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Record Information
Version1.0
Creation Date2016-09-30 22:43:08 UTC
Update Date2020-05-21 16:28:28 UTC
BMDB IDBMDB0001254
Secondary Accession Numbers
  • BMDB01254
Metabolite Identification
Common NameGlucosamine 6-phosphate
DescriptionGlucosamine 6-phosphate, also known as GLCN-6-p or glucose-6-phosphoric acid, 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. Glucosamine 6-phosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Glucosamine 6-phosphate exists in all living species, ranging from bacteria to humans. Glucosamine 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Glucosamine 6-phosphate and acetic acid can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme putative N-acetylglucosamine-6-phosphate deacetylase. In addition, Glucosamine 6-phosphate can be converted into N-acetyl-D-glucosamine 6-phosphate; which is catalyzed by the enzyme glucosamine 6-phosphate N-acetyltransferase. In cattle, glucosamine 6-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.
Structure
Thumb
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 NameNot Available
Traditional NameNot Available
CAS Registry Number3616-42-0
SMILESNot Available
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
Biospecimen Locations
  • Epidermis
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001254
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
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. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

General function:
Cell wall/membrane/envelope biogenesis
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 (By similarity).
Gene Name:
GFPT2
Uniprot ID:
Q08DQ2
Molecular weight:
77081.0
Reactions
Fructose 6-phosphate + L-Glutamine → Glucosamine 6-phosphate + L-Glutamic aciddetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
Glucosamine + Adenosine triphosphate → Glucosamine 6-phosphate + ADPdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GNPDA2
Uniprot ID:
Q17QL1
Molecular weight:
31165.0
General function:
Carbohydrate transport and metabolism
Specific function:
Hydrolyzes the N-glycolyl group from N-glycolylglucosamine 6-phosphate (GlcNGc-6-P) in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway.
Gene Name:
AMDHD2
Uniprot ID:
A7MBC0
Molecular weight:
43496.0
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate + Water → Glucosamine 6-phosphate + Acetic aciddetails
General function:
Not Available
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:
A4FV08
Molecular weight:
32580.0
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
GNPNAT1
Uniprot ID:
Q08DV2
Molecular weight:
20776.0
Reactions
Acetyl-CoA + Glucosamine 6-phosphate → N-Acetyl-D-Glucosamine 6-Phosphate + Coenzyme Adetails