d8e500581f7a4754be471c74",
"parentId": "4101",
"isLeaf": false,
"molecule": {
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"inchikey": "UJOLMBCBEPDZSF-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)N(c1ccc([N+](=O)[O-])cc1I)S(C)(=O)=O"
},
"smiles": "CS(=O)(=O)N(c1ccc([N+](=O)[O-])cc1I)S(C)(=O)=O",
"reactionStepId": "sa_4f819a84bd529d21e403f061",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158269A1;0172;1384415\",\"rsmi\":\"CCN(CC)C[CH3:17].Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1>ClCCl.Cl.N>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]([c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1)[S:16]([CH3:17])(=[O:18])=[O:19]\"},\"mapped_reaction_smiles\":\"CCN(CC)C[CH3:17].Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1>ClCCl.Cl.N>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]([c:6]1[c:7]([I:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1)[S:16]([CH3:17])(=[O:18])=[O:19]\"}",
"reactionStep": {
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"reactionHash": "a427a162ac314bf08adea24ad59cef655a858929d82599fa573af13a11855f1c"
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"children": [
{
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"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_d1f98e7510933968e4854e00",
"parentId": "4102",
"isLeaf": true,
"molecule": {
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"inchikey": "LOLSEMNGXKAZBZ-UHFFFAOYSA-N",
"smiles": "Nc1ccc([N+](=O)[O-])cc1I"
},
"smiles": "Nc1ccc([N+](=O)[O-])cc1I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4104",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "4102",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4105",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_fb8ad87f20d9aab2ea35051a",
"parentId": "4102",
"isLeaf": true,
"molecule": {
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"inchikey": "ZMANZCXQSJIPKH-UHFFFAOYSA-N",
"smiles": "CCN(CC)CC"
},
"smiles": "CCN(CC)CC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "4106",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_0164270b3014af74caeccb5b",
"parentId": "4100",
"isLeaf": true,
"molecule": {
"id": "sa_0164270b3014af74caeccb5b",
"inchikey": "SSDZYLQUYMOSAK-UHFFFAOYSA-N",
"smiles": "C#CC1CCCCC1"
},
"smiles": "C#CC1CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "4107",
"routeId": "sa_0a22a5a5bbfa8f4b1a57f410",
"moleculeId": "sa_ba4021c610c673105b10b53d",
"parentId": "4098",
"isLeaf": true,
"molecule": {
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"inchikey": "HVTICUPFWKNHNG-UHFFFAOYSA-N",
"smiles": "CCI"
},
"smiles": "CCI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}