Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCOCC(C)(C)c1ccc(N)cc1O
InChiKey
SHPHNUIANIATEF-UHFFFAOYSA-N
Route Signature
d7022c57e5e36290757b02662df83fd13a4bb12f57d978c6c34ea185e1436413
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_bfc8536aa157f191efb80d4b",
"signature": "d7022c57e5e36290757b02662df83fd13a4bb12f57d978c6c34ea185e1436413",
"contentHash": "a6194894302cc9fa97f5b0cb6ebd0c86cf31b20ff9a11e89490fa168c7bc14ea",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_5593d23299acefdb27f5a388",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00481",
"moleculeId": "sa_8d8a48ada9cd3963fae20b16",
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_8d8a48ada9cd3963fae20b16",
"inchikey": "SHPHNUIANIATEF-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13355",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_8d8a48ada9cd3963fae20b16",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_8d8a48ada9cd3963fae20b16",
"inchikey": "SHPHNUIANIATEF-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1O"
},
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1O",
"reactionStepId": "sa_a24795cc8b892b54e3694d19",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121208A1;0562;1519971\",\"rsmi\":\"CC(=O)[NH:15][c:14]1[cH:13][c:11]([OH:12])[c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:17][cH:16]1>Cl.O=C(O)O.[Na+].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([OH:12])[cH:13][c:14]([NH2:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CC(=O)[NH:15][c:14]1[cH:13][c:11]([OH:12])[c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:17][cH:16]1>Cl.O=C(O)O.[Na+].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([OH:12])[cH:13][c:14]([NH2:15])[cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_a24795cc8b892b54e3694d19",
"reactionHash": "1f4d9982336252203758b9a87a5c2ad6e18ab7b009af100009a0f39e508becfa"
},
"children": [
{
"id": "13356",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_a16072754c4e94c4d02c257a",
"parentId": "13355",
"isLeaf": false,
"molecule": {
"id": "sa_a16072754c4e94c4d02c257a",
"inchikey": "UZAFWIUCYUCYLC-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(NC(C)=O)cc1O"
},
"smiles": "COCCOCC(C)(C)c1ccc(NC(C)=O)cc1O",
"reactionStepId": "sa_a1b99b5a51d941fd0b502eec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121208A1;0561;1519970\",\"rsmi\":\"N[c:11]1[c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:20][cH:19][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:13]1.ON=[O:12]>O=S(=O)(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([OH:12])[cH:13][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"N[c:11]1[c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:20][cH:19][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:13]1.ON=[O:12]>O=S(=O)(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([OH:12])[cH:13][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_a1b99b5a51d941fd0b502eec",
"reactionHash": "9012dad21bd2b220959ddd7480908d160ea2aed837903d0f9670ab11d9cc3b17"
},
"children": [
{
"id": "13357",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_81c0446884d57a7253ff6b54",
"parentId": "13356",
"isLeaf": true,
"molecule": {
"id": "sa_81c0446884d57a7253ff6b54",
"inchikey": "IOVCWXUNBOPUCH-UHFFFAOYSA-N",
"smiles": "[O-]N=[OH+]"
},
"smiles": "O=NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13358",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_96ad716b3a6f24ba00b6540e",
"parentId": "13356",
"isLeaf": false,
"molecule": {
"id": "sa_96ad716b3a6f24ba00b6540e",
"inchikey": "WTGHJMVUIFYGIU-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(NC(C)=O)cc1N"
},
"smiles": "COCCOCC(C)(C)c1ccc(NC(C)=O)cc1N",
"reactionStepId": "sa_b904f1cf0e29eb00bea75658",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121208A1;0560;1519969\",\"rsmi\":\"O=[N+:12]([O-])[c:11]1[c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:20][cH:19][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:13]1>CO.[Ni]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([NH2:12])[cH:13][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[N+:12]([O-])[c:11]1[c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:20][cH:19][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:13]1>CO.[Ni]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([NH2:12])[cH:13][c:14]([NH:15][C:16]([CH3:17])=[O:18])[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_b904f1cf0e29eb00bea75658",
"reactionHash": "879ce0be0aed2cd096bacdb296f3539481b98eba535bb6e49320f3bf0de211ac"
},
"children": [
{
"id": "13359",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_a43793c5637424036901a8a3",
"parentId": "13358",
"isLeaf": false,
"molecule": {
"id": "sa_a43793c5637424036901a8a3",
"inchikey": "IYAKGFXKXACMQC-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(NC(C)=O)cc1[N+](=O)[O-]"
},
"smiles": "COCCOCC(C)(C)c1ccc(NC(C)=O)cc1[N+](=O)[O-]",
"reactionStepId": "sa_8a13679dcfb6185eeab8ed99",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121208A1;0559;1519968\",\"rsmi\":\"Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([NH2:17])[cH:21][cH:22]1>ClCCl.O.O=C(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([NH:17][C:18]([CH3:19])=[O:20])[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Cl[C:18]([CH3:19])=[O:20].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([NH2:17])[cH:21][cH:22]1>ClCCl.O.O=C(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([NH:17][C:18]([CH3:19])=[O:20])[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_8a13679dcfb6185eeab8ed99",
"reactionHash": "eb595c1d686f9caed4db694c6f4e20b15925467216c7a2a46c4ea8f6592781b1"
},
"children": [
{
"id": "13360",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_f11042fbb86f32268c2783a8",
"parentId": "13359",
"isLeaf": false,
"molecule": {
"id": "sa_f11042fbb86f32268c2783a8",
"inchikey": "LAUXSWDHTBBXMZ-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1[N+](=O)[O-]"
},
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1[N+](=O)[O-]",
"reactionStepId": "sa_a14efe3ba0062401cd8fc4a6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121208A1;0558;1519967\",\"rsmi\":\"O=[N+:12]([OH:13])[O-:14].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][cH:15][c:16]([NH2:17])[cH:18][cH:19]1>O=S(=O)(O)O.[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([NH2:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"O=[N+:12]([OH:13])[O-:14].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][cH:15][c:16]([NH2:17])[cH:18][cH:19]1>O=S(=O)(O)O.[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([NH2:17])[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_a14efe3ba0062401cd8fc4a6",
"reactionHash": "f10476f668a1b7c0ffcd8d4f8f1f61c9e776749e3e95bdc307affa6d7b07d590"
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"children": [
{
"id": "13361",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "13360",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13362",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_ba3e370a4ede0772ca33abb3",
"parentId": "13360",
"isLeaf": false,
"molecule": {
"id": "sa_ba3e370a4ede0772ca33abb3",
"inchikey": "GTCDTIAHTJHQEA-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1"
},
"smiles": "COCCOCC(C)(C)c1ccc(N)cc1",
"reactionStepId": "sa_5528a22c7b5a07364c740854",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140121208A1;0557;1519966\",\"rsmi\":\"O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:16][cH:15]1>CO.[Ni]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]([C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH3:8])[CH3:9])[cH:16][cH:15]1>CO.[Ni]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "3461866871ceac6dbf2ff5b750dfe07fbe77d2bd88b2477264a4db26dcd072ee"
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"children": [
{
"id": "13363",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_c15d57af4a3ad08651634515",
"parentId": "13362",
"isLeaf": true,
"molecule": {
"id": "sa_c15d57af4a3ad08651634515",
"inchikey": "QWPSMHWZUCWTRI-UHFFFAOYSA-N",
"smiles": "COCCOCC(C)(C)c1ccc([N+](=O)[O-])cc1"
},
"smiles": "COCCOCC(C)(C)c1ccc([N+](=O)[O-])cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13364",
"routeId": "sa_bfc8536aa157f191efb80d4b",
"moleculeId": "sa_7992c61d309177eaaf95fc6b",
"parentId": "13359",
"isLeaf": true,
"molecule": {
"id": "sa_7992c61d309177eaaf95fc6b",
"inchikey": "WETWJCDKMRHUPV-UHFFFAOYSA-N",
"smiles": "CC(=O)Cl"
},
"smiles": "CC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}