oleoylethanolamide oleoylethanolamide oleoylethanolamide (oea) is an endogenous peroxisome proliferator-activated receptor alpha (ppar-α) agonist. it is a naturally occurring ethanolamide lipid that regulates feeding and body weight in vertebrates ranging from mice to pythons. oleoylethanolamide names preferred iupac name (9z)-n-(2-hydroxyethyl)octadec-9-enamide identifiers cas number 111-58-0 y 3d model (jsmol) interactive image chebi chebi:77362 chemspider 4446574 n echa infocard 100.003.532 iuphar/bps 2661 pubchem cid 5283454 unii 1hi5j9n8e6 y comptox dashboard (epa) dtxsid1044516 inchi inchi=1s/c20h39no2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22h,2-8,11-19h2,1h3,(h,21,23)/b10-9- nkey: bowvqlfmwhzbef-ktkrtigzsa-n ninchi=1/c20h39no2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22h,2-8,11-19h2,1h3,(h,21,23)/b10-9-key: bowvqlfmwhzbef-ktkrtigzbw smiles cccccccc\c=c/cccccccc(=o)ncco properties chemical formula c20h39no2 molar mass 325.537 g·mol−1 appearance white solid melting point 59–60 °c (138–140 °f; 332–333 k) solubility in ethanol and dmso soluble except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references oea is a shorter, monounsaturated analogue of the endocannabinoid anandamide, but unlike anandamide it acts independently of the cannabinoid pathway, regulating ppar-α activity to stimulate lipolysis. oea is produced by the small intestine following feeding in two steps. first an n-acyl transferase (nat) activity joins the free amino terminus of phosphatidylethanolamine (pe) to the oleoyl group (one variety of acyl group) derived from sn-1-oleoyl-phosphatidylcholine, which contains the fatty acid oleic acid at the sn-1 position. this produces an n-acylphosphatidylethanolamine, which is then split (hydrolyzed) by n-acyl phosphatidylethanolamine-specific phospholipase d (nape-pld) into phosphatidic acid and oea. the biosynthesis of oea and other bioactive lipid amides is modulated by bile acids. oea has been demonstrated to bind to the novel cannabinoid receptor gpr119. oea has been suggested to be the receptor's endogenous ligand. oea has been hypothesized to play a key role in the inhibition of food seeking behavior and in the lipolysis of brown bears "ursus arctos" during the hibernation season together with the alteration of the endocannabinoid system required for the metabolic changes for hibernation. oea has been reported to lengthen the life span of the roundworm caenorhabditis elegans through interactions with lysomal molecules.