(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-octahydroimidazolidino[1,2-a]pyridine-2,3-dione

• ChemBase ID: 172134
• Molecular Formular: C8H12N2O6
• Molecular Mass: 232.19068
• Monoisotopic Mass: 232.06953611
• SMILES: [C@@H]1([C@@H]([C@H](N2[C@@H]([C@H]1O)NC(=O)C2=O)CO)O)O
• Canonical SMILES: OC[C@@H]1[C@@H](O)[C@H](O)[C@@H]([C@@H]2N1C(=O)C(=O)N2)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
• InChIKey: OIURYJWYVIAOCW-PQMKYFCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-octahydroimidazolidino[1,2-a]pyridine-2,3-dione
• IUPAC Traditional name: (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-hexahydroimidazolidino[1,2-a]pyridine-2,3-dione
• Synonyms: [5R-(5α,6β,7α,8α,8aα)]-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione; (+)-Kifunensine; FR 900494; Kifunensine

Database IDs

• CAS Number: 109944-15-2
• PubChem SID: 164228044
• PubChem CID: 130611

CALCULATED PROPERTIES

• Acid pKa: 9.940488
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.745134
• LogD (pH = 7.4): -3.746227
• Log P: -3.7451203
• Molar Refractivity: 47.4227 cm^3
• Polarizability: 19.296642 Å^3
• Polar Surface Area: 130.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Water
• Apperance: White Solid
• Melting Point: >280°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Desiccate and Store at -20°C

DETAILS

Toronto Research Chemicals - K450000

Kifunensine 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

REFERENCES

• Kayakiri, H., et al.: Chem. Pharm. Bull., 39(1987)
• 1378 (1991)
• Iwami, M., et al.: J. Antibiotic., 40, 612 (1987)
• Elbein, A.D., et al.: J. Biol. Chem., 265, 15599 (1987)
• Elbein, A.D., et al.: Archives of Biochem & Biophys., 288, 1, 177 (1987)