3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

• ChemBase ID: 169552
• Molecular Formular: C6H14ClNO5
• Molecular Mass: 215.63206
• Monoisotopic Mass: 215.05605023
• SMILES: C1(C(C(C(OC1CO)O)N)O)O.Cl
• Canonical SMILES: OCC1OC(O)C(C(C1O)O)N.Cl
• InChI: InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H
• InChIKey: QKPLRMLTKYXDST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride
• IUPAC Traditional name: glucosamine hydrochloride
• Synonyms: 2-Amino-2-deoxy-D-galactose Hydrochloride; Chondrosamine Hydrochloride; D-Galactosamine, Hydrochloride

Database IDs

• CAS Number: 1772-03-8
• PubChem SID: 162263684
• PubChem CID: 2830832

CALCULATED PROPERTIES

• Acid pKa: 11.726975
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.5965767
• LogD (pH = 7.4): -3.9292529
• Log P: -3.039421
• Molar Refractivity: 37.5809 cm^3
• Polarizability: 15.959335 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >185°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G155000

Specifically inhibits COX-2 by preventing COX-2 N-glycosylation and by increasing COX-2 protein turnover in a proteasome-dependent manner.

REFERENCES

• Inoue, H., et al.: J. Biol. Chem., 270, 24965 (1995)
• Smith, W., et al.: Adv. Immunol., 62, 167 (1995)
• Nemeth, J., et al.: Biochemistry, 40, 3109 (1995)
• Tamura, M., et al.: J. Clin. Endocrinol. Metab., 87, 3263 (1995)