Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:58 UTC
HMDB IDHMDB01254
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlucosamine 6-phosphate
DescriptionGlucosamine 6-phosphate is normally produced in endothelial cells via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus. (PMID 11270676 , 11842094 ).
Structure
Thumb
Synonyms
  1. 2-Amino-2-deoxy-D-glucose 6-phosphate
  2. 2-Amino-2-deoxyglucose 6-phosphate
  3. 2-Amino-D-glucose-6-phosphate
  4. D-Glucosamine 6-phosphate
  5. D-Glucosamine phosphate
  6. D-Glucosamine-6-phosphate
  7. Glucosamine 6 -phosphate
  8. Glucosamine 6-Phosphate
  9. Glucosamine-6-P
  10. Glucosamine-6-phosphate
  11. Glucose-6-phosphorate
  12. Glucose-6-phosphoric acid
  13. Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester
Chemical FormulaC6H14NO8P
Average Molecular Weight259.151
Monoisotopic Molecular Weight259.045702941
IUPAC Name{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number3616-42-0
SMILES
N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1
InChI KeyXHMJOUIAFHJHBW-UKFBFLRUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • 2-amino-2-deoxy-D-glucopyranose 6-phosphate(ChEBI)
  • Aliphatic Heteromonocyclic Compounds
  • Amino Sugars
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Aminoalcohol
  • 1,2 Diol
  • Hemiacetal
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Glutamate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility34.8 g/LALOGPS
logP-2.6ALOGPS
logP-4.2ChemAxon
logS-0.87ALOGPS
pKa (strongest acidic)1.22ChemAxon
pKa (strongest basic)8.23ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count6ChemAxon
polar surface area162.7ChemAxon
rotatable bond count3ChemAxon
refractivity48.45ChemAxon
polarizability20.95ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
Biofluid LocationsNot Available
Tissue Location
  • Endothelium: Skin
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
Glutamate MetabolismSMP00072map00250
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022515
KNApSAcK IDNot Available
Chemspider ID388356
KEGG Compound IDC00352
BioCyc IDD-GLUCOSAMINE-6-P
BiGG ID34709
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01254
Metagene LinkHMDB01254
METLIN ID6111
PubChem Compound439217
PDB IDGLP
ChEBI ID15873
References
Synthesis ReferenceCacioppo, F.; Pandolfo, L.; Arena, E. Synthesis of glucosamine 6-phosphate in tissues of rachitic rats. Giorn. Biochim. (1964), 13(4), 249-55.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wu G, Haynes TE, Yan W, Meininger CJ: Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine. Diabetologia. 2001 Feb;44(2):196-202. Pubmed: 11270676
  2. Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP: Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate. J Biol Chem. 2002 Apr 26;277(17):14764-70. Epub 2002 Feb 12. Pubmed: 11842094

Enzymes

Gene Name:
GNPNAT1
Uniprot ID:
Q96EK6
Reactions
Acetyl-CoA + Glucosamine 6-phosphate unknown Coenzyme A + N-Acetyl-D-Glucosamine 6-Phosphatedetails
Gene Name:
GCK
Uniprot ID:
P35557
Gene Name:
GNPDA1
Uniprot ID:
P46926
Reactions
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammoniadetails
Gene Name:
HK3
Uniprot ID:
P52790
Reactions
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphatedetails
Gene Name:
HK2
Uniprot ID:
P52789
Reactions
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphatedetails
Gene Name:
GFPT2
Uniprot ID:
O94808
Reactions
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphatedetails
Gene Name:
HK1
Uniprot ID:
P19367
Reactions
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphatedetails
Gene Name:
GFPT1
Uniprot ID:
Q06210
Reactions
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphatedetails
Gene Name:
AMDHD2
Uniprot ID:
Q9Y303
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate + Water unknown Glucosamine 6-phosphate + Acetic aciddetails
Gene Name:
GNPDA2
Uniprot ID:
Q8TDQ7
Reactions
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammoniadetails
Gene Name:
HKDC1
Uniprot ID:
Q2TB90
Reactions
Adenosine triphosphate + Glucosamine unknown ADP + Glucosamine 6-phosphatedetails