Details of Metabolite

General Information of MET (ID: META00244)
Name UDP-GalNAc
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Acetylgalactosamine, UDP; Acetylglucosamine, UDP; Diphosphate N-acetylgalactosamine, uridine; Diphosphate N-acetylglucosamine, uridine; Diphospho-N-acetylglucosamine, uridine; N-Acetylgalactosamine, uridine diphosphate; N-Acetylglucosamine, uridine diphosphate; 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]ethanimidate; Pyrophosphoacetylglucosamine, uridine; UDP Acetylgalactosamine; UDP Acetylglucosamine; UDP-N-Acetyl-D-galactosamine; UDP-N-Acetyl-delta-galactosamine; UDP-N-Acetylgalactosamine', Uridine 5'-diphospho-N-acetylgalactosamine, 'Uridine diphosphate-N-acetyl-D-galactosamine; UDPGNAc; Uridine diphosphate N acetylgalactosamine; Uridine diphosphate N acetylglucosamine; Uridine diphosphate N-acetylgalactosamine; Uridine diphosphate N-acetylglucosamine; Uridine diphosphate-N-acetyl-delta-galactosamine; Uridine diphospho N acetylglucosamine; Uridine diphospho-2-acetamido-2-deoxy-D-galactose; Uridine diphospho-2-acetamido-2-deoxy-delta-galactose; Uridine diphospho-N-acetylgalactosamine; Uridine diphospho-N-acetylglucosamine; Uridine diphosphoacetylgalactosamine; Uridine diphosphoric acid-N-acetylgalactosamine; Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-galactopyranosyl ester; Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl ester; Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl ester; Uridine pyrophosphate N-acetyl-a-D-chondrosamine ester; Uridine pyrophosphate N-acetyl-alpha-D-chondrosamine ester; Uridine pyrophosphate N-acetyl-alpha-delta-chondrosamine ester; Uridine pyrophosphoacetylgalactosamine; Uridine pyrophosphoacetylglucosamine
Source Endogenous;Food
Structure Type   Pyrimidine nucleotide sugars  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Pyrimidine nucleotides
Pyrimidine nucleotide sugars
PubChem CID
1167
HMDB ID
HMDB0000304
Formula
C17H27N3O17P2
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00203
FooDB ID
FDB021933
ChemSpider ID
1134
METLIN ID
5293
Physicochemical Properties Molecular Weight 607.4 Topological Polar Surface Area 300
XlogP -6.6 Complexity 1080
Heavy Atom Count 39 Rotatable Bond Count 10
Hydrogen Bond Donor Count 9 Hydrogen Bond Acceptor Count 17
Function
Uridine 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. 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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            Forkhead box protein O1 (FOXO1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of Foxo1
                      Induced Change UDP-GalNAc concentration: decrease (FC = 0.70)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Foxo1 leads to the decrease of UDP-GalNAc levels compared with control group.
References
1 Metabolomic analysis of C2C12 myoblasts induced by the transcription factor FOXO1. FEBS Lett. 2019 Jun;593(12):1303-1312.

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