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Identification
YMDB IDYMDB00737
NameN-acetyl-D-glucosamine 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-Acetyl-D-Glucosamine 6-Phosphate, also known as N-acetyl-D-glucosamine-6-p or GLCNAC6P, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-Glucosamine 6-Phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-Glucosamine 6-Phosphate exists in all living species, ranging from bacteria to humans. Within yeast, N-acetyl-D-glucosamine 6-phosphate participates in a number of enzymatic reactions. In particular, N-acetyl-D-glucosamine 6-phosphate can be biosynthesized from glucosamine 6-phosphate and acetyl-CoA; which is catalyzed by the enzyme glucosamine-phosphate N-acetyltransferase. In addition, N-acetyl-D-glucosamine 6-phosphate can be converted into N-acetyl-glucosamine 1-phosphate through its interaction with the enzyme phosphoacetylglucosamine mutase. In yeast, N-acetyl-D-glucosamine 6-phosphate is involved in the metabolic pathway called the amino sugar and nucleotide sugar metabolism pathway.
Structure
Thumb
Synonyms
  • N-Acetyl-D-Glucosamine 6-Phosphate
  • N-Acetyl-D-Glucosamine 6-Phosphic acid
  • n-acetyl-d-glucosamine-6-p
  • N-acetyl-D-glucosamine-6-phosphate
  • n-acetyl-glucosamine-6-p
  • n-acetyl-glucosamine-6-phosphate
  • n-acetylglucosamine-6-p
  • 2-Acetamido-2-deoxy-6-O-phosphono-D-glucopyranose
  • N-Acetyl-D-glucosamine 6-phosphoric acid
  • N-Acetylglucosamine 6-phosphate
  • GlcNAc6p
CAS number102029-88-9
WeightAverage: 301.1877
Monoisotopic: 301.056267627
InChI KeyBRGMHAYQAZFZDJ-RTRLPJTCSA-N
InChIInChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
Chemical FormulaC8H16NO9P
SMILESCC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Acetamide
  • 1,2-diol
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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 Solubility17.6 g/LALOGPS
logP-2ALOGPS
logP-3.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
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
Polarizability25.8 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
Glucosamine 6-phosphate + Acetyl-CoACoenzyme A + hydron + N-acetyl-D-glucosamine 6-phosphate
N-acetyl-D-glucosamine 6-phosphateN-Acetyl-glucosamine 1-phosphate
KEGG Reactions
Acetyl-CoA + Glucosamine 6-phosphateN-acetyl-D-glucosamine 6-phosphate + hydron + Coenzyme A
N-acetyl-D-glucosamine 6-phosphateN-acetyl-alpha-D-glucosamine 1-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Mio, T., Yamada-Okabe, T., Arisawa, M., Yamada-Okabe, H. (1999). "Saccharomyces cerevisiae GNA1, an essential gene encoding a novel acetyltransferase involved in UDP-N-acetylglucosamine synthesis." J Biol Chem 274:424-429.9867860
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15784
HMDB IDHMDB01062
Pubchem Compound ID440996
Kegg IDC00357
ChemSpider ID389821
FOODB IDFDB022401
Wikipedia IDNot Available
BioCyc IDN-ACETYL-D-GLUCOSAMINE-6-P

Enzymes

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.
General function:
Involved in N-acetyltransferase activity
Specific function:
Acetyl-CoA + D-glucosamine 6-phosphate = CoA + N-acetyl-D-glucosamine 6-phosphate
Gene Name:
GNA1
Uniprot ID:
P43577
Molecular weight:
18134.80078
Reactions
Acetyl-CoA + D-glucosamine 6-phosphate → CoA + N-acetyl-D-glucosamine 6-phosphate.