14,15-EET
Cif (cystic fibrosis transmembrane conductance regulator inhibitory factor) rapidly hydrolyzes 14,15-EET into its cognate diol 14,15-Dihydroxyeicosatrienoic acid
General
Type : Epoxide, Fatty acid, Epoxy-fatty-acid
Chemical_Nomenclature : 13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid
Canonical SMILES : CCCCCC1C(O1)CC=CCC=CCC=CCCCC(=O)O
InChI : InChI=1S\/C20H32O3\/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22\/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)
InChIKey : JBSCUHKPLGKXKH-UHFFFAOYSA-N
Other name(s) : 13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid || 14,15-Epoxy-5,8,11-eicosatrienoic acid || 14(15)-EpETrE || (+\/-)14,15-EPOXYEICOSA-5Z,8Z,11Z-TRIENOIC ACID || 105304-92-5
MW : 320.47
Formula : C20H32O3
CAS_number : 81276-03-1
PubChem : 1431
UniChem : JBSCUHKPLGKXKH-UHFFFAOYSA-N
Target
Structures : 5JYC
Families : Epoxide_hydrolase, CFTR-inhibitory-factor_Cif
References (11)
| Title : Hepatic soluble epoxide hydrolase activity regulates cerebral Abeta metabolism and the pathogenesis of Alzheimer's disease in mice - Wu_2023_Neuron__ |
| Author(s) : Wu Y , Dong JH , Dai YF , Zhu MZ , Wang MY , Zhang Y , Pan YD , Yuan XR , Guo ZX , Wang CX , Li YQ , Zhu XH |
| Ref : Neuron , : , 2023 |
| Abstract : |
| PubMedSearch : Wu_2023_Neuron__ |
| PubMedID: 37402372 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Pseudomonas aeruginosa sabotages the generation of host proresolving lipid mediators - Flitter_2017_Proc.Natl.Acad.Sci.U.S.A_114_136 |
| Author(s) : Flitter BA , Hvorecny KL , Ono E , Eddens T , Yang J , Kwak DH , Bahl CD , Hampton TH , Morisseau C , Hammock BD , Liu X , Lee JS , Kolls JK , Levy BD , Madden DR , Bomberger JM |
| Ref : Proc Natl Acad Sci U S A , 114 :136 , 2017 |
| Abstract : |
| PubMedSearch : Flitter_2017_Proc.Natl.Acad.Sci.U.S.A_114_136 |
| PubMedID: 27980032 |
| Gene_locus related to this paper: pseae-PA2934 |
| Title : Vasopressin lowers renal epoxyeicosatrienoic acid levels by activating soluble epoxide hydrolase - Boldt_2016_Am.J.Physiol.Renal.Physiol_311_F1198 |
| Author(s) : Boldt C , Roeschel T , Himmerkus N , Plain A , Bleich M , Labes R , Blum M , Krause H , Magheli A , Giesecke T , Mutig K , Rothe M , Weldon SM , Dragun D , Schunck WH , Bachmann S , Paliege A |
| Ref : American Journal of Physiology Renal Physiol , :ajprenal 00062 2016 , 2016 |
| Abstract : |
| PubMedSearch : Boldt_2016_Am.J.Physiol.Renal.Physiol_311_F1198 |
| PubMedID: 27681558 |
| Title : Arg287Gln variant of EPHX2 and epoxyeicosatrienoic acids are associated with insulin sensitivity in humans - Ramirez_2014_Prostaglandins.Other.Lipid.Mediat_113-115_38 |
| Author(s) : Ramirez CE , Shuey MM , Milne GL , Gilbert K , Hui N , Yu C , Luther JM , Brown NJ |
| Ref : Prostaglandins Other Lipid Mediat , 113-115 :38 , 2014 |
| Abstract : |
| PubMedSearch : Ramirez_2014_Prostaglandins.Other.Lipid.Mediat_113-115_38 |
| PubMedID: 25173047 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Role of soluble epoxide hydrolase in age-related vascular cognitive decline - Nelson_2014_Prostaglandins.Other.Lipid.Mediat_113-115_30 |
| Author(s) : Nelson JW , Young JM , Borkar RN , Woltjer RL , Quinn JF , Silbert LC , Grafe MR , Alkayed NJ |
| Ref : Prostaglandins Other Lipid Mediat , 113-115 :30 , 2014 |
| Abstract : |
| PubMedSearch : Nelson_2014_Prostaglandins.Other.Lipid.Mediat_113-115_30 |
| PubMedID: 25277097 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides - Decker_2012_J.Lipid.Res_53_2038 |
| Author(s) : Decker M , Adamska M , Cronin A , Di Giallonardo F , Burgener J , Marowsky A , Falck JR , Morisseau C , Hammock BD , Gruzdev A , Zeldin DC , Arand M |
| Ref : J Lipid Res , 53 :2038 , 2012 |
| Abstract : |
| PubMedSearch : Decker_2012_J.Lipid.Res_53_2038 |
| PubMedID: 22798687 |
| Gene_locus related to this paper: human-EPHX3 , human-EPHX4 |
| Title : Polymorphisms in the human soluble epoxide hydrolase gene EPHX2 linked to neuronal survival after ischemic injury - Koerner_2007_J.Neurosci_27_4642 |
| Author(s) : Koerner IP , Jacks R , DeBarber AE , Koop D , Mao P , Grant DF , Alkayed NJ |
| Ref : Journal of Neuroscience , 27 :4642 , 2007 |
| Abstract : |
| PubMedSearch : Koerner_2007_J.Neurosci_27_4642 |
| PubMedID: 17460077 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Effect of soluble epoxide hydrolase inhibition on epoxyeicosatrienoic acid metabolism in human blood vessels - Fang_2004_Am.J.Physiol.Heart.Circ.Physiol_287_H2412 |
| Author(s) : Fang X , Weintraub NL , McCaw RB , Hu S , Harmon SD , Rice JB , Hammock BD , Spector AA |
| Ref : American Journal of Physiology Heart Circ Physiol , 287 :H2412 , 2004 |
| Abstract : |
| PubMedSearch : Fang_2004_Am.J.Physiol.Heart.Circ.Physiol_287_H2412 |
| PubMedID: 15284062 |
| Title : Pathways of epoxyeicosatrienoic acid metabolism in endothelial cells. Implications for the vascular effects of soluble epoxide hydrolase inhibition - Fang_2001_J.Biol.Chem_276_14867 |
| Author(s) : Fang X , Kaduce TL , Weintraub NL , Harmon S , Teesch LM , Morisseau C , Thompson DA , Hammock BD , Spector AA |
| Ref : Journal of Biological Chemistry , 276 :14867 , 2001 |
| Abstract : |
| PubMedSearch : Fang_2001_J.Biol.Chem_276_14867 |
| PubMedID: 11278979 |
| Title : Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids - Yu_2000_Circ.Res_87_992 |
| Author(s) : Yu Z , Xu F , Huse LM , Morisseau C , Draper AJ , Newman JW , Parker C , Graham L , Engler MM , Hammock BD , Zeldin DC , Kroetz DL |
| Ref : Circulation Research , 87 :992 , 2000 |
| Abstract : |
| PubMedSearch : Yu_2000_Circ.Res_87_992 |
| PubMedID: 11090543 |
| Title : Epoxide hydrolases regulate epoxyeicosatrienoic acid incorporation into coronary endothelial phospholipids - Weintraub_1999_Am.J.Physiol_277_H2098 |
| Author(s) : Weintraub NL , Fang X , Kaduce TL , VanRollins M , Chatterjee P , Spector AA |
| Ref : American Journal of Physiology , 277 :H2098 , 1999 |
| Abstract : |
| PubMedSearch : Weintraub_1999_Am.J.Physiol_277_H2098 |
| PubMedID: 10564166 |