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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:27:05 UTC
Update Date2019-07-23 07:14:31 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). UDP-N-acetyl-alpha-D-galactosamine exists in all living organisms, ranging from bacteria to humans. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Structure
Data?1563866071
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]oxyphosphinic 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
Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13 g/LALOGPS
logP-1.4ALOGPS
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
Polarizability51.05 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0itc-5952736000-d36d9e2016c3cc3efc48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-5332109000-51407a00f408770ec019Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05cr-5796100000-28a7cdf50cd872a70c19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-1960000000-6ceaa442b144ea3c15f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910020000-b4f448790a5adc1b2231Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-b1ea97b129b6c701887eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-af36b4483c7d5529ce86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-9801421000-87db24d9515a2033d9b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-9605020000-323a53bc8a8e293636d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-aee8e2f7d665fa10b3b1Spectrum
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 ID
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.