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Showing metabocard for Glucosamine 6-phosphate (HMDB0001254)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (11) Show 11 proteinsXML
enzymes (11) Show 11 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-07-17 20:52:09 UTC
HMDB IDHMDB0001254
Secondary Accession Numbers
  • HMDB01254
Metabolite Identification
Common NameGlucosamine 6-phosphate
DescriptionGlucosamine 6-phosphate (CAS: 3616-42-0) is normally produced in endothelial cells via 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
Data?1595019129
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranoseChEBI
alpha-D-Glucosamine 6-(dihydrogen phosphate)ChEBI
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranoseGenerator
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranoseGenerator
Glucosamine 6-phosphoric acidGenerator
a-D-Glucosamine 6-(dihydrogen phosphate)Generator
a-D-Glucosamine 6-(dihydrogen phosphoric acid)Generator
alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)Generator
α-D-Glucosamine 6-(dihydrogen phosphate)Generator
α-D-Glucosamine 6-(dihydrogen phosphoric acid)Generator
2-Amino-2-deoxy-D-glucose 6-phosphateHMDB
2-Amino-2-deoxyglucose 6-phosphateHMDB
2-Amino-D-glucose-6-phosphateHMDB
D-Glucosamine 6-phosphateHMDB
D-Glucosamine phosphateHMDB
D-Glucosamine-6-phosphateHMDB
Glucosamine 6 -phosphateHMDB
Glucosamine-6-PHMDB
Glucosamine-6-phosphateHMDB
Glucose-6-phosphorateHMDB
Glucose-6-phosphoric acidHMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) esterHMDB
GLCN-6-PMeSH, HMDB
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 Nameα-D-glucosamine 6-phosphate
CAS Registry Number55722-81-1
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
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Amino saccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Hemiacetal
  • 1,2-diol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Area162.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability21.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9320000000-54466a568e39d51598c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ik9-3912400000-c198d10e982d681785edSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0970000000-095ba413dfd29c80b445Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9500000000-e4e82ba86236d6046d0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-bd232a0933f76298e943Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0190000000-778d1a36aaf5c9b3c846Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-08i0-1690000000-f08f9e49e698f1aa134dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9010000000-8a6a96ec67621a842ce8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9010000000-8a6a96ec67621a842ce8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0190000000-280711606909adbb8814Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-08i0-1690000000-f08f9e49e698f1aa134dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-818ec0fe39e531f561a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9850000000-40bb2cfef099c426fcbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmj-9500000000-9bb59bf1855e5fa76305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0699-8950000000-68f380f4fab22160c728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-4f7a2c18e5b29f9e6076Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6fc65d9a14f58d847a4fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02657
Phenol Explorer Compound IDNot Available
FooDB IDFDB022515
KNApSAcK IDNot Available
Chemspider ID388356
KEGG Compound IDC00352
BioCyc IDD-GLUCOSAMINE-6-P
BiGG ID34709
Wikipedia LinkNot Available
METLIN ID6111
PubChem Compound439217
PDB IDNot Available
ChEBI ID15873
Food Biomarker OntologyNot Available
VMH IDGAM6P
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)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 ]
  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 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Glucosamine 6-phosphate N-acetyltransferase
General function:
Involved in N-acetyltransferase activity
Specific function:
Not Available
Gene Name:
GNPNAT1
Uniprot ID:
Q96EK6
Molecular weight:
20748.965
Reactions
Acetyl-CoA + Glucosamine 6-phosphate → Coenzyme A + N-Acetyl-D-Glucosamine 6-Phosphatedetails
Enzyme Details
2. Glucokinase
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
Enzyme Details
3. Glucosamine-6-phosphate isomerase 1
General function:
Involved in carbohydrate metabolic process
Specific function:
Seems to trigger calcium oscillations in mammalian eggs. These oscillations serve as the essential trigger for egg activation and early development of the embryo (By similarity).
Gene Name:
GNPDA1
Uniprot ID:
P46926
Molecular weight:
32668.29
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails
Enzyme Details
4. Hexokinase-3
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
Enzyme Details
5. Hexokinase-2
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
Enzyme Details
6. Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT2
Uniprot ID:
O94808
Molecular weight:
76929.885
Reactions
L-Glutamine + Fructose 6-phosphate → L-Glutamic acid + Glucosamine 6-phosphatedetails
Enzyme Details
7. Hexokinase-1
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
Enzyme Details
8. Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT1
Uniprot ID:
Q06210
Molecular weight:
78805.81
Reactions
L-Glutamine + Fructose 6-phosphate → L-Glutamic acid + Glucosamine 6-phosphatedetails
Enzyme Details
9. Putative N-acetylglucosamine-6-phosphate deacetylase
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes the N-glycolyl group from N-glycolylglucosamine 6-phosphate (GlcNGc-6-P) in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway. Although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
Gene Name:
AMDHD2
Uniprot ID:
Q9Y303
Molecular weight:
63594.415
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate + Water → Glucosamine 6-phosphate + Acetic aciddetails
Enzyme Details
10. Glucosamine-6-phosphate isomerase 2
General function:
Involved in carbohydrate metabolic process
Specific function:
Not Available
Gene Name:
GNPDA2
Uniprot ID:
Q8TDQ7
Molecular weight:
27090.845
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters