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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. Within yeast, N-acetyl-glucosamine 1-phosphate participates in a number of enzymatic reactions. 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; which is mediated by the enzyme UDP-N-acetylglucosamine pyrophosphorylase. In yeast, N-acetyl-glucosamine 1-phosphate is involved in the metabolic pathway called the amino sugar and nucleotide sugar metabolism pathway.
Structure
Thumb
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-phosphateN-Acetyl-glucosamine 1-phosphate
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + hydronPyrophosphate + 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 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
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

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.
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.