5-Oxo-eicosatetraenoic acid

5-Oxo-eicosatetraenoic acid
Names
Preferred IUPAC name
(6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoic acid
Other names
  • 5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoate
  • 5-oxo-ETE
  • 5-oxoETE
  • 5-KETE
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
    Key: MEASLHGILYBXFO-XTDASVJISA-N
  • CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O
Properties
C20H30O3
Molar mass 318.457 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Oxo-eicosatetraenoic acid (i.e. 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid; also termed 5-oxo-ETE and 5-oxoETE) is a nonclassic eicosanoid metabolite of arachidonic acid and the most potent naturally occurring member of the 5-HETE family of cell signaling agents. Like other cell signaling agents, 5-oxo-ETE is made by a cell and then feeds back to stimulate its parent cell (see Autocrine signaling) and/or exits this cell to stimulate nearby cells (see Paracrine signaling). 5-Oxo-ETE can stimulate various cell types particularly human leukocytes but possesses its highest potency and power in stimulating the human eosinophil type of leukocyte. It is therefore suggested to be formed during and to be an important contributor to the formation and progression of eosinophil-based allergic reactions;[1][2] it is also suggested that 5-oxo-ETE contributes to the development of inflammation, cancer cell growth, and other pathological and physiological events.[1][3]

  1. ^ a b Powell WS, Rokach J (April 2015). "Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1851 (4): 340–55. doi:10.1016/j.bbalip.2014.10.008. PMC 5710736. PMID 25449650.
  2. ^ Cossette C, Gravel S, Reddy CN, Gore V, Chourey S, Ye Q, Snyder NW, Mesaros CA, Blair IA, Lavoie JP, Reinero CR, Rokach J, Powell WS (August 2015). "Biosynthesis and actions of 5-oxoeicosatetraenoic acid (5-oxo-ETE) on feline granulocytes". Biochemical Pharmacology. 96 (3): 247–55. doi:10.1016/j.bcp.2015.05.009. PMC 4830392. PMID 26032638.
  3. ^ Cite error: The named reference Prog Lipid Res 2013. p 19 was invoked but never defined (see the help page).