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Chemical Compound Review

MOLI001158     pentanoic acid

Synonyms: AC1L9P26
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Disease relevance of MOLI001158

  • Gemfibrozil, a novel hypolipidemic agent identified chemically as 2,2-dimethyl-5-(2,5-xylyoxy) valeric acid, was evaluated for mutagenic potential in in vitro assays with Salmonella typhimurium [1].
  • The fact that valproic acid, a derivative of pentanoic acid, also induces gamma-globin expression suggests that short-chain fatty acid derivatives that are already approved for human use may possess the property of gamma-globin inducibility and may be of therapeutic relevance to the beta-chain hemoglobinopathies [2].
  • BW12C (5-[2-formyl-3-hydroxypenoxyl] pentanoic acid) stabilizes oxyhaemoglobin, causing a reversible left-shift of the oxygen saturation curve (OSC) and tissue hypoxia [3].
  • We report a method for rapid extraction of the outer membrane protein, OmpF, from freeze-dried Escherichia coli cells using valeric acid, alleviating the effort and time in sample preparation [4].
  • The disposition of the antidepressant tianeptine and its MC5 metabolite (pentanoic acid analogue of tianeptine) was studied following a single 12.5 mg oral dose of tianeptine sodium salt in 20 patients with chronic renal failure [5].

Psychiatry related information on MOLI001158

  • The response latencies to stimulation with a malodour (valeric acid) and pleasant odorant (amyl acetate) were compared over a range of different stimulus strengths [6].

High impact information on MOLI001158


Chemical compound and disease context of MOLI001158


Biological context of MOLI001158


Anatomical context of MOLI001158


Associations of MOLI001158 with other chemical compounds

  • When 2,2-dimethyl 3-(2'-naphthyl 6'-hydroxy) pentanoic acid, an artificial estrogen of the allenolic acid group, was added to an exponential-phase growth culture of Neurospora crassa (in Horowitz medium), it was transformed into its hydroxylated derivative, 2,2-dimethyl 3-(2'-naphthyl 4',6'-dihydroxy)pentaoic acid [23].
  • Pretreatment with DL-2-amino-5-phosphono valeric acid (2-APV) (an NMDA receptor selective antagonist, 5 nmol) also abolished the pressor response induced by NMDA [24].
  • Pretreatment of the rats with a CysLT1 receptor antagonist (pranlukast) failed to reduce the elevation of airway resistance, and pretreatment with a BLT receptor antagonist (ONO-4057; 5-[2-(2-carboxyethyl)-3-[6-(4-methoxyphenyl)-5E-hexenyl]- oxyphenoxy] valeric acid) also produced no decrease [25].
  • 6-Aminohexanoic acid, pentylamine, pentanoic acid and arginine were used for investigation of the ligand specificity of isolated kringle 1 prepared by pepsin hydrolysis of kringle 1 + 2 + 3 [17].
  • The effect of leukotriene B4 (0.03 nmol/site) started within 3 min, peaked in the second 10-min period, had almost subsided by 30 min, and was inhibited by the simultaneous injection of the leukotriene B4 receptor antagonist ONO-4057, 5-[2-(2carboxyethyl)-3-(6-( p-methoxyphenyl)-5E-hexenyl) oxyphenyoxy] valeric acid [26].

Gene context of MOLI001158


Analytical, diagnostic and therapeutic context of MOLI001158


  1. Carcinogen bioassay and mutagenicity studies with the hypolipidemic agent gemfibrozil. Fitzgerald, J.E., Sanyer, J.L., Schardein, J.L., Lake, R.S., McGuire, E.J., de la Iglesia, F.A. J. Natl. Cancer Inst. (1981) [Pubmed]
  2. Stimulation of fetal hemoglobin production by short chain fatty acids. Liakopoulou, E., Blau, C.A., Li, Q., Josephson, B., Wolf, J.A., Fournarakis, B., Raisys, V., Dover, G., Papayannopoulou, T., Stamatoyannopoulos, G. Blood (1995) [Pubmed]
  3. Phase II study of the oxygen saturation curve left shifting agent BW12C in combination with the hypoxia activated drug mitomycin C in advanced colorectal cancer. Propper, D.J., Levitt, N.C., O'Byrne, K., Braybrooke, J.P., Talbot, D.C., Ganesan, T.S., Thompson, C.H., Rajagopalan, B., Littlewood, T.J., Dixon, R.M., Harris, A.L. Br. J. Cancer (2000) [Pubmed]
  4. A rapid selective extraction procedure for the outer membrane protein (OmpF) from Escherichia coli. Arcidiacono, S., Butler, M.M., Mello, C.M. Protein Expr. Purif. (2002) [Pubmed]
  5. Tianeptine and its main metabolite. Disposition in chronic renal failure and haemodialysis. Salvadori, C., Merdjan, H., Brouard, R., Baumelou, A., Nicot, G., Friès, D. Fundamental & clinical pharmacology. (1990) [Pubmed]
  6. A new method for measuring reaction times for odour detection at iso-intensity: Comparison between an unpleasant and pleasant odour. Jacob, T.J., Wang, L. Physiol. Behav. (2006) [Pubmed]
  7. N-methyl-D-aspartate receptor regulation of uncompetitive antagonist binding in rat brain membranes: kinetic analysis. Bonhaus, D.W., McNamara, J.O. Mol. Pharmacol. (1988) [Pubmed]
  8. Spiropentaneacetic acid as a specific inhibitor of medium-chain acyl-CoA dehydrogenase. Tserng, K.Y., Jin, S.J., Hoppel, C.L. Biochemistry (1991) [Pubmed]
  9. Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1). Tateoka, R., Abe, H., Miyauchi, S., Shuto, S., Matsuda, A., Kobayashi, M., Miyazaki, K., Kamo, N. Bioconjug. Chem. (2001) [Pubmed]
  10. Sensitization, desensitization and stimulus-induced recovery of trigeminal neuronal responses to oral capsaicin and nicotine. Dessirier, J.M., Simons, C.T., Sudo, M., Sudo, S., Carstens, E. J. Neurophysiol. (2000) [Pubmed]
  11. Ridogrel: a selective inhibitor of the cytochrome P450-dependent thromboxane synthesis. Vanden Bossche, H., Willemsens, G., Bellens, D., Janssen, P.A. Biochem. Pharmacol. (1992) [Pubmed]
  12. Production of polyhydroxyalkanoates from methanol by a new methylotrophic bacterium Methylobacterium sp. GW2. Yezza, A., Fournier, D., Halasz, A., Hawari, J. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  13. Combined therapy of L1210 leukemia with Damvar and cytostatics. Pujman, V., Cernochová, S. Neoplasma (1979) [Pubmed]
  14. Effect of valproic acid, its unsaturated metabolites and some structurally related fatty acids on the binding of warfarin and dansylsarcosine to human albumin. Panjehshahin, M.R., Bowmer, C.J., Yates, M.S. Biochem. Pharmacol. (1991) [Pubmed]
  15. Transport kinetics of plasma free fatty acid, very low density lipoprotein triglycerides and apoprotein in patients with endogenous hypertriglyceridaemia: effects of 2,2-dimethyl, 5(2, 5-xylyoxy) valeric acid therapy. Kissebah, A.H., Alfarsi, S., Adams, P.W., Seed, M., Folkard, J., Wynn, V. Atherosclerosis (1976) [Pubmed]
  16. Lipase specificity toward some acetylenic and olefinic alcohols in the esterification of pentanoic and stearic acids. Lie Ken Jie, M.S., Xun, F. Lipids (1998) [Pubmed]
  17. Fluorescence spectroscopic analysis of ligand binding to kringle 1 + 2 + 3 and kringle 1 fragments from human plasminogen. Matsuka, Y.V., Novokhatny, V.V., Kudinov, S.A. Eur. J. Biochem. (1990) [Pubmed]
  18. The effects of short-chain fatty acids on the neuronal membrane functions of Helix pomatia. II. Cholinoreceptive properties. Arvanov, V.L., Takenaka, T., Dadalian, S.S., Ayrapetyan, S.N. Cell. Mol. Neurobiol. (1986) [Pubmed]
  19. Activation of neurons in trigeminal caudalis by noxious oral acidic or salt stimuli is not reduced by amiloride. Sudo, S., Sudo, M., Simons, C.T., Dessirier, J.M., Iodi Carstens, M., Carstens, E. Brain Res. (2003) [Pubmed]
  20. Effects of hydrochloric, valeric, and other volatile fatty acids on pathogenesis of ulcers in the nonglandular portion of the stomach of horses. Nadeau, J.A., Andrews, F.M., Patton, C.S., Argenzio, R.A., Mathew, A.G., Saxton, A.M. Am. J. Vet. Res. (2003) [Pubmed]
  21. Pentanoic acid, a novel protein synthesis stimulant for Chinese Hamster Ovary (CHO) cells. Liu, C., Chu, I., Hwang, S. J. Biosci. Bioeng. (2001) [Pubmed]
  22. Hepatic and intestinal blood flow following thermal injury. Carter, E.A., Tompkins, R.G., Burke, J.F. The Journal of burn care & rehabilitation. (1988) [Pubmed]
  23. Microbial transformation of artificial estrogens of the allenolic group. Maugras, M., Lorrain, M., Lematre, J., Granger, P. J. Bacteriol. (1975) [Pubmed]
  24. Involvement of endothelin in the pressor response following injection of NMDA to the periaqueductal gray area of rats. D'Amico, M., Warner, T.D. Br. J. Pharmacol. (1995) [Pubmed]
  25. Synergistic effects of pranlukast and leukotriene B4 receptor antagonist on antigen-induced pulmonary reaction. Sakurada, T., Abe, M., Kodani, M., Sakata, N., Katsuragi, T. Eur. J. Pharmacol. (1999) [Pubmed]
  26. Intradermal leukotriene B4, but not prostaglandin E2, induces itch-associated responses in mice. Andoh, T., Kuraishi, Y. Eur. J. Pharmacol. (1998) [Pubmed]
  27. Inhibitors of polyamine biosynthesis VI: 2,5-Diamino-2-(cyanomethyl) pentanoic acid, a potential irreversible inhibitor of ornithine decarboxylase. Abdel-Monem, M.M., Mikhail, E.A. Journal of pharmaceutical sciences. (1978) [Pubmed]
  28. Measurement of phenytoin in serum using in-house reagents employing the Syva enzyme-multiplied immunoassay technique principle. Colbert, D.L. Therapeutic drug monitoring. (1992) [Pubmed]
  29. A new series of S-adenosyl-L-methionine synthetase inhibitors. Lavrador, K., Allart, B., Guillerm, D., Guillerm, G. J. Enzym. Inhib. (1998) [Pubmed]
  30. Acyloxymethyl acidic drug derivatives: in vitro hydrolytic reactivity. Redden, P.R., Melanson, R.L., Douglas, J.A., Dick, A.J. International journal of pharmaceutics. (1999) [Pubmed]
  31. Evidence for a compound in Comstock-Kellog glands modulating premating behavior in male desert locust, Schistocerca gregaria. Njagi, P.G., Torto, B. J. Chem. Ecol. (2002) [Pubmed]
  32. Performance responses and indicators of gastrointestinal health in early-weaned pigs fed low-protein amino acid-supplemented diets. Nyachoti, C.M., Omogbenigun, F.O., Rademacher, M., Blank, G. J. Anim. Sci. (2006) [Pubmed]
  33. Measurement of the amino acid metabolite of phencyclidine by selected ion monitoring. Syracuse, C.D., Kuhnert, B.R., Golden, N.L., Bagby, B.S. Biomed. Environ. Mass Spectrom. (1986) [Pubmed]
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