Record Information
Version1.0
Creation date2011-09-21 00:05:24 UTC
Update date2015-10-09 22:29:27 UTC
Primary IDFDB021930
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
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 diphosphate (non-preferred name)ChEBI
UDP-GlcNAcChEBI
UDP-N-Acetyl-D-glucosamineChEBI
UDP-N-AcetylglucosamineChEBI
URIDINE-diphosphATE-N-acetylglucosamineChEBI
(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 diphosphoric acid (non-preferred name)Generator
URIDINE-diphosphoric acid-N-acetylglucosamineGenerator
Uridine diphosphoric acid-N-acetylglucosamineGenerator
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-N-Acetyl-delta-glucosamineHMDB
UDP-N-Acetyl-glucosamineHMDB
UPPAGHMDB
Uridine 5'-diphospho-N-acetlyglucosamineHMDB
Uridine 5'-diphospho-N-acetylglucosamineHMDB
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 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
[[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
Acetylglucosamine, UDPHMDB
Diphosphate N-acetylglucosamine, uridineHMDB
Diphospho-N-acetylglucosamine, uridineHMDB
N-Acetylglucosamine, uridine diphosphateHMDB
Pyrophosphoacetylglucosamine, uridineHMDB
UDP AcetylglucosamineHMDB
UDPGNAcHMDB
Uridine diphosphate N acetylglucosamineHMDB
Uridine diphospho N acetylglucosamineHMDB
(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-N-acetyl-D-glucosaminehmdb
UDP-N-acetyl-delta-glucosaminehmdb
UDP-N-acetyl-glucosaminehmdb
UDP-N-acetylglucosaminehmdb
Uridine 5'-dio-N-acetlyglucosamineHMDB
Uridine 5'-dio-N-acetylglucosamineHMDB
Uridine 5'-Diphospho-N-Acetlyglucosaminehmdb
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 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-diATE-N-acetylglucosamineChEBI
URIDINE-diic acid-N-acetylglucosamineGenerator
Predicted Properties
PropertyValueSource
Water Solubility11.4 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
Polarizability50.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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 Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS)splash10-00di-9620000000-18841b4db9b69a91db36JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-18841b4db9b69a91db36JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5501619000-8584f57aecb61fc3e5b6JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-5543009000-8a176d160a1f074ab319JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-05cr-4796000000-6c09aa3a2dac66281973JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-5543009000-8a176d160a1f074ab319JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05cr-4796000000-6c09aa3a2dac66281973JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910020000-b4f448790a5adc1b2231JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-b1ea97b129b6c701887eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-af36b4483c7d5529ce86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-9801421000-87db24d9515a2033d9b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-9605020000-323a53bc8a8e293636d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-aee8e2f7d665fa10b3b1JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID393240
ChEMBL IDNot Available
KEGG Compound IDC00043
Pubchem Compound ID445675
Pubchem Substance IDNot Available
ChEBI ID16264
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00290
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33638
KNApSAcK IDNot Available
HET IDUD1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDUDP-N-acetylglucosamine
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
N-acetylglucosamine-1-phosphotransferase subunits alpha/betaGNPTABQ3T906
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinaseGNEQ9Y223
UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunitOGTO15294
Beta-1,3-N-acetylglucosaminyltransferase bGnT-2bGnT-2Q9NY97
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferaseDPAGT1Q9H3H5
Alpha-1,6-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferaseMGAT2Q10469
Exostosin-1EXT1Q16394
Exostosin-like 3EXTL3O43909
Exostosin-2EXT2Q93063
Exostosin-like 1EXTL1Q92935
N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferaseB3GNT1O43505
Alpha-1,6-mannosylglycoprotein 6-beta-N-acetylglucosaminyltransferase AMGAT5Q09328
Beta-1,4-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferaseMGAT3Q09327
N-acetyllactosaminide beta-1,6-N-acetylglucosaminyl-transferase, isoform BGCNT2Q06430
Exostosin-like 2EXTL2Q9UBQ6
Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase AMGAT4AQ9UM21
Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase BMGAT4BQ9UQ53
UDP-N-acetylglucosamine transferase subunit ALG13 homologALG13Q9NP73
UDP-N-acetylhexosamine pyrophosphorylaseUAP1Q16222
UDP-N-acetylglucosamine transporterSLC35A3Q9Y2D2
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference