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

• ChemBase ID: 1148
• Molecular Formular: C6H13NO5
• Molecular Mass: 179.17112
• Monoisotopic Mass: 179.07937252
• SMILES: O1[C@@H]([C@@H](O)[C@H](O)[C@@H](N)C1O)CO
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([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-IVMDWMLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
• IUPAC Traditional name: glucosamine
• Synonyms: Glucosamine

Database IDs

• CAS Number: 3416-24-8
• PubChem SID: 160964611; 46506420
• PubChem CID: 439213

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.73
• LOG S: 0.49
• Solubility (Water): 5.51e+02 g/l

DETAILS

DrugBank - DB01296

• Drug Groups: approved
• Description: Glucosamine is commonly used as a treatment for osteoarthritis, although its acceptance as a medical therapy varies. It is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis.
• References: Towheed TE, Maxwell L, Anastassiades TP, Shea B, Houpt J, Robinson V, Hochberg MC, Wells G: Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD002946. [Pubmed] ; Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. [Pubmed] ; GHOSH S, BLUMENTHAL HJ, DAVIDSON E, ROSEMAN S: Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate. J Biol Chem. 1960 May;235:1265-73. [Pubmed] ; Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. [Pubmed] ; Laverty S, Sandy JD, Celeste C, Vachon P, Marier JF, Plaas AH: Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses. Arthritis Rheum. 2005 Jan;52(1):181-91. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Towheed TE, Maxwell L, Anastassiades TP, Shea B, Houpt J, Robinson V, Hochberg MC, Wells G: Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD002946. Pubmed
• Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. Pubmed
• GHOSH S, BLUMENTHAL HJ, DAVIDSON E, ROSEMAN S: Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate. J Biol Chem. 1960 May;235:1265-73. Pubmed
• Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. Pubmed
• Laverty S, Sandy JD, Celeste C, Vachon P, Marier JF, Plaas AH: Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses. Arthritis Rheum. 2005 Jan;52(1):181-91. Pubmed