Human Metabolome Database Version 3.5

Showing metabocard for Glucosamine (HMDB01514)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-15 14:01:42 -0600
HMDB ID HMDB01514
Secondary Accession Numbers
  • HMDB06479
  • HMDB15410
Metabolite Identification
Common Name Glucosamine
Description In 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H13NO5
Average Molecular Weight 179.1711
Monoisotopic Molecular Weight 179.079372531
IUPAC Name (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Traditional IUPAC Name glucosamine
CAS Registry Number 3416-24-8
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 Key MSWZFWKMSRAUBD-IVMDWMLBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Endogenous
  • Food
Biofunction
  • Component of Aminosugars metabolism
  • Component of Glutamate metabolism
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 88 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 330 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 551 g/L ALOGPS
LogP -2.73 ALOGPS
LogP -3 ChemAxon
LogS 0.49 ALOGPS
pKa (strongest acidic) 11.73 ChemAxon
pKa (strongest basic) 8.23 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 116.17 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 37.58 ChemAxon
Polarizability 16.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Epidermis
  • Platelet
  • Cartilage
Pathways
Name SMPDB Link KEGG Link
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.29 (0.0-0.6) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.45 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01296 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022668
KNApSAcK ID Not Available
Chemspider ID 388352 Link_out
KEGG Compound ID C00329 Link_out
BioCyc ID GLUCOSAMINE Link_out
BiGG ID 34633 Link_out
Wikipedia Link Glucosamine Link_out
NuGOwiki Link HMDB01514 Link_out
Metagene Link HMDB01514 Link_out
METLIN ID 266 Link_out
PubChem Compound 439213 Link_out
PDB ID 1QGI Link_out
ChEBI ID 5417 Link_out
References
Synthesis Reference Li, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  16. Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. Pubmed: 11553646 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Glucokinase
Reactions: Not Available
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphate details
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphate details
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-1
Reactions:
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphate details
Gene Name: HK1
Uniprot ID: P19367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-sulphoglucosamine sulphohydrolase
Reactions:
N-Sulfo-D-glucosamine + Water unknown Glucosamine + Oat gum details
Gene Name: SGSH
Uniprot ID: P51688 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Tumor necrosis factor
Reactions: Not Available
Gene Name: TNF
Uniprot ID: P01375 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Di-N-acetylchitobiase
Reactions: Not Available
Gene Name: CTBS
Uniprot ID: Q01459 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase
Reactions: Not Available
Gene Name: NGLY1
Uniprot ID: Q96IV0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative hexokinase HKDC1
Reactions:
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphate details
Gene Name: HKDC1
Uniprot ID: Q2TB90 Link_out
Protein Sequence: FASTA