6-(1,2-dihydroxyethyl)-2-methyloxane-2,4,5-triol

• ChemBase ID: 165994
• Molecular Formular: C8H16O6
• Molecular Mass: 208.20904
• Monoisotopic Mass: 208.09468823
• SMILES: C1(C(CC(OC1C(O)CO)(O)C)O)O
• Canonical SMILES: OCC(C1OC(C)(O)CC(C1O)O)O
• InChI: InChI=1S/C8H16O6/c1-8(13)2-4(10)6(12)7(14-8)5(11)3-9/h4-7,9-13H,2-3H2,1H3
• InChIKey: IIJASIDKCOUAQO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(1,2-dihydroxyethyl)-2-methyloxane-2,4,5-triol
• IUPAC Traditional name: 6-(1,2-dihydroxyethyl)-2-methyloxane-2,4,5-triol
• Synonyms: 2-Keto-3-deoxyoctonate Ammonium Salt; 3-Deoxyoctulosonic Acid Ammonim Salt; KDO Ammonium Salt; 3-Deoxyoctulosonic Acid; 3-Deoxy-2-octulosonic Acid Monoammonium Salt; 3-Deoxyoctulosonic Acid KDO; 3-Deoxy-D-manno-2-octulosonic Acid Ammonium Salt

Database IDs

• CAS Number: 103404-70-2
• PubChem SID: 162260127
• PubChem CID: 71315501

CALCULATED PROPERTIES

• Acid pKa: 12.139641
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.4141734
• LogD (pH = 7.4): -2.4141812
• Log P: -2.4141734
• Molar Refractivity: 45.397 cm^3
• Polarizability: 18.75511 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Crystalline Solid
• Melting Point: 122-124°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D242000

A ketosidic component in all lipopolysaccharides of Gram-negative bacteria and has been identified in several acidic exopolysaccharides (K-antigens). Synthetic analogues of KDO may be studied for their potential to disrupt the biosynthesis of bacterial ce

REFERENCES

• Altschul, S., et al.: J. Mol. Biol., 215, 403 (1990)
• Baumann, H., et al.: Biochemistry, 31, 4081 (1990)
• Hashimoto, M., et al.: Eur. J. Biochem., 268, 3139 (1990)
• Kodar, K., et al.: Immunol. Invest., 38, 704 (1990)