Human Metabolome Database Version 3.5

Showing metabocard for Glucosamine 6-phosphate (HMDB01254)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:58 -0600
HMDB ID HMDB01254
Secondary Accession Numbers None
Metabolite Identification
Common Name Glucosamine 6-phosphate
Description Glucosamine 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 Link_out, 11842094 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H14NO8P
Average Molecular Weight 259.151
Monoisotopic Molecular Weight 259.045702941
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 Number 3616-42-0
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 Key XHMJOUIAFHJHBW-UKFBFLRUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Glutamate metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 34.8 g/L ALOGPS
LogP -2.60 ALOGPS
LogP -4.2 ChemAxon
LogS -0.87 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) 8.23 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 162.7 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 48.45 ChemAxon
Polarizability 20.95 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
Biofluid Locations Not Available
Tissue Location
  • Endothelium: Skin
Pathways
Name SMPDB Link KEGG Link
Amino Sugar Metabolism SMP00045 map00520 Link_out
Glutamate Metabolism SMP00072 map00250 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022515
KNApSAcK ID Not Available
Chemspider ID 388356 Link_out
KEGG Compound ID C00352 Link_out
BioCyc ID D-GLUCOSAMINE-6-P Link_out
BiGG ID 34709 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01254 Link_out
Metagene Link HMDB01254 Link_out
METLIN ID 6111 Link_out
PubChem Compound 439217 Link_out
PDB ID GLP Link_out
ChEBI ID 15873 Link_out
References
Synthesis Reference Cacioppo, 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) Download (PDF)
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 Link_out
  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 Link_out

Enzymes
Name: Glucosamine 6-phosphate N-acetyltransferase
Reactions:
Acetyl-CoA + Glucosamine 6-phosphate unknown Coenzyme A + N-Acetyl-D-Glucosamine 6-Phosphate details
Gene Name: GNPNAT1
Uniprot ID: Q96EK6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucokinase
Reactions: Not Available
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosamine-6-phosphate isomerase 1
Reactions:
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammonia details
Gene Name: GNPDA1
Uniprot ID: P46926 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: Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2
Reactions:
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphate details
Gene Name: GFPT2
Uniprot ID: O94808 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: Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1
Reactions:
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphate details
Gene Name: GFPT1
Uniprot ID: Q06210 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative N-acetylglucosamine-6-phosphate deacetylase
Reactions:
N-Acetyl-D-Glucosamine 6-Phosphate + Water unknown Glucosamine 6-phosphate + Acetic acid details
Gene Name: AMDHD2
Uniprot ID: Q9Y303 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosamine-6-phosphate isomerase 2
Reactions:
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammonia details
Gene Name: GNPDA2
Uniprot ID: Q8TDQ7 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