Glucosamine

Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country.

Glucosamine
Names
IUPAC name
(3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
Other names
2-Amino-2-deoxy-glucose
Chitosamine
Identifiers
3D model (JSmol)
1723616
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.020.284
EC Number
  • 222-311-2
720725
KEGG
MeSH Glucosamine
PubChem CID
UNII
  • 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 N
    Key: MSWZFWKMSRAUBD-SPZCMYQFSA-N N
SMILES
  • N[C@H]1C(O)OC(CO)[C@@H](O)[C@@H]1O
Properties
C6H13NO5
Molar mass 179.172 g·mol−1
Density 1.563 g/mL
Melting point 150 °C (302 °F; 423 K)
log P -2.175
Acidity (pKa) 7.5
Basicity (pKb) 4.5
Pharmacology
M01AX05 (WHO)
Legal status
  • EU: Authorized
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug.

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