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N-Acetyl-glucosamine 1-phosphate (YMDB00043)

Identification
YMDB IDYMDB00043
NameN-Acetyl-glucosamine 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-Acetyl-glucosamine 1-phosphate, also known as glcnac-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 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-(acetylamino)-2-Deoxy-D-glucopyranose 1-(dihydrogen phosphate)
  • 2-(acetylamino)-2-Deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid)
  • 2-acetamido-2-Deoxy-1-O-phosphono-D-glucopyranose
  • D-glucosamine 1-phosphate
  • delta-glucosamine 1-phosphate
  • GlcNAc-1-phosphate
  • N-acetyl-alpha-D-glucosamine 1-phosphate
  • N-acetyl-alpha-delta-glucosamine 1-phosphate
  • N-acetyl-D-glucosamine 1-phosphate
  • N-Acetyl-D-glucosamine 1-phosphoric acid
  • N-acetyl-delta-glucosamine 1-phosphate
  • N-Acetyl-glucosamine 1-phosphate
  • N-Acetyl-glucosamine 1-phosphic acid
  • N-Acetyl-glucosamine 1-phosphoric acid
  • N-acetyl-glucosamine-1-phosphate
  • N-Acetylglucosamine-1-phosphate
  • N-Acetylglucosamine-1-phosphoric acid
CAS number901851-43-2
WeightAverage: 301.1877
Monoisotopic: 301.056267627
InChI KeyFZLJPEPAYPUMMR-RTRLPJTCSA-N
InChIInChI=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
IUPAC Name{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
Chemical FormulaC8H16NO9P
SMILES[H]OC([H])([H])[C@@]1([H])OC([H])(OP(=O)(O[H])O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility18.4 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
SMPDB Reactions
N-acetyl-D-glucosamine 6-phosphate → N-Acetyl-glucosamine 1-phosphate
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + hydron → Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007k-9230000000-37cdd3ef185356d03c19JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-9211240000-817e06893a2ccced098bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1094000000-f1e04aaf05d431b8b0abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-6290000000-6ff96a8c8bf54d5e8bfaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-9620000000-3e2ee2ffc3801abdb7daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-9211000000-7f3631860a58ca188060JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-9614f2b717f8fb17cc08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1a4f6aa02a49053d5b95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0269000000-3075b429edd6182c13baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0559000000-4ca1cd5a6e65977c0024JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-6900000000-1cb673f71135d27b87a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1019000000-7dfe9f6a1a82e9cc6643JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9021000000-405c928cec60fc405bdbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9000000000-5c37c1fa0342ac32c556JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Mio, T., Yabe, T., Arisawa, M., Yamada-Okabe, H. (1998). "The eukaryotic UDP-N-acetylglucosamine pyrophosphorylases. Gene cloning, protein expression, and catalytic mechanism." J Biol Chem 273:14392-14397.9603950
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID7125
HMDB IDHMDB01367
Pubchem Compound ID900
Kegg IDC04256
ChemSpider ID389248
FOODB IDFDB022581
Wikipedia IDNot Available
BioCyc IDN-ACETYL-D-GLUCOSAMINE-1-P

Enzymes

Protein Details
1. UDP-N-acetylglucosamine pyrophosphorylase
General function:
Involved in UDP-N-acetylglucosamine diphosphorylase act
Specific function:
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine
Gene Name:
QRI1
Uniprot ID:
P43123
Molecular weight:
53475.60156
Reactions
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate → diphosphate + UDP-N-acetyl-D-glucosamine.
Protein Details
2. Phosphoacetylglucosamine mutase
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Interconverts GlcNAc-6-P and GlcNAc-1-P
Gene Name:
PCM1
Uniprot ID:
P38628
Molecular weight:
62066.10156
Reactions
N-acetyl-alpha-D-glucosamine 1-phosphate → N-acetyl-D-glucosamine 6-phosphate.