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

• ChemBase ID: 169667
• Molecular Formular: C6H13NO5
• Molecular Mass: 179.17112
• Monoisotopic Mass: 179.07937252
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)N)O)O
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1O)O)N
• InChI: InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2?,3?,4-,5-,6?/m1/s1
• InChIKey: MSWZFWKMSRAUBD-BKAHITNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
• IUPAC Traditional name: (4R,5S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
• Synonyms: 2-Amino-2-deoxy-D-glucose Sulfate; Arthro; Cevolox; Chitosamine Sulfate; D-Glucosamine Sulfate; DONA; Glucosamine Sulfate; Glucosamine Sulfate Salt; D-Glucosamine Sulfate Salt

Database IDs

• CAS Number: 29031-19-4
• PubChem SID: 162263799
• PubChem CID: 68011877

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

• Apperance: White Powder

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G515100

Novel application of glucosamine to prepare medical agent for treating vertigo. Found in chitin, in mucoproteins, and in mucopolysaccharides. Antiarthritic.

REFERENCES

• Cox, J., et al.: Nature, 143, 894 (1939)
• Vajarudal, Y., et al.: Clin. Ther., 3, 336 (1939)
• Setnikar, I., et al.: Arzneim.-Forsch., 36, 729 (1939)
• Anderson, J.W., et al.: Food Chem. Toxicol., 43, 187 (1939)