Record Information
Version2.0
Creation Date2012-05-31 14:07:18 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB04171
Identification
Name:UDP-Glucose
DescriptionUDP-glucose is key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of lipopolysaccharides.
Structure
Thumb
Synonyms:
  • (UDP)glucose
  • (UPD)-glucose
  • GDP-Glc
  • UDP Glucose
  • UDP-a-D-Glucose
  • UDP-a-delta-Glucose
  • UDP-a-δ-Glucose
  • UDP-alpha-D-Glucose
  • UDP-alpha-delta-Glucose
  • UDP-D-Glucose
  • UDP-delta-Glucose
  • UDP-Glc
  • UDP-Glucose
  • UDP-α-D-Glucose
  • UDP-α-δ-Glucose
  • UDP-δ-Glucose
  • UDPG
  • UDPglucose
  • Uridine 5'-diphosphate glucose
  • Uridine 5'-diphospho-a-D-glucose
  • Uridine 5'-diphospho-a-delta-glucose
  • Uridine 5'-diphospho-a-δ-glucose
  • Uridine 5'-diphospho-alpha-D-glucose
  • Uridine 5'-diphospho-alpha-delta-glucose
  • Uridine 5'-diphospho-α-D-glucose
  • Uridine 5'-diphospho-α-δ-glucose
  • Uridine 5'-diphosphoglucose
  • Uridine 5'-diphosphoric acid glucose
  • Uridine 5'-pyrophosphate a-D-glucopyranosyl ester
  • Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester
  • Uridine 5'-pyrophosphate a-δ-glucopyranosyl ester
  • Uridine 5'-pyrophosphoric acid a-D-glucopyranosyl ester
  • Uridine 5'-pyrophosphoric acid a-delta-glucopyranosyl ester
  • Uridine 5'-pyrophosphoric acid a-δ-glucopyranosyl ester
  • Uridine diphosphate-glucose
  • Uridine diphospho-D-glucose
  • Uridine diphospho-delta-glucose
  • Uridine diphospho-δ-glucose
  • Uridine diphosphoglucose
  • Uridine diphosphoric acid-glucose
  • Uridine pyrophosphate-glucose
  • Uridine pyrophosphoric acid-glucose
Chemical Formula:C15H24N2O17P2
Weight:Average: 566.3018
Monoisotopic: 566.055020376
InChI Key:HSCJRCZFDFQWRP-LPTOLDDLSA-N
InChI:InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14?/m0/s1
CAS number:133-89-1
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,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name:udp-α-D-glucose
SMILES:OC[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)N2C=CC(=O)NC2=O)[C@@H](O)[C@H](O)[C@H]1O
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
  • 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
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Lactam
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility15 g/LALOGPS
logP-1.4ALOGPS
logP-5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area291.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m³·mol⁻¹ChemAxon
Polarizability45.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + UDP-Glucose > Glucose 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Galactose 1-phosphate + UDP-Glucose <> Glucose 1-phosphate + Uridine diphosphategalactose
UDP-Glucose <> Uridine diphosphategalactose
Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose
Glucose 6-phosphate + UDP-Glucose > Hydrogen ion + Trehalose 6-phosphate + Uridine 5'-diphosphate
Water + 2 NAD + UDP-Glucose <>3 Hydrogen ion +2 NADH + Uridine diphosphate glucuronic acid + UDP-Glucuronic acid
O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + UDP-Glucose > Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Hydrogen ion + Uridine 5'-diphosphate
glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A + UDP-Glucose > glucosyl-glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate
galactosyl-glucosyl-inner core oligosaccharide lipid A + UDP-Glucose > glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate
glucosyl-inner core oligosaccharide lipid A + UDP-Glucose > galactosyl-glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate
inner core oligosaccharide lipid A (E coli) + UDP-Glucose > glucosyl-inner core oligosaccharide lipid A + Hydrogen ion + Uridine 5'-diphosphate
UDP-Glucose + Water + 2 NAD <> Uridine diphosphate glucuronic acid +2 NADH +2 Hydrogen ion
UDP-Glucose + Water <> Uridine 5'-monophosphate + Glucose 1-phosphate
Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose
UDP-Glucose + LPS (1-O-antigen) <> Uridine 5'-diphosphate + D-Glucosyllipopolysaccharide
UDP-Glucose + Glucose 6-phosphate <> Uridine 5'-diphosphate + Trehalose 6-phosphate
UDP-Glucose + Cellulose <> Uridine 5'-diphosphate + Cellulose
GDP-L-Fucose + UDP-Glucose + Uridine diphosphate glucuronic acid + Uridine diphosphategalactose colanic acid
UDP-Glucose + a lipopolysaccharide D-glucosyl-lipopolysaccharide + Uridine 5'-diphosphate
Hydrogen ion + Glucose 1-phosphate + Uridine triphosphate > UDP-Glucose + Pyrophosphate
UDP-Glucose + Heptosyl2-KDO2-lipid A > Hydrogen ion + Glucosyl-heptosyl2-KDO2-lipid A + Uridine 5'-diphosphate
UDP-Glucose + Galactosyl-glucosyl-heptosyl3-KDO2-lipid A-bisphosphate > Hydrogen ion + Galactosyl-glucosyl2-heptosyl3-KDO2-lipid A-bisphosphate + Uridine 5'-diphosphate
UDP-Glucose + Galactosyl-glucosyl2-heptosyl3-KDO2-lipid A-bisphosphate > Hydrogen ion + Galactosyl-glucosyl3-heptosyl3-KDO2-lipid A-bisphosphate + Uridine 5'-diphosphate
UDP-Glucose + &alpha;-D-glucose 6-phosphate > Hydrogen ion + Uridine 5'-diphosphate + Trehalose 6-phosphate
UDP-Glucose + Water + NAD > Hydrogen ion + NADH + Uridine diphosphate glucuronic acid
UDP-Glucose + (1,4-beta-D-glucosyl)(n) > Uridine 5'-diphosphate + (1,4-beta-D-glucosyl)(n+1)
UDP-Glucose + Galactose 1-phosphate > Alpha-D-glucose 1-phosphate + Uridine diphosphategalactose
UDP-Glucose > Uridine diphosphategalactose
Uridine triphosphate + Alpha-D-glucose 1-phosphate > Pyrophosphate + UDP-Glucose
UDP-Glucose + Glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate
UDP-Glucose + LPS (1-O-antigen) > Uridine 5'-diphosphate + D-glucosyl-lipopolysaccharide
UDP-Glucose + 2 NAD + Water > UDP-Glucuronic acid +2 NADH
UDP-Glucose <> Uridine 5'-diphosphate
UDP-Glucose + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + alpha-D-Glucopyranosyl-diphospho-ditrans,octacis-undecaprenol
Glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose
β-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > UDP-Glucose + Pyrophosphate
Alpha-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose
UDP-Glucose > Uridine diphosphategalactose + Uridine diphosphategalactose
Galactose 1-phosphate + UDP-Glucose + Galactose 1-phosphate > Uridine diphosphategalactose + Glucose 1-phosphate + Uridine diphosphategalactose
Alpha-D-glucose 1-phosphate + UDP-galactose > UDP-Glucose + Galactose 1-phosphate + Galactose 1-phosphate
UDP-Glucose <> Uridine diphosphategalactose + Uridine diphosphategalactose
(heptosyl)2-Kdo2-lipid A + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A
galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate
galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP-Glucose > Uridine 5'-diphosphate + Hydrogen ion + galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate
UDP-Glucose + 2 NAD + Water > UDP-Glucuronic acid +2 NADH +3 Hydrogen ion
UDP-Glucose + Alpha-D-glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate + Hydrogen ion + Uridine 5'-diphosphate
UDP-Glucose + D-Fructose + D-Fructose <> Sucrose + Phosphate
UDP-Glucose + Mannose 6-phosphate > alpha,alpha-Trehalose 6-phosphate + Uridine 5'-diphosphate + Hydrogen ion
UDP-Glucose <> Uridine diphosphategalactose
Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose
Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose
UDP-Glucose <> Uridine diphosphategalactose
More...

SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIPW000887 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
colanic acid building blocks biosynthesisPW000951 ThumbThumb?image type=greyscaleThumb?image type=simple
galactose degradation/Leloir PathwayPW000884 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
trehalose biosynthesis IPW002088 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
2500± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1120± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
553± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1910± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-4942706000-3a83736296429f83adeeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Uridine diphosphate glucose,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000090000-1692ab5f5dad1cf7e436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-015a-0439510000-69e7cd4c2c365a24706bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0109-5753970000-03f34041208ba93ef87aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00fr-9257000000-73b85a465d99ce92467dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00ba-9333000000-b57dc1340555f1a997b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00fr-9257000000-ba1e6c754b8f04d5b659View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-9bd63595c19dbe18d143View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-4b94aa10fd96d2d9c505View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-996cd4acdaa34c877460View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e77963110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa84737530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0000960000-6404d8d944e1ae6f30e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07e1-2322960000-6af539ce21752f9023baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9732000000-b0c81adc41b1d799e1e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8cab8f2bc0fb9e9e8ba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057j-9203870000-d60681ff91f741bdb867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3519000000-67ca2f9355ef7f94a47dView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
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  • Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  • Raila J, Wirth K, Chen F, Buscher U, Dudenhausen JW, Schweigert FJ: Excretion of vitamin A in urine of women during normal pregnancy and pregnancy complications. Ann Nutr Metab. 2004 Sep-Oct;48(5):357-64. Epub 2004 Nov 9. Pubmed: 15542927
  • Reynolds TH 4th, Pak Y, Harris TE, Manchester J, Barrett EJ, Lawrence JC Jr: Effects of insulin and transgenic overexpression of UDP-glucose pyrophosphorylase on UDP-glucose and glycogen accumulation in skeletal muscle fibers. J Biol Chem. 2005 Feb 18;280(7):5510-5. Epub 2004 Dec 13. Pubmed: 15596435
  • Schwartz AL, Rall TW: Hormonal regulation of glycogen metabolism in human fetal liver. II. Regulation of glycogen synthase activity. Diabetes. 1975 Dec;24(12):1113-22. Pubmed: 811498
  • Tarantino G, Morelli L, Califano C: [Uridine diphosphate glucose (UDPG) in the treatment of hepatic disease from chronic alcohol abuse] Riv Eur Sci Med Farmacol. 1990 Apr;12(2):109-17. Pubmed: 2080308
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Burma, D. P.; Mortimer, D. C. Biosynthesis of uridine diphosphate glucose and sucrose in sugar-beet leaf. Archives of Biochemistry and Biophysics (1956), 62 16-28.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID46229
HMDB IDHMDB00286
Pubchem Compound ID439156
Kegg IDC00029
ChemSpider IDNot Available
WikipediaUridine diphosphate glucose
BioCyc IDUDP-GLUCOSE
EcoCyc IDUDP-GLUCOSE

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in catalytic activity
Specific function:
UDP-glucose = UDP-galactose
Gene Name:
galE
Uniprot ID:
P09147
Molecular weight:
37265
Reactions
UDP-glucose = UDP-galactose.
General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
Gene Name:
galT
Uniprot ID:
P09148
Molecular weight:
39645
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose.
General function:
Involved in enzyme regulator activity
Specific function:
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose
Gene Name:
galF
Uniprot ID:
P0AAB6
Molecular weight:
32829
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase activity
Specific function:
May play a role in stationary phase survival
Gene Name:
galU
Uniprot ID:
P0AEP3
Molecular weight:
32942
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
mazG
Uniprot ID:
P0AEY3
Molecular weight:
30412
Reactions
ATP + H(2)O = AMP + diphosphate.
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
UDP-glucose + lipopolysaccharide = UDP + D- glucosyl-lipopolysaccharide
Gene Name:
rfaJ
Uniprot ID:
P27129
Molecular weight:
39040
Reactions
UDP-glucose + lipopolysaccharide = UDP + D-glucosyl-lipopolysaccharide.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Essential for viability of the cells at low temperatures and at elevated osmotic strength
Gene Name:
otsA
Uniprot ID:
P31677
Molecular weight:
53611
Reactions
UDP-glucose + D-glucose 6-phosphate = UDP + alpha,alpha-trehalose 6-phosphate.
General function:
Involved in cellulose synthase activity
Specific function:
Catalytic subunit of cellulose synthase. It polymerizes uridine 5'-diphosphate glucose to cellulose, which is produced as an extracellular component for mechanical and chemical protection at the onset of the stationary phase, when the cells exhibit multicellular behavior (rdar morphotype). Coexpression of cellulose and thin aggregative fimbriae leads to a hydrophobic network with tightly packed cells embedded in a highly inert matrix
Gene Name:
bcsA
Uniprot ID:
P37653
Molecular weight:
99784
Reactions
UDP-glucose + (1,4-beta-D-glucosyl)(n) = UDP + (1,4-beta-D-glucosyl)(n+1).
General function:
Involved in catalytic activity
Specific function:
Sucrose + phosphate = D-fructose + alpha-D- glucose 1-phosphate
Gene Name:
ycjM
Uniprot ID:
P76041
Molecular weight:
64185
Reactions
Sucrose + phosphate = D-fructose + alpha-D-glucose 1-phosphate.
General function:
Involved in oxidation-reduction process
Specific function:
UDP-glucose + 2 NAD(+) + H(2)O = UDP- glucuronate + 2 NADH
Gene Name:
ugd
Uniprot ID:
P76373
Molecular weight:
43656
Reactions
UDP-glucose + 2 NAD(+) + H(2)O = UDP-glucuronate + 2 NADH.
General function:
Involved in biosynthetic process
Specific function:
Involved in the addition of the first glucose residue to the lipopolysaccharide core
Gene Name:
rfaG
Uniprot ID:
P25740
Molecular weight:
42284
General function:
Involved in biosynthetic process
Specific function:
Adds a galactose goup to a glucose group of LPS
Gene Name:
rfaB
Uniprot ID:
P27127
Molecular weight:
40826
General function:
Involved in biosynthetic process
Specific function:
May be a glycosyltransferase involved in the transfer of UDP-GalF and UDP-glucose
Gene Name:
yefI
Uniprot ID:
P37751
Molecular weight:
43188
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
UDP-galactose + lipopolysaccharide = UDP + 3- alpha-D-galactosyl-[lipopolysaccharide glucose]
Gene Name:
rfaI
Uniprot ID:
P27128
Molecular weight:
39423
Reactions
UDP-galactose + lipopolysaccharide = UDP + 3-alpha-D-galactosyl-[lipopolysaccharide glucose].

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368