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Chemical Compound Review

NSC-165     3,4,5,6-tetrahydroxyoxane-2- carboxylic acid

Synonyms: AGN-PC-0069X1, NSC165, NSC-9248, SureCN2519396, NSC9248, ...
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Disease relevance of glucuronic acid


Psychiatry related information on glucuronic acid

  • There was an exception: even though both rutin and orcinol are detoxified via conjugation with GA, the feeding behavior of possums did not suggest competition for detoxification pathways [6].

High impact information on glucuronic acid


Chemical compound and disease context of glucuronic acid


Biological context of glucuronic acid

  • Capsule size was quantitated physically by measuring cell volume, and chemically by determining the content of a capsular monosaccharide, glucuronate [17].
  • Other bile acids will be esterified with glucuronate and secreted into bile, but undergo little enterohepatic circulation [18].
  • Chemically desulfated SGNL lipid retained binding activity for L- and P-selectin chimeras, while methyl esterification of the glucuronic acid eliminated binding [19].
  • Furthermore, substrate specificity analysis using a soluble chimeric form of GlcAT-D revealed that GlcAT-D transfers a GlcA not only to Galbeta1-4GlcNAcbeta1-3Galbeta1-4Glc-pyridylamine++ + but also to Galbeta1-3GlcNAcbeta1-3Galbeta1-4Glc-pyridylamine++ + [20].
  • Hyaluronan (HA), a functionally essential glycosaminoglycan in vertebrate tissues and a putative virulence factor in certain pathogenic bacteria, is an extended linear polymer composed of alternating units of glucuronic acid (GlcUA) and N-acetylglucosamine (GlcNAc) [21].

Anatomical context of glucuronic acid


Associations of glucuronic acid with other chemical compounds


Gene context of glucuronic acid

  • The UDP-glucuronosyltransferase, UGT1A1, is the critical enzyme responsible for detoxification of the potentially neurotoxic bilirubin by conjugating it with glucuronic acid [32].
  • Defects in glucuronate biosynthesis disrupt Wingless signaling in Drosophila [33].
  • We found that in the case of MRP2, ATP-dependent vesicular bile acid transport was increased by E217betaG, and the results indicated an allosteric cross-stimulation, probably a co-transport of bile acids and glucuronate conjugates through this protein [34].
  • In contrast, incubations with recombinant EXT2 resulted in the addition of a single glucuronic acid but no further polymerization [35].
  • Many lipophilic compounds conjugated with glutathione, glucuronate, or sulfate are substrates for export pumps of the MRP family [36].

Analytical, diagnostic and therapeutic context of glucuronic acid


  1. Bilirubin secretion and conjujation in the Crigler-Najjar syndrome type II. Gordon, E.R., Shaffer, E.A., Sass-Kortsak, A. Gastroenterology (1976) [Pubmed]
  2. Glycoside conjugation in microsomes from hepatic and renal carcinoma of man. Matern, H., Fiebig, H.H., Matern, S. Hepatology (1987) [Pubmed]
  3. Novel O-methylated terminal glucuronic acid characterizes the polar glycopeptidolipids of Mycobacterium habana strain TMC 5135. Khoo, K.H., Chatterjee, D., Dell, A., Morris, H.R., Brennan, P.J., Draper, P. J. Biol. Chem. (1996) [Pubmed]
  4. First molecular characterization of a uridine diphosphate galacturonate 4-epimerase: an enzyme required for capsular biosynthesis in Streptococcus pneumoniae type 1. Muñoz, R., López, R., de Frutos, M., García, E. Mol. Microbiol. (1999) [Pubmed]
  5. Autopsy-proven amyotrophic lateral sclerosis, Waldenström's macroglobulinemia, and antibodies to sulfated glucuronic acid paragloboside. Rowland, L.P., Sherman, W.L., Hays, A.P., Lange, D.J., Latov, N., Trojaborg, W., Younger, D.S. Neurology (1995) [Pubmed]
  6. Conflicting demands on detoxification pathways influence how common brushtail possums choose their diets. Marsh, K.J., Wallis, I.R., McLean, S., Sorensen, J.S., Foley, W.J. Ecology (2006) [Pubmed]
  7. Spontaneous glycosylation of glycosaminoglycan substrates by adherent fibroblasts. Turley, E.A., Roth, S. Cell (1979) [Pubmed]
  8. A nutrient-permeable channel on the intraerythrocytic malaria parasite. Desai, S.A., Krogstad, D.J., McCleskey, E.W. Nature (1993) [Pubmed]
  9. Odorant signal termination by olfactory UDP glucuronosyl transferase. Lazard, D., Zupko, K., Poria, Y., Nef, P., Lazarovits, J., Horn, S., Khen, M., Lancet, D. Nature (1991) [Pubmed]
  10. Two distinct mechanisms for bilirubin glucuronide transport by rat bile canalicular membrane vesicles. Demonstration of defective ATP-dependent transport in rats (TR-) with inherited conjugated hyperbilirubinemia. Nishida, T., Gatmaitan, Z., Roy-Chowdhry, J., Arias, I.M. J. Clin. Invest. (1992) [Pubmed]
  11. Sialic acid storage diseases. A multiple lysosomal transport defect for acidic monosaccharides. Mancini, G.M., Beerens, C.E., Aula, P.P., Verheijen, F.W. J. Clin. Invest. (1991) [Pubmed]
  12. Immunogenic properties of octasaccharide-protein conjugates derived from Klebsiella serotype 11 capsular polysaccharide. Zigterman, J.W., van Dam, J.E., Snippe, H., Rotteveel, F.T., Jansze, M., Willers, J.M., Kamerling, J.P., Vliegenthart, J.F. Infect. Immun. (1985) [Pubmed]
  13. Escherichia coli F-18 and E. coli K-12 eda mutants do not colonize the streptomycin-treated mouse large intestine. Sweeney, N.J., Laux, D.C., Cohen, P.S. Infect. Immun. (1996) [Pubmed]
  14. Defective glucuronic acid transport from lysosomes of infantile free sialic acid storage disease fibroblasts. Blom, H.J., Andersson, H.C., Seppala, R., Tietze, F., Gahl, W.A. Biochem. J. (1990) [Pubmed]
  15. Evidence for an electrogenic 3-deoxy-2-oxo-D-gluconate--proton co-transport driven by the protonmotive force in Escherichia coli K12. Lagarde, A. Biochem. J. (1977) [Pubmed]
  16. Estrogen regulation of the glucuronidation enzyme UGT2B15 in estrogen receptor-positive breast cancer cells. Harrington, W.R., Sengupta, S., Katzenellenbogen, B.S. Endocrinology (2006) [Pubmed]
  17. Virulence of Cryptococcus neoformans. Regulation of capsule synthesis by carbon dioxide. Granger, D.L., Perfect, J.R., Durack, D.T. J. Clin. Invest. (1985) [Pubmed]
  18. Defective bile acid amidation: predicted features of a new inborn error of metabolism. Hofmann, A.F., Strandvik, B. Lancet (1988) [Pubmed]
  19. The HNK-1 reactive sulfoglucuronyl glycolipids are ligands for L-selectin and P-selectin but not E-selectin. Needham, L.K., Schnaar, R.L. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  20. Cloning and expression of a novel galactoside beta1, 3-glucuronyltransferase involved in the biosynthesis of HNK-1 epitope. Shimoda, Y., Tajima, Y., Nagase, T., Harii, K., Osumi, N., Sanai, Y. J. Biol. Chem. (1999) [Pubmed]
  21. Biosynthesis of hyaluronan: direction of chain elongation. Bodevin-Authelet, S., Kusche-Gullberg, M., Pummill, P.E., DeAngelis, P.L., Lindahl, U. J. Biol. Chem. (2005) [Pubmed]
  22. Glycoconjugates as noninvasive probes of intrahepatic metabolism: pathways of glucose entry into compartmentalized hepatic UDP-glucose pools during glycogen accumulation. Hellerstein, M.K., Greenblatt, D.J., Munro, H.N. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  23. Human breast cell-mediated mutagenesis of mammalian cells by polycyclic aromatic hydrocarbons. Gould, M.N., Cathers, L.E., Moore, C.J. Cancer Res. (1982) [Pubmed]
  24. Interspecies comparison of polycyclic aromatic hydrocarbon metabolism in human and rat mammary epithelial cells. Moore, C.J., Tricomi, W.A., Gould, M.N. Cancer Res. (1986) [Pubmed]
  25. Benzo(a)pyrene disposition and metabolism in rats following intratracheal instillation. Weyand, E.H., Bevan, D.R. Cancer Res. (1986) [Pubmed]
  26. A novel, highly modified, bacteriophage DNA in which thymine is partly replaced by a phosphoglucuronate moiety covalently bound to 5-(4',5'-dihydroxypentyl)uracil. Ehrlich, M., Ehrlich, K.C. J. Biol. Chem. (1981) [Pubmed]
  27. Engineering increased vitamin C levels in plants by overexpression of a D-galacturonic acid reductase. Agius, F., González-Lamothe, R., Caballero, J.L., Muñoz-Blanco, J., Botella, M.A., Valpuesta, V. Nat. Biotechnol. (2003) [Pubmed]
  28. Evidence for C-H cleavage by an iron-superoxide complex in the glycol cleavage reaction catalyzed by myo-inositol oxygenase. Xing, G., Diao, Y., Hoffart, L.M., Barr, E.W., Prabhu, K.S., Arner, R.J., Reddy, C.C., Krebs, C., Bollinger, J.M. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  29. The human multidrug resistance protein 2 gene: functional characterization of the 5'-flanking region and expression in hepatic cells. Tanaka, T., Uchiumi, T., Hinoshita, E., Inokuchi, A., Toh, S., Wada, M., Takano, H., Kohno, K., Kuwano, M. Hepatology (1999) [Pubmed]
  30. Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Zeng, H., Chen, Z.S., Belinsky, M.G., Rea, P.A., Kruh, G.D. Cancer Res. (2001) [Pubmed]
  31. Isolation and characterization of proteoglycans from human nonepithelial tumors. Sobue, M., Takeuchi, J., Yoshida, K., Akao, S., Fukatsu, T., Nagasaka, T., Nakashima, N. Cancer Res. (1987) [Pubmed]
  32. The phenobarbital response enhancer module in the human bilirubin UDP-glucuronosyltransferase UGT1A1 gene and regulation by the nuclear receptor CAR. Sugatani, J., Kojima, H., Ueda, A., Kakizaki, S., Yoshinari, K., Gong, Q.H., Owens, I.S., Negishi, M., Sueyoshi, T. Hepatology (2001) [Pubmed]
  33. Defects in glucuronate biosynthesis disrupt Wingless signaling in Drosophila. Haerry, T.E., Heslip, T.R., Marsh, J.L., O'Connor, M.B. Development (1997) [Pubmed]
  34. Differential modulation of the human liver conjugate transporters MRP2 and MRP3 by bile acids and organic anions. Bodo, A., Bakos, E., Szeri, F., Varadi, A., Sarkadi, B. J. Biol. Chem. (2003) [Pubmed]
  35. In vitro polymerization of heparan sulfate backbone by the EXT proteins. Busse, M., Kusche-Gullberg, M. J. Biol. Chem. (2003) [Pubmed]
  36. Export pumps for glutathione S-conjugates. Keppler, D. Free Radic. Biol. Med. (1999) [Pubmed]
  37. Lignans in man and in animal species. Setchell, K.D., Lawson, A.M., Mitchell, F.L., Adlercreutz, H., Kirk, D.N., Axelson, M. Nature (1980) [Pubmed]
  38. Major urinary metabolites in hamsters and rats treated with N-nitroso(2-hydroxypropyl)(2-oxopropyl)amine. Kokkinakis, D.M., Hollenberg, P.F., Scarpelli, D.G. Cancer Res. (1985) [Pubmed]
  39. Formation of glucuronic acid conjugates of 7,12-dimethylbenz(a)anthracene phenols in 7,12-dimethylbenz(a)anthracene-treated hamster embryo cell cultures. Baird, W.M., Chemerys, R., Chern, C.J., Diamond, L. Cancer Res. (1978) [Pubmed]
  40. The discovery of a lipid-linked glucuronide and its synthesis by chicken liver. Cummings, R.D., Roth, S. J. Biol. Chem. (1982) [Pubmed]
  41. Molecular cloning and characterization of a novel chondroitin sulfate glucuronyltransferase that transfers glucuronic acid to N-acetylgalactosamine. Gotoh, M., Yada, T., Sato, T., Akashima, T., Iwasaki, H., Mochizuki, H., Inaba, N., Togayachi, A., Kudo, T., Watanabe, H., Kimata, K., Narimatsu, H. J. Biol. Chem. (2002) [Pubmed]
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