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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:25:28 UTC
HMDB IDHMDB0000853
Secondary Accession Numbers
  • HMDB00853
Metabolite Identification
Common NameN-Acetyl-b-D-galactosamine
DescriptionN-Acetyl-b-D-galactosamine is an oligosaccharide residue found in the lining and glandular epithelium, the stroma and the vessels (capillary and large vessels of the human postmenopausal endometrium. (PMID: 8930627 ). It is suspected that N-Acetyl-b-D-galactosamine is a molecule that binds to IgA in the glomerular mesangium in Henoch-Schoenlein purpura associated nephropathy (the most common vasculitis of childhood). (PMID: 10732728 ).
Structure
Thumb
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 GalactopyranoseMeSH
2-acetamido-2-Deoxy-D-galactoseMeSH
2 acetamido 2 Deoxy D galactoseMeSH
2-acetamido-2-D-GalactopyranoseMeSH
AcetylgalactosamineMeSH
2 acetamido 2 DeoxygalactoseMeSH
N-Acetyl-D-galactosamineMeSH
2-acetamido-2-DeoxygalactoseMeSH
N Acetyl D galactosamineMeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility254 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-6920000000-c07df80c6fb758af9cd2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3331900000-c6fab10d67507eecce65View in MoNA
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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022279
KNApSAcK IDNot Available
Chemspider ID389452
KEGG Compound IDC05021
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5816
PubChem Compound440552
PDB IDNGA
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 References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Removes terminal alpha-N-acetylgalactosamine residues from glycolipids and glycopeptides. Required for the breakdown of glycolipids.
Gene Name:
NAGA
Uniprot ID:
P17050
Molecular weight:
Not Available
Reactions
Water + IV3GalNAca-Gb4Cer → N-Acetyl-b-D-galactosamine + Globosidedetails
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name:
HEXB
Uniprot ID:
P07686
Molecular weight:
Not Available
Reactions
+ Water → + N-Acetyl-b-D-galactosaminedetails
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
Gene Name:
HEXA
Uniprot ID:
P06865
Molecular weight:
Not Available
Reactions
+ Water → + N-Acetyl-b-D-galactosaminedetails
General function:
Involved in galactokinase activity
Specific function:
Acts on GalNAc. Also acts as a galactokinase when galactose is present at high concentrations. May be involved in a salvage pathway for the reutilization of free GalNAc derived from the degradation of complex carbohydrates.
Gene Name:
GALK2
Uniprot ID:
Q01415
Molecular weight:
49234.57
Reactions
Adenosine triphosphate + N-Acetyl-b-D-galactosamine → ADP + N-acetyl-alpha-D-galactosamine 1-phosphatedetails