Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:26 UTC
HMDB IDHMDB00304
Secondary Accession NumbersNone
Metabolite Identification
Common NameUridine diphosphate-N-acetylgalactosamine
DescriptionUridine diphosphate-N-acetylgalactosamine (UDP-GalNAc) is a sugar donor metabolite, transferring N-acetylgalactosamine (GalNAc, an O-glycan) from UDP-GalNAc to serine and threonine residues, forming an alpha anomeric linkage in a reaction catalyzed by enzymes known as UDP-N-acetylgalactosamine: polypeptide N-acetylgalactosaminyltransferases; addition of GalNAc to serine or threonine represents the first committed step in mucin biosynthesis. O-glycans impart unique structural features to mucin glycoproteins and numerous membrane receptors, and resistance to thermal change and proteolytic attack in a number of diverse proteins. O-linked carbohydrate side chains function as ligands for receptors; lymphocyte and leukocyte homing and as signals for protein sorting. (PMID: 12634319 ). Animal studies suggest that overactivity of the hexosamine pathway, resulting in increased UDP-hexosamines [i.e.: UDP-N-acetylgalactosamine (UDP-GalNAc)] is an important mechanism by which hyperglycemia causes insulin resistance. However, to date, human studies concerning the role of the hexosamine pathway in hyperglycemia-induced insulin resistance are scarce and restricted to measurements of glutamine fructose-6-phosphate amidotransferase (GFAT) enzyme activity. Both positive and negative correlations between GFAT activity in human muscle tissue from patients with type 2 DM and glucose disposal rate have been reported. (PMID: 12414889 ).
Structure
Thumb
Synonyms
  1. UDP-N-Acetyl-D-galactosamine
  2. UDP-N-Acetyl-delta-galactosamine
  3. UDP-N-Acetylgalactosamine
  4. Uridine 5'-diphospho-N-acetylgalactosamine
  5. Uridine diphosphate-N-acetyl-D-galactosamine
  6. Uridine diphosphate-N-acetyl-delta-galactosamine
  7. Uridine diphospho-2-acetamido-2-deoxy-D-galactose
  8. Uridine diphospho-2-acetamido-2-deoxy-delta-galactose
  9. Uridine diphospho-N-acetylgalactosamine
  10. Uridine diphosphoacetylgalactosamine
  11. Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-galactopyranosyl ester
  12. Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl ester
  13. Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl ester
  14. Uridine pyrophosphate N-acetyl-a-D-chondrosamine ester
  15. Uridine pyrophosphate N-acetyl-alpha-D-chondrosamine ester
  16. Uridine pyrophosphate N-acetyl-alpha-delta-chondrosamine ester
  17. Uridine pyrophosphoacetylgalactosamine
Chemical FormulaC17H27N3O17P2
Average Molecular Weight607.3537
Monoisotopic Molecular Weight607.081569477
IUPAC Name{[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry Number7277-98-7
SMILES
CC(=O)NC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)
InChI KeyLFTYTUAZOPRMMI-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Nucleotide Sugars
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Pyrimidine Ribonucleoside Diphosphates
Substituents
  • 1,2 Diol
  • Carboxamide Group
  • Disaccharide Phosphate
  • Glucosamine
  • Glycosyl Compound
  • Hydropyrimidine
  • Mannosamine
  • Mixed Pentose/Hexose Disaccharide
  • N Acetyl Alpha Hexosamine 1 Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxane
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentPyrimidine Nucleotide Sugars
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Ganglioside biosynthesis
  • Component of Globoside metabolism
  • Component of O-Glycan biosynthesis
ApplicationNot Available
Cellular locations
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
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 solubility11.4 g/LALOGPS
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (strongest acidic)1.74ChemAxon
pKa (strongest basic)-3.5ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count14ChemAxon
hydrogen donor count9ChemAxon
polar surface area300.41ChemAxon
rotatable bond count10ChemAxon
refractivity117.56ChemAxon
polarizability50.69ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid LocationsNot Available
Tissue Location
  • Adipose Tissue
  • Muscle
PathwaysNot Available
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 IDFDB021933
KNApSAcK IDNot Available
Chemspider ID1134
KEGG Compound IDC00203
BioCyc IDUDP-N-ACETYL-GALACTOSAMINE
BiGG ID34247
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00304
Metagene LinkHMDB00304
METLIN ID5293
PubChem Compound1167
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceYamamoto, Kenji; Kawai, Hiroyasu; Tochikura, Tatsurokurou. Preparation of uridine diphosphate-N-acetylgalactosamine from uridine diphosphate-N-acetylglucosamine by using microbial enzymes. Applied and Environmental Microbiology (1981), 41(2), 392-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Forrest CM, Youd P, Kennedy A, Gould SR, Darlington LG, Stone TW: Purine, kynurenine, neopterin and lipid peroxidation levels in inflammatory bowel disease. J Biomed Sci. 2002 Sep-Oct;9(5):436-42. Pubmed: 12218359
  2. Ten Hagen KG, Fritz TA, Tabak LA: All in the family: the UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferases. Glycobiology. 2003 Jan;13(1):1R-16R. Epub 2002 Nov 1. Pubmed: 12634319
  3. Pouwels MJ, Span PN, Tack CJ, Olthaar AJ, Sweep CG, van Engelen BG, de Jong JG, Lutterman JA, Hermus AR: Muscle uridine diphosphate-hexosamines do not decrease despite correction of hyperglycemia-induced insulin resistance in type 2 diabetes. J Clin Endocrinol Metab. 2002 Nov;87(11):5179-84. Pubmed: 12414889

Enzymes

Gene Name:
CSGALNACT1
Uniprot ID:
Q8TDX6
Reactions
Uridine diphosphate-N-acetylgalactosamine + beta-D-glucuronyl-(1->3)-D-galactosyl-proteoglycan unknown Uridine 5'-diphosphate + N-acetyl-D-galactosaminyl-(1->4)-beta-D-glucuronyl-(1->3)-beta-D-galactosylproteoglycandetails
Gene Name:
GALNT7
Uniprot ID:
Q86SF2
Gene Name:
CHSY3
Uniprot ID:
Q70JA7
Reactions
Uridine diphosphate-N-acetylgalactosamine + D-Glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycan unknown Uridine 5'-diphosphate + N-Acetyl-beta-D-galactosaminyl-1,4-beta-D-glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycandetails
Gene Name:
CHPF
Uniprot ID:
Q8IZ52
Reactions
Uridine diphosphate-N-acetylgalactosamine + D-Glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycan unknown Uridine 5'-diphosphate + N-Acetyl-beta-D-galactosaminyl-1,4-beta-D-glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycandetails
Gene Name:
CHSY1
Uniprot ID:
Q86X52
Reactions
Uridine diphosphate-N-acetylgalactosamine + D-Glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycan unknown Uridine 5'-diphosphate + N-Acetyl-beta-D-galactosaminyl-1,4-beta-D-glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycandetails
Gene Name:
CSGALNACT2
Uniprot ID:
Q8N6G5
Reactions
Uridine diphosphate-N-acetylgalactosamine + beta-D-glucuronyl-(1->3)-D-galactosyl-proteoglycan unknown Uridine 5'-diphosphate + N-acetyl-D-galactosaminyl-(1->4)-beta-D-glucuronyl-(1->3)-beta-D-galactosylproteoglycandetails
Gene Name:
GALNT20
Uniprot ID:
Q2L4S5