Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cn[nH]c4)ccc32)CC1
InChiKey
MRBNYWQYLMPQAG-UHFFFAOYSA-N
Route Signature
bda9d5a4bc09a0ff7fe0a6c2362dfc9163277c5fea7621f7cc2b882e5d62b81e
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"signature": "bda9d5a4bc09a0ff7fe0a6c2362dfc9163277c5fea7621f7cc2b882e5d62b81e",
"contentHash": "6236b9343269a5ee8f366566c10eb9c908ce696394411a795e40e5bbf2ea1bf8",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_73152082ab345f9b40e04af9",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-06333",
"moleculeId": "sa_9f2346aeb7c3768a7cfa6b3f",
"smiles": "O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cn[nH]c4)ccc32)CC1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_9f2346aeb7c3768a7cfa6b3f",
"inchikey": "MRBNYWQYLMPQAG-UHFFFAOYSA-N",
"smiles": "O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cn[nH]c4)ccc32)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "15907",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_9f2346aeb7c3768a7cfa6b3f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_9f2346aeb7c3768a7cfa6b3f",
"inchikey": "MRBNYWQYLMPQAG-UHFFFAOYSA-N",
"smiles": "O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cn[nH]c4)ccc32)CC1"
},
"smiles": "O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cn[nH]c4)ccc32)CC1",
"reactionStepId": "sa_5e3537b2d44effbd147199cf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024086A1;0350;1827504\",\"rsmi\":\"C1CCC([n:23]2[cH:22][c:21](-[c:20]3[n:19][c:18]4[cH:17][cH:16][n:15]([CH2:14][CH:13]5[CH2:12][CH2:11][N:10]([S:2](=[O:1])(=[O:3])[c:4]6[cH:5][cH:6][cH:7][cH:8][cH:9]6)[CH2:30][CH2:29]5)[c:28]4[cH:27][cH:26]3)[cH:25][n:24]2)OC1>CO.Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][CH:13]([CH2:14][n:15]2[cH:16][cH:17][c:18]3[n:19][c:20](-[c:21]4[cH:22][nH:23][n:24][cH:25]4)[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1\"},\"mapped_reaction_smiles\":\"C1CCC([n:23]2[cH:22][c:21](-[c:20]3[n:19][c:18]4[cH:17][cH:16][n:15]([CH2:14][CH:13]5[CH2:12][CH2:11][N:10]([S:2](=[O:1])(=[O:3])[c:4]6[cH:5][cH:6][cH:7][cH:8][cH:9]6)[CH2:30][CH2:29]5)[c:28]4[cH:27][cH:26]3)[cH:25][n:24]2)OC1>CO.Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][CH:13]([CH2:14][n:15]2[cH:16][cH:17][c:18]3[n:19][c:20](-[c:21]4[cH:22][nH:23][n:24][cH:25]4)[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1\"}",
"reactionStep": {
"id": "sa_5e3537b2d44effbd147199cf",
"reactionHash": "98be996c99a990393c0b6790aeb918db0012c49e582904d1e618b984779501e6"
},
"children": [
{
"id": "15908",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_4ef320f7c74b9fd7ebe14cce",
"parentId": "15907",
"isLeaf": false,
"molecule": {
"id": "sa_4ef320f7c74b9fd7ebe14cce",
"inchikey": "HGBNDWBHFSKJEC-UHFFFAOYSA-N",
"smiles": "O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cnn(C5CCCCO5)c4)ccc32)CC1"
},
"smiles": "O=S(=O)(c1ccccc1)N1CCC(Cn2ccc3nc(-c4cnn(C5CCCCO5)c4)ccc32)CC1",
"reactionStepId": "sa_e58a75f2b69f18cb5a5eeeaf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024086A1;0348;1827503\",\"rsmi\":\"Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[NH:10]1[CH2:11][CH2:12][CH:13]([CH2:14][n:15]2[cH:16][cH:17][c:18]3[n:19][c:20](-[c:21]4[cH:22][n:23]([CH:24]5[CH2:25][CH2:26][CH2:27][CH2:28][O:29]5)[n:30][cH:31]4)[cH:32][cH:33][c:34]23)[CH2:35][CH2:36]1>CCN(CC)CC.CO.ClCCl.O>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][CH:13]([CH2:14][n:15]2[cH:16][cH:17][c:18]3[n:19][c:20](-[c:21]4[cH:22][n:23]([CH:24]5[CH2:25][CH2:26][CH2:27][CH2:28][O:29]5)[n:30][cH:31]4)[cH:32][cH:33][c:34]23)[CH2:35][CH2:36]1\"},\"mapped_reaction_smiles\":\"Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[NH:10]1[CH2:11][CH2:12][CH:13]([CH2:14][n:15]2[cH:16][cH:17][c:18]3[n:19][c:20](-[c:21]4[cH:22][n:23]([CH:24]5[CH2:25][CH2:26][CH2:27][CH2:28][O:29]5)[n:30][cH:31]4)[cH:32][cH:33][c:34]23)[CH2:35][CH2:36]1>CCN(CC)CC.CO.ClCCl.O>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][CH:13]([CH2:14][n:15]2[cH:16][cH:17][c:18]3[n:19][c:20](-[c:21]4[cH:22][n:23]([CH:24]5[CH2:25][CH2:26][CH2:27][CH2:28][O:29]5)[n:30][cH:31]4)[cH:32][cH:33][c:34]23)[CH2:35][CH2:36]1\"}",
"reactionStep": {
"id": "sa_e58a75f2b69f18cb5a5eeeaf",
"reactionHash": "609f7c6a0987b31cab5761674096335f9f327e440d13b6484578b53c8648eb7c"
},
"children": [
{
"id": "15909",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_2e449791516bfe12bcac6036",
"parentId": "15908",
"isLeaf": true,
"molecule": {
"id": "sa_2e449791516bfe12bcac6036",
"inchikey": "CSKNSYBAZOQPLR-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccccc1"
},
"smiles": "O=S(=O)(Cl)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15910",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_5a25cf0fb9b0f1688559c3ac",
"parentId": "15908",
"isLeaf": false,
"molecule": {
"id": "sa_5a25cf0fb9b0f1688559c3ac",
"inchikey": "KYKIBVAKXCZILG-UHFFFAOYSA-N",
"smiles": "c1nn(C2CCCCO2)cc1-c1ccc2c(ccn2CC2CCNCC2)n1"
},
"smiles": "c1nn(C2CCCCO2)cc1-c1ccc2c(ccn2CC2CCNCC2)n1",
"reactionStepId": "sa_bcb82fbc59db304ca9be841f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024086A1;0294;1827486\",\"rsmi\":\"O=C(OCc1ccccc1)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][n:3]2[cH:2][cH:1][c:27]3[c:11]2[cH:12][cH:13][c:14](-[c:15]2[cH:16][n:17]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:23]4)[n:24][cH:25]2)[n:26]3)[CH2:10][CH2:9]1>CCO.CO.ClCCl>[cH:1]1[cH:2][n:3]([CH2:4][CH:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][n:17]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:23]4)[n:24][cH:25]3)[n:26][c:27]12\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][n:3]2[cH:2][cH:1][c:27]3[c:11]2[cH:12][cH:13][c:14](-[c:15]2[cH:16][n:17]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:23]4)[n:24][cH:25]2)[n:26]3)[CH2:10][CH2:9]1>CCO.CO.ClCCl>[cH:1]1[cH:2][n:3]([CH2:4][CH:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][n:17]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:23]4)[n:24][cH:25]3)[n:26][c:27]12\"}",
"reactionStep": {
"id": "sa_bcb82fbc59db304ca9be841f",
"reactionHash": "0288fc1c790c0d8de89929193a7fa58f992a064562a6929dd337f250fde9ce4d"
},
"children": [
{
"id": "15911",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_4c426f411ad18983d5a7019a",
"parentId": "15910",
"isLeaf": false,
"molecule": {
"id": "sa_4c426f411ad18983d5a7019a",
"inchikey": "IGYLBSHQPMAVME-UHFFFAOYSA-N",
"smiles": "O=C(OCc1ccccc1)N1CCC(Cn2ccc3nc(-c4cnn(C5CCCCO5)c4)ccc32)CC1"
},
"smiles": "O=C(OCc1ccccc1)N1CCC(Cn2ccc3nc(-c4cnn(C5CCCCO5)c4)ccc32)CC1",
"reactionStepId": "sa_29e96c3d18dea36222e8aa90",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160024086A1;0293;1827485\",\"rsmi\":\"Cc1ccc(S(=O)(=O)O[CH2:15][CH:14]2[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:37][CH2:36]2)cc1.[nH:16]1[cH:17][cH:18][c:19]2[n:20][c:21](-[c:22]3[cH:23][n:24]([CH:25]4[CH2:26][CH2:27][CH2:28][CH2:29][O:30]4)[n:31][cH:32]3)[cH:33][cH:34][c:35]12>CCCCCC.CCOC(C)=O.CN(C)C=O.[HH].[Na+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][n:16]2[cH:17][cH:18][c:19]3[n:20][c:21](-[c:22]4[cH:23][n:24]([CH:25]5[CH2:26][CH2:27][CH2:28][CH2:29][O:30]5)[n:31][cH:32]4)[cH:33][cH:34][c:35]23)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"Cc1ccc(S(=O)(=O)O[CH2:15][CH:14]2[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[CH2:37][CH2:36]2)cc1.[nH:16]1[cH:17][cH:18][c:19]2[n:20][c:21](-[c:22]3[cH:23][n:24]([CH:25]4[CH2:26][CH2:27][CH2:28][CH2:29][O:30]4)[n:31][cH:32]3)[cH:33][cH:34][c:35]12>CCCCCC.CCOC(C)=O.CN(C)C=O.[HH].[Na+]>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([CH2:15][n:16]2[cH:17][cH:18][c:19]3[n:20][c:21](-[c:22]4[cH:23][n:24]([CH:25]5[CH2:26][CH2:27][CH2:28][CH2:29][O:30]5)[n:31][cH:32]4)[cH:33][cH:34][c:35]23)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_29e96c3d18dea36222e8aa90",
"reactionHash": "86ae6d92a6ca70153cc6f7135a7c494e8a380864a91b5b5a5e3140ed7354c2b5"
},
"children": [
{
"id": "15912",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_d0a9456c594a75113d8956a2",
"parentId": "15911",
"isLeaf": true,
"molecule": {
"id": "sa_d0a9456c594a75113d8956a2",
"inchikey": "JLWNIBRSVNTKHT-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OCc3ccccc3)CC2)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OCc3ccccc3)CC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "15913",
"routeId": "sa_c9ba2a4a6d0cdbf1ab9a6d9e",
"moleculeId": "sa_a2607bc5b2014e7ebb37afb4",
"parentId": "15911",
"isLeaf": true,
"molecule": {
"id": "sa_a2607bc5b2014e7ebb37afb4",
"inchikey": "RSMKPJQHHQTTPE-UHFFFAOYSA-N",
"smiles": "c1cc2nc(-c3cnn(C4CCCCO4)c3)ccc2[nH]1"
},
"smiles": "c1cc2nc(-c3cnn(C4CCCCO4)c3)ccc2[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}