![(5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione](https://resource.bocsci.com/structure/109944-15-2.gif)
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| IUPAC Name: | (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridine-2,3-dione |
| Description: | (5R,6R,7S,8R,8aS)-6,7,8-Trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione (CAS# 109944-15-2) is an alkaloid produced by the fungus, Kitasatosporia kifunense, and has been shown to be a weak inhibitor of aryl mannosidase. It is a unique oxamide derivative of mannojirimycin and a potent inhibitor of the glycoprotein processing enzyme mannosidase I. Kifunenesine is ineffective in inhibiting either mannosidase II or the endoplasmic reticulum (ER) a-mannosidase. It also possesses immunomodulating properties based on chemical, physicochemical and x-ray crystallographic analysis.When tested in cell culture using influenza virus-infected MDCK cells, kifunensine, at 1 mg/ml or less, caused almost complete inhibition of complex chain formation with the accumulation of Man9(GlcNAc)2. Thus, kifunensine was proven to be 50 to 100 times more effective than deoxymannojirimycin. |
| Molecular Weight: | 232.19 |
| Molecular Formula: | C8H12N2O6 |
| Canonical SMILES: | C(C1C(C(C(C2N1C(=O)C(=O)N2)O)O)O)O |
| InChI: | InChI=1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1 |
| InChI Key: | OIURYJWYVIAOCW-PQMKYFCFSA-N |
| Melting Point: | >208°C (dec.) |
| Density: | 1.85±0.1 g/cm3 (Predicted) |
| Solubility: | Soluble in DMSO (Slightly, Heated), Methanol (Very Slightly, Heated, Sonicated), Water (Very Slightly) |
| Appearance: | White to Off-white Solid |
| Storage: | Store at -20°C |
| MDL: | MFCD00270017 |
| LogP: | -4.00520 |
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