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Chemical Compound Review

zoomarate     (Z)-hexadec-9-enoate

Synonyms: palmitoleate, CPD-9245, CHEBI:32372, AC1NUU1V, palmitolinoleate, ...
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Disease relevance of palmitoleic acid

  • Palmitoleate is not present in lipid A isolated from Escherichia coli grown at 30 degrees C or higher, but it comprises approximately 11% of the fatty acyl chains of lipid A in cells grown at 12 degrees C. The appearance of palmitoleate at 12 degrees C is accompanied by a decline in laurate from approximately 18% to approximately 5.5% [1].
  • Liver microsomal fatty-acid composition in hyperthyroidism is altered with significantly increased proportions of stearate and arachidonate and decreased proportions of palmitate, palmitoleate, linoleate (C18:2) and eicosa-8,11,14-trienoate (C20:3) [2].

High impact information on palmitoleic acid


Biological context of palmitoleic acid


Anatomical context of palmitoleic acid


Associations of palmitoleic acid with other chemical compounds


Gene context of palmitoleic acid

  • Stearoyl-CoA desaturase (SCD) is a microsomal enzyme required for the biosynthesis of oleate (C18:1) and palmitoleate (C16:1) which are the major monounsaturated fatty acids of membrane phospholipids, triglycerides and cholesterol esters [12].
  • Stearoyl-CoA desaturase (SCD) is expressed at high levels in several human tissues and is required for the biosynthesis of oleate (18:1) and palmitoleate (16:1) [13].
  • Comparison of Arrhenius plots of the oxidation of [U-14C]palmitoleate by whole cells and acyl-CoA synthetase activity with palmitoleate as substrate demonstrated that the two exhibited virtually identical Arrhenius activation energies and temperature optima [14].
  • Palmitoleate inhibited remarkably LDH, MDH, ICDH and G6P-DH [15].

Analytical, diagnostic and therapeutic context of palmitoleic acid

  • The crystal structure of the palmitoleate-bound A264E mutant reveals that substrate binding promotes heme ligation by Glu(264), with little other difference from the palmitoleate-bound wild-type structure observable [16].


  1. Effect of cold shock on lipid A biosynthesis in Escherichia coli. Induction At 12 degrees C of an acyltransferase specific for palmitoleoyl-acyl carrier protein. Carty, S.M., Sreekumar, K.R., Raetz, C.R. J. Biol. Chem. (1999) [Pubmed]
  2. Fatty-acid desaturation and microsomal lipid fatty-acid composition in experimental hyperthyroidism. Faas, F.H., Carter, W.J. Biochem. J. (1981) [Pubmed]
  3. Saturated, but Not Unsaturated, Fatty Acids Induce Apoptosis of Human Coronary Artery Endothelial Cells via Nuclear Factor-{kappa}B Activation. Staiger, K., Staiger, H., Weigert, C., Haas, C., H??ring, H.U., Kellerer, M. Diabetes (2006) [Pubmed]
  4. A triple mutant of Escherichia coli lacking secondary acyl chains on lipid A. Vorachek-Warren, M.K., Ramirez, S., Cotter, R.J., Raetz, C.R. J. Biol. Chem. (2002) [Pubmed]
  5. The biosynthesis of hepatic cholesterol esters and triglycerides is impaired in mice with a disruption of the gene for stearoyl-CoA desaturase 1. Miyazaki, M., Kim, Y.C., Gray-Keller, M.P., Attie, A.D., Ntambi, J.M. J. Biol. Chem. (2000) [Pubmed]
  6. Lack of stearoyl-CoA desaturase 1 upregulates basal thermogenesis but causes hypothermia in a cold environment. Lee, S.H., Dobrzyn, A., Dobrzyn, P., Rahman, S.M., Miyazaki, M., Ntambi, J.M. J. Lipid Res. (2004) [Pubmed]
  7. Differential protective effects of palmitoleic acid and cAMP on caspase activation and cell viability in pancreatic beta-cells exposed to palmitate. Welters, H.J., Diakogiannaki, E., Mordue, J.M., Tadayyon, M., Smith, S.A., Morgan, N.G. Apoptosis (2006) [Pubmed]
  8. Regulation of stearoyl-CoA desaturase genes: role in cellular metabolism and preadipocyte differentiation. Kim, Y.C., Ntambi, J.M. Biochem. Biophys. Res. Commun. (1999) [Pubmed]
  9. Differential effects of palmitate and palmitoleate on insulin action and glucose utilization in rat L6 skeletal muscle cells. Dimopoulos, N., Watson, M., Sakamoto, K., Hundal, H.S. Biochem. J. (2006) [Pubmed]
  10. Stimulation of strontium accumulation in linoleate-enriched Saccharomyces cerevisiae is a result of reduced Sr2+ efflux. Avery, S.V., Smith, S.L., Ghazi, A.M., Hoptroff, M.J. Appl. Environ. Microbiol. (1999) [Pubmed]
  11. Mechanism of biosynthesis of unsaturated fatty acids in Pseudomonas sp. strain E-3, a psychrotrophic bacterium. Wada, M., Fukunaga, N., Sasaki, S. J. Bacteriol. (1989) [Pubmed]
  12. Cloning and characterization of the human stearoyl-CoA desaturase gene promoter: transcriptional activation by sterol regulatory element binding protein and repression by polyunsaturated fatty acids and cholesterol. Bené, H., Lasky, D., Ntambi, J.M. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  13. Relationship between stearoyl-CoA desaturase activity and plasma triglycerides in human and mouse hypertriglyceridemia. Attie, A.D., Krauss, R.M., Gray-Keller, M.P., Brownlie, A., Miyazaki, M., Kastelein, J.J., Lusis, A.J., Stalenhoef, A.F., Stoehr, J.P., Hayden, M.R., Ntambi, J.M. J. Lipid Res. (2002) [Pubmed]
  14. The effect of temperature and membrane lipid composition on the rate of beta-oxidation by Escherichia coli. O'Brien, W.J., Frerman, F.E. Biochim. Biophys. Acta (1980) [Pubmed]
  15. The palmitoleate: a natural selective denaturant of enzymes. Vincenzini, M.T., Favilli, F., Treves, C., Vanni, P., Baccari, V. Int. J. Biochem. (1983) [Pubmed]
  16. A single mutation in cytochrome P450 BM3 induces the conformational rearrangement seen upon substrate binding in the wild-type enzyme. Joyce, M.G., Girvan, H.M., Munro, A.W., Leys, D. J. Biol. Chem. (2004) [Pubmed]
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