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Showing metabocard for N-Acetyl-glucosamine 1-phosphate (BMDB0001367)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:48 UTC
Update Date2020-05-21 16:28:28 UTC
BMDB IDBMDB0001367
Secondary Accession Numbers
  • BMDB01367
Metabolite Identification
Common NameN-Acetyl-glucosamine 1-phosphate
DescriptionN-Acetyl-glucosamine 1-phosphate, also known as n-acetyl-glucosamine 1-phosphate, belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-Acetyl-glucosamine 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-glucosamine 1-phosphate exists in all eukaryotes, ranging from yeast to humans. N-Acetyl-glucosamine 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-glucosamine 1-phosphate can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is catalyzed by the enzyme phosphoacetylglucosamine mutase. In addition, N-Acetyl-glucosamine 1-phosphate and uridine triphosphate can be converted into uridine diphosphate-N-acetylglucosamine through its interaction with the enzyme UDP-N-acetylhexosamine pyrophosphorylase. In cattle, N-acetyl-glucosamine 1-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphate)ChEBI
2-Acetamido-2-deoxy-1-O-phosphono-D-glucopyranoseChEBI
N-Acetyl-D-glucosamine 1-phosphateChEBI
N-Acetylglucosamine-1-phosphateChEBI
2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid)Generator
N-Acetyl-D-glucosamine 1-phosphoric acidGenerator
N-Acetylglucosamine-1-phosphoric acidGenerator
N-Acetyl-glucosamine 1-phosphoric acidGenerator
D-Glucosamine 1-phosphateHMDB
delta-Glucosamine 1-phosphateHMDB
N-Acetyl-alpha-D-glucosamine 1-phosphateHMDB
N-Acetyl-alpha-delta-glucosamine 1-phosphateHMDB
N-Acetyl-delta-glucosamine 1-phosphateHMDB
N-Acetyl-glucosamine-1-phosphateHMDB
GlcNAc-1-phosphateHMDB
Chemical FormulaC8H16NO9P
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
IUPAC Name{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional Name[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
CAS Registry Number6866-69-9
SMILES
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O
InChI Identifier
InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1
InChI KeyFZLJPEPAYPUMMR-RTRLPJTCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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-2ALOGPS
logP-3.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m³·mol⁻¹ChemAxon
Polarizability25.41 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, Positivesplash10-007k-9230000000-37cdd3ef185356d03c19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-9211240000-817e06893a2ccced098bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1094000000-f1e04aaf05d431b8b0abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-6290000000-6ff96a8c8bf54d5e8bfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-9620000000-3e2ee2ffc3801abdb7daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-9211000000-7f3631860a58ca188060View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-9614f2b717f8fb17cc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1a4f6aa02a49053d5b95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0269000000-3075b429edd6182c13baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0559000000-4ca1cd5a6e65977c0024View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-6900000000-1cb673f71135d27b87a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1019000000-7dfe9f6a1a82e9cc6643View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9021000000-405c928cec60fc405bdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9000000000-5c37c1fa0342ac32c556View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001367
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022581
KNApSAcK IDC00019581
Chemspider ID389248
KEGG Compound IDC04256
BioCyc IDN-ACETYL-D-GLUCOSAMINE-1-P
BiGG ID43457
Wikipedia LinkNot Available
METLIN ID6194
PubChem Compound440272
PDB IDNot Available
ChEBI ID7125
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphoacetylglucosamine mutase
General function:
Not Available
Specific function:
Catalyzes the conversion of GlcNAc-6-P into GlcNAc-1-P during the synthesis of uridine diphosphate/UDP-GlcNAc, a sugar nucleotide critical to multiple glycosylation pathways including protein N- and O-glycosylation.
Gene Name:
PGM3
Uniprot ID:
F1MS56
Molecular weight:
59950.0
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate → N-Acetyl-glucosamine 1-phosphatedetails
Enzyme Details
2. UDP-N-acetylglucosamine pyrophosphorylase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
UAP1
Uniprot ID:
F1MJP7
Molecular weight:
58623.0
Reactions
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate → Uridine diphosphate-N-acetylglucosamine + Pyrophosphatedetails