Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)CC(O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1
InChiKey
RXXHBNWDBDXXIK-UHFFFAOYSA-N
Route Signature
384349643a83665d627ea57c1aa3be03082c0757f73ae252abd663d583745d68
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_378b6534ce9f10b17fac5047",
"signature": "384349643a83665d627ea57c1aa3be03082c0757f73ae252abd663d583745d68",
"contentHash": "6822b13ace73765e33ce17538c1a29a4f974e299b7a5f0ac3b45056e172401b9",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_31acc0f2c71cb20a9f5a8254",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00616",
"moleculeId": "sa_5ee81cedf0ac3c9c52b56dac",
"smiles": "CCOC(=O)CC(O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_5ee81cedf0ac3c9c52b56dac",
"inchikey": "RXXHBNWDBDXXIK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CC(O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13597",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_5ee81cedf0ac3c9c52b56dac",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5ee81cedf0ac3c9c52b56dac",
"inchikey": "RXXHBNWDBDXXIK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CC(O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "CCOC(=O)CC(O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"reactionStepId": "sa_a2deefc798d4c3c785f0d0c8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US05070206;;241627\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][CH:10]([OH:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1>C1CCOC1.CCB(CC)CC.CO.B.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[CH2:9][CH:10]([OH:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][CH:10]([OH:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1>C1CCOC1.CCB(CC)CC.CO.B.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[CH2:9][CH:10]([OH:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1\"}",
"reactionStep": {
"id": "sa_a2deefc798d4c3c785f0d0c8",
"reactionHash": "36e6ea21df49372bd07ca4694367f8b8d4128706f63dd9b31946d8becb2b275a"
},
"children": [
{
"id": "13598",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_b9782ed179814781218a722b",
"parentId": "13597",
"isLeaf": false,
"molecule": {
"id": "sa_b9782ed179814781218a722b",
"inchikey": "QZVYQAJDHISQFY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CC(=O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "CCOC(=O)CC(=O)CC(O)C=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"reactionStepId": "sa_80b85f648c0e40e3ebfab737",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US05070206;;241626\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH3:9].[CH:10](=[O:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][CH:10]([OH:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH3:9].[CH:10](=[O:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][CH:10]([OH:11])[CH:12]=[CH:13][C:14](=[C:15]([c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[n:30]1[cH:31][n:32][n:33][n:34]1\"}",
"reactionStep": {
"id": "sa_80b85f648c0e40e3ebfab737",
"reactionHash": "43be61b651df428d99f99c959ac3f2fb141b269a24495428063d63a4a5209fff"
},
"children": [
{
"id": "13599",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_440e1fa4ba75ae3f97503685",
"parentId": "13598",
"isLeaf": false,
"molecule": {
"id": "sa_440e1fa4ba75ae3f97503685",
"inchikey": "JRBCLZODOKQGIQ-UHFFFAOYSA-N",
"smiles": "O=CC=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "O=CC=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"reactionStepId": "sa_5d6a97baad2fccb2919d8062",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US05070206;;241625\",\"rsmi\":\"O=[CH:4][C:5](=[C:6]([c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[n:21]1[cH:22][n:23][n:24][n:25]1.c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:3][CH:2]=[O:1])cc1>c1ccccc1>[O:1]=[CH:2][CH:3]=[CH:4][C:5](=[C:6]([c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[n:21]1[cH:22][n:23][n:24][n:25]1\"},\"mapped_reaction_smiles\":\"O=[CH:4][C:5](=[C:6]([c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[n:21]1[cH:22][n:23][n:24][n:25]1.c1ccc(P(c2ccccc2)(c2ccccc2)=[CH:3][CH:2]=[O:1])cc1>c1ccccc1>[O:1]=[CH:2][CH:3]=[CH:4][C:5](=[C:6]([c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[n:21]1[cH:22][n:23][n:24][n:25]1\"}",
"reactionStep": {
"id": "sa_5d6a97baad2fccb2919d8062",
"reactionHash": "f91301ecfe9ba0e490c247ebd356e5e1605f1afd69dd23d94e26432781944e2f"
},
"children": [
{
"id": "13600",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_719a79ec86c709ecd8f819d1",
"parentId": "13599",
"isLeaf": true,
"molecule": {
"id": "sa_719a79ec86c709ecd8f819d1",
"inchikey": "CQCAYWAIRTVXIY-UHFFFAOYSA-N",
"smiles": "O=CC=P(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "O=CC=P(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13601",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_a74fcc11e8d68b64163c3681",
"parentId": "13599",
"isLeaf": false,
"molecule": {
"id": "sa_a74fcc11e8d68b64163c3681",
"inchikey": "YYOZLUSDYWSDAC-UHFFFAOYSA-N",
"smiles": "O=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "O=CC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"reactionStepId": "sa_c64af7311c59dd8c3a485adf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US05070206;;241624\",\"rsmi\":\"[OH:1][CH2:2][C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1>ClCCl.O=[Cr](=O)(O)Cl.c1ccncc1>[O:1]=[CH:2][C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1\"},\"mapped_reaction_smiles\":\"[OH:1][CH2:2][C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1>ClCCl.O=[Cr](=O)(O)Cl.c1ccncc1>[O:1]=[CH:2][C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1\"}",
"reactionStep": {
"id": "sa_c64af7311c59dd8c3a485adf",
"reactionHash": "b1a42e175ead67312776e9027e320df621bb9ab0bcc40f4096b587948d63bf5f"
},
"children": [
{
"id": "13602",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_6a9b1a8cccfdc4554ccd0af9",
"parentId": "13601",
"isLeaf": false,
"molecule": {
"id": "sa_6a9b1a8cccfdc4554ccd0af9",
"inchikey": "QXEBHFUSNTZOMK-UHFFFAOYSA-N",
"smiles": "OCC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "OCC(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"reactionStepId": "sa_5a7fcb775d6d842bf5b0b22f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US05070206;;241623\",\"rsmi\":\"O[C:2](=[O:1])[C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1>O=C(Cl)C(=O)Cl.[Al+3].[HH].[HH].[HH].[HH].[Li+].c1ccccc1.c1ccncc1>[OH:1][CH2:2][C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1>O=C(Cl)C(=O)Cl.[Al+3].[HH].[HH].[HH].[HH].[Li+].c1ccccc1.c1ccncc1>[OH:1][CH2:2][C:3](=[C:4]([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[n:19]1[cH:20][n:21][n:22][n:23]1\"}",
"reactionStep": {
"id": "sa_5a7fcb775d6d842bf5b0b22f",
"reactionHash": "0930572a7fc933820e7acfaf93d62ba22ce08b2a07f08677f9a30ed5b2f4cb9b"
},
"children": [
{
"id": "13603",
"routeId": "sa_378b6534ce9f10b17fac5047",
"moleculeId": "sa_30ab93b9912f6378dab5daa9",
"parentId": "13602",
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"molecule": {
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"inchikey": "XVMZFSCRELXCHW-UHFFFAOYSA-N",
"smiles": "O=C(O)C(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "O=C(O)C(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
"reactionStepId": "sa_efc9f967d7080148f60053e7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US05070206;;241622\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[C:4](=[C:5]([c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1)[n:20]1[cH:21][n:22][n:23][n:24]1>CCO.O.[Li+].O>[O:1]=[C:2]([OH:3])[C:4](=[C:5]([c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1)[n:20]1[cH:21][n:22][n:23][n:24]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[C:4](=[C:5]([c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1)[n:20]1[cH:21][n:22][n:23][n:24]1>CCO.O.[Li+].O>[O:1]=[C:2]([OH:3])[C:4](=[C:5]([c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1)[n:20]1[cH:21][n:22][n:23][n:24]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "AKFCLHYUPVOIFU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1"
},
"smiles": "CCOC(=O)C(=C(c1ccc(F)cc1)c1ccc(F)cc1)n1cnnn1",
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"template": null,
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}
]
}
]
}
]
}
]
},
{
"id": "13605",
"routeId": "sa_378b6534ce9f10b17fac5047",
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"parentId": "13598",
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"molecule": {
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"inchikey": "XYIBRDXRRQCHLP-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CC(C)=O"
},
"smiles": "CCOC(=O)CC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}