File:Glucosamine_Structural_Formulae_V.1.svg · Wikimedia Commons · See Wikimedia Commons
D-glucosamine
Sign in to saveAlso known as 2-Amino-2-deoxy-D-glucose, Chitosamine, Mannosamin, 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. It is produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. Glucosamine has various names depending on the country and its intended use.
Chemical data
- Formula
- C6H13NO5
- Molecular weight
- 179.17 g/mol
- IUPAC name
- (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
- SMILES
- C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)N)O)O)O
- InChIKey
- MSWZFWKMSRAUBD-IVMDWMLBSA-N
- XLogP
- -2.8
- Polar surface area
- 116 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- hydrogen
- Mass
- 179.079373
- Has use
- medication
Show 9 more facts
- found in taxon
- Cannabis sativa
- chemical formula
- C₆H₁₃NO₅
- medical condition treated
- osteoarthritis
- canonical SMILES
- C(C1C(C(C(C(O1)O)N)O)O)O
- isomeric SMILES
- C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)N)O)O)O
- defined daily dose
- 1.5
- native label
- Glucosamine
- Commons category
- Glucosamine
- significant drug interaction
- rac-warfarin
via Wikidata · CC0
~12 min read
Encyclopedic overview
20 sectionsContents
- Absence of clinical recommendations
- Recommendations against use
- Dietary supplement
- Adverse effects and drug interactions
- Biochemistry
- Manufacturing
- History
- Legal status
- United States
- Europe
- Class-action lawsuits
- Research
- Humans
- Bioavailability
- Veterinary medicine
- Dogs
- Horses
- See also
- References
- External links
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. It is produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. Glucosamine has various names depending on the country and its intended use.
Although a common dietary supplement, there is little clinical evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug in most countries, although it is listed as a medicinal product in Europe. Worldwide, there are no clinical organizations that recommend use of glucosamine as a treatment for arthritis.
Excerpted from Wikipedia’s “D-glucosamine” article, available under the CC BY-SA 4.0 licence.