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

• ChemBase ID: 169662
• Molecular Formular: C6H14ClNO5
• Molecular Mass: 215.63206
• Monoisotopic Mass: 215.05605023
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)N)O)O.Cl
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1O)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/t2?,3?,4-,5-,6?;/m1./s1
• InChIKey: QKPLRMLTKYXDST-NPDXWMOGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride
• IUPAC Traditional name: (4R,5S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride
• Synonyms: 2-Amino-2-deoxy-D-glucose Hydrochloride; 2-Deoxy-2-amino-D-glucose Hydrochloride; Chitosamine Hydrochloride; Cosamin; D-(+)-Glucosamine Hydrochloride; D-Glucosamine Chloride; Glucosamine hydrochloride; NSC 234443; NSC 758; D-Glucosamine Hydrochloride; 2-Amino-2-deoxy-D-mannose Hydrochloride; D-Mannosamine Hydrochloride

Database IDs

• CAS Number: 5505-63-5; 66-84-2
• PubChem SID: 162263794
• PubChem CID: 71317088

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: Water
• Apperance: White Solid; White to Off-White Solid
• Melting Point: >160°C (dec.); 180-183°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G514950

Novel application of glucosamine to prepare medical agent for treating vertigo. Found in chitin, in mucoproteins, and in mucopolysaccharides. Antiarthritic. Recent studies show that its chondroprotective activity is related to its antiapoptic properties.

Toronto Research Chemicals - M167000

A pharmaceutical compound used in the development of mannosylated liposomes for bioadhesive oral drug delivery via M cells of Peyer's patches.

REFERENCES

• Zupanets, I.A. et al.: Klin. Farmat., 15, 67 (2011)
• Vajarudal, Y., et al.: Clin. Ther., 3, 336 (2011)
• Setnikar, I., et al.: Arzneim.-Forsch., 36, 729 (2011)
• Pukanud, P. et al.: Drug Delivery, 16, 289 (2009)
• Knowles, D.J. et al.: J. Gen. Microbiol., 108, 17 (2009)