N-Acetyl-b-D-galactosamine (PAMDB000193)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000193
Identification
Name: N-Acetyl-b-D-galactosamine
Description:N-Acetyl-b-D-galactosamine is one of the eight essential sugars. It is important for cell communication. In galactose metabolism pathway, it is converted to N-Acetyl-b-D-galactosamine-6P by N-acetylgalactosamine-specific phosphotransferase enzyme B (EC 2.7.1.69).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Deoxy-2-acetamido-b-D-galactopyranose
  • 2-Deoxy-2-acetamido-b-delta-galactopyranose
  • 2-Deoxy-2-acetamido-b-δ-galactopyranose
  • 2-Deoxy-2-acetamido-beta-D-galactopyranose
  • 2-Deoxy-2-acetamido-beta-delta-galactopyranose
  • 2-Deoxy-2-acetamido-β-D-galactopyranose
  • 2-Deoxy-2-acetamido-β-δ-galactopyranose
  • B-D-2-Acetamido-2-deoxy-Galactopyranose
  • b-delta-2-acetamido-2-Deoxy-galactopyranose
  • B-N-Acetyl-D-galactosamine
  • b-N-Acetyl-delta-galactosamine
  • b-N-Acetyl-δ-galactosamine
  • B-N-Acetylgalactosamine
  • b-δ-2-acetamido-2-Deoxy-galactopyranose
  • Beta-D-2-Acetamido-2-deoxy-Galactopyranose
  • Beta-delta-2-Acetamido-2-deoxy-Galactopyranose
  • Beta-N-Acetyl-D-galactosamine
  • Beta-N-Acetyl-delta-galactosamine
  • Beta-N-Acetylgalactosamine
  • β-D-2-acetamido-2-Deoxy-galactopyranose
  • β-N-Acetyl-D-galactosamine
  • β-N-Acetyl-δ-galactosamine
  • β-N-Acetylgalactosamine
  • β-δ-2-acetamido-2-Deoxy-galactopyranose
Chemical Formula: C8H15NO6
Average Molecular Weight: 221.2078
Monoisotopic Molecular Weight: 221.089937217
InChI Key: OVRNDRQMDRJTHS-JAJWTYFOSA-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: 14131-60-3
IUPAC Name:N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional IUPAC Name: N-acetyl-β-D-galactosamine
SMILES:CC(=O)N[C@H]1[C@H](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: Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability21.04 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Globoside <> N-Acetyl-b-D-galactosamine + Globotriaosylceramide
GM2 + Water <> GM3 + N-Acetyl-b-D-galactosamine
G13033 + Water <> G08421 + N-Acetyl-b-D-galactosamine
G06780 + Water <> G08421 + N-Acetyl-b-D-galactosamine
N-Acetyl-b-D-galactosamine + Protein N(pi)-phospho-L-histidine <> N-Acetyl-D-galactosamine 6-phosphate + Protein histidine
Pathways:
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:
  • Barbas C, Garcia A, de Miguel L, Simo C: Evaluation of filter paper collection of urine samples for detection and measurement of organic acidurias by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 15;780(1):73-82. Pubmed: 12383482
  • Garcia A, Barbas C, Aguilar R, Castro M: Capillary electrophoresis for rapid profiling of organic acidurias. Clin Chem. 1998 Sep;44(9):1905-11. Pubmed: 9732975
  • Gheri G, Bryk SG, Taddei G, Moncini D, Noci I: Sugar residues content and distribution in atrophic and hyperplastic postmenopausal human endometrium: lectin histochemistry. Histol Histopathol. 1996 Oct;11(4):861-7. Pubmed: 8930627
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  • Sediva A, Stejskal J, Bartunkova J, Smetana K Jr, Gabius HJ: Detection of alpha(beta)-N-acetyl-D-galactosamine-binding sites in kidney--relation to Henoch-Schonlein-associated IgA nephropathy. Folia Biol (Praha). 1999;45(4):147-50. Pubmed: 10732728
Synthesis Reference: Chaplin, 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 biotransformat
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28497
HMDB IDHMDB00853
Pubchem Compound ID440552
Kegg IDC05021
ChemSpider ID389452
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoNGA

Enzymes

Protein Details
• Beta-hexosaminidase
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:
nagZ
Locus Tag:
PA3005
Molecular weight:
36.1 kDa
Reactions
Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.

Transporters