5-oxo-eicosatetraenoic acid

5-oxo-eicosatetraenoic acid

Names
IUPAC name 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoate
Other names 5-oxo-ETE, 5-oxoETE, 5-KETE
Identifiers
CAS Number	106154-18-1
3D model (Jmol)	Interactive image
ChEBI	CHEBI:52449
ChemSpider	4446283
KEGG	C14732
PubChem CID	5283159
InChI 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
SMILES CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O
Properties
Chemical formula	C20H30O3
Molar mass	318.45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 in made by a cell and then feeds back to stimulate its parent cell (see ) 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; it is also suggested that 5-oxo-ETE may also contribute inflammation, cancer cell growth, and other pathophysiological responses.

In the most common means for its production, cells make 5-oxo-ETE in a four step pathway that involves their stimulus-induced activation of the following pathway: a) the release of arachidonic acid (i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid) from its storage sites in membrane phospholipids due to the activation of phospholipase A2 enzymes; b) oxygenation of this arachidonic acid with by activated arachidonate 5-lipoxygenase (ALOX5) to form 5(S)-hydroperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5(S)-HpETE); c) reduction of this 5(S)-HpETE by ubiquitous cellular peroxidases to form 5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5(S)-HETE); and (d) the oxidation of 5(S)-HETE by a microsome-bound nicotinamide adenine dinucleotide phosphate (NADP⁺)-dependent dehydrogenase enzyme viz., (5-Hydroxyeicosanoid dehydrogenase or 5-HEDH) to form 5-oxo-ETE: