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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:27:05 UTC
Update Date2022-03-07 03:17:46 UTC
HMDB IDHMDB0060522
Secondary Accession Numbers
  • HMDB60522
Metabolite Identification
Common NameUDP-N-acetyl-alpha-D-galactosamine
DescriptionUDP-N-acetyl-alpha-D-galactosamine, also known as UDP-galnac or acetylgalactosamine, UDP, 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. UDP-N-acetyl-alpha-D-galactosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). A UDP-N-acetyl-D-galactosamine in which the anomeric centre of the galactosamine moiety has alpha-configuration. UDP-N-acetyl-alpha-D-galactosamine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4R,5R,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)ChEBI
UDP-GalNacChEBI
URIDINE-diphosphATE-N-acetylgalactosamineChEBI
(2R,3R,4R,5R,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)Generator
URIDINE-diphosphoric acid-N-acetylgalactosamineGenerator
UDP-N-Acetyl-a-D-galactosamineGenerator
UDP-N-Acetyl-α-D-galactosamineGenerator
Acetylgalactosamine, UDPHMDB
Diphosphate N-acetylgalactosamine, uridineHMDB
N-Acetylgalactosamine, uridine diphosphateHMDB
UDP AcetylgalactosamineHMDB
Uridine diphosphate N acetylgalactosamineHMDB
Uridine diphosphate N-acetylgalactosamineHMDB
Chemical FormulaC17H27N3O17P2
Average Molecular Weight607.3537
Monoisotopic Molecular Weight607.081569477
IUPAC Name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Name{[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[P@](O)(=O)O[P@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)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)/t7-,8-,10-,11+,12-,13-,14-,15-,16-/m1/s1
InChI KeyLFTYTUAZOPRMMI-NESSUJCYSA-N
Chemical Taxonomy
Description 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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02196
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID22161
KEGG Compound IDNot Available
BioCyc IDUDP-N-ACETYL-GALACTOSAMINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23700
PDB IDUD2
ChEBI ID67168
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Only showing the first 10 proteins. There are 26 proteins in total.

Enzymes

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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl-(1<->1)-ceramide → Uridine 5'-diphosphate + O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1->4)-O-(N-acetyl-alpha-neuraminyl-(2->3))-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl-(1<->1)-ceramidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails
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:
WBSCR17
Uniprot ID:
Q6IS24
Molecular weight:
67750.455
Reactions
UDP-N-acetyl-alpha-D-galactosamine + polypeptide → Uridine 5'-diphosphate + N-acetyl-alpha-D-galactosaminyl-polypeptidedetails

Only showing the first 10 proteins. There are 26 proteins in total.