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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
SynonymSource
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
UDP-N-acetyl-D-galactosaminehmdb
UDP-N-acetyl-delta-galactosaminehmdb
UDP-N-acetylgalactosaminehmdb
Uridine 5'-dio-N-acetylgalactosamineHMDB
Uridine diate-N-acetyl-D-galactosamineHMDB
Uridine diate-N-acetyl-delta-galactosamineHMDB
Uridine dio-2-acetamido-2-deoxy-D-galactoseHMDB
Uridine dio-2-acetamido-2-deoxy-delta-galactoseHMDB
Uridine dio-N-acetylgalactosamineHMDB
Uridine dioacetylgalactosamineHMDB
Uridine pyroate 2-acetamido-2-deoxy-a-D-galactopyranosyl esterHMDB
Uridine pyroate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl esterHMDB
Uridine pyroate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl esterHMDB
Uridine pyroate N-acetyl-a-D-chondrosamine esterHMDB
Uridine pyroate N-acetyl-alpha-D-chondrosamine esterHMDB
Uridine pyroate N-acetyl-alpha-delta-chondrosamine esterHMDB
Uridine pyrooacetylgalactosamineHMDB
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
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunitOGTO15294
Polypeptide N-acetylgalactosaminyltransferase 13GALNT13Q68VI8
Pp-GalNAc-transferase 20GALNT20Q2L4S5
Chondroitin sulfate N-acetylgalactosaminyltransferase 2CSGALNACT2Q8N6G5
Chondroitin sulfate N-acetylgalactosaminyltransferase 1CSGALNACT1Q8TDX6
Beta-1,4 N-acetylgalactosaminyltransferase 1B4GALNT1Q00973
Beta-1,4-N-acetylgalactosaminyltransferase 3B4GALNT3Q6L9W6
N-acetyl-beta-glucosaminyl-glycoprotein 4-beta-N-acetylgalactosaminyltransferase 1B4GALNT4Q76KP1
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference