Showing metabocard for Beta-N-Acetylglucosamine (BMDB0000803)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:49 UTC
Update Date2020-04-22 15:05:23 UTC
BMDB IDBMDB0000803
Secondary Accession Numbers
  • BMDB00803
Metabolite Identification
Common NameBeta-N-Acetylglucosamine
Descriptionbeta-N-Acetylglucosamine, also known as N-acetyl-D-glucosamine or glcnac-beta, 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. Based on a literature review a significant number of articles have been published on beta-N-Acetylglucosamine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Acetamido-2-deoxy-D-glucoseChEBI
2-Acetylamino-2-deoxy-D-glucoseChEBI
AcetylglucosamineChEBI
BetaGlcNAcChEBI
GlcNAc-betaChEBI
N-Acetyl-D-glucosamineChEBI
N-AcetylglucosamineChEBI
WURCS=2.0/1,1,0/[a2122h-1b_1-5_2*ncc/3=o]/1/ChEBI
GlcNAc-bGenerator
GlcNAc-βGenerator
b-N-AcetylglucosamineGenerator
Β-N-acetylglucosamineGenerator
N-Acetyl-b-D-glucosamineHMDB
N-Acetyl-β-D-glucosamineHMDB
N Acetyl D glucosamineHMDB
2 Acetamido 2 deoxyglucoseHMDB
2 Acetamido 2 deoxy D glucoseHMDB
2-Acetamido-2-deoxyglucoseHMDB
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-beta-D-glucosamineHMDB
N-Acetyl 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
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
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000803
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022253
KNApSAcK IDC00053525
Chemspider ID22563
KEGG Compound IDC03878
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5767
PubChem Compound24139
PDB IDNot Available
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Hyaluronidase-2
General function:
Involved in hyalurononglucosaminidase activity
Specific function:
Hydrolyzes high molecular weight hyaluronic acid to produce an intermediate-sized product which is further hydrolyzed by sperm hyaluronidase to give small oligosaccharides. Displays very low levels of activity. Associates with and negatively regulates MST1R (By similarity).
Gene Name:
HYAL2
Uniprot ID:
Q8SQG8
Molecular weight:
53881.0
Enzyme Details
2. Hyaluronidase-1
General function:
Involved in hyalurononglucosaminidase activity
Specific function:
May have a role in promoting tumor progression. May block the TGFB1-enhanced cell growth (By similarity).
Gene Name:
HYAL1
Uniprot ID:
Q5E985
Molecular weight:
50508.0