Showing metabocard for N-Acetyl-b-D-galactosamine (BMDB0000853)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:32 UTC
Update Date2020-04-22 15:05:37 UTC
BMDB IDBMDB0000853
Secondary Accession Numbers
  • BMDB00853
Metabolite Identification
Common NameN-Acetyl-b-D-galactosamine
DescriptionN-Acetyl-b-D-galactosamine, also known as beta-galnac or β-galnac, belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-Acetyl-b-D-galactosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-b-D-galactosamine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Acetamido-2-deoxy-beta-D-galactopyranosideChEBI
beta-GalNAcChEBI
BGalNAcChEBI
2-Acetamido-2-deoxy-b-D-galactopyranosideGenerator
2-Acetamido-2-deoxy-β-D-galactopyranosideGenerator
b-GalNAcGenerator
Β-galnacGenerator
2-Deoxy-2-acetamido-b-D-galactopyranoseHMDB
2-Deoxy-2-acetamido-beta-D-galactopyranoseHMDB
2-Deoxy-2-acetamido-beta-delta-galactopyranoseHMDB
b-D-2-Acetamido-2-deoxy-galactopyranoseHMDB
b-N-Acetyl-D-galactosamineHMDB
b-N-AcetylgalactosamineHMDB
beta-D-2-Acetamido-2-deoxy-galactopyranoseHMDB
beta-delta-2-Acetamido-2-deoxy-galactopyranoseHMDB
beta-N-Acetyl-D-galactosamineHMDB
beta-N-Acetyl-delta-galactosamineHMDB
beta-N-AcetylgalactosamineHMDB
2 Acetamido 2 D galactopyranoseHMDB
2-Acetamido-2-deoxy-D-galactoseHMDB
2 Acetamido 2 deoxy D galactoseHMDB
2-Acetamido-2-D-galactopyranoseHMDB
AcetylgalactosamineHMDB
2 Acetamido 2 deoxygalactoseHMDB
N-Acetyl-D-galactosamineHMDB
2-Acetamido-2-deoxygalactoseHMDB
N Acetyl D galactosamineHMDB
N-Acetyl-β-D-galactosamineHMDB
N-Acetyl-b-D-galactosamineGenerator
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-acetyl-β-D-galactosamine
CAS Registry Number14131-60-3
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-JAJWTYFOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Hemiacetal
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability21.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000853
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031024
KNApSAcK IDNot Available
Chemspider ID389452
KEGG Compound IDC05021
BioCyc IDCPD-12557
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5816
PubChem Compound440552
PDB IDNot Available
ChEBI ID28497
References
Synthesis ReferenceChaplin, David; Crout, David H. G.; Bornemann, Stephen; Hutchinson, David W.; Khan, Riaz. Conversion of 2-acetamido-2-deoxy-b-D-glucopyranose (N-acetylglucosamine) into 2-acetamido-2-deoxy-b-D-galactopyranose (N-acetylgalactosamine using a biotransformation to generate a selectively deprotected substrate for SN2 inversion. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1992), (2), 235-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available