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Uridine diphosphate-N-acetylglucosamine (PC000251)

Record Information
Version1.0
Creation date2015-10-09 22:29:27 UTC
Update date2017-01-19 02:36:18 UTC
FoodComEx IDPC000251
FoodDB RecordFDB021930
Chemical Information
NameUridine diphosphate-N-acetylglucosamine
DescriptionUridine 5'-diphosphate-GlcNAc (UDP-Glc-NAc )respond to nutrient excess to activate O-GlcNAcylation (addition of O-linked N-acetylglucosamine) in the hexosamine signaling pathway (HSP). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114) The incidence of type 2 diabetes (non-insulin-dependent diabetes mellitus) has increased to epidemic proportions, being described as a disease of 'chronic overnutrition'. Due to the chemical makeup of UDP-GlcNAc,it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. UDP-Glc-NAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake. (PMID: 12678487) [HMDB]
CAS Number528-04-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2R,3R,4R,5S,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 diate (non-preferred name)ChEBI
(2R,3R,4R,5S,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 diic acid (non-preferred name)Generator
[[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inateHMDB
[[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inic acidHMDB
[[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinatehmdb
[[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acidhmdb
N-[2-[[[5-[(2,4-dioxo-1H-Pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-inoyl]oxy-hydroxy-inoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamideHMDB
N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamidehmdb
UDP-a-D-N-acetylglucosaminehmdb
UDP-acetyl-D-glucosaminehmdb
UDP-acetyl-delta-glucosaminehmdb
UDP-acetylglucosaminehmdb
UDP-alpha-D-N-acetylglucosaminehmdb
UDP-alpha-delta-N-acetylglucosaminehmdb
UDP-GlcNAchmdb
UDP-N-acetyl-D-glucosaminehmdb
UDP-N-acetyl-delta-glucosaminehmdb
UDP-N-acetyl-glucosaminehmdb
UDP-N-acetylglucosaminehmdb
UPPAGhmdb
Uridine 5'-dio-N-acetlyglucosamineHMDB
Uridine 5'-dio-N-acetylglucosamineHMDB
Uridine 5'-Diphospho-N-Acetlyglucosaminehmdb
Uridine 5'-diphospho-N-acetylglucosaminehmdb
Uridine diate N-acetyl-D-glucosamineHMDB
Uridine diate N-acetyl-delta-glucosamineHMDB
Uridine diate N-acetylglucosamineHMDB
Uridine dio-2-acetamido-2-deoxy-D-glucoseHMDB
Uridine dio-2-acetamido-2-deoxy-delta-glucoseHMDB
Uridine dio-N-acetyl-D-glucosamineHMDB
Uridine dio-N-acetyl-delta-glucosamineHMDB
Uridine dio-N-acetylglucosamineHMDB
Uridine dioacetylglucosamineHMDB
Uridine diphosphate N-acetyl-D-glucosaminehmdb
Uridine diphosphate N-acetyl-delta-glucosaminehmdb
Uridine diphosphate N-acetylglucosaminehmdb
Uridine diphospho-2-acetamido-2-deoxy-D-glucosehmdb
Uridine diphospho-2-acetamido-2-deoxy-delta-glucosehmdb
Uridine diphospho-N-acetyl-D-glucosaminehmdb
Uridine diphospho-N-acetyl-delta-glucosaminehmdb
Uridine diphospho-N-acetylglucosaminehmdb
uridine diphosphoacetylglucosaminehmdb
Uridine pyroate 2-acetamido-2-deoxy-a-D-glucopyranosyl esterHMDB
Uridine pyroate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl esterHMDB
Uridine pyroate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl esterHMDB
Uridine pyrooacetylglucosamineHMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl esterhmdb
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl esterhmdb
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl esterhmdb
Uridine pyrophosphoacetylglucosaminehmdb
URIDINE-diATE-N-acetylglucosamineChEBI
URIDINE-diic acid-N-acetylglucosamineGenerator
Chemical FormulaC17H27N3O17P2
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,5S,6R)-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)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
InChI KeyLFTYTUAZOPRMMI-CFRASDGPSA-N
Isomeric SMILESCC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O
Average Molecular Weight607.3537
Monoisotopic Molecular Weight607.081569477
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 20 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available