Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001956
Identification
Name: N-Acetylglucosamine
Description:N-Acetyl-D-Glucosamine (N-acetlyglucosamine, GlcNAc) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. It is part of peptidoglycan, a biopolymer in bacterial cell walls, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks.
Structure
Thumb
Synonyms:
  • 2-(acetylamino)-2-Deoxy-b-D-glucopyranose
  • 2-(Acetylamino)-2-deoxy-beta-D-glucopyranose
  • 2-(Acetylamino)-2-deoxy-D-Glucose
  • 2-(acetylamino)-2-Deoxy-β-D-glucopyranose
  • 2-(Acetylamino)-2-deoxyhexose
  • 2-(Acetylamino)-2-deoxyhexose (ACD/Name 4.0)
  • 2-acetamido-2-Deoxy-b-D-glucopyranose
  • 2-Acetamido-2-deoxy-beta-D-glucopyranose
  • 2-Acetamido-2-deoxy-D-glucose
  • 2-acetamido-2-Deoxy-β-D-glucopyranose
  • 2-Acetamido-2-deoxyglucose
  • 2-Acetamido-2-deoxyhexopyranose
  • 2-Acetamido-D-glucose
  • 2-Acetylamino-2-deoxy-D-glucose
  • N-acetylglucosamine
  • Acetylglucosamine
  • BetaGlcNAc
  • D-N-Acetylglucosamine
  • Glcnac
  • GlcNAc-b
  • GlcNAc-beta
  • GlcNAc-β
  • Glucosamine Complex
  • N-Acetyl-b-D-glucosamine
  • N-Acetyl-beta-D-glucosamine
  • N-Acetyl-D-glucosamine
  • N-Acetyl-D-hexosamine
  • N-Acetyl-β-D-glucosamine
  • N-Acetylchitosamine
  • N-Acetylglucosamine
  • NAcGlc
  • NAG
Chemical Formula: C8H15NO6
Average Molecular Weight: 221.2078
Monoisotopic Molecular Weight: 221.089937217
InChI Key: OVRNDRQMDRJTHS-RTRLPJTCSA-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: 7512-17-6
IUPAC Name:N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional IUPAC Name: GlcNAc
SMILES:CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct Parent Acylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Oxane
  • Monosaccharide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 210 °C
Experimental Properties:
PropertyValueSource
Water Solubility:167 mg/mLPhysProp
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
Polarizability20.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1490000000-40dfe33adabe6ad7a7a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il0-2940000000-880c7b1fb58ed63f0ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9400000000-e1f07558d7921e9f24e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-8920000000-d504941e0508d1593f33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9820000000-753556be259b7e745ba7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-bad102d081eb3bbc006bView in MoNA
References
References:
  • Collard CD, Montalto MC, Reenstra WR, Buras JA, Stahl GL: Endothelial oxidative stress activates the lectin complement pathway: role of cytokeratin 1. Am J Pathol. 2001 Sep;159(3):1045-54. Pubmed: 11549596
  • Hatcher VB, Schwarzmann GO, Jeanloz RW, McArthur JW: Changes in the sialic acid concentration in the major cervical glycoprotein from the bonnet monkey (Macaca radiata) during a hormonally induced cycle. Fertil Steril. 1977 Jun;28(6):682-8. Pubmed: 405259
  • Kottgen E, Hell B, Muller C, Kainer F, Tauber R: Developmental changes in the glycosylation and binding properties of human fibronectins. Characterization of the glycan structures and ligand binding of human fibronectins from adult plasma, cord blood and amniotic fluid. Biol Chem Hoppe Seyler. 1989 Dec;370(12):1285-94. Pubmed: 2619923
  • Madrid JF, Castells MT, Martinez-Menarguez JA, Aviles M, Hernandez F, Ballesta J: Subcellular characterization of glycoproteins in the principal cells of human gallbladder. A lectin cytochemical study. Histochemistry. 1994 Mar;101(3):195-204. Pubmed: 8056619
  • Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76. Pubmed: 1366057
  • Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. Pubmed: 3757018
  • Percheron F: [Beta-D-mannosidase] Bull Acad Natl Med. 1995 May;179(5):881-91; discussion 892. Pubmed: 7583460
  • Slawson, C., Housley, M. P., Hart, G. W. (2006). "O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks." J Cell Biochem 97:71-83. Pubmed: 16237703
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Weiner B, Fischer T, Waxman S: Hemostasis in the era of the chronic anticoagulated patient. J Invasive Cardiol. 2003 Nov;15(11):669-73; quiz 674. Pubmed: 14608143
  • Yates AD, Watkins WM: Enzymes involved in the biosynthesis of glycoconjugates. A UDP-2-acetamido-2-deoxy-D-glucose: beta-D-galactopyranosyl-(1 leads to 4)-saccharide (1 leads to 3)-2-acetamido-2-deoxy-beta-D- glucopyranosyltransferase in human serum. Carbohydr Res. 1983 Aug 16;120:251-68. Pubmed: 6226355
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28009
HMDB IDHMDB00215
Pubchem Compound ID439174
Kegg IDC00140
ChemSpider ID388319
WikipediaN-Acetylglucosamine
BioCyc IDN-ACETYL-D-GLUCOSAMINE
EcoCyc IDN-ACETYL-D-GLUCOSAMINE