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Chemical Compound Review

PHENYLACETIC ACID     potassium 2-phenylethanoate

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Disease relevance of 7188-16-1


Psychiatry related information on 7188-16-1


High impact information on 7188-16-1

  • Treatment of a patient deficient in carbamyl phosphate synthetase with benzoate or phenylacetic acid resulted in an increase in urinary nitrogen, which could be accounted for by the respective amino acid acylation product, hippurate or phenylacetylgultamine [11].
  • Diclofenac sodium, a phenylacetic acid-derived nonsteroidal anti-inflammatory drug (NSAID) recently released in the United States, was associated with the development of significant hepatitis in seven patients, with one associated death [12].
  • Authentic phenylacetic acid inhibited iNOS expression in a dose-dependent manner [2].
  • Although a recent report indicates that MHC expression influences the ratio of volatile compounds such as phenylacetic acid, so far no other means than studying the behavior of mice or rats has been available to assess odor types [13].
  • This catabolic pathway appears to be organized in three contiguous operons that contain the following functional units: (i) a transport system, (ii) a phenylacetic acid activating enzyme, (iii) a ring-hydroxylation complex, (iv) a ring-opening protein, (v) a beta-oxidation-like system, and (vi) two regulatory genes [3].

Chemical compound and disease context of 7188-16-1


Biological context of 7188-16-1


Anatomical context of 7188-16-1


Associations of 7188-16-1 with other chemical compounds


Gene context of 7188-16-1

  • Chronic kidney diseases are accompanied by the accumulation of substances like asymmetric dimethylarginine, phenylacetic acid, homocysteine, and advanced glycation end products, known to either inhibit endothelial nitric oxide synthase (eNOS) or uncouple it, consequently limiting the amount of available nitric oxide (NO) [31].
  • The expression of the divergently transcribed paaZ and paaABCDEFGHIJK catabolic operons, which are responsible for phenylacetic acid (PA) degradation in Escherichia coli, is driven by the Pz and Pa promoters, respectively [32].
  • Here we report that an engineered microbial cytochrome P450 BM-3 (CYP102A subfamily) efficiently catalyzes the alpha-hydroxylation of phenylacetic acid esters [33].
  • Effect of heterologous expression of phaG [(R)-3-hydroxyacyl-ACP-CoA transferase] on polyhydroxyalkanoate accumulation from the aromatic hydrocarbon phenylacetic acid in Pseudomonas species [34].
  • Purification and biochemical characterization of phenylacetyl-CoA ligase from Pseudomonas putida. A specific enzyme for the catabolism of phenylacetic acid [35].

Analytical, diagnostic and therapeutic context of 7188-16-1


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  2. Increased plasma phenylacetic acid in patients with end-stage renal failure inhibits iNOS expression. Jankowski, J., van der Giet, M., Jankowski, V., Schmidt, S., Hemeier, M., Mahn, B., Giebing, G., Tolle, M., Luftmann, H., Schluter, H., Zidek, W., Tepel, M. J. Clin. Invest. (2003) [Pubmed]
  3. Molecular characterization of the phenylacetic acid catabolic pathway in Pseudomonas putida U: the phenylacetyl-CoA catabolon. Olivera, E.R., Miñambres, B., García, B., Muñiz, C., Moreno, M.A., Ferrández, A., Díaz, E., García, J.L., Luengo, J.M. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  4. Diclofenac sodium: a review of its pharmacological properties and therapeutic use in rheumatic diseases and pain of varying origin. Brogden, R.N., Heel, R.C., Pakes, G.E., Speight, T.M., Avery, G.S. Drugs (1980) [Pubmed]
  5. Differentiation of Bacteroides fragilis species by gas chromatographic detection of phenylacetic acid. van Assche, P.F. J. Clin. Microbiol. (1978) [Pubmed]
  6. Phenylacetic acid as an indicator in bipolar affective disorders. Sabelli, H., Fawcett, J., Gusovsky, F., Edwards, J., Jeffriess, H., Javaid, J. Journal of clinical psychopharmacology. (1983) [Pubmed]
  7. Urinary phenylacetic acid in panic disorder with and without depression. Sabelli, H.C., Javaid, J.I., Fawcett, J., Kravitz, H.M., Wynn, P. Acta psychiatrica Scandinavica. (1990) [Pubmed]
  8. Correlations of plasma and urinary phenylacetic acid and phenylethylamine concentrations with eating behavior and mood rating scores in brofaromine-treated women with bulimia nervosa. Davis, B.A., Kennedy, S.H., D'Souza, J., Durden, D.A., Goldbloom, D.S., Boulton, A.A. Journal of psychiatry & neuroscience : JPN. (1994) [Pubmed]
  9. A high-pressure liquid chromatographic method for plasma phenylacetic acid, a putative marker for depressive disorders. Gusovsky, F., Fawcett, J., Javaid, J.I., Jeffriess, H., Sabelli, H. Anal. Biochem. (1985) [Pubmed]
  10. CSF phenylacetic acid and hostility in paranoid schizophrenia. Faull, K.F., King, R.J., Barchas, J.D., Csernansky, J.G. Psychiatry research. (1989) [Pubmed]
  11. Amino acid acylation: a mechanism of nitrogen excretion in inborn errors of urea synthesis. Brusilow, S., Tinker, J., Batshaw, M.L. Science (1980) [Pubmed]
  12. Diclofenac-associated hepatotoxicity. Helfgott, S.M., Sandberg-Cook, J., Zakim, D., Nestler, J. JAMA (1990) [Pubmed]
  13. "Electronic nose" detects major histocompatibility complex-dependent prerenal and postrenal odor components. Montag, S., Frank, M., Ulmer, H., Wernet, D., Göpel, W., Rammensee, H.G. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  14. Characterization of dimethylguanosine, phenylethylamine, and phenylacetic acid as inhibitors of Ca2+ ATPase in end-stage renal failure. Jankowski, J., Luftmann, H., Tepel, M., Leibfritz, D., Zidek, W., Schlüter, H. J. Am. Soc. Nephrol. (1998) [Pubmed]
  15. Clinical studies on the phenylethylamine hypothesis of affective disorder: urine and blood phenylacetic acid and phenylalanine dietary supplements. Sabelli, H.C., Fawcett, J., Gusovsky, F., Javaid, J.I., Wynn, P., Edwards, J., Jeffriess, H., Kravitz, H. The Journal of clinical psychiatry. (1986) [Pubmed]
  16. Genetic characterization of the styrene lower catabolic pathway of Pseudomonas sp. strain Y2. Alonso, S., Bartolomé-Martín, D., del Alamo, M., Díaz, E., García, J.L., Perera, J. Gene (2003) [Pubmed]
  17. Kinetic study of penicillin acylase from Alcaligenes faecalis. Svedas, V., Guranda, D., van Langen, L., van Rantwijk, F., Sheldon, R. FEBS Lett. (1997) [Pubmed]
  18. Anaplerosis via pyruvate carboxylase is required for the fuel-induced rise in the ATP:ADP ratio in rat pancreatic islets. Fransson, U., Rosengren, A.H., Schuit, F.C., Renström, E., Mulder, H. Diabetologia (2006) [Pubmed]
  19. Detection of H2O2 release from vascular endothelial cells. Panus, P.C., Radi, R., Chumley, P.H., Lillard, R.H., Freeman, B.A. Free Radic. Biol. Med. (1993) [Pubmed]
  20. Rapid burst kinetics in the hydrolysis of 4-nitrophenyl acetate by penicillin G acylase from Kluyvera citrophila. Effects of mutation F360V on rate constants for acylation and de-acylation. Roa, A., Goble, M.L., García, J.L., Acebal, C., Virden, R. Biochem. J. (1996) [Pubmed]
  21. Characterization of a second functional gene cluster for the catabolism of phenylacetic acid in Pseudomonas sp. strain Y2. Bartolomé-Martín, D., Martínez-García, E., Mascaraque, V., Rubio, J., Perera, J., Alonso, S. Gene (2004) [Pubmed]
  22. Strategy for cloning large gene assemblages as illustrated using the phenylacetate and polyhydroxyalkanoate gene clusters. García, B., Olivera, E.R., Sandoval, A., Arias-Barrau, E., Arias, S., Naharro, G., Luengo, J.M. Appl. Environ. Microbiol. (2004) [Pubmed]
  23. Differential gene regulation in human versus rodent hepatocytes by peroxisome proliferator-activated receptor (PPAR) alpha. PPAR alpha fails to induce peroxisome proliferation-associated genes in human cells independently of the level of receptor expresson. Lawrence, J.W., Li, Y., Chen, S., DeLuca, J.G., Berger, J.P., Umbenhauer, D.R., Moller, D.E., Zhou, G. J. Biol. Chem. (2001) [Pubmed]
  24. Phenylacetic acid in human body fluids: high correlation between plasma and cerebrospinal fluid concentration values. Sandler, M., Ruthven, C.R., Goodwin, B.L., Lees, A., Stern, G.M. J. Neurol. Neurosurg. Psychiatr. (1982) [Pubmed]
  25. Oxygen dependency of monoamine oxidase activity in the intact lung. Audi, S.H., Dawson, C.A., Ahlf, S.B., Roerig, D.L. Am. J. Physiol. Lung Cell Mol. Physiol. (2001) [Pubmed]
  26. In vitro and in vivo suppression of gluconeogenesis by inhibition of pyruvate carboxylase. Bahl, J.J., Matsuda, M., DeFronzo, R.A., Bressler, R. Biochem. Pharmacol. (1997) [Pubmed]
  27. Carbon regulation and the role in nature of the Escherichia coli penicillin acylase (pac) gene. Merino, E., Balbás, P., Recillas, F., Becerril, B., Valle, F., Bolivar, F. Mol. Microbiol. (1992) [Pubmed]
  28. Ligand-induced conformational change in penicillin acylase. Done, S.H., Brannigan, J.A., Moody, P.C., Hubbard, R.E. J. Mol. Biol. (1998) [Pubmed]
  29. Bromfenac (Duract)-associated hepatic failure requiring liver transplantation. Hunter, E.B., Johnston, P.E., Tanner, G., Pinson, C.W., Awad, J.A. Am. J. Gastroenterol. (1999) [Pubmed]
  30. Decarboxylation of metastable methyl benzoate molecular ions. Dechamps, N., Flammang, R., Gerbaux, P., Nam, P.C., Nguyen, M.T. J. Am. Soc. Mass Spectrom. (2006) [Pubmed]
  31. Chronic NOS inhibition actuates endothelial-mesenchymal transformation. O'riordan, E., Mendelev, N., Patschan, S., Patschan, D., Eskander, J., Cohen-Gould, L., Chander, P., Goligorsky, M.S. Am. J. Physiol. Heart Circ. Physiol. (2007) [Pubmed]
  32. Transcriptional regulation of the divergent paa catabolic operons for phenylacetic acid degradation in Escherichia coli. Ferrández, A., García, J.L., Díaz, E. J. Biol. Chem. (2000) [Pubmed]
  33. Enantioselective alpha-Hydroxylation of 2-Arylacetic Acid Derivatives and Buspirone Catalyzed by Engineered Cytochrome P450 BM-3. Landwehr, M., Hochrein, L., Otey, C.R., Kasrayan, A., Bäckvall, J.E., Arnold, F.H. J. Am. Chem. Soc. (2006) [Pubmed]
  34. Effect of heterologous expression of phaG [(R)-3-hydroxyacyl-ACP-CoA transferase] on polyhydroxyalkanoate accumulation from the aromatic hydrocarbon phenylacetic acid in Pseudomonas species. Tobin, K.M., O'leary, N.D., Dobson, A.D., O'connor, K.E. FEMS Microbiol. Lett. (2007) [Pubmed]
  35. Purification and biochemical characterization of phenylacetyl-CoA ligase from Pseudomonas putida. A specific enzyme for the catabolism of phenylacetic acid. Martínez-Blanco, H., Reglero, A., Rodriguez-Aparicio, L.B., Luengo, J.M. J. Biol. Chem. (1990) [Pubmed]
  36. Assay of urinary phenylacetic acid by high-performance liquid chromatography. Pennings, E.J., Verhagen, J.C., van Kempen, G.M. J. Chromatogr. (1985) [Pubmed]
  37. Aerobic metabolism of phenylacetic acids in Azoarcus evansii. Mohamed, M.e.l.-.S., Ismail, W., Heider, J., Fuchs, G. Arch. Microbiol. (2002) [Pubmed]
  38. Hyperargininemia: clinical course and treatment with sodium benzoate and phenylacetic acid. Mizutani, N., Maehara, M., Hayakawa, C., Kato, T., Watanabe, K., Suzuki, S. Brain Dev. (1983) [Pubmed]
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