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 (15)
| Title : Effects of 17,18-Epoxyeicosatetraenoic Acid and 19,20-Epoxydocosapentaenoic Acid Combined with Soluble Epoxide Hydrolase Inhibitor t-TUCB on Brown Adipogenesis and Mitochondrial Respiration - Yang_2025_Nutrients_17_936 |
| Author(s) : Yang Y , Wu H , Xu X , Morisseau C , Lee KSS , Hammock BD , Chen J , Zhao L |
| Ref : Nutrients , 17 :936 , 2025 |
| Abstract : |
| PubMedSearch : Yang_2025_Nutrients_17_936 |
| PubMedID: 40289939 |
| Title : Endothelial soluble epoxide hydrolase links polyunsaturated fatty acid metabolism to oxidative stress and atherosclerosis progression - Cao_2025_Redox.Biol_85_103730 |
| Author(s) : Cao M , Li M , Li X , Li Y , Chen Y , Drekolia MK , Cheng X , Lagos FD , Bibli SI , Hu J |
| Ref : Redox Biol , 85 :103730 , 2025 |
| Abstract : |
| PubMedSearch : Cao_2025_Redox.Biol_85_103730 |
| PubMedID: 40554101 |
| Gene_locus related to this paper: human-EPHX2 , mouse-hyes |
| Title : Endothelial soluble epoxide hydrolase links polyunsaturated fatty acid metabolism to oxidative stress and atherosclerosis progression - Cao_2025_Redox.Biol_85_103730 |
| Author(s) : Cao M , Li M , Li X , Li Y , Chen Y , Drekolia MK , Cheng X , Lagos FD , Bibli SI , Hu J |
| Ref : Redox Biol , 85 :103730 , 2025 |
| Abstract : |
| PubMedSearch : Cao_2025_Redox.Biol_85_103730 |
| PubMedID: 40554101 |
| Gene_locus related to this paper: human-EPHX2 , mouse-hyes |
| Title : Effects of 17,18-Epoxyeicosatetraenoic Acid and 19,20-Epoxydocosapentaenoic Acid Combined with Soluble Epoxide Hydrolase Inhibitor t-TUCB on Brown Adipogenesis and Mitochondrial Respiration - Yang_2025_Nutrients_17_936 |
| Author(s) : Yang Y , Wu H , Xu X , Morisseau C , Lee KSS , Hammock BD , Chen J , Zhao L |
| Ref : Nutrients , 17 :936 , 2025 |
| Abstract : |
| PubMedSearch : Yang_2025_Nutrients_17_936 |
| PubMedID: 40289939 |
| Title : Endothelial soluble epoxide hydrolase links polyunsaturated fatty acid metabolism to oxidative stress and atherosclerosis progression - Cao_2025_Redox.Biol_85_103730 |
| Author(s) : Cao M , Li M , Li X , Li Y , Chen Y , Drekolia MK , Cheng X , Lagos FD , Bibli SI , Hu J |
| Ref : Redox Biol , 85 :103730 , 2025 |
| Abstract : |
| PubMedSearch : Cao_2025_Redox.Biol_85_103730 |
| PubMedID: 40554101 |
| Gene_locus related to this paper: human-EPHX2 , mouse-hyes |
| Title : Effects of 17,18-Epoxyeicosatetraenoic Acid and 19,20-Epoxydocosapentaenoic Acid Combined with Soluble Epoxide Hydrolase Inhibitor t-TUCB on Brown Adipogenesis and Mitochondrial Respiration - Yang_2025_Nutrients_17_936 |
| Author(s) : Yang Y , Wu H , Xu X , Morisseau C , Lee KSS , Hammock BD , Chen J , Zhao L |
| Ref : Nutrients , 17 :936 , 2025 |
| Abstract : |
| PubMedSearch : Yang_2025_Nutrients_17_936 |
| PubMedID: 40289939 |
| 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 : 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 : 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 : 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 : 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 |
| 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 |
| 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 |