Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C=CC(=O)NCCC1CCN(C(=O)CNc2cc(Cl)c(Cl)cc2O)CC1
InChiKey
OGIPQDLZWWDKEM-UHFFFAOYSA-N
Route Signature
897b5a76f440b7d371b7369ee7dc35f606ea1fcb2228948c0722125dfc6d3905
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_41f7f2ee166229a69b31d1f9",
"signature": "897b5a76f440b7d371b7369ee7dc35f606ea1fcb2228948c0722125dfc6d3905",
"contentHash": "7834bbeb9e1f46c076f0a6b83943b2ca4019a2da2717d6f227fc606b8be50c8a",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_4b11a4736410d9f00a36cef0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00195",
"moleculeId": "sa_27d2b5c705e07e3c7cdba6f6",
"smiles": "C=CC(=O)NCCC1CCN(C(=O)CNc2cc(Cl)c(Cl)cc2O)CC1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_27d2b5c705e07e3c7cdba6f6",
"inchikey": "OGIPQDLZWWDKEM-UHFFFAOYSA-N",
"smiles": "C=CC(=O)NCCC1CCN(C(=O)CNc2cc(Cl)c(Cl)cc2O)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "352",
"routeId": "sa_41f7f2ee166229a69b31d1f9",
"moleculeId": "sa_27d2b5c705e07e3c7cdba6f6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_27d2b5c705e07e3c7cdba6f6",
"inchikey": "OGIPQDLZWWDKEM-UHFFFAOYSA-N",
"smiles": "C=CC(=O)NCCC1CCN(C(=O)CNc2cc(Cl)c(Cl)cc2O)CC1"
},
"smiles": "C=CC(=O)NCCC1CCN(C(=O)CNc2cc(Cl)c(Cl)cc2O)CC1",
"reactionStepId": "sa_2988f2d131489acb9665d7d8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0520;1587064\",\"rsmi\":\"O[C:12](=[O:13])[CH2:14][NH:15][c:16]1[c:17]([OH:18])[cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]1.[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:25][CH2:26]1>CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][NH:15][c:16]2[c:17]([OH:18])[cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]2)[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"O[C:12](=[O:13])[CH2:14][NH:15][c:16]1[c:17]([OH:18])[cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]1.[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:25][CH2:26]1>CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][NH:15][c:16]2[c:17]([OH:18])[cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]2)[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_2988f2d131489acb9665d7d8",
"reactionHash": "d1c14a0c327f8f0434e9de4e34132589dd589b1ca3a424d6235b494f06ce9a81"
},
"children": [
{
"id": "353",
"routeId": "sa_41f7f2ee166229a69b31d1f9",
"moleculeId": "sa_490d41e9b763b1fe58e2a0a0",
"parentId": "352",
"isLeaf": false,
"molecule": {
"id": "sa_490d41e9b763b1fe58e2a0a0",
"inchikey": "AOWRVWWARBBCHK-UHFFFAOYSA-N",
"smiles": "O=C(O)CNc1cc(Cl)c(Cl)cc1O"
},
"smiles": "O=C(O)CNc1cc(Cl)c(Cl)cc1O",
"reactionStepId": "sa_93f345ebeeacb8a886cf6d92",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0458;1587020\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[CH2:4][NH:5][c:6]1[c:7]([OH:8])[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1>C1CCOC1.Cl.O.O.[Li]O>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][c:6]1[c:7]([OH:8])[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[CH2:4][NH:5][c:6]1[c:7]([OH:8])[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1>C1CCOC1.Cl.O.O.[Li]O>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][c:6]1[c:7]([OH:8])[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1\"}",
"reactionStep": {
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"reactionHash": "ae71c044503b5b11a746b0c5104169cb2fbe1784b4b3b29ad25dc42ba1d4dc9f"
},
"children": [
{
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"moleculeId": "sa_a34469f05309b038ab99ee76",
"parentId": "353",
"isLeaf": false,
"molecule": {
"id": "sa_a34469f05309b038ab99ee76",
"inchikey": "OAGSACLWERICLI-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CNc1cc(Cl)c(Cl)cc1O"
},
"smiles": "CCOC(=O)CNc1cc(Cl)c(Cl)cc1O",
"reactionStepId": "sa_3d12a84a4ca57d8eab266a8b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0457;1587019\",\"rsmi\":\"O=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:7][c:8]1[c:9]([OH:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[c:9]([OH:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"O=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:7][c:8]1[c:9]([OH:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[c:9]([OH:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_3d12a84a4ca57d8eab266a8b",
"reactionHash": "f5e70c90089c8bfb7ec2b8855add78092da1cb3a796e493303d16fd94faa97ac"
},
"children": [
{
"id": "355",
"routeId": "sa_41f7f2ee166229a69b31d1f9",
"moleculeId": "sa_75236846fd7a02ef331ec5f9",
"parentId": "354",
"isLeaf": true,
"molecule": {
"id": "sa_75236846fd7a02ef331ec5f9",
"inchikey": "DBPFRRFGLYGEJI-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C=O"
},
"smiles": "CCOC(=O)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "356",
"routeId": "sa_41f7f2ee166229a69b31d1f9",
"moleculeId": "sa_0bfb7a3d10aa920ce0653628",
"parentId": "354",
"isLeaf": false,
"molecule": {
"id": "sa_0bfb7a3d10aa920ce0653628",
"inchikey": "UVIBWGFLURLRHR-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)c(Cl)cc1O"
},
"smiles": "Nc1cc(Cl)c(Cl)cc1O",
"reactionStepId": "sa_045b8c0766db9a219f4ae5df",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0456;1587018\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[c:3]([OH:4])[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]1>CC(=O)O.O.[Fe]>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[c:3]([OH:4])[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]1>CC(=O)O.O.[Fe]>[NH2:1][c:2]1[c:3]([OH:4])[cH:5][c:6]([Cl:7])[c:8]([Cl:9])[cH:10]1\"}",
"reactionStep": {
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"reactionHash": "47577aff730d7c6765fa8ce28c740ad07608daa44af70ce1aaad381e5e6a2201"
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"children": [
{
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"routeId": "sa_41f7f2ee166229a69b31d1f9",
"moleculeId": "sa_4eb71f899b3ed39e10cf633a",
"parentId": "356",
"isLeaf": false,
"molecule": {
"id": "sa_4eb71f899b3ed39e10cf633a",
"inchikey": "CEFFUJIHZMPDID-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1O"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1O",
"reactionStepId": "sa_c8cd44df59079e70cc0ebf1a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0455;1587017\",\"rsmi\":\"O[N+:2](=[O:1])[O-:3].[cH:4]1[c:5]([OH:6])[cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1>ClCCl.O=S(=O)(O)O>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([OH:6])[cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O[N+:2](=[O:1])[O-:3].[cH:4]1[c:5]([OH:6])[cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1>ClCCl.O=S(=O)(O)O>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([OH:6])[cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1\"}",
"reactionStep": {
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"reactionHash": "c3868f0ee7573b673d4a1fbd458032acaee3e173111ff81866ecd8e70411ff5c"
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"children": [
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"moleculeId": "sa_edac0a7fd043198784a28dd9",
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"isLeaf": true,
"molecule": {
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"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "359",
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"moleculeId": "sa_36f362ee561abc8b7e68de06",
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"isLeaf": true,
"molecule": {
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"inchikey": "WDNBURPWRNALGP-UHFFFAOYSA-N",
"smiles": "Oc1ccc(Cl)c(Cl)c1"
},
"smiles": "Oc1ccc(Cl)c(Cl)c1",
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"template": null,
"metadata": null,
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}
]
}
]
}
]
}
]
},
{
"id": "360",
"routeId": "sa_41f7f2ee166229a69b31d1f9",
"moleculeId": "sa_2bf97ef58f9d4a0fbafba406",
"parentId": "352",
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"molecule": {
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"inchikey": "TXYJSFXETJLSGB-UHFFFAOYSA-N",
"smiles": "C=CC(=O)NCCC1CCNCC1"
},
"smiles": "C=CC(=O)NCCC1CCNCC1",
"reactionStepId": "sa_9eec770c14f870d48650923b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0519;1587063\",\"rsmi\":\"CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][NH:5][C:3]([CH:2]=[CH2:1])=[O:4])[CH2:13][CH2:12]1>CO.Cl>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][NH:5][C:3]([CH:2]=[CH2:1])=[O:4])[CH2:13][CH2:12]1>CO.Cl>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1\"}",
"reactionStep": {
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"molecule": {
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"smiles": "C=CC(=O)NCCC1CCN(C(=O)OC(C)(C)C)CC1"
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"smiles": "C=CC(=O)NCCC1CCN(C(=O)OC(C)(C)C)CC1",
"reactionStepId": "sa_7d4b1135a25c2b32128725bd",
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"metadata": "{\"annotations\":{\"ID\":\"US20140288045A1;0518;1587062\",\"rsmi\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1>CCN(CC)CC.ClCCl.O>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1>CCN(CC)CC.ClCCl.O>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1\"}",
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"smiles": "C=CC(=O)Cl"
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{
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"smiles": "CC(C)(C)OC(=O)N1CCC(CCN)CC1",
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}
}