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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 00:32:32 UTC
HMDB IDHMDB0000803
Secondary Accession Numbers
  • HMDB00803
Metabolite Identification
Common Namebeta-N-Acetylglucosamine
DescriptionAll animals and plants dynamically attach and remove beta-N-acetylglucosamine at serine and threonine residues on myriad nuclear and cytoplasmic proteins. beta-N-Acetylglucosamine cycling, which is tightly regulated by the concerted actions of two highly conserved enzymes, serves as a nutrient and stress sensor. On some proteins, beta-N-acetylglucosamine competes directly with phosphate for serine/threonine residues. beta-N-Acetylglucosamine's subcellular localization in hepatocytes establishes that it is highly concentrated at the nuclear envelope, particularly at the nuclear pore complex, but is also abundant and widespread within chromatin. However, several cytosolic and cytoskeletal proteins are also found to be glycosylated with beta-N-acetylglucosamine. beta-N-Acetylglucosamination is in many ways distinct from "classical" protein glycosylation. First, it is found mostly within the cytoplasm or nucleoplasm. Second, unlike the extraordinarily complex array of glycans found on extracellular glycoproteins, beta-N-acetylglucosamine is not elongated or further modified. Third, beta-N-acetylglucosamine cycles by means of mechanisms and on a timescale similar to those of phosphorylation which is quite different from the cycling of complex extracellular glycans. beta-N-Acetylglucosamination is one of the most common post-translational modifications. In terms of high-energy compounds, the intracellular concentration of the direct donor for beta-N-acetylglucosamination, UDP-GlcNAc, is second only to that of ATP, with 2-5% of all glucose being used to generate this sugar nucleotide. beta-N-Acetylglucosaminated proteins can be found in almost every intracellular compartment, and there are proteins in almost every functional class that are subject to beta-N-acetylglucosamination (PMID: 17460662 ).
Structure
Thumb
Synonyms
ValueSource
2-acetamido-2-Deoxy-D-glucoseChEBI
2-acetylamino-2-Deoxy-D-glucoseChEBI
AcetylglucosamineChEBI
BetaGlcNAcChEBI
GlcNAc-betaChEBI
N-Acetyl-D-glucosamineChEBI
N-AcetylglucosamineChEBI
N-Acetyl glucosamineChEMBL
GlcNAc-bGenerator
GlcNAc-βGenerator
b-N-AcetylglucosamineGenerator
Β-N-acetylglucosamineGenerator
2 acetamido 2 DeoxyglucoseMeSH
2 acetamido 2 Deoxy D glucoseMeSH
2-acetamido-2-DeoxyglucoseMeSH
N Acetyl D glucosamineMeSH
2-acetamido-2-Deoxy-b-D-glucoseHMDB
2-acetamido-2-Deoxy-beta-D-glucoseHMDB
2-acetamido-2-Deoxy-beta-delta-glucoseHMDB
b-N-Acetyl-D-glucosamineHMDB
beta-N-Acetyl-D-glucosamineHMDB
beta-N-Acetyl-delta-glucosamineHMDB
N-Acetyl-b-D-glucosamineHMDB
N-Acetyl-beta-D-glucosamineHMDB
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-acetyl-D-glucosamine
CAS Registry Number14131-68-1
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1
InChI KeyOVRNDRQMDRJTHS-FMDGEEDCSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility254 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability21.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0ue9-6920000000-c07df80c6fb758af9cd2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3331900000-c6fab10d67507eecce65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f79-0950000000-61c83c523f164fae3cc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001a-9700000000-ea1c503f19d4401abae9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053v-9000000000-e3255df1a993bd7f2b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0390000000-ce54c5d356ec2fc8ab9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-2940000000-f88941018e49a26c37beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9400000000-ebc784f7cee5c3483d94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-8920000000-5889786c5b50003455d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9820000000-15d2a7694c2cca4aa77eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-69f7eb5167a70a24f71aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022253
KNApSAcK IDNot Available
Chemspider ID22563
KEGG Compound IDC03878
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5767
PubChem Compound24139
PDB IDNAG
ChEBI ID28009
References
Synthesis ReferenceKuk, J. H.; Jung, W. J.; Jo, G. H.; Kim, Y. C.; Kim, K. Y.; Park, R. D. Production of N-acetyl-b-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Applied Microbiology and Biotechnology (2005), 68(3), 384-389.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yao AY, Tang HY, Wang Y, Feng MF, Zhou RL: Inhibition of the activating signals in NK92 cells by recombinant GST-sHLA-G1a chain. Cell Res. 2004 Apr;14(2):155-60. [PubMed:15115617 ]
  2. Kum K, Khanna R, Vinayak VK: Characterization of surface associated antigens of axenic Giardia lamblia trophozoites & their recognition by human sera. Indian J Med Res. 1991 Jan;93:40-6. [PubMed:2022401 ]
  3. Hart GW, Housley MP, Slawson C: Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins. Nature. 2007 Apr 26;446(7139):1017-22. [PubMed:17460662 ]