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19,20-EDP

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 : Epoxide, Epoxy-fatty-acid, Fatty acid

Chemical_Nomenclature : (4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid

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

InChI : InChI=1S\/C22H32O3\/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24\/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)\/b4-3-,9-7-,10-8-,15-13-,16-14-

InChIKey : OSXOPUBJJDUAOJ-MBYQGORISA-N

Other name(s) : 19(20)-EpDPE  ||  19(20)-EpDPA  ||  (+\/-)-19(20)-epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid  ||  Epox 22:6n3  ||  19(20)-epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid  ||  19(20)-EpDoPE  ||  SCHEMBL3411078

MW : 344.49

Formula : C22H32O3

CAS_number :

PubChem : 11631565

UniChem : OSXOPUBJJDUAOJ-MBYQGORISA-N

Target

Structures : 5TNF

Families : CFTR-inhibitory-factor_Cif, Epoxide_hydrolase

References (3)

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

Title : Active-Site Flexibility and Substrate Specificity in a Bacterial Virulence Factor: Crystallographic Snapshots of an Epoxide Hydrolase - Hvorecny_2017_Structure_25_697
Author(s) : Hvorecny KL , Bahl CD , Kitamura S , Lee KSS , Hammock BD , Morisseau C , Madden DR
Ref : Structure , 25 :697 , 2017
Abstract :
PubMedSearch : Hvorecny_2017_Structure_25_697
PubMedID: 28392259
Gene_locus related to this paper: pseae-PA2934