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Showing Compound Uridine diphosphate-N-acetylgalactosamine (FDB021933)

Record Information
Version1.0
Creation date2011-09-21 00:05:27 UTC
Update date2015-07-21 06:56:53 UTC
Primary IDFDB021933
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number7277-98-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H27N3O17P2
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
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
Isomeric SMILESCC(=O)NC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O
Average Molecular Weight607.3537
Monoisotopic Molecular Weight607.081569477
Classification
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
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSUridine diphosphate-N-acetylgalactosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373Spectrum
Predicted GC-MSUridine diphosphate-N-acetylgalactosamine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fu-5926205000-cdab8d90ff64fb776a15Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-05e9-8897100000-095b6091bd84d37fd58b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000l-2900000000-82a9c4130de4b3125fd72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000l-2900000000-4d24529e74ad2fa21c052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1930010000-55436553b484e5220f192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1490000000-ac1c456c4492cae878a22021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910010000-188f1b92ae056d7c7cd02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-ce6262fadd328364b3762015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-b91dd47ef36e2cad815b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06ri-9502321000-f502248d5c26ca57aecb2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9605010000-08fa474eedca91ebd68f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-55e7efddb090fc85714a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0000095000-b04755a1d58b540399312021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4201191000-b741fdd379d9a2afcc612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-5719010000-abc6f96328a6d0fbfbb82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0000914000-04cfea1597e2554c0ff82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1412944000-aafe333f4e24af5bf0922021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h3r-9231000000-e1c43f13a820bf095dda2021-09-24View Spectrum
NMRNot Available
ChemSpider ID1134
ChEMBL IDNot Available
KEGG Compound IDC00203
Pubchem Compound ID1167
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00304
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34247
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference