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N-acetyl-alpha-D-glucosamine 1-phosphate (YMDB00751)

Identification
YMDB IDYMDB00751
NameN-acetyl-alpha-D-glucosamine 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-acetyl-α-D-glucosamine 1-phosphate, also known as alpha-glcnac-(1->o)PO3H2 or glcnac1alpha-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-α-D-glucosamine 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). N-acetyl-α-D-glucosamine 1-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-(N-acetyl-alpha-D-glucosamine) phosphate
  • 2-(ACETYLAMINO)-2-DEOXY-1-O-PHOSPHONO-ALPHA-D-GLUCOPYRANOSE
  • 2-acetamido-2-deoxy-1-O-phosphono-alpha-D-glucopyranose
  • 2-N-acetylglucosamine 1-phosphate
  • alpha-GlcNAc-(1->O)PO3H2
  • alpha-GlcNAc-1-P
  • GlcNAc1alpha-phosphate
  • N-acetyl-alpha-D-glucosamine 1-(dihydrogen phosphate)
  • N-acetyl-alpha-D-glucosamine 1-phosphate
  • N-acetylglucosamine-1-phosphate
  • 1-(N-Acetyl-a-D-glucosamine) phosphate
  • 1-(N-Acetyl-a-D-glucosamine) phosphoric acid
  • 1-(N-Acetyl-alpha-D-glucosamine) phosphoric acid
  • 1-(N-Acetyl-α-D-glucosamine) phosphate
  • 1-(N-Acetyl-α-D-glucosamine) phosphoric acid
  • 2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-a-D-glucopyranose
  • 2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-α-D-glucopyranose
  • 2-Acetamido-2-deoxy-1-O-phosphono-a-D-glucopyranose
  • 2-Acetamido-2-deoxy-1-O-phosphono-α-D-glucopyranose
  • 2-N-Acetylglucosamine 1-phosphoric acid
  • a-GlcNAc-(1->o)PO3H2
  • Α-glcnac-(1->o)PO3H2
  • a-GlcNAc-1-p
  • Α-glcnac-1-p
  • GlcNAc1a-phosphate
  • GlcNAc1a-phosphoric acid
  • GlcNAc1alpha-phosphoric acid
  • GlcNAc1α-phosphate
  • GlcNAc1α-phosphoric acid
  • N-Acetyl-a-D-glucosamine 1-(dihydrogen phosphate)
  • N-Acetyl-a-D-glucosamine 1-(dihydrogen phosphoric acid)
  • N-Acetyl-alpha-D-glucosamine 1-(dihydrogen phosphoric acid)
  • N-Acetyl-α-D-glucosamine 1-(dihydrogen phosphate)
  • N-Acetyl-α-D-glucosamine 1-(dihydrogen phosphoric acid)
  • N-Acetylglucosamine-1-phosphoric acid
  • N-Acetyl-α-D-glucosamine 1-phosphoric acid
  • N-Acetyl-a-D-glucosamine 1-phosphate
  • N-Acetyl-a-D-glucosamine 1-phosphoric acid
  • N-Acetyl-alpha-D-glucosamine 1-phosphoric acid
  • N-Acetyl-α-D-glucosamine 1-phosphate
  • GlcNAc-1-phosphate
CAS numberNot Available
WeightAverage: 301.1877
Monoisotopic: 301.056267627
InChI KeyFZLJPEPAYPUMMR-FMDGEEDCSA-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{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC NameD-glucosamine 1-phosphate
Chemical FormulaC8H16NO9P
SMILESCC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O
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
  • 2-acetamido-2-deoxy-D-glucopyranose 1-phosphate (CHEBI:16446 )
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
logP-3.3ChemAxon
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m³·mol⁻¹ChemAxon
Polarizability25.31 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 ReactionsNot Available
KEGG Reactions
N-acetyl-D-glucosamine 6-phosphate ↔ N-acetyl-alpha-D-glucosamine 1-phosphate
Uridine triphosphate + N-acetyl-alpha-D-glucosamine 1-phosphate + hydron ↔ Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
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 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:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Milewski, S., Gabriel, I., Olchowy, J. (2006). "Enzymes of UDP-GlcNAc biosynthesis in yeast." Yeast 23:1-14.16408321
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16446
HMDB IDNot Available
Pubchem Compound ID25243937
Kegg IDC04501
ChemSpider ID389323
FOODB IDFDB031023
Wikipedia IDNot Available
BioCyc IDNot Available

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.