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17,18-EEQ

N-3 epoxy fatty acids (EpFAs) are bioactive metabolites generated by cytochrome P-450 (CYP450) epoxygenases from n-3 polyunsaturated fatty acids (PUFAs). 17,18-Epoxyeicosatetraenoic acids (17,18-EEQ) and 19,20-epoxydocosapentaenoic acids (19,20-EDP) are the major EpFAs derived from eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Epoxy-fatty-acids modulate angiogenesis, vascular dilation, inflammation, and cell growth and differentiation, and are implicated in tumor growth and metastasis, cardiovascular disease, diabetes, metabolic syndromes, and pain. Many of the beneficial effects of these EpFAs were potentiated by co-administration of an sEH inhibitor

General

Type : Epoxy-fatty-acid, Epoxide, Fatty acid

Chemical_Nomenclature : (5Z,8Z,11Z,14Z)-16-[(2R,3S)-3-ethyloxiran-2-yl]hexadeca-5,8,11,14-tetraenoic acid, (5Z,8Z,11Z,14Z)-16-[(2S,3R)-3-ethyloxiran-2-yl]hexadeca-5,8,11,14-tetraenoic acid

Canonical SMILES : CCC1C(O1)CC=CCC=CCC=CCC=CCCCC(=O)O

InChI : InChI=1S\/C20H30O3\/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22\/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)\/b5-3-,8-6-,11-9-,14-12-\/t18-,19+\/m0\/s1 || InChI=1S\/C20H30O3\/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22\/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)\/b5-3-,8-6-,11-9-,14-12-\/t18-,19+\/m1\/s1

InChIKey : GPQVVJQEBXAKBJ-VDTDYMMTSA-N || GPQVVJQEBXAKBJ-YQLHGUCYSA-N

Other name(s) : 17,18-Epoxyeicosatetraenoic acid  ||  17R,18S-EpETE  ||  17(R),18(S)-EETeTr  ||  CHEBI:76953  ||  (5Z,8Z,11Z,14Z)-(17R,18S)-17,18-Epoxyicosa-5,8,11,14-tetraenoic acid  ||  17R,18S-epoxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid  ||  CHEMBL1802675  ||  (+\/-)17(18)-EpETE  ||  17(S),18(R)-EETeTr  ||  CHEBI:76955  ||  17,18-EETeTr  ||  17(18)-epoxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid  ||  CHEMBL1802676

MW : 318.4

Formula : C20H30O3

CAS_number :

PubChem : 5282277,    27076755

UniChem : GPQVVJQEBXAKBJ-VDTDYMMTSA-N,    GPQVVJQEBXAKBJ-YQLHGUCYSA-N

Target

Structures : No structure

Families : Epoxide_hydrolase

References (2)

Title : Differential Effects of 17,18-EEQ and 19,20-EDP Combined with Soluble Epoxide Hydrolase Inhibitor t-TUCB on Diet-Induced Obesity in Mice - Yang_2021_Int.J.Mol.Sci_22_
Author(s) : Yang Y , Xu X , Wu H , Yang J , Chen J , Morisseau C , Hammock BD , Bettaieb A , Zhao L
Ref : Int J Mol Sci , 22 : , 2021
Abstract :
PubMedSearch : Yang_2021_Int.J.Mol.Sci_22_
PubMedID: 34361032

Title : Epoxy Fatty Acids Are Promising Targets for Treatment of Pain, Cardiovascular Disease and Other Indications Characterized by Mitochondrial Dysfunction, Endoplasmic Stress and Inflammation - McReynolds_2020_Adv.Exp.Med.Biol_1274_71
Author(s) : McReynolds C , Morisseau C , Wagner K , Hammock B
Ref : Advances in Experimental Medicine & Biology , 1274 :71 , 2020
Abstract :
PubMedSearch : McReynolds_2020_Adv.Exp.Med.Biol_1274_71
PubMedID: 32894508