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Showing metabocard for Uridine diphosphate-N-acetylgalactosamine (HMDB00304)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:16 -0700
HMDB ID HMDB00304
Secondary Accession Numbers None
Metabolite Identification
Common Name Uridine diphosphate-N-acetylgalactosamine
Description 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; 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 Link_out). 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C17H27N3O17P2
Average Molecular Weight 607.3537
Monoisotopic Molecular Weight 607.081569477
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 Number 7277-98-7
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 Key LFTYTUAZOPRMMI-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyrimidine Nucleotides
Sub Class Pyrimidine 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 Parent Pyrimidine Nucleotide Sugars
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Ganglioside biosynthesis
  • Component of Globoside metabolism
  • Component of O-Glycan biosynthesis
Application Not Available
Cellular locations
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 11.4 g/L ALOGPS
LogP -1.41 ALOGPS
LogP -5.3 ChemAxon
LogS -1.72 ALOGPS
pKa (strongest acidic) 1.74 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
Hydrogen Acceptor Count 14 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 300.41 A2 ChemAxon
Rotatable Bond Count 10 ChemAxon
Refractivity 117.56 ChemAxon
Polarizability 50.69 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations Not Available
Tissue Location
  • Muscle
  • Adipose Tissue
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021933
KNApSAcK ID Not Available
Chemspider ID 1134 Link_out
KEGG Compound ID C00203 Link_out
BioCyc ID UDP-N-ACETYL-GALACTOSAMINE Link_out
BiGG ID 34247 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB00304 Link_out
Metagene Link HMDB00304 Link_out
METLIN ID 5293 Link_out
PubChem Compound 1167 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Yamamoto, 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 Link_out
Enzymes
Name: Chondroitin sulfate N-acetylgalactosaminyltransferase 1
Reactions:
  • UDP-N-acetyl-D-galactosamine + beta-D-glucuronyl-(1->3)-D-galactosyl-proteoglycan = UDP + N-acetyl-D-galactosaminyl-(1->4)-beta-D-glucuronyl-(1->3)-beta-D- galactosylproteoglycan [RN:R05929]
Gene Name: CSGALNACT1
Uniprot ID: Q8TDX6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4 N-acetylgalactosaminyltransferase 1
Reactions:
  • UDP-N-acetyl-D-galactosamine + 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D- galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide = UDP + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1->4)-O-[N- acetyl-alpha-neuraminosyl-(2->3)]-O-beta-D-galactopyranosyl-(1->4)- beta-D-glucopyranosyl]-ceramide [RN:R04584 R05939]
Gene Name: B4GALNT1
Uniprot ID: Q00973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 11
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNT11
Uniprot ID: Q8NCW6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 4
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNT4
Uniprot ID: Q8N4A0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 3
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNT3
Uniprot ID: Q14435 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Probable polypeptide N-acetylgalactosaminyltransferase 8
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNT8
Uniprot ID: Q9NY28 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase-like protein 2
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNTL2
Uniprot ID: Q8N3T1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 1
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNTL1
Uniprot ID: Q8N428 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 10
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNT10
Uniprot ID: Q86SR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Polypeptide N-acetylgalactosaminyltransferase 13
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNT13
Uniprot ID: Q8IUC8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 3
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: WBSCR17
Uniprot ID: Q6IS24 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 4
Reactions:
  • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
Gene Name: GALNTL4
Uniprot ID: Q6P9A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acetylgalactosaminyltransferase 7
Reactions:
    Gene Name: GALNT7
    Uniprot ID: Q86SF2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polypeptide N-acetylgalactosaminyltransferase 6
    Reactions:
    • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
    Gene Name: GALNT6
    Uniprot ID: Q8NCL4 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polypeptide N-acetylgalactosaminyltransferase 14
    Reactions:
    • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
    Gene Name: GALNT14
    Uniprot ID: Q96FL9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polypeptide N-acetylgalactosaminyltransferase 2
    Reactions:
    • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
    Gene Name: GALNT2
    Uniprot ID: Q10471 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polypeptide N-acetylgalactosaminyltransferase 12
    Reactions:
    • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
    Gene Name: GALNT12
    Uniprot ID: Q8IXK2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polypeptide N-acetylgalactosaminyltransferase 1
    Reactions:
    • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
    Gene Name: GALNT1
    Uniprot ID: Q10472 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Polypeptide N-acetylgalactosaminyltransferase 5
    Reactions:
    • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
    Gene Name: GALNT5
    Uniprot ID: Q7Z7M9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-GalNAc:beta-1,3-N-acetylgalactosaminyltransferase 1
    Reactions:
    • UDP-N-acetyl-D-galactosamine + alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosyl- (11)-ceramide = UDP + N-acetyl-beta-D-galactosaminyl-(1->3)-alpha-D-galactosyl-(1->4)- beta-D-galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide [RN:R05631 R05962]
    Gene Name: B3GALNT1
    Uniprot ID: O75752 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Histo-blood group ABO system transferase
    Reactions:
    • UDP-N-acetyl-D-galactosamine + glycoprotein-alpha-L-fucosyl-(1->2)-D-galactose = UDP + glycoprotein-N-acetyl-alpha-D-galactosaminyl-(1->3)-[alpha-L- fucosyl-(1->2)]-D-galactose [RN:R04423]
    Gene Name: ABO
    Uniprot ID: P16442 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Chondroitin sulfate synthase 3
    Reactions:
    • UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
    Gene Name: CHSY3
    Uniprot ID: Q70JA7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Chondroitin sulfate synthase 2
    Reactions:
    • UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
    Gene Name: CHPF
    Uniprot ID: Q8IZ52 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Chondroitin sulfate synthase 1
    Reactions:
    • UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
    Gene Name: CHSY1
    Uniprot ID: Q86X52 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunit
    Reactions:
      Gene Name: OGT
      Uniprot ID: O15294 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Polypeptide N-acetylgalactosaminyltransferase 13
      Reactions:
        Gene Name: GALNT13
        Uniprot ID: Q68VI8 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Chondroitin sulfate N-acetylgalactosaminyltransferase 2
        Reactions:
        • UDP-N-acetyl-D-galactosamine + beta-D-glucuronyl-(1->3)-D-galactosyl-proteoglycan = UDP + N-acetyl-D-galactosaminyl-(1->4)-beta-D-glucuronyl-(1->3)-beta-D- galactosylproteoglycan [RN:R05929]
        Gene Name: CSGALNACT2
        Uniprot ID: Q8N6G5 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Polypeptide N-acetylgalactosaminyltransferase 9
        Reactions:
        • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
        Gene Name: GALNT9
        Uniprot ID: Q9HCQ5 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Polypeptide N-acetylgalactosaminyltransferase-like 6
        Reactions:
        • UDP-N-acetyl-D-galactosamine + polypeptide = UDP + N-acetyl-D-galactosaminyl-polypeptide [RN:R02183]
        Gene Name: GALNTL6
        Uniprot ID: Q49A17 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Putative polypeptide N-acetylgalactosaminyltransferase-like protein 5
        Reactions:
          Gene Name: GALNTL5
          Uniprot ID: Q7Z4T8 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: N-acetyl-beta-glucosaminyl-glycoprotein 4-beta-N-acetylgalactosaminyltransferase 2
          Reactions:
          • UDP-N-acetyl-D-galactosamine + N-acetyl-beta-D-glucosaminyl group = UDP + N-acetyl-beta-D-galactosaminyl-(1->4)-N-acetyl-beta-D-glucosaminyl group
          Gene Name: B4GALNT3
          Uniprot ID: Q6L9W6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: N-acetyl-beta-glucosaminyl-glycoprotein 4-beta-N-acetylgalactosaminyltransferase 1
          Reactions:
          • UDP-N-acetyl-D-galactosamine + N-acetyl-beta-D-glucosaminyl group = UDP + N-acetyl-beta-D-galactosaminyl-(1->4)-N-acetyl-beta-D-glucosaminyl group
          Gene Name: B4GALNT4
          Uniprot ID: Q76KP1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Pp-GalNAc-transferase 20
          Reactions:
            Gene Name: GALNT20
            Uniprot ID: Q2L4S5 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA