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Chemical Compound Review

AC1O5PIQ     (2E,4E,6E,8E,10E)-docosa- 2,4,6,8,10...

Synonyms: LMFA04000049, C22:5n-12,14,16,18,20, Docosapentaenoic acid (VAN), 2E,4E,6E,8E,10E-docosapentaenoic acid
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Disease relevance of docosapentaenoic acid


Psychiatry related information on docosapentaenoic acid


High impact information on docosapentaenoic acid


Biological context of docosapentaenoic acid


Anatomical context of docosapentaenoic acid


Associations of docosapentaenoic acid with other chemical compounds


Gene context of docosapentaenoic acid


Analytical, diagnostic and therapeutic context of docosapentaenoic acid

  • The decrease was accompanied by an increase in docosapentaenoic acid (22:5n-6) content, which replaced the 22:6n-3 phospholipids with 22:5n-6 molecular species, as demonstrated using HPLC/electrospray mass spectrometry [32].


  1. Serum levels of polyunsaturated fatty acids and risk of colorectal cancer: a prospective study. Kojima, M., Wakai, K., Tokudome, S., Suzuki, K., Tamakoshi, K., Watanabe, Y., Kawado, M., Hashimoto, S., Hayakawa, N., Ozasa, K., Toyoshima, H., Suzuki, S., Ito, Y., Tamakoshi, A. Am. J. Epidemiol. (2005) [Pubmed]
  2. Fatty acid composition of serum phospholipid of premenopausal women and postmenopausal women receiving and not receiving hormone replacement therapy. Stark, K.D., Park, E.J., Holub, B.J. Menopause (New York, N.Y.) (2003) [Pubmed]
  3. Flaxseed oil increases the plasma concentrations of cardioprotective (n-3) fatty acids in humans. Harper, C.R., Edwards, M.J., DeFilipis, A.P., Jacobson, T.A. J. Nutr. (2006) [Pubmed]
  4. Synthesis of structured lipids containing medium-chain and omega-3 fatty acids. Hamam, F., Shahidi, F. J. Agric. Food Chem. (2006) [Pubmed]
  5. Essential-fatty-acid metabolites in plasma phospholipids in patients with ichthyosis vulgaris, acne vulgaris and psoriasis. Grattan, C., Burton, J.L., Manku, M., Stewart, C., Horrobin, D.F. Clin. Exp. Dermatol. (1990) [Pubmed]
  6. An extraordinary degree of structural specificity is required in neural phospholipids for optimal brain function: n-6 docosapentaenoic acid substitution for docosahexaenoic acid leads to a loss in spatial task performance. Lim, S.Y., Hoshiba, J., Salem, N. J. Neurochem. (2005) [Pubmed]
  7. Docosahexaenoic acid: a positive modulator of Akt signaling in neuronal survival. Akbar, M., Calderon, F., Wen, Z., Kim, H.Y. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  8. Reduced Brain DHA Content After a Single Reproductive Cycle in Female Rats Fed a Diet Deficient in N-3 Polyunsaturated Fatty Acids. Levant, B., Radel, J.D., Carlson, S.E. Biol. Psychiatry (2006) [Pubmed]
  9. n-6 Docosapentaenoic acid is not a predictor of low docosahexaenoic acid status in Canadian preschool children. Innis, S.M., Vaghri, Z., King, D.J. Am. J. Clin. Nutr. (2004) [Pubmed]
  10. Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Francois, C.A., Connor, S.L., Bolewicz, L.C., Connor, W.E. Am. J. Clin. Nutr. (2003) [Pubmed]
  11. Significantly reduced docosahexaenoic and docosapentaenoic acid concentrations in erythrocyte membranes from schizophrenic patients compared with a carefully matched control group. Assies, J., Lieverse, R., Vreken, P., Wanders, R.J., Dingemans, P.M., Linszen, D.H. Biol. Psychiatry (2001) [Pubmed]
  12. Effects of highly purified eicosapentaenoic acid and docosahexaenoic acid on hemodynamics in humans. Grimsgaard, S., Bønaa, K.H., Hansen, J.B., Myhre, E.S. Am. J. Clin. Nutr. (1998) [Pubmed]
  13. The protection of long chain polyunsaturated fatty acids by melatonin during nonenzymatic lipid peroxidation of rat liver microsomes. Leaden, P., Barrionuevo, J., Catalá, A. J. Pineal Res. (2002) [Pubmed]
  14. Influence of an algal triacylglycerol containing docosahexaenoic acid (22 : 6n-3) and docosapentaenoic acid (22 : 5n-6) on cardiovascular risk factors in healthy men and women. Sanders, T.A., Gleason, K., Griffin, B., Miller, G.J. Br. J. Nutr. (2006) [Pubmed]
  15. Involvement of lipoxygenase pathway in docosapentaenoic acid-induced inhibition of platelet aggregation. Akiba, S., Murata, T., Kitatani, K., Sato, T. Biol. Pharm. Bull. (2000) [Pubmed]
  16. Docosahexaenoic acid enrichment can reduce L929 cell necrosis induced by tumor necrosis factor. Kishida, E., Tajiri, M., Masuzawa, Y. Biochim. Biophys. Acta (2006) [Pubmed]
  17. Dietary n-3 fatty acid restriction during gestation in rats: neuronal cell body and growth-cone fatty acids. Auestad, N., Innis, S.M. Am. J. Clin. Nutr. (2000) [Pubmed]
  18. Incorporation and clearance of omega-3 Fatty acids in erythrocyte membranes and plasma phospholipids. Cao, J., Schwichtenberg, K.A., Hanson, N.Q., Tsai, M.Y. Clin. Chem. (2006) [Pubmed]
  19. Rabbit photoreceptor outer segments contain high levels of docosapentaenoic acid. Nielsen, J.C., Maude, M.B., Hughes, H., Anderson, R.E. Invest. Ophthalmol. Vis. Sci. (1986) [Pubmed]
  20. Docosahexaenoic acid promotes neurite growth in hippocampal neurons. Calderon, F., Kim, H.Y. J. Neurochem. (2004) [Pubmed]
  21. N-3 fatty acid deficiency in the rat pineal gland: effects on phospholipid molecular species composition and endogenous levels of melatonin and lipoxygenase products. Zhang, H., Hamilton, J.H., Salem, N., Kim, H.Y. J. Lipid Res. (1998) [Pubmed]
  22. Anti-lipoperoxidation action of food restriction. Laganiere, S., Yu, B.P. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  23. Low-dose eicosapentaenoic or docosahexaenoic acid administration modifies fatty acid composition and does not affect susceptibility to oxidative stress in rat erythrocytes and tissues. Calviello, G., Palozza, P., Franceschelli, P., Bartoli, G.M. Lipids (1997) [Pubmed]
  24. Electrospray/tandem mass spectrometry for quantitative analysis of lipid remodeling in essential fatty acid deficient mice. Duffin, K., Obukowicz, M., Raz, A., Shieh, J.J. Anal. Biochem. (2000) [Pubmed]
  25. Docosapentaenoic acid (22:5,n-3): metabolism and effect on prostacyclin production in endothelial cells. Bénistant, C., Achard, F., Ben Slama, S., Lagarde, M. Prostaglandins Leukot. Essent. Fatty Acids (1996) [Pubmed]
  26. Polyunsaturated fatty acids in the diet and breast milk of lactating icelandic women with traditional fish and cod liver oil consumption. Olafsdottir, A.S., Thorsdottir, I., Wagner, K.H., Elmadfa, I. Ann. Nutr. Metab. (2006) [Pubmed]
  27. Oxygenation of polyunsaturated long chain fatty acids by recombinant CYP4F8 and CYP4F12 and catalytic importance of Tyr-125 and Gly-328 of CYP4F8. Stark, K., Wongsud, B., Burman, R., Oliw, E.H. Arch. Biochem. Biophys. (2005) [Pubmed]
  28. Blood phospholipid fatty acid analysis of adults with and without attention deficit/hyperactivity disorder. Young, G.S., Maharaj, N.J., Conquer, J.A. Lipids (2004) [Pubmed]
  29. Fatty acid composition of the testes of zinc-deficient rats: the effect of docosapentaenoic acid supplementation. Chanmugam, P., Wheeler, C., Hwang, D.H. J. Nutr. (1984) [Pubmed]
  30. Effect of exercise on FA profiles in n-3 FA-supplemented and -nonsupplemented premenopausal women. Conquer, J.A., Roelfsema, H., Zecevic, J., Graham, T.E., Holub, B.J. Lipids (2002) [Pubmed]
  31. Evidence of increased flux to n-6 docosapentaenoic acid in phospholipids of pancreas from cftr-/- knockout mice. Ollero, M., Laposata, M., Zaman, M.M., Blanco, P.G., Andersson, C., Zeind, J., Urman, Y., Kent, G., Alvarez, J.G., Freedman, S.D. Metab. Clin. Exp. (2006) [Pubmed]
  32. Effect of docosahexaenoic acid on the synthesis of phosphatidylserine in rat brain in microsomes and C6 glioma cells. Garcia, M.C., Ward, G., Ma, Y.C., Salem, N., Kim, H.Y. J. Neurochem. (1998) [Pubmed]
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