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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:01 UTC
HMDB IDHMDB0000304
Secondary Accession Numbers
  • HMDB00304
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
ValueSource
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
UDP AcetylglucosamineMeSH
Uridine diphospho-N-acetylglucosamineMeSH
Acetylgalactosamine, UDPMeSH
diphospho-N-Acetylglucosamine, uridineMeSH
Uridine diphosphate N acetylgalactosamineMeSH
Uridine diphosphate N acetylglucosamineMeSH
Uridine diphosphate N-acetylglucosamineMeSH
Diphosphate N-acetylglucosamine, uridineMeSH
UDPGNAcMeSH
Uridine diphosphate N-acetylgalactosamineMeSH
Acetylglucosamine, UDPMeSH
N-Acetylgalactosamine, uridine diphosphateMeSH
UDP AcetylgalactosamineMeSH
Uridine pyrophosphoacetylglucosamineMeSH
Uridine diphospho N acetylglucosamineMeSH
Diphosphate N-acetylgalactosamine, uridineMeSH
N-Acetylglucosamine, uridine diphosphateMeSH
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}(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(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
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Acetamide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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-1.7ALOGPS
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 Area300.41 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m³·mol⁻¹ChemAxon
Polarizability51.59 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03fu-5926205000-cdab8d90ff64fb776a15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-05e9-8897100000-095b6091bd84d37fd58bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000l-2900000000-82a9c4130de4b3125fd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910010000-188f1b92ae056d7c7cd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-ce6262fadd328364b376View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-b91dd47ef36e2cad815bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06ri-9502321000-f502248d5c26ca57aecbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9605010000-08fa474eedca91ebd68fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-55e7efddb090fc85714aView in MoNA
Biological Properties
Cellular Locations
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biospecimen LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Muscle
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021933
KNApSAcK IDNot Available
Chemspider ID1134
KEGG Compound IDC00203
BioCyc IDUDP-N-ACETYL-GALACTOSAMINE
BiGG ID34247
Wikipedia LinkNot Available
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 ]

Only showing the first 10 proteins. There are 33 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Transfers 1,4-N-acetylgalactosamine (GalNAc) from UDP-GalNAc to the non-reducing end of glucuronic acid (GlcUA). Required for addition of the first GalNAc to the core tetrasaccharide linker and for elongation of chondroitin chains. Important role in chondroitin chain biosynthesis in cartilage.
Gene Name:
CSGALNACT1
Uniprot ID:
Q8TDX6
Molecular weight:
61294.005
Reactions
Uridine diphosphate-N-acetylgalactosamine + beta-D-glucuronyl-(1->3)-D-galactosyl-proteoglycan → Uridine 5'-diphosphate + N-acetyl-D-galactosaminyl-(1->4)-beta-D-glucuronyl-(1->3)-beta-D-galactosylproteoglycandetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in the biosynthesis of gangliosides GM2, GD2 and GA2.
Gene Name:
B4GALNT1
Uniprot ID:
Q00973
Molecular weight:
58881.78
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Displays the same enzyme activity toward Muc1, Muc4.1, and EA2 than GALNT1. Does not appear to be involved in glycosylation of erythropoietin.
Gene Name:
GALNT11
Uniprot ID:
Q8NCW6
Molecular weight:
68918.365
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has a highest activity toward Muc7, EA2 and Muc2, with a lowest activity than GALNT2. Glycosylates 'Thr-57' of SELPLG.
Gene Name:
GALNT4
Uniprot ID:
Q8N4A0
Molecular weight:
45701.465
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has activity toward HIV envelope glycoprotein gp120, EA2, Muc2 and Muc5. Probably glycosylates fibronectin in vivo. Glycosylates FGF23. Plays a central role in phosphate homeostasis.
Gene Name:
GALNT3
Uniprot ID:
Q14435
Molecular weight:
72609.79
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Probably catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor (By similarity).
Gene Name:
GALNT8
Uniprot ID:
Q9NY28
Molecular weight:
72850.77
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Although it displays a much weaker activity toward all substrates tested compared to GALNT2, it is able to transfer up to seven GalNAc residues to the Muc5AC peptide, suggesting that it can fill vicinal Thr/Ser residues in cooperation with other GALNT proteins. Prefers Muc1a as substrate.
Gene Name:
GALNTL2
Uniprot ID:
Q8N3T1
Molecular weight:
73062.79
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
May catalyze the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor (By similarity).
Gene Name:
GALNTL1
Uniprot ID:
Q8N428
Molecular weight:
63073.595
General function:
Involved in metal ion binding
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has activity toward Muc5Ac and EA2 peptide substrates.
Gene Name:
GALNT10
Uniprot ID:
Q86SR1
Molecular weight:
68991.22
General function:
Involved in polypeptide N-acetylgalactosaminyltransfera
Specific function:
Catalyzes the initial reaction in O-linked oligosaccharide biosynthesis, the transfer of an N-acetyl-D-galactosamine residue to a serine or threonine residue on the protein receptor. Has a much stronger activity than GALNT1 to transfer GalNAc to mucin peptides, such as Muc5Ac and Muc7. Able to glycosylate SDC3. May be responsible for the synthesis of Tn antigen in neuronal cells.
Gene Name:
GALNT13
Uniprot ID:
Q8IUC8
Molecular weight:
64050.095

Only showing the first 10 proteins. There are 33 proteins in total.