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Chemical Compound Review

Orotic acid     2,6-dioxo-3H-pyrimidine-4- carboxylic acid

Synonyms: Orotonin, Oroturic, Lactinium, Orotonsan, Orotsaure, ...
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Disease relevance of Orotic acid


Psychiatry related information on Orotic acid


High impact information on Orotic acid


Chemical compound and disease context of Orotic acid

  • Expression of human UMP synthase cDNAs containing these mutations in pyrimidine auxotrophic Escherichia coli and in recombinant baculovirus-infected Sf21 cells demonstrates impaired activity presumably associated with the urinary orotic acid substrate accumulations observed in vivo [13].
  • The depletion of UTP pools could be reversed within 10 min by the addition of uridine; orotate or uracil were completely ineffective in these hepatoma cells [14].
  • Recombinant adenoviruses deleted in E1 and containing a human OTC cDNA expressed little functional OTC enzyme in vivo and had no observable impact on the underlying metabolic abnormalities of the OTC-deficient mouse (i.e. elevated urinary orotate and serum glutamine) [15].
  • Dihydroorotate dehydrogenase (DHOD) from Escherichia coli is a monomeric membrane-associated flavoprotein that catalyzes the oxidation of dihydroorotate to orotate [16].
  • Orotate phosphoribosyltransferase gene polymorphism predicts toxicity in patients treated with bolus 5-fluorouracil regimen [17].

Biological context of Orotic acid


Anatomical context of Orotic acid


Associations of Orotic acid with other chemical compounds


Gene context of Orotic acid


Analytical, diagnostic and therapeutic context of Orotic acid


  1. Selection of catalytic antibodies for a biosynthetic reaction from a combinatorial cDNA library by complementation of an auxotrophic Escherichia coli: antibodies for orotate decarboxylation. Smiley, J.A., Benkovic, S.J. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  2. Promotion by orotic acid of liver carcinogenesis in rats initiated by 1,2-dimethylhydrazine. Laurier, C., Tatematsu, M., Rao, P.M., Rajalakshmi, S., Sarma, D.S. Cancer Res. (1984) [Pubmed]
  3. N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy. Elpeleg, O., Shaag, A., Ben-Shalom, E., Schmid, T., Bachmann, C. Ann. Neurol. (2002) [Pubmed]
  4. Effects of 6-azauridine on nucleotides, orotic acid, and orotidine in L5178Y mouse lymphoma cells in vitro. Janeway, C.M., Cha, S. Cancer Res. (1977) [Pubmed]
  5. Postnatal orotate treatment: effects on learning and memory in adult rats. Rüthrich, H.L., Wetzel, W., Matthies, H. Psychopharmacology (Berl.) (1979) [Pubmed]
  6. Orotic acid excretion during starvation and refeeding in normal men. Jeevanandam, M., Shoemaker, J.D., Horowitz, G.D., Lowry, S.F., Brennan, M.F. Metab. Clin. Exp. (1985) [Pubmed]
  7. Hereditary orotic aciduria heterozygotes accompanied with neurological symptoms. Imaeda, M., Sumi, S., Imaeda, H., Suchi, M., Kidouchi, K., Togari, H., Wada, Y. Tohoku J. Exp. Med. (1998) [Pubmed]
  8. Chemical evolution from hydrogen cyanide: photochemical decarboxylation of orotic acid and orotate derivatives. Ferris, J.P., Joshi, P.C. Science (1978) [Pubmed]
  9. Pyrimidine salvage in Giardia lamblia. Aldritt, S.M., Tien, P., Wang, C.C. J. Exp. Med. (1985) [Pubmed]
  10. Orotic aciduria in two unrelated patients with inherited deficiencies of purine nucleoside phosphorylase. Cohen, A., Staal, G.E., Ammann, A.J., Martin, D.W. J. Clin. Invest. (1977) [Pubmed]
  11. Protein and RNA synthesis in pituitary tumors from F344 rats given implants of estrogen. Kaplan, S.E., De Nicola, A.F. J. Natl. Cancer Inst. (1976) [Pubmed]
  12. Hypoxanthine-guanine phosphoribosyltransferase. Characterization of a mutant in a patient with gout. Fox, I.H., Dwosh, I.L., Marchant, P.J., Lacroix, S., Moore, M.R., Omura, S., Wyhofsky, V. J. Clin. Invest. (1975) [Pubmed]
  13. Molecular cloning of the human UMP synthase gene and characterization of point mutations in two hereditary orotic aciduria families. Suchi, M., Mizuno, H., Kawai, Y., Tsuboi, T., Sumi, S., Okajima, K., Hodgson, M.E., Ogawa, H., Wada, Y. Am. J. Hum. Genet. (1997) [Pubmed]
  14. Uridine triphosphate deficiency, growth inhibition, and death in ascites hepatoma cells induced by a combination of pyrimidine biosynthesis inhibition with uridylate trapping. Keppler, D.O. Cancer Res. (1977) [Pubmed]
  15. Prolonged metabolic correction in adult ornithine transcarbamylase-deficient mice with adenoviral vectors. Ye, X., Robinson, M.B., Batshaw, M.L., Furth, E.E., Smith, I., Wilson, J.M. J. Biol. Chem. (1996) [Pubmed]
  16. Multiple states of the Tyr318Leu mutant of dihydroorotate dehydrogenase revealed by single-molecule kinetics. Shi, J., Palfey, B.A., Dertouzos, J., Jensen, K.F., Gafni, A., Steel, D. J. Am. Chem. Soc. (2004) [Pubmed]
  17. Orotate phosphoribosyltransferase gene polymorphism predicts toxicity in patients treated with bolus 5-fluorouracil regimen. Ichikawa, W., Takahashi, T., Suto, K., Sasaki, Y., Hirayama, R. Clin. Cancer Res. (2006) [Pubmed]
  18. Activation of transcription by metabolic intermediates of the pyrimidine biosynthetic pathway. Flynn, P.J., Reece, R.J. Mol. Cell. Biol. (1999) [Pubmed]
  19. Occurrence of cell death (apoptosis) in preneoplastic and neoplastic liver cells. A sequential study. Columbano, A., Ledda-Columbano, G.M., Rao, P.M., Rajalakshmi, S., Sarma, D.S. Am. J. Pathol. (1984) [Pubmed]
  20. Characterization of the rodent genes for arylacetamide deacetylase, a putative microsomal lipase, and evidence for transcriptional regulation. Trickett, J.I., Patel, D.D., Knight, B.L., Saggerson, E.D., Gibbons, G.F., Pease, R.J. J. Biol. Chem. (2001) [Pubmed]
  21. The chemistry of the reaction determines the invariant amino acids during the evolution and divergence of orotidine 5'-monophosphate decarboxylase. Traut, T.W., Temple, B.R. J. Biol. Chem. (2000) [Pubmed]
  22. Orotic acid, nucleotide-pool imbalance, and liver-tumor promotion: a possible mechanism for the mitoinhibitory effects of orotic acid in isolated rat hepatocytes. Manjeshwar, S., Sheikh, A., Pichiri-Coni, G., Coni, P., Rao, P.M., Rajalakshmi, S., Pediaditakis, P., Michalopoulos, G., Sarma, D.S. Cancer Res. (1992) [Pubmed]
  23. Potentiation of 5-fluoro-2'-deoxyuridine antineoplastic activity by the uridine phosphorylase inhibitors benzylacyclouridine and benzyloxybenzylacyclouridine. Chu, M.Y., Naguib, F.N., Iltzsch, M.H., el Kouni, M.H., Chu, S.H., Cha, S., Calabresi, P. Cancer Res. (1984) [Pubmed]
  24. Nitrogen-stimulated orotic acid synthesis and nucleotide imbalance. Visek, W.J. Cancer Res. (1992) [Pubmed]
  25. Orotic acid enhancement of preneoplastic and neoplastic lesions induced in the pancreas and liver of hamsters by N-nitroso(2-hydroxypropyl) (2-oxopropyl)amine. Kokkinakis, D.M., Albores-Saavedra, J. Cancer Res. (1994) [Pubmed]
  26. Transit and sorting of apolipoprotein B within the endoplasmic reticulum and Golgi compartments of isolated hepatocytes from normal and orotic acid-fed rats. Cartwright, I.J., Hebbachi, A.M., Higgins, J.A. J. Biol. Chem. (1993) [Pubmed]
  27. Pyrimidine metabolism in Tritrichomonas foetus. Wang, C.C., Verham, R., Tzeng, S.F., Aldritt, S., Cheng, H.W. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  28. Isolation and partial characterization of a 5'-nucleotidase specific for orotidine-5'-monophosphate. El Kouni, M.H., Cha, S. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  29. Superoxide production and electron transport in mitochondrial oxidation of dihydroorotic acid. Forman, J.H., Kennedy, J. J. Biol. Chem. (1975) [Pubmed]
  30. Purification, size, and properties of the complex of orotate phosphoribosyltransferase: orotidylate decarboxylase from mouse Ehrlich ascites carcinoma. Kavipurapu, P.R., Jones, M.E. J. Biol. Chem. (1976) [Pubmed]
  31. Both gene expression for orotate phosphoribosyltransferase and its ratio to dihydropyrimidine dehydrogenase influence outcome following fluoropyrimidine-based chemotherapy for metastatic colorectal cancer. Ichikawa, W., Uetake, H., Shirota, Y., Yamada, H., Takahashi, T., Nihei, Z., Sugihara, K., Sasaki, Y., Hirayama, R. Br. J. Cancer (2003) [Pubmed]
  32. Isolation and confirmation of function of the Coccidioides immitis URA5 (orotate phosphoribosyl transferase) gene. Yu, J.J., Zheng, L., Thomas, P.W., Szaniszlo, P.J., Cole, G.T. Gene (1999) [Pubmed]
  33. Utilization of orotate as a pyrimidine source by Salmonella typhimurium and Escherichia coli requires the dicarboxylate transport protein encoded by dctA. Baker, K.E., Ditullio, K.P., Neuhard, J., Kelln, R.A. J. Bacteriol. (1996) [Pubmed]
  34. Sequence analysis of the DdPYR5-6 gene coding for UMP synthase in Dictyostelium discoideum and comparison with orotate phosphoribosyl transferases and OMP decarboxylases. Jacquet, M., Guilbaud, R., Garreau, H. Mol. Gen. Genet. (1988) [Pubmed]
  35. Cloning and sequencing of URA10, a second gene encoding orotate phosphoribosyl transferase in Saccharomyces cerevisiae. de Montigny, J., Kern, L., Hubert, J.C., Lacroute, F. Curr. Genet. (1990) [Pubmed]
  36. Rat liver and small intestine produce proapolipoprotein A-I which is slowly processed to apolipoprotein A-I in the circulation. Sliwkowski, M.B., Windmueller, H.G. J. Biol. Chem. (1984) [Pubmed]
  37. Studies on a pyrimidine phosphoribosyltransferase from murine leukemia P1534J. Partial purification, substrate specificity, and evidence for its existence as a bifunctional complex with orotidine 5-phosphate decarboxylase. Reyes, P., Guganig, M.E. J. Biol. Chem. (1975) [Pubmed]
  38. Helicobacter pylori-selective antibacterials based on inhibition of pyrimidine biosynthesis. Copeland, R.A., Marcinkeviciene, J., Haque, T.S., Kopcho, L.M., Jiang, W., Wang, K., Ecret, L.D., Sizemore, C., Amsler, K.A., Foster, L., Tadesse, S., Combs, A.P., Stern, A.M., Trainor, G.L., Slee, A., Rogers, M.J., Hobbs, F. J. Biol. Chem. (2000) [Pubmed]
  39. Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues. Palfey, B.A., Björnberg, O., Jensen, K.F. J. Med. Chem. (2001) [Pubmed]
  40. Conditions affecting the colorimetry of orotic acid and orotidine in urine. Harris, M.L., Oberholzer, V.G. Clin. Chem. (1980) [Pubmed]
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