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Substrate Report for: 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 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
IUPHAR|
Wikipedia|

Target
Families | 19,20-EDP ligand of proteins in family: CFTR-inhibitory-factor_Cif, Epoxide_hydrolase
Stucture | 1 structure: 5TNF: Crystal structure of the E153Q mutant of the CFTR inhibitory factor Cif containing the adducted 19,20-EDP (epoxy-docosapentaenoic acid)
Protein | pseae-PA2934, mouse-hyes

References:
Search PubMed for references concerning: 19,20-EDP
    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 Y, Xu X, Wu H, Yang J, Chen J, Morisseau C, Hammock BD, Bettaieb A, Zhao L
    Ref: Int J Mol Sci, 22:, 2021 : PubMed

            

    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 C, Morisseau C, Wagner K, Hammock B
    Ref: Advances in Experimental Medicine & Biology, 1274:71, 2020 : PubMed

            

    Title: Active-Site Flexibility and Substrate Specificity in a Bacterial Virulence Factor: Crystallographic Snapshots of an Epoxide Hydrolase
    Hvorecny KL, Bahl CD, Kitamura S, Lee KSS, Hammock BD, Morisseau C, Madden DR
    Ref: Structure, 25:697, 2017 : PubMed