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Chemical Compound Review

Homogentisic acid     2-(2,5- dihydroxyphenyl)ethanoic acid

Synonyms: Alcapton, homogentisate, Melanic acid, H0751_ALDRICH, SureCN155333, ...
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Disease relevance of Homogentisic acid


High impact information on Homogentisic acid


Chemical compound and disease context of Homogentisic acid


Biological context of Homogentisic acid


Anatomical context of Homogentisic acid


Associations of Homogentisic acid with other chemical compounds


Gene context of Homogentisic acid


Analytical, diagnostic and therapeutic context of Homogentisic acid


  1. In vitro inhibition of chick embryo lysyl hydroxylase by homogentisic acid. A proposed connective tissue defect in alkaptonuria. Murray, J.C., Lindberg, K.A., Pinnell, S.R. J. Clin. Invest. (1977) [Pubmed]
  2. Oral loading of homogentisic acid in controls and in obligate heterozygotes for hereditary tyrosinemia type I. Laberge, C., Lescault, A., Grenier, A., Morrisette, J., Gagné, R., Gadbois, P., Halket, J. Am. J. Hum. Genet. (1990) [Pubmed]
  3. Hepatocyte injury in tyrosinemia type 1 is induced by fumarylacetoacetate and is inhibited by caspase inhibitors. Kubo, S., Sun, M., Miyahara, M., Umeyama, K., Urakami, K., Yamamoto, T., Jakobs, C., Matsuda, I., Endo, F. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  4. Minocycline-induced hyperpigmentation masquerading as alkaptonuria in individuals with joint pain. Suwannarat, P., Phornphutkul, C., Bernardini, I., Turner, M., Gahl, W.A. Arthritis Rheum. (2004) [Pubmed]
  5. Complementation of the Arabidopsis pds1 mutation with the gene encoding p-hydroxyphenylpyruvate dioxygenase. Norris, S.R., Shen, X., DellaPenna, D. Plant Physiol. (1998) [Pubmed]
  6. Genetic dissection of carotenoid synthesis in arabidopsis defines plastoquinone as an essential component of phytoene desaturation. Norris, S.R., Barrette, T.R., DellaPenna, D. Plant Cell (1995) [Pubmed]
  7. In vivo suppressor mutations correct a murine model of hereditary tyrosinemia type I. Manning, K., Al-Dhalimy, M., Finegold, M., Grompe, M. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  8. Isolation and functional analysis of homogentisate phytyltransferase from Synechocystis sp. PCC 6803 and Arabidopsis. Collakova, E., DellaPenna, D. Plant Physiol. (2001) [Pubmed]
  9. The Sinorhizobium meliloti nutrient-deprivation-induced tyrosine degradation gene hmgA is controlled by a novel member of the arsR family of regulatory genes. Milcamps, A., Struffi, P., de Bruijn, F.J. Appl. Environ. Microbiol. (2001) [Pubmed]
  10. A Streptomyces avermitilis gene encoding a 4-hydroxyphenylpyruvic acid dioxygenase-like protein that directs the production of homogentisic acid and an ochronotic pigment in Escherichia coli. Denoya, C.D., Skinner, D.D., Morgenstern, M.R. J. Bacteriol. (1994) [Pubmed]
  11. Application of the Synechococcus nirA promoter to establish an inducible expression system for engineering the Synechocystis tocopherol pathway. Qi, Q., Hao, M., Ng, W.O., Slater, S.C., Baszis, S.R., Weiss, J.D., Valentin, H.E. Appl. Environ. Microbiol. (2005) [Pubmed]
  12. Use of nitisinone in patients with alkaptonuria. Suwannarat, P., O'Brien, K., Perry, M.B., Sebring, N., Bernardini, I., Kaiser-Kupfer, M.I., Rubin, B.I., Tsilou, E., Gerber, L.H., Gahl, W.A. Metab. Clin. Exp. (2005) [Pubmed]
  13. A two-component hydroxylase involved in the assimilation of 3-hydroxyphenyl acetate in Pseudomonas putida. Arias-Barrau, E., Sandoval, A., Naharro, G., Olivera, E.R., Luengo, J.M. J. Biol. Chem. (2005) [Pubmed]
  14. Isolation and characterization of homogentisate phytyltransferase genes from Synechocystis sp. PCC 6803 and Arabidopsis. Savidge, B., Weiss, J.D., Wong, Y.H., Lassner, M.W., Mitsky, T.A., Shewmaker, C.K., Post-Beittenmiller, D., Valentin, H.E. Plant Physiol. (2002) [Pubmed]
  15. Renal proximal tubular cells acquire resistance to cell death stimuli in mice with hereditary tyrosinemia type 1. Luijerink, M.C., van Beurden, E.A., Malingré, H.E., Jacobs, S.M., Grompe, M., Klomp, L.W., Berger, R., van den Berg, I.E. Kidney Int. (2004) [Pubmed]
  16. Oxidative DNA damage induced by homogentisic acid, a tyrosine metabolite. Hiraku, Y., Yamasaki, M., Kawanishi, S. FEBS Lett. (1998) [Pubmed]
  17. In vivo genetic selection of renal proximal tubules. Held, P.K., Al-Dhalimy, M., Willenbring, H., Akkari, Y., Jiang, S., Torimaru, Y., Olson, S., Fleming, W.H., Finegold, M., Grompe, M. Mol. Ther. (2006) [Pubmed]
  18. Conversion of 4-hydroxyphenylpyruvic acid into homogentisic acid at the thylakoid membrane of Lemna gibba. Löffelhardt, W., Kindl, H. FEBS Lett. (1979) [Pubmed]
  19. Chondrocyte growth inhibition induced by homogentisic acid and its partial prevention with ascorbic acid. Angeles, A.P., Badger, R., Gruber, H.E., Seegmiller, J.E. J. Rheumatol. (1989) [Pubmed]
  20. Analysis of homogentisic acid in body fluids by high-performance liquid chromatography. Akesson, B., Forslind, K., Wollheim, F. J. Chromatogr. (1987) [Pubmed]
  21. Chronic liver disease in murine hereditary tyrosinemia type 1 induces resistance to cell death. Vogel, A., van Den Berg, I.E., Al-Dhalimy, M., Groopman, J., Ou, C.N., Ryabinina, O., Iordanov, M.S., Finegold, M., Grompe, M. Hepatology (2004) [Pubmed]
  22. Homogentisic acid autoxidation and oxygen radical generation: implications for the etiology of alkaptonuric arthritis. Martin, J.P., Batkoff, B. Free Radic. Biol. Med. (1987) [Pubmed]
  23. Cryptococcus neoformans Can Utilize the Bacterial Melanin Precursor Homogentisic Acid for Fungal Melanogenesis. Frases, S., Salazar, A., Dadachova, E., Casadevall, A. Appl. Environ. Microbiol. (2007) [Pubmed]
  24. Styrene metabolism in Exophiala jeanselmei and involvement of a cytochrome P-450-dependent styrene monooxygenase. Cox, H.H., Faber, B.W., Van Heiningen, W.N., Radhoe, H., Doddema, H.J., Harder, W. Appl. Environ. Microbiol. (1996) [Pubmed]
  25. Kidneys of mice with hereditary tyrosinemia type I are extremely sensitive to cytotoxicity. Jacobs, S.M., van Beurden, D.H., Klomp, L.W., Berger, R., van den Berg, I.E. Pediatr. Res. (2006) [Pubmed]
  26. The protein encoded by the Shewanella colwelliana melA gene is a p-hydroxyphenylpyruvate dioxygenase. Ruzafa, C., Solano, F., Sanchez-Amat, A. FEMS Microbiol. Lett. (1994) [Pubmed]
  27. The Lly protein protects Legionella pneumophila from light but does not directly influence its intracellular survival in Hartmannella vermiformis. Steinert, M., Engelhard, H., Flügel, M., Wintermeyer, E., Hacker, J. Appl. Environ. Microbiol. (1995) [Pubmed]
  28. Determination of homogentisic acid in serum and urine by liquid chromatography with amperometric detection. Zoutendam, P.H., Bruntlett, C.S., Kissinger, P.T. Anal. Chem. (1976) [Pubmed]
  29. Homogentisic acid determined in biological fluids by HPLC. Bory, C., Boulieu, R., Chantin, C., Mathieu, M. Clin. Chem. (1989) [Pubmed]
  30. Exacerbation of the ochronosis of alkaptonuria due to renal insufficiency and improvement after renal transplantation. Introne, W.J., Phornphutkul, C., Bernardini, I., McLaughlin, K., Fitzpatrick, D., Gahl, W.A. Mol. Genet. Metab. (2002) [Pubmed]
  31. Alkaptonuria diagnosed by flexible bronchoscopy. Parambil, J.G., Daniels, C.E., Zehr, K.J., Utz, J.P. Chest (2005) [Pubmed]
  32. Knee arthropathy in ochronosis: diagnosis by arthroscopy with ultrastructural features. Lurie, D.P., Musil, G. J. Rheumatol. (1984) [Pubmed]
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