Record Information
Version2.0
Creation Date2012-05-31 14:07:02 -0600
Update Date2015-06-03 15:54:49 -0600
Secondary Accession Numbers
  • ECMDB04166
Identification
Name:Uridine diphosphate glucuronic acid
DescriptionUridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. It is made from UDP-glucose by UDP-glucose 6-dehydrogenase (EC 1.1.1.22) using NAD+ as a cofactor. It is the source of the glucuronosyl group in glucuronosyltransferase reactions. (Wikipedia)
Structure
Thumb
Synonyms:
  • (UDP-GlcA)1
  • A-D-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • a-D-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
  • A-D-Glucopyranuronate ester with uridine 5'-pyrophosphate
  • A-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
  • a-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • A-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphate
  • a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
  • a-delta-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • a-delta-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
  • a-delta-Glucopyranuronate ester with uridine 5'-pyrophosphate
  • a-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
  • a-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • a-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
  • a-δ-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • a-δ-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
  • a-δ-Glucopyranuronate ester with uridine 5'-pyrophosphate
  • a-δ-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
  • a-δ-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • a-δ-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
  • Alpha-D-Glucopyranuronate 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
  • Alpha-D-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
  • alpha-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • Alpha-delta-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • Alpha-delta-Glucopyranuronate 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
  • Alpha-delta-Glucopyranuronate ester with uridine 5'-pyrophosphate
  • Alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
  • Alpha-delta-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
  • alpha-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • Alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphate
  • alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
  • GDP-GlcA
  • Glucopyranuronate 1-ester with uridine 5'-pyrophosphate
  • Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate
  • Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphoric acid
  • UDP Glucuronate
  • UDP Glucuronic acid
  • UDP-a-D-Glucuronate
  • UDP-a-D-Glucuronic acid
  • UDP-a-delta-Glucuronate
  • UDP-a-delta-Glucuronic acid
  • UDP-a-δ-Glucuronate
  • UDP-a-δ-Glucuronic acid
  • UDP-alpha-D-Glucuronate
  • UDP-alpha-D-Glucuronic acid
  • UDP-alpha-delta-Glucuronate
  • UDP-alpha-delta-Glucuronic acid
  • UDP-D-Glucuronate
  • UDP-D-Glucuronic acid
  • UDP-delta-Glucuronate
  • UDP-delta-Glucuronic acid
  • UDP-GlcUA
  • UDP-Glucuronate
  • UDP-Glucuronic acid
  • UDP-L-Iduronate
  • UDP-L-Iduronic acid
  • UDP-α-D-Glucuronate
  • UDP-α-D-Glucuronic acid
  • UDP-α-δ-Glucuronate
  • UDP-α-δ-Glucuronic acid
  • UDP-δ-Glucuronate
  • UDP-δ-Glucuronic acid
  • UDPGA
  • UDPglucuronate
  • UDPglucuronic acid
  • UGA
  • Uridine 5'-diphospho-a-D-glucuronate
  • Uridine 5'-diphospho-a-D-glucuronic acid
  • Uridine 5'-diphospho-a-delta-glucuronate
  • Uridine 5'-diphospho-a-delta-glucuronic acid
  • Uridine 5'-diphospho-a-δ-glucuronate
  • Uridine 5'-diphospho-a-δ-glucuronic acid
  • Uridine 5'-diphospho-alpha-delta-glucuronate
  • Uridine 5'-diphospho-alpha-delta-glucuronic acid
  • Uridine 5'-diphospho-glucuronate
  • Uridine 5'-diphospho-glucuronic acid
  • Uridine 5'-diphospho-α-δ-glucuronate
  • Uridine 5'-diphospho-α-δ-glucuronic acid
  • Uridine 5'-diphosphoglucuronate
  • Uridine 5'-diphosphoglucuronic acid
  • Uridine 5'-[3-(D-glucopyranosyloxyuronate) dihydrogen diphosphate]
  • Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]
  • Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphoric acid]
  • Uridine diphosphate glucuronate
  • Uridine diphosphate glucuronic acid
  • Uridine diphosphate-glucuronate
  • Uridine diphosphate-glucuronic acid
  • Uridine diphospho-D-glucuronate
  • Uridine diphospho-D-glucuronic acid
  • Uridine diphospho-delta-glucuronate
  • Uridine diphospho-delta-glucuronic acid
  • Uridine diphospho-δ-glucuronate
  • Uridine diphospho-δ-glucuronic acid
  • Uridine diphosphoglucuronate
  • Uridine diphosphoglucuronic acid
  • Uridine diphosphoric acid glucuronic acid
  • Uridine diphosphoric acid-glucuronic acid
  • Uridine pyrophosphoglucuronate
  • Uridine pyrophosphoglucuronic acid
  • Uridinediphosphoglucuronate
  • Uridinediphosphoglucuronic acid
  • α-D-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
  • α-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • α-δ-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
  • α-δ-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
  • α-δ-Glucopyranuronate ester with uridine 5'-pyrophosphate
  • α-δ-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
  • α-δ-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
  • α-δ-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
Chemical Formula:C15H22N2O18P2
Weight:Average: 580.2853
Monoisotopic: 580.034284934
InChI Key:HDYANYHVCAPMJV-LXQIFKJMSA-N
InChI:InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1
CAS number:2616-64-0
IUPAC Name:(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name:udp-α-D-glucuronic acid
SMILES:O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility18.1 g/LALOGPS
logP-1.2ALOGPS
logP-4.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area308.61 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.32 m³·mol⁻¹ChemAxon
Polarizability45.33 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Ascorbate and aldarate metabolism ec00053
  • Pentose and glucuronate interconversions ec00040
  • Starch and sucrose metabolism ec00500
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
83± 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
566± 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
375± 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
188± 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
296± 12 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
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, Positivesplash10-0w29-3322930000-0ce18416678ea80bec67View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004r-4862914000-b91973e084ab99d92364View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Uridine diphosphate glucuronic acid,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 - 20V, Negativesplash10-0fb9-0135690000-0ff1e6a4900ecdc6a915View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0000090000-1cdeb28950f03fda28eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0r29-5934300000-e5fcfe66852c383b82d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-bc00d530c5ce60dfe672View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3922200000-353e174f91c8b182064cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-d434fad6ebdd7797c473View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-b27e8f43f987aadd35fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-6c8ee9c73e164f9ccf76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imu-4601190000-7a0e82462b874f18b2c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9817020000-a72141b1bee762a83bc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvl-4901000000-5d52b1b8f03063646a7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001090000-c773521e9e340d5e6564View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-055e-9424840000-deea5ee6888efff36f31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-3936510000-b41af0ea55c95b9da1e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1700490000-7f9159b24d34e9358740View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4921760000-cd1fe2a62f343b8eb5baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0209-6940100000-aa916ad8a0ed15e6eb2aView in MoNA
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Alkharfy KM, Frye RF: High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. J Chromatogr B Biomed Sci Appl. 2001 Apr 5;753(2):303-8. Pubmed: 11334344
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Cappiello M, Giuliani L, Pacifici GM: Distribution of UDP-glucuronosyltransferase and its endogenous substrate uridine 5'-diphosphoglucuronic acid in human tissues. Eur J Clin Pharmacol. 1991;41(4):345-50. Pubmed: 1804651
  • Cappiello M, Giuliani L, Rane A, Pacifici GM: Uridine 5'-diphosphoglucuronic acid (UDPGLcUA) in the human fetal liver, kidney and placenta. Eur J Drug Metab Pharmacokinet. 2000 Jul-Dec;25(3-4):161-3. Pubmed: 11420884
  • Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990
  • Fondeur-Gelinotte M, Lattard V, Oriol R, Mollicone R, Jacquinet JC, Mulliert G, Gulberti S, Netter P, Magdalou J, Ouzzine M, Fournel-Gigleux S: Phylogenetic and mutational analyses reveal key residues for UDP-glucuronic acid binding and activity of beta1,3-glucuronosyltransferase I (GlcAT-I). Protein Sci. 2006 Jul;15(7):1667-78. Pubmed: 16815917
  • Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20. Pubmed: 14977865
  • Hagenauer B, Salamon A, Thalhammer T, Kunert O, Haslinger E, Klingler P, Senderowicz AM, Sausville EA, Jager W: In vitro glucuronidation of the cyclin-dependent kinase inhibitor flavopiridol by rat and human liver microsomes: involvement of UDP-glucuronosyltransferases 1A1 and 1A9. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):407-14. Pubmed: 11259324
  • Huskey SW, Doss GA, Miller RR, Schoen WR, Chiu SH: N-glucuronidation reactions. II. Relative N-glucuronidation reactivity of methylbiphenyl tetrazole, methylbiphenyl triazole, and methylbiphenyl imidazole in rat, monkey, and human hepatic microsomes. Drug Metab Dispos. 1994 Jul-Aug;22(4):651-8. Pubmed: 7956743
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Quintus J, Kovar KA, Link P, Hamacher H: Urinary excretion of arbutin metabolites after oral administration of bearberry leaf extracts. Planta Med. 2005 Feb;71(2):147-52. Pubmed: 15729623
  • 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:Simon, Ethan S.; Grabowski, Sven; Whitesides, George M. Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose. Journal
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17200
HMDB IDHMDB00935
Pubchem Compound ID17473
Kegg IDC00167
ChemSpider ID16522
WikipediaUridine diphosphate glucuronic acid
BioCyc IDUDP-GLUCURONATE
EcoCyc IDUDP-GLUCURONATE
Ligand ExpoUGA

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 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 hydroxymethyl-, formyl- and related transferase activity
Specific function:
Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto- arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4- amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido- arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnA
Uniprot ID:
P77398
Molecular weight:
74288
Reactions
UDP-alpha-D-glucuronate + NAD(+) = UDP-beta-L-threo-pentapyranos-4-ulose + CO(2) + NADH.
10-formyltetrahydrofolate + UDP-4-amino-4-deoxy-beta-L-arabinose = 5,6,7,8-tetrahydrofolate + UDP-4-deoxy-4-formamido-beta-L-arabinose.

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