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Record Information
Version1.0
Creation Date2016-09-30 22:26:48 UTC
Update Date2020-06-04 20:21:31 UTC
MCDB ID BMDB0000212
Secondary Accession Numbers
  • BMDB00212
Metabolite Identification
Common NameN-Acetylgalactosamine
DescriptionN-Acetylgalactosamine, also known as Tn or alpha-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-Acetylgalactosamine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Structure
Thumb
Synonyms
ValueSource
2-(Acetylamino)-2-deoxy-alpha-D-galactopyranoseChEBI
alpha-GalNAcChEBI
alpha-GalpNAcChEBI
GalNAc-alphaChEBI
TnChEBI
TN Antigen saccharideChEBI
TN Antigen saccharide componentChEBI
TN SaccharideChEBI
TN Saccharide componentChEBI
2-(Acetylamino)-2-deoxy-a-D-galactopyranoseGenerator
2-(Acetylamino)-2-deoxy-α-D-galactopyranoseGenerator
a-GalNAcGenerator
Α-galnacGenerator
a-GalpNAcGenerator
Α-galpnacGenerator
GalNAc-aGenerator
GalNAc-αGenerator
2-Acetamido-2-deoxy-a-D-allopyranoseHMDB
2-Acetamido-2-deoxy-a-D-glucopyranoseHMDB
2-Acetamido-2-deoxy-alpha-D-allopyranoseHMDB
2-Acetamido-2-deoxy-alpha-D-glucopyranoseHMDB
2-Acetamido-2-deoxy-alpha-delta-allopyranoseHMDB
2-Acetamido-2-deoxy-alpha-delta-glucopyranoseHMDB
2-Acetamido-2-deoxy-b-D-glucopyranoseHMDB
2-Acetamido-2-deoxy-beta-D-glucopyranoseHMDB
2-Acetamido-2-deoxy-beta-delta-glucopyranoseHMDB
2-Acetamido-2-desoxy-b-D-talofuranoseHMDB
2-Acetamido-2-desoxy-beta-D-talofuranoseHMDB
2-Acetamido-2-desoxy-beta-delta-talofuranoseHMDB
2-Acetamino-2-deoxy-a-D-glucoseHMDB
2-Acetamino-2-deoxy-alpha-D-glucoseHMDB
2-Acetamino-2-deoxy-alpha-delta-glucoseHMDB
2-Acetamino-2-desoxy-a-D-glucopyranoseHMDB
2-Acetamino-2-desoxy-alpha-D-glucopyranoseHMDB
2-Acetamino-2-desoxy-alpha-delta-glucopyranoseHMDB
2-Acetamino-2-desoxy-D-galaktoseHMDB
2-Acetamino-2-desoxy-D-glucoseHMDB
2-Acetamino-2-desoxy-delta-galaktoseHMDB
2-Acetamino-2-desoxy-delta-glucoseHMDB
2-Acetylamino-2-deoxy-a-D-galactopyranoseHMDB
2-Acetylamino-2-deoxy-a-D-glucopyranoseHMDB
2-Acetylamino-2-deoxy-a-D-mannopyranoseHMDB
2-Acetylamino-2-deoxy-alpha-D-galactopyranoseHMDB
2-Acetylamino-2-deoxy-alpha-D-glucopyranoseHMDB
2-Acetylamino-2-deoxy-alpha-D-mannopyranoseHMDB
2-Acetylamino-2-deoxy-alpha-delta-galactopyranoseHMDB
2-Acetylamino-2-deoxy-alpha-delta-glucopyranoseHMDB
2-Acetylamino-2-deoxy-alpha-delta-mannopyranoseHMDB
2-Acetylamino-2-deoxy-b-D-allopyranoseHMDB
2-Acetylamino-2-deoxy-b-D-altropyranoseHMDB
2-Acetylamino-2-deoxy-b-D-galactopyranoseHMDB
2-Acetylamino-2-deoxy-b-D-glucopyranoseHMDB
2-Acetylamino-2-deoxy-b-D-mannopyranoseHMDB
2-Acetylamino-2-deoxy-beta-D-allopyranoseHMDB
2-Acetylamino-2-deoxy-beta-D-altropyranoseHMDB
2-Acetylamino-2-deoxy-beta-D-galactopyranoseHMDB
2-Acetylamino-2-deoxy-beta-D-glucopyranoseHMDB
2-Acetylamino-2-deoxy-beta-D-mannopyranoseHMDB
2-Acetylamino-2-deoxy-beta-delta-allopyranoseHMDB
2-Acetylamino-2-deoxy-beta-delta-altropyranoseHMDB
2-Acetylamino-2-deoxy-beta-delta-galactopyranoseHMDB
2-Acetylamino-2-deoxy-beta-delta-glucopyranoseHMDB
2-Acetylamino-2-deoxy-beta-delta-mannopyranoseHMDB
2-Acetylamino-2-desoxy-a-D-galaktoseHMDB
2-Acetylamino-2-desoxy-a-D-mannoseHMDB
2-Acetylamino-2-desoxy-alpha-D-galaktoseHMDB
2-Acetylamino-2-desoxy-alpha-D-mannoseHMDB
2-Acetylamino-2-desoxy-alpha-delta-galaktoseHMDB
2-Acetylamino-2-desoxy-alpha-delta-mannoseHMDB
2-Acetylamino-2-desoxy-b-D-galaktoseHMDB
2-Acetylamino-2-desoxy-b-D-mannoseHMDB
2-Acetylamino-2-desoxy-beta-D-galaktoseHMDB
2-Acetylamino-2-desoxy-beta-D-mannoseHMDB
2-Acetylamino-2-desoxy-beta-delta-galaktoseHMDB
2-Acetylamino-2-desoxy-beta-delta-mannoseHMDB
2-Acetylamino-2-desoxy-D-mannoseHMDB
2-Acetylamino-2-desoxy-delta-mannoseHMDB
2-Acetylamino-2-desoxy-DL-glucopyranoseHMDB
2-Acetylamino-a-D-2-deoxy-galactopyranoseHMDB
2-Acetylamino-a-D-2-deoxy-glucopyranoseHMDB
2-Acetylamino-a-D-2-deoxy-glucoseHMDB
2-Acetylamino-a-D-2-deoxy-mannopyranoseHMDB
2-Acetylamino-alpha-D-2-deoxy-galactopyranoseHMDB
2-Acetylamino-alpha-D-2-deoxy-glucopyranoseHMDB
2-Acetylamino-alpha-D-2-deoxy-glucoseHMDB
2-Acetylamino-alpha-D-2-deoxy-mannopyranoseHMDB
2-Acetylamino-alpha-delta-2-deoxy-galactopyranoseHMDB
2-Acetylamino-alpha-delta-2-deoxy-glucopyranoseHMDB
2-Acetylamino-alpha-delta-2-deoxy-glucoseHMDB
2-Acetylamino-alpha-delta-2-deoxy-mannopyranoseHMDB
2-Acetylamino-b-D-2-deoxy-galactopyranoseHMDB
2-Acetylamino-b-D-2-deoxy-glucopyranoseHMDB
2-Acetylamino-b-D-2-deoxy-mannopyranoseHMDB
2-Acetylamino-beta-D-2-deoxy-galactopyranoseHMDB
2-Acetylamino-beta-D-2-deoxy-glucopyranoseHMDB
2-Acetylamino-beta-D-2-deoxy-mannopyranoseHMDB
2-Acetylamino-beta-delta-2-deoxy-galactopyranoseHMDB
2-Acetylamino-beta-delta-2-deoxy-glucopyranoseHMDB
2-Acetylamino-beta-delta-2-deoxy-mannopyranoseHMDB
2-Acetylamino-D-2-deoxy-galactoseHMDB
2-Acetylamino-D-2-deoxy-glucoseHMDB
2-Acetylamino-D-2-deoxy-guloseHMDB
2-Acetylamino-D-2-deoxy-idoseHMDB
2-Acetylamino-D-2-deoxy-mannoseHMDB
2-Acetylamino-D-2-deoxy-taloseHMDB
2-Acetylamino-delta-2-deoxy-galactoseHMDB
2-Acetylamino-delta-2-deoxy-glucoseHMDB
2-Acetylamino-delta-2-deoxy-guloseHMDB
2-Acetylamino-delta-2-deoxy-idoseHMDB
2-Acetylamino-delta-2-deoxy-mannoseHMDB
2-Acetylamino-delta-2-deoxy-taloseHMDB
2-Acetylamino-L-2-deoxy-galactoseHMDB
2-Acetylamino-L-2-deoxy-mannoseHMDB
a-2-Acetamido-2-deoxy-D-galactoseHMDB
alpha-2-Acetamido-2-deoxy-D-galactoseHMDB
alpha-2-Acetamido-2-deoxy-delta-galactoseHMDB
GalNAcHMDB
N-(2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamideHMDB
N-Acetyl-a-D-glucosamineHMDB
N-Acetyl-alpha-D-glucosamineHMDB
N-Acetyl-alpha-delta-glucosamineHMDB
N-Acetyl-D-allosamineHMDB
N-Acetyl-D-galactosamineHMDB
N-Acetyl-delta-allosamineHMDB
N-Acetyl-delta-galactosamineHMDB
N-AcetylgalactosaminHMDB
N-AcetylglucosaminHMDB
N-AcetylgluosaminHMDB
N-AcetylmannosaminHMDB
2 Acetamido 2 deoxy D galactoseHMDB
2-Acetamido-2-D-galactopyranoseHMDB
AcetylgalactosamineHMDB
2-Acetamido-2-deoxygalactoseHMDB
N Acetyl D galactosamineHMDB
2 Acetamido 2 D galactopyranoseHMDB
2 Acetamido 2 deoxygalactoseHMDB
2-Acetamido-2-deoxy-D-galactoseHMDB
N-Acetyl-a-D-galactosamineHMDB
N-Acetyl-α-D-galactosamineHMDB
a-N-Acetyl-D-galactosamineHMDB
Α-N-acetyl-D-galactosamineHMDB
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(2S,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional Nameα-GalNAc
CAS Registry Number1811-31-0
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-CBQIKETKSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172 - 173 °CNot 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
Polarizability20.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified158 (127-371) uM
  • Esperanza Troyano...
details
HMDB IDHMDB0000212
DrugBank IDDB03567
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031022
KNApSAcK IDNot Available
Chemspider ID76020
KEGG Compound IDC01074
BioCyc IDCPD-3604
BiGG ID36880
Wikipedia LinkN-Acetylgalactosamine
METLIN ID5222
PubChem Compound84265
PDB IDNot Available
ChEBI ID40356
References
Synthesis ReferenceCardini, C. E.; Leloir, Luis F. Enzymic formation of acetylgalactosamine. Journal of Biological Chemistry (1957), 225 317-24.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]