You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.

Showing metabocard for Glucosamine 6-phosphate (BMDB0001254)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
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
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 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
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 Properties
PropertyValueSource
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9320000000-54466a568e39d51598c7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ik9-3912400000-c198d10e982d681785edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0970000000-095ba413dfd29c80b445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9500000000-e4e82ba86236d6046d0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-bd232a0933f76298e943View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0190000000-778d1a36aaf5c9b3c846View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-08i0-1690000000-f08f9e49e698f1aa134dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9010000000-8a6a96ec67621a842ce8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9010000000-8a6a96ec67621a842ce8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0190000000-280711606909adbb8814View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-08i0-1690000000-f08f9e49e698f1aa134dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-3190000000-0f9d6942fba86f12422eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03fr-2790000000-7fe42a3d5900a5984d04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-818ec0fe39e531f561a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9850000000-40bb2cfef099c426fcbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmj-9500000000-9bb59bf1855e5fa76305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0699-8950000000-68f380f4fab22160c728View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-4f7a2c18e5b29f9e6076View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6fc65d9a14f58d847a4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0790000000-d9873144345380710376View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9810000000-32a2cffa4a376910fdb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-9000000000-7be390edddedcba28a23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-9040000000-fd7b28df2dbc578cfc0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9010000000-f0f082b70bb688bd4b38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
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

Enzyme Details
1. Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2
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
Enzyme Details
2. Hexokinase-1
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
Enzyme Details
3. Glucosamine-6-phosphate isomerase 2
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GNPDA2
Uniprot ID:
Q17QL1
Molecular weight:
31165.0
Enzyme Details
4. N-acetylglucosamine-6-phosphate deacetylase
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
Enzyme Details
5. Glucosamine-6-phosphate isomerase 1
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
Enzyme Details
6. Glucosamine 6-phosphate N-acetyltransferase
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