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Chemical Compound Review

MOLI001155     hexadecanoic acid

Synonyms: AC1L9P23
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Disease relevance of hexadecanoic acid

  • In this report, we examined the ability of peptides, covalently coupled to palmitic acid and incorporated into liposomes, to induce virus-specific T cell responses that confer protection against a lethal challenge of HSV-2 [1].
  • The three vaccine components included HBV core antigen peptide 18-27 as the CTL epitope, tetanus toxoid peptide 830-843 as the T helper peptide, and two palmitic acid molecules as the lipids [2].
  • Studies on the attachment of myristic and palmitic acid to cell proteins in human squamous carcinoma cell lines: evidence for two pathways [3].
  • This contrasted with Harvey sarcoma virus, in which two forms of p21v-H-ras contained palmitic acid [4].
  • A CTL epitope derived from the hepatitis B core protein amino acids 18-27 has been incorporated into a vaccine also comprised of a T-helper cell epitope and 2 palmitic acid residues (CY-1899) [5].

Psychiatry related information on hexadecanoic acid


High impact information on hexadecanoic acid


Chemical compound and disease context of hexadecanoic acid


Biological context of hexadecanoic acid


Anatomical context of hexadecanoic acid


Associations of hexadecanoic acid with other chemical compounds


Gene context of hexadecanoic acid

  • The extension by three residues, -Val-Leu-Ser, generating a ras-typical C-terminal end, did not interfere with the mutant YPT1 protein's function although it resulted in a reduced labelling with palmitic acid [30].
  • In rodents, the principal fatty acid produced by FAS is palmitic acid (16:0) [34].
  • Constitutive liver beta-oxidation of the long chain fatty acid, palmitic acid, was lower in the PPARalpha null mice as compared with wild type mice, indicating defective mitochondrial fatty acid catabolism [35].
  • Exogenous radioactive palmitic acid is incorporated post-translationally into the HLA-B and -DR heavy chains, but not HLA-A heavy chains or -DR light chains of the human B lymphoblastoid cells JY and T51 . Protease digestions localize the label to the transmembrane region of the B7 heavy chain [36].
  • CYP2C8 crystallized as a symmetric dimer formed by the interaction of helices F, F', G', and G. Two molecules of palmitic acid are bound in the dimer interface [37].

Analytical, diagnostic and therapeutic context of hexadecanoic acid


  1. A synthetic peptide induces long-term protection from lethal infection with herpes simplex virus 2. Watari, E., Dietzschold, B., Szokan, G., Heber-Katz, E. J. Exp. Med. (1987) [Pubmed]
  2. Development of a lipopeptide-based therapeutic vaccine to treat chronic HBV infection. I. Induction of a primary cytotoxic T lymphocyte response in humans. Vitiello, A., Ishioka, G., Grey, H.M., Rose, R., Farness, P., LaFond, R., Yuan, L., Chisari, F.V., Furze, J., Bartholomeuz, R. J. Clin. Invest. (1995) [Pubmed]
  3. Studies on the attachment of myristic and palmitic acid to cell proteins in human squamous carcinoma cell lines: evidence for two pathways. McIlhinney, R.A., Pelly, S.J., Chadwick, J.K., Cowley, G.P. EMBO J. (1985) [Pubmed]
  4. Direct identification of palmitic acid as the lipid attached to p21ras. Buss, J.E., Sefton, B.M. Mol. Cell. Biol. (1986) [Pubmed]
  5. A pilot study of the CY-1899 T-cell vaccine in subjects chronically infected with hepatitis B virus. The CY1899 T Cell Vaccine Study Group. Heathcote, J., McHutchison, J., Lee, S., Tong, M., Benner, K., Minuk, G., Wright, T., Fikes, J., Livingston, B., Sette, A., Chestnut, R. Hepatology (1999) [Pubmed]
  6. Increased mitochondrial glycerol-3-phosphate acyltransferase protein and enzyme activity in rat epididymal fat upon cessation of wheel running. Kump, D.S., Laye, M.J., Booth, F.W. Am. J. Physiol. Endocrinol. Metab. (2006) [Pubmed]
  7. Determination of free fatty acids as pentafluorobenzyl esters by electron capture gas chromatography. Gyllenhaal, O., Brötell, H., Hartvig, P. J. Chromatogr. (1976) [Pubmed]
  8. Induction of a latency period in the time-course of phospholipase A2 action on dipalmitoylphosphatidylcholine liposomes in the gel phase. González-Martínez, M.T., Fernández, M.S. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  9. Reduced labeling of brain phosphatidylinositol, triacylglycerols, and diacylglycerols by [1-14C]arachidonic acid after electroconvulsive shock: potentiation of the effect by adrenergic drugs and comparison with palmitic acid labeling. Pediconi, M.F., Rodriguez de Turco, E.B., Bazan, N.G. Neurochem. Res. (1986) [Pubmed]
  10. The effect of digitonin and altered thyroid status on palmitic acid oxidation by isolated rat liver mitochondria. Pointer, R.H., Gipson, V.A., Mitchell, W.A. Endocr. Res. (1993) [Pubmed]
  11. Conversion of a secretory protein into a transmembrane protein results in its transport to the Golgi complex but not to the cell surface. Guan, J.L., Rose, J.K. Cell (1984) [Pubmed]
  12. T-cell antigen receptor transmembrane peptides modulate T-cell function and T cell-mediated disease. Manolios, N., Collier, S., Taylor, J., Pollard, J., Harrison, L.C., Bender, V. Nat. Med. (1997) [Pubmed]
  13. Diacylglycerol in large alpha-actinin/actin complexes and in the cytoskeleton of activated platelets. Burn, P., Rotman, A., Meyer, R.K., Burger, M.M. Nature (1985) [Pubmed]
  14. Membrane fluidity of a fatty acid auxotroph grown with palmitic acid. Hauser, H., Hazlewood, G.P., Dawson, R.M. Nature (1979) [Pubmed]
  15. Rat very-long-chain acyl-CoA dehydrogenase, a novel mitochondrial acyl-CoA dehydrogenase gene product, is a rate-limiting enzyme in long-chain fatty acid beta-oxidation system. cDNA and deduced amino acid sequence and distinct specificities of the cDNA-expressed protein. Aoyama, T., Ueno, I., Kamijo, T., Hashimoto, T. J. Biol. Chem. (1994) [Pubmed]
  16. Comparison of the lipoprotein gene among the enterobacteriaceae. DNA sequence of Morganella morganii lipoprotein gene and its expression in Escherichia coli. Huang, Y.X., Ching, G., Inouye, M. J. Biol. Chem. (1983) [Pubmed]
  17. Pyruvylated glycolipids from Mycobacterium smegmatis. Nature and location of the lipid components. Kamisango, K., Saadat, S., Dell, A., Ballou, C.E. J. Biol. Chem. (1985) [Pubmed]
  18. Conformational changes associated with complex formation between a mycobacterial polymethylpolysaccharide and palmitic acid. Yabusaki, K.K., Cohen, R.E., Ballou, C.E. J. Biol. Chem. (1979) [Pubmed]
  19. Retention and clearance of C-11 palmitic acid in ischemic and reperfused canine myocardium. Schwaiger, M., Schelbert, H.R., Keen, R., Vinten-Johansen, J., Hansen, H., Selin, C., Barrio, J., Huang, S.C., Phelps, M.E. J. Am. Coll. Cardiol. (1985) [Pubmed]
  20. Accessibility to proteases of the cytoplasmic G protein domain of vesicular stomatitis virus is increased during intracellular transport. Mack, D., Kluxen, B., Kruppa, J. J. Cell Biol. (1989) [Pubmed]
  21. Amino-terminal deletion mutants of the Rous sarcoma virus glycoprotein do not block signal peptide cleavage but can block intracellular transport. Hardwick, J.M., Shaw, K.E., Wills, J.W., Hunter, E. J. Cell Biol. (1986) [Pubmed]
  22. Triglyceride accumulation protects against fatty acid-induced lipotoxicity. Listenberger, L.L., Han, X., Lewis, S.E., Cases, S., Farese, R.V., Ory, D.S., Schaffer, J.E. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  23. Inhibition of calcium-independent phospholipase A2 prevents arachidonic acid incorporation and phospholipid remodeling in P388D1 macrophages. Balsinde, J., Bianco, I.D., Ackermann, E.J., Conde-Frieboes, K., Dennis, E.A. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  24. Saturated fatty acids inhibit induction of insulin gene transcription by JNK-mediated phosphorylation of insulin-receptor substrates. Solinas, G., Naugler, W., Galimi, F., Lee, M.S., Karin, M. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  25. Cell membrane-binding properties of group A streptococcal lipoteichoic acid. Ofek, I., Beachey, E.H., Jefferson, W., Campbell, G.L. J. Exp. Med. (1975) [Pubmed]
  26. Purification of human very-long-chain acyl-coenzyme A dehydrogenase and characterization of its deficiency in seven patients. Aoyama, T., Souri, M., Ushikubo, S., Kamijo, T., Yamaguchi, S., Kelley, R.I., Rhead, W.J., Uetake, K., Tanaka, K., Hashimoto, T. J. Clin. Invest. (1995) [Pubmed]
  27. Novel inhibitory action of tunicamycin homologues suggests a role for dynamic protein fatty acylation in growth cone-mediated neurite extension. Patterson, S.I., Skene, J.H. J. Cell Biol. (1994) [Pubmed]
  28. Inhibition of the mitochondrial oxidation of fatty acids by tetracycline in mice and in man: possible role in microvesicular steatosis induced by this antibiotic. Fréneaux, E., Labbe, G., Letteron, P., The Le Dinh, n.u.l.l., Degott, C., Genève, J., Larrey, D., Pessayre, D. Hepatology (1988) [Pubmed]
  29. Distinct effects of fatty acids on translocation of gamma- and epsilon-subspecies of protein kinase C. Shirai, Y., Kashiwagi, K., Yagi, K., Sakai, N., Saito, N. J. Cell Biol. (1998) [Pubmed]
  30. A carboxyl-terminal cysteine residue is required for palmitic acid binding and biological activity of the ras-related yeast YPT1 protein. Molenaar, C.M., Prange, R., Gallwitz, D. EMBO J. (1988) [Pubmed]
  31. The transfer of myristic and other fatty acids on lipid and viral protein acceptors in cultured cells infected with Semliki Forest and influenza virus. Schmidt, M.F. EMBO J. (1984) [Pubmed]
  32. Lignoceric acid is oxidized in the peroxisome: implications for the Zellweger cerebro-hepato-renal syndrome and adrenoleukodystrophy. Singh, I., Moser, A.E., Goldfischer, S., Moser, H.W. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  33. Arachidonic acid mediates interleukin-1 and tumor necrosis factor-alpha-induced activation of the c-jun amino-terminal kinases in stromal cells. Rizzo, M.T., Carlo-Stella, C. Blood (1996) [Pubmed]
  34. Identification of a mammalian long chain fatty acyl elongase regulated by sterol regulatory element-binding proteins. Moon, Y.A., Shah, N.A., Mohapatra, S., Warrington, J.A., Horton, J.D. J. Biol. Chem. (2001) [Pubmed]
  35. Altered constitutive expression of fatty acid-metabolizing enzymes in mice lacking the peroxisome proliferator-activated receptor alpha (PPARalpha). Aoyama, T., Peters, J.M., Iritani, N., Nakajima, T., Furihata, K., Hashimoto, T., Gonzalez, F.J. J. Biol. Chem. (1998) [Pubmed]
  36. Cysteines in the transmembrane region of major histocompatibility complex antigens are fatty acylated via thioester bonds. Kaufman, J.F., Krangel, M.S., Strominger, J.L. J. Biol. Chem. (1984) [Pubmed]
  37. Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding site. Schoch, G.A., Yano, J.K., Wester, M.R., Griffin, K.J., Stout, C.D., Johnson, E.F. J. Biol. Chem. (2004) [Pubmed]
  38. Generation of lyso-phospholipids from surfactant in acute lung injury is mediated by type-II phospholipase A2 and inhibited by a direct surfactant protein A-phospholipase A2 protein interaction. Arbibe, L., Koumanov, K., Vial, D., Rougeot, C., Faure, G., Havet, N., Longacre, S., Vargaftig, B.B., Béréziat, G., Voelker, D.R., Wolf, C., Touqui, L. J. Clin. Invest. (1998) [Pubmed]
  39. Cloning of human very-long-chain acyl-coenzyme A dehydrogenase and molecular characterization of its deficiency in two patients. Aoyama, T., Souri, M., Ueno, I., Kamijo, T., Yamaguchi, S., Rhead, W.J., Tanaka, K., Hashimoto, T. Am. J. Hum. Genet. (1995) [Pubmed]
  40. A single N-linked oligosaccharide at either of the two normal sites is sufficient for transport of vesicular stomatitis virus G protein to the cell surface. Machamer, C.E., Florkiewicz, R.Z., Rose, J.K. Mol. Cell. Biol. (1985) [Pubmed]
  41. Differential fatty acid selection during biosynthetic S-acylation of a transmembrane protein (HEF) and other proteins in insect cells (Sf9) and in mammalian cells (CV1). Reverey, H., Veit, M., Ponimaskin, E., Schmidt, M.F. J. Biol. Chem. (1996) [Pubmed]
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