Uridine diphosphate-N-acetylgalactosamine (CHEM034791)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:13:31 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034791
Identification
Common NameUridine diphosphate-N-acetylgalactosamine
ClassSmall Molecule
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) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Uridine diphosphoric acid-N-acetylgalactosamineGenerator
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, HMDB
UDP AcetylglucosamineMeSH, HMDB
Uridine diphospho-N-acetylglucosamineMeSH, HMDB
Acetylgalactosamine, UDPMeSH, HMDB
diphospho-N-Acetylglucosamine, uridineMeSH, HMDB
Uridine diphosphate N acetylgalactosamineMeSH, HMDB
Uridine diphosphate N acetylglucosamineMeSH, HMDB
Uridine diphosphate N-acetylglucosamineMeSH, HMDB
Diphosphate N-acetylglucosamine, uridineMeSH, HMDB
UDPGNAcMeSH, HMDB
Uridine diphosphate N-acetylgalactosamineMeSH, HMDB
Acetylglucosamine, UDPMeSH, HMDB
N-Acetylgalactosamine, uridine diphosphateMeSH, HMDB
UDP AcetylgalactosamineMeSH, HMDB
Uridine pyrophosphoacetylglucosamineMeSH, HMDB
Uridine diphospho N acetylglucosamineMeSH, HMDB
Diphosphate N-acetylgalactosamine, uridineMeSH, HMDB
N-Acetylglucosamine, uridine diphosphateMeSH, HMDB
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]ethanimidateGenerator, HMDB
Chemical FormulaC17H27N3O17P2
Average Molecular Mass607.354 g/mol
Monoisotopic Mass607.082 g/mol
CAS Registry Number7277-98-7
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
SMILESCC(=O)NC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O
InChI IdentifierInChI=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
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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility13 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
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, Positivesplash10-03fu-5926205000-cdab8d90ff64fb776a15Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-05e9-8897100000-095b6091bd84d37fd58bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000l-2900000000-82a9c4130de4b3125fd7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000l-2900000000-4d24529e74ad2fa21c05Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1930010000-55436553b484e5220f19Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1490000000-ac1c456c4492cae878a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910010000-188f1b92ae056d7c7cd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-ce6262fadd328364b376Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-b91dd47ef36e2cad815bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06ri-9502321000-f502248d5c26ca57aecbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9605010000-08fa474eedca91ebd68fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-55e7efddb090fc85714aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0000095000-b04755a1d58b54039931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4201191000-b741fdd379d9a2afcc61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-5719010000-abc6f96328a6d0fbfbb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0000914000-04cfea1597e2554c0ff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1412944000-aafe333f4e24af5bf092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h3r-9231000000-e1c43f13a820bf095ddaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0259722
FooDB IDFDB021933
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID1134
ChEBI IDNot Available
PubChem Compound ID1167
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available