Uridine diphosphate glucuronic acid (PAMDB000646)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000646
Identification
Name: Uridine diphosphate glucuronic acid
Description:Uridine 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 580.2853
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Glucuronic acid or derivatives
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Monoalkyl phosphate
  • Pyrimidone
  • Beta-hydroxy acid
  • Alkyl phosphate
  • Pyrimidine
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility18.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.32 m3·mol-1ChemAxon
Polarizability45.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Uridine diphosphate glucuronic acid > D-Glucuronate 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Water + 2 NAD + UDP-Glucose <>3 Hydrogen ion +2 NADH + Uridine diphosphate glucuronic acid + UDP-Glucuronic acid
NAD + Uridine diphosphate glucuronic acid > Carbon dioxide + NADH + UDP-4-Keto-pyranose
UDP-Glucose + Water + 2 NAD <> Uridine diphosphate glucuronic acid +2 NADH +2 Hydrogen ion
Uridine diphosphate glucuronic acid + NAD <> UDP-4-Keto-pyranose + Carbon dioxide + NADH + Hydrogen ion
GDP-L-Fucose + UDP-Glucose + Uridine diphosphate glucuronic acid + Uridine diphosphategalactose colanic acid
Pathways:
  • Amino sugar and nucleotide sugar metabolism pae00520
  • Ascorbate and aldarate metabolism pae00053
  • Pentose and glucuronate interconversions pae00040
  • Starch and sucrose metabolism pae00500
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
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

Protein Details
• Bifunctional polymyxin resistance protein ArnA
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
Locus Tag:
PA3554
Molecular weight:
74.4 kDa
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