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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-15 20:01:42 UTC
HMDB IDHMDB01514
Secondary Accession Numbers
  • HMDB06479
  • HMDB15410
Metabolite Identification
Common NameGlucosamine
DescriptionIn the United States, glucosamine is not approved by the Food and Drug Administration for medical use in humans. Since glucosamine is classified as a dietary supplement, evidence of safety and efficacy is not required as long as it is not advertised as a treatment for a medical condition. Nevertheless, glucosamine is a popular alternative medicine used by consumers for the treatment of osteoarthritis. Glucosamine is also extensively used in veterinary medicine as an unregulated but widely accepted supplement (Nolen RS, 2002). Treatment with oral glucosamine is commonly used for the treatment of osteoarthritis. 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. However, there is little evidence that any clinical effect of glucosamine works this way (Laverty et al., 2005; Biggee et al., 2005). Its use as a therapy for osteoarthritis appears safe but there is conflicting evidence as to its effectiveness. Glucosamine (C6H14NO5) is an amino sugar that is an important precursor in the biochemical synthesis of glycosylated proteins and lipids.
Structure
Thumb
Synonyms
  1. (+)-2-amino-2-deoxy-D-glucopyranose
  2. (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
  3. 2-Amino-2-deoxy-D-glucopyranose
  4. 2-Amino-2-deoxy-D-Glucose
  5. 2-Amino-2-deoxyglucose
  6. 2-Aminoglucose
  7. 2-Deoxy-2-amino-D-glucose
  8. 2-Deoxy-2-aminoglucose
  9. Chitosamine
  10. Cosamin
  11. D-(+)-Glucosamine
  12. D-Glucosamine
Chemical FormulaC6H13NO5
Average Molecular Weight179.1711
Monoisotopic Molecular Weight179.079372531
IUPAC Name(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Traditional IUPAC Nameglucosamine
CAS Registry Number3416-24-8
SMILES
N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyMSWZFWKMSRAUBD-IVMDWMLBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Amino Sugars
  • Amino sugars(KEGG)
  • Carbohydrates and Carbohydrate Conjugates
  • D-galactosamine(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • 1,2 Diol
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Endogenous
  • Food
Biofunction
  • Component of Aminosugars metabolism
  • Component of Glutamate metabolism
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility330 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility551 g/LALOGPS
logP-2.7ALOGPS
logP-3ChemAxon
logS0.49ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area116.17ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.58ChemAxon
Polarizability16.87ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Cartilage
  • Epidermis
  • Fibroblasts
  • Intestine
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.29 (0.0-0.6) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.45 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01296
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022668
KNApSAcK IDNot Available
Chemspider ID388352
KEGG Compound IDC00329
BioCyc IDGLUCOSAMINE
BiGG ID34633
Wikipedia LinkGlucosamine
NuGOwiki LinkHMDB01514
Metagene LinkHMDB01514
METLIN ID266
PubChem Compound439213
PDB ID1QGI
ChEBI ID5417
References
Synthesis ReferenceLi, Nan; Li, Jiheng. Preparation of D-glucosamine hydrochloride. Zhongguo Yaoke Daxue Xuebao (1997), 28(1), 56-58.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Thatte HS, Zagarins S, Khuri SF, Fischer TH: Mechanisms of poly-N-acetyl glucosamine polymer-mediated hemostasis: platelet interactions. J Trauma. 2004 Jul;57(1 Suppl):S13-21. Pubmed: 15280745
  2. Ruoslahti E, Engvall E, Hayman EG, Spiro RG: Comparative studies on amniotic fluid and plasma fibronectins. Biochem J. 1981 Jan 1;193(1):295-9. Pubmed: 7305927
  3. Rhodes M, Allen A, Dowling RH, Murphy G, Lennard TW: Inhibition of human gall bladder mucus synthesis in patients undergoing cholecystectomy. Gut. 1992 Aug;33(8):1113-7. Pubmed: 1398238
  4. Cibere J, Thorne A, Kopec JA, Singer J, Canvin J, Robinson DB, Pope J, Hong P, Grant E, Lobanok T, Ionescu M, Poole AR, Esdaile JM: Glucosamine sulfate and cartilage type II collagen degradation in patients with knee osteoarthritis: randomized discontinuation trial results employing biomarkers. J Rheumatol. 2005 May;32(5):896-902. Pubmed: 15868627
  5. Morita H, Kettlewell MG, Jewell DP, Kent PW: Glycosylation and sulphation of colonic mucus glycoproteins in patients with ulcerative colitis and in healthy subjects. Gut. 1993 Jul;34(7):926-32. Pubmed: 8344580
  6. Zhang LJ, Huang TM, Fang XL, Li XN, Wang QS, Zhang ZW, Sha XY: Determination of glucosamine sulfate in human plasma by precolumn derivatization using high performance liquid chromatography with fluorescence detection: its application to a bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):8-12. Epub 2006 Jun 5. Pubmed: 16740419
  7. Hoffer LJ, Kaplan LN, Hamadeh MJ, Grigoriu AC, Baron M: Sulfate could mediate the therapeutic effect of glucosamine sulfate. Metabolism. 2001 Jul;50(7):767-70. Pubmed: 11436179
  8. Huang TM, Cai L, Yang B, Zhou MX, Shen YF, Duan GL: Liquid chromatography with electrospray ionization mass spectrometry method for the assay of glucosamine sulfate in human plasma: validation and application to a pharmacokinetic study. Biomed Chromatogr. 2006 Mar;20(3):251-6. Pubmed: 16145658
  9. Biggee BA, Blinn CM, McAlindon TE, Nuite M, Silbert JE: Low levels of human serum glucosamine after ingestion of glucosamine sulphate relative to capability for peripheral effectiveness. Ann Rheum Dis. 2006 Feb;65(2):222-6. Epub 2005 Aug 3. Pubmed: 16079170
  10. McCarty MF: Enhanced synovial production of hyaluronic acid may explain rapid clinical response to high-dose glucosamine in osteoarthritis. Med Hypotheses. 1998 Jun;50(6):507-10. Pubmed: 9710325
  11. Uitterlinden EJ, Jahr H, Koevoet JL, Jenniskens YM, Bierma-Zeinstra SM, Degroot J, Verhaar JA, Weinans H, van Osch GJ: Glucosamine decreases expression of anabolic and catabolic genes in human osteoarthritic cartilage explants. Osteoarthritis Cartilage. 2006 Mar;14(3):250-7. Epub 2005 Nov 18. Pubmed: 16300972
  12. Cope GF, Heatley RV, Kelleher J, Axon AT: In vitro mucus glycoprotein production by colonic tissue from patients with ulcerative colitis. Gut. 1988 Feb;29(2):229-34. Pubmed: 3345934
  13. McCarty MF: Glucosamine may retard atherogenesis by promoting endothelial production of heparan sulfate proteoglycans. Med Hypotheses. 1997 Mar;48(3):245-51. Pubmed: 9140889
  14. Cheung HS, Nicoloff JT, Kamiel MB, Spolter L, Nimni ME: Stimulation of fibroblast biosynthetic activity by serum of patients with pretibial myxedema. J Invest Dermatol. 1978 Jul;71(1):12-7. Pubmed: 355562
  15. Valeri CR, Srey R, Tilahun D, Ragno G: In vitro effects of poly-N-acetyl glucosamine on the activation of platelets in platelet-rich plasma with and without red blood cells. J Trauma. 2004 Jul;57(1 Suppl):S22-5; discussion S25. Pubmed: 15280746
  16. Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. Pubmed: 11553646
  17. 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: 13827775
  18. 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: 15641100
  19. 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: 15846645
  20. Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. Pubmed: 16339923

Enzymes

General function:
Involved in ATP binding
Specific function:
Catalyzes the initial step in utilization of glucose by the beta-cell and liver at physiological glucose concentration. Glucokinase has a high Km for glucose, and so it is effective only when glucose is abundant. The role of GCK is to provide G6P for the synthesis of glycogen. Pancreatic glucokinase plays an important role in modulating insulin secretion. Hepatic glucokinase helps to facilitate the uptake and conversion of glucose by acting as an insulin-sensitive determinant of hepatic glucose usage.
Gene Name:
GCK
Uniprot ID:
P35557
Molecular weight:
52191.07
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
Reactions
Adenosine triphosphate + Glucosamine → ADP + Glucosamine 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
Reactions
Adenosine triphosphate + Glucosamine → ADP + Glucosamine 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK1
Uniprot ID:
P19367
Molecular weight:
102485.1
Reactions
Adenosine triphosphate + Glucosamine → ADP + Glucosamine 6-phosphatedetails
General function:
Inorganic ion transport and metabolism
Specific function:
Not Available
Gene Name:
SGSH
Uniprot ID:
P51688
Molecular weight:
56694.875
Reactions
N-Sulfo-D-glucosamine + Water → Glucosamine + Oat gumdetails
General function:
Involved in tumor necrosis factor receptor binding
Specific function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:
TNF
Uniprot ID:
P01375
Molecular weight:
25644.1
General function:
Involved in chitinase activity
Specific function:
Involved in the degradation of asparagine-linked glycoproteins. Hydrolyze of N-acetyl-beta-D-glucosamine (1-4)N- acetylglucosamine chitobiose core from the reducing end of the bond, it requires prior cleavage by glycosylasparaginase
Gene Name:
CTBS
Uniprot ID:
Q01459
Molecular weight:
43759.4
General function:
Involved in protein binding
Specific function:
Specifically deglycosylates the denatured form of N- linked glycoproteins in the cytoplasm and assists their proteasome-mediated degradation. Cleaves the beta-aspartyl- glucosamine (GlcNAc) of the glycan and the amide side chain of Asn, converting Asn to Asp. Prefers proteins containing high- mannose over those bearing complex type oligosaccharides. Can recognize misfolded proteins in the endoplasmic reticulun that are exported in the cytosol to be destroyed and deglycosylate them, while it has no activity toward native proteins. Deglycosylation is prerequisite for subsequent proteasome-mediated degradation of some, but not all, misfolded glycoproteins
Gene Name:
NGLY1
Uniprot ID:
Q96IV0
Molecular weight:
74389.4
General function:
Not Available
Specific function:
Not Available
Gene Name:
HKDC1
Uniprot ID:
Q2TB90
Molecular weight:
102513.88
Reactions
Adenosine triphosphate + Glucosamine → ADP + Glucosamine 6-phosphatedetails