Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:14:21 UTC
Update Date2024-04-30 20:32:09 UTC
Metabolite IDMMDBc0047907
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. The 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-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
Synonyms
ValueSource
Uridine diphosphoric acid-N-acetylgalactosamineGenerator
UDP-N-Acetyl-D-galactosamineHMDB
UDP-N-Acetyl-delta-galactosamineHMDB
UDP-N-AcetylgalactosamineHMDB
Uridine 5'-diphospho-N-acetylgalactosamineHMDB
Uridine diphosphate-N-acetyl-D-galactosamineHMDB
Uridine diphosphate-N-acetyl-delta-galactosamineHMDB
Uridine diphospho-2-acetamido-2-deoxy-D-galactoseHMDB
Uridine diphospho-2-acetamido-2-deoxy-delta-galactoseHMDB
Uridine diphospho-N-acetylgalactosamineHMDB
Uridine diphosphoacetylgalactosamineHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-galactopyranosyl esterHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl esterHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl esterHMDB
Uridine pyrophosphate N-acetyl-a-D-chondrosamine esterHMDB
Uridine pyrophosphate N-acetyl-alpha-D-chondrosamine esterHMDB
Uridine pyrophosphate N-acetyl-alpha-delta-chondrosamine esterHMDB
Uridine pyrophosphoacetylgalactosamineHMDB
Pyrophosphoacetylglucosamine, uridineMeSH, HMDB
UDP AcetylglucosamineMeSH, HMDB
Uridine diphospho-N-acetylglucosamineMeSH, HMDB
Acetylgalactosamine, UDPMeSH, HMDB
diphospho-N-Acetylglucosamine, uridineMeSH, HMDB
Uridine diphosphate N acetylgalactosamineMeSH, HMDB
Uridine diphosphate N acetylglucosamineMeSH, HMDB
Uridine diphosphate N-acetylglucosamineMeSH, HMDB
Diphosphate N-acetylglucosamine, uridineMeSH, HMDB
UDPGNAcMeSH, HMDB
Uridine diphosphate N-acetylgalactosamineMeSH, HMDB
Acetylglucosamine, UDPMeSH, HMDB
N-Acetylgalactosamine, uridine diphosphateMeSH, HMDB
UDP AcetylgalactosamineMeSH, HMDB
Uridine pyrophosphoacetylglucosamineMeSH, HMDB
Uridine diphospho N acetylglucosamineMeSH, HMDB
Diphosphate N-acetylgalactosamine, uridineMeSH, HMDB
N-Acetylglucosamine, uridine diphosphateMeSH, HMDB
N-[2-({[({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidateGenerator, HMDB
Molecular FormulaC17H27N3O17P2
Average Mass607.3537
Monoisotopic Mass607.081569477
IUPAC Name[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Name{[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid
CAS Registry Number7277-98-7
SMILES
CC(O)=NC1C(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(O)=NC2=O)OC(CO)C(O)C1O
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