N-acetyl-β-D-glucosamine (PAMDB120154)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120154
Identification
Name: N-acetyl-β-D-glucosamine
Description:An N-acetyl-D-glucosamine having β-configuration at the anomeric centre.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Acetamido-2-deoxy-D-glucose
  • 2-Acetylamino-2-deoxy-D-glucose
  • Acetylglucosamine
  • βGlcNAc
  • GlcNAc-β
  • N-Acetyl-beta-D-glucosamine
  • N-acetyl-β-D-glucosamine
  • N-Acetyl-D-glucosamine
  • N-acetylglucosamine
Chemical Formula: C8H15NO6
Average Molecular Weight: 221.21
Monoisotopic Molecular Weight: 221.08994
InChI Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N
InChI: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
CAS number: 14131-68-1
IUPAC Name:2-acetamido-2-deoxy-β-D-glucopyranose
Traditional IUPAC Name: N-acetyl-D-glucosamine
SMILES:CC(=O)NC1(C(O)OC(CO)C(O)C(O)1)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Acylaminosugars
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 Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility254.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m3·mol-1ChemAxon
Polarizability21.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
N-acetyl-β-D-glucosamine(anhydrous)-N-acetylmuramate + Water → N-acetyl-β-D-glucosamine + 1,6-anhydro-N-acetyl-β-muramate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Zajonc DM, Savage PB, Bendelac A, Wilson IA, Teyton L (2008)Crystal structures of mouse CD1d-iGb3 complex and its cognate Valpha14 T cell receptor suggest a model for dual recognition of foreign and self glycolipids. Journal of molecular biology 377, Pubmed: 18295796
  • Obukhova P, Rieben R, Bovin N (2007)Normal human serum contains high levels of anti-Gal alpha 1-4GlcNAc antibodies. Xenotransplantation 14, Pubmed: 17991151
  • von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. The Journal of allergy and clinical immunology 123, Pubmed: 19443021
  • Kuk JH, Jung WJ, Jo GH, Kim YC, Kim KY, Park RD (2005)Production of N-acetyl-beta-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Applied microbiology and biotechnology 68, Pubmed: 15692805
  • Wu D, Zajonc DM, Fujio M, Sullivan BA, Kinjo Y, Kronenberg M, Wilson IA, Wong CH (2006)Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d. Proceedings of the National Academy of Sciences of the United States of America 103, Pubmed: 16537470
  • Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S (2015)The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites. Science translational medicine 7, Pubmed: 25568069
  • Cooper DK, Good AH, Koren E, Oriol R, Malcolm AJ, Ippolito RM, Neethling FA, Ye Y, Romano E, Zuhdi N (1993)Identification of alpha-galactosyl and other carbohydrate epitopes that are bound by human anti-pig antibodies: relevance to discordant xenografting in man. Transplant immunology 1, Pubmed: 7521740
Synthesis Reference: Kuk, 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)
External Links:
ResourceLink
METABOLIGHTSMTBLC28009
HMDBHMDB00803
BIGG34006
CHEMSPIDER22563
LIGAND-CPDC03878
CHEBI28009
PUBCHEM24139
CAS7512-17-6