(4R,5S)-2,4,5-trihydroxy-6-[hydroxy(13C)methyl](2,3,4,5,6-13C5)oxan-3-aminium chloride

• ChemBase ID: 169668
• Molecular Formular: C6H14ClNO5
• Molecular Mass: 221.58798903
• Monoisotopic Mass: 221.07617926
• SMILES: [13C@@H]1([13C@@H]([13CH]([13CH](O[13CH]1[13CH2]O)O)[NH3+])O)O.[Cl-]
• Canonical SMILES: O[13CH2][13CH]1O[13CH](O)[13CH]([13C@H]([13C@@H]1O)O)[NH3+].[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/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: QKPLRMLTKYXDST-KCUZVKRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-2,4,5-trihydroxy-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-3-aminium chloride
• IUPAC Traditional name: (4R,5S)-2,4,5-trihydroxy-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-3-aminium chloride
• Synonyms: 2-Amino-2-deoxy-D-[UL-13C6]glucose Hydrochloride; D-[UL-13C6]Glucosamine Hydrochloride

Database IDs

• PubChem SID: 162263800
• PubChem CID: 71317092

CALCULATED PROPERTIES

• Acid pKa: 11.726975
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -5.5965767
• LogD (pH = 7.4): -3.9292529
• Log P: -3.039421
• Molar Refractivity: 48.8737 cm^3
• Polarizability: 15.922577 Å^3
• Polar Surface Area: 117.79 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >185°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G515102

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)