Coronaric-acid
(CYP2C/CYP2J) CYP-derived oxidized linoleic acid metabolite epoxy octadecenoic acid. The epoxide is transformed in the diol by soluble epoxide hydrolse (sEH EPHX2) the resulting 9,10-DiHOME (12,13-DiHOME ) mediates thermal hyperalgesia during inflammatory pain (9,10-DiHOME) 12,13-DiHOME induces thermal pain hypersensitivity via TRPV1
General
Type : Epoxide, Fatty acid, Epoxy-fatty-acid
Chemical_Nomenclature : 8-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]octanoic acid, 8-[3-[(Z)-oct-2-enyl]oxiran-2-yl]octanoic acid
Canonical SMILES : CCCCCC=CCC1C(O1)CCCCCCCC(=O)O
InChI : InChI=1S\/C18H32O3\/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20\/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)\/b10-7-\/t16-,17+\/m0\/s1 || InChI=1S\/C18H32O3\/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20\/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)\/b10-7-
InChIKey : FBUKMFOXMZRGRB-SQGUUQMOSA-N || FBUKMFOXMZRGRB-YFHOEESVSA-N
Other name(s) : 9R,10S-EpOME || Leukotoxin || (9R,10S)-(12Z)-9,10-Epoxyoctadecenoic acid || 9R,10S-epoxy-12Z-octadecenoic acid || 9(10)-EpOME || AC1NSTU0 || UNII-7U94YS1WZ0 || LEUKOTOXIN A || Coronaric acid || 9,10-epoxy-12Z-octadecenoic acid || 9,10-Epoxyoctadecenoic acid || CHEBI:34494 || SCHEMBL2566928 || CHEMBL1903868 || Coronarsaeure || (+)-CORONARIC ACID || (?)9(10)-EpOME || 8-(3-oct-2-enyloxiran-2-yl)octanoic acid || cis-9,10-Epoxy-12(Z)-octadecenoic acid
MW : 296.45
Formula : C18H32O3
CAS_number :
PubChem : 5316080, 6246154, 12097313, 1929
UniChem : FBUKMFOXMZRGRB-SQGUUQMOSA-N, FBUKMFOXMZRGRB-YFHOEESVSA-N
Target
Structures : No structure
Families : Epoxide_hydrolase
References (12)
| Title : Epoxide hydrolase 3 (Ephx3) gene disruption reduces ceramide linoleate epoxide hydrolysis and impairs skin barrier function - Edin_2021_J.Biol.Chem_296_100198 |
| Author(s) : Edin ML , Yamanashi H , Boeglin WE , Graves JP , DeGraff LM , Lih FB , Zeldin DC , Brash AR |
| Ref : Journal of Biological Chemistry , 296 :100198 , 2021 |
| Abstract : |
| PubMedSearch : Edin_2021_J.Biol.Chem_296_100198 |
| PubMedID: 33334892 |
| Gene_locus related to this paper: human-EPHX3 , mouse-ephx3 |
| Title : Epoxide hydrolase 3 (Ephx3) gene disruption reduces ceramide linoleate epoxide hydrolysis and impairs skin barrier function - Edin_2021_J.Biol.Chem_296_100198 |
| Author(s) : Edin ML , Yamanashi H , Boeglin WE , Graves JP , DeGraff LM , Lih FB , Zeldin DC , Brash AR |
| Ref : Journal of Biological Chemistry , 296 :100198 , 2021 |
| Abstract : |
| PubMedSearch : Edin_2021_J.Biol.Chem_296_100198 |
| PubMedID: 33334892 |
| Gene_locus related to this paper: human-EPHX3 , mouse-ephx3 |
| Title : Epoxide hydrolase 3 (Ephx3) gene disruption reduces ceramide linoleate epoxide hydrolysis and impairs skin barrier function - Edin_2021_J.Biol.Chem_296_100198 |
| Author(s) : Edin ML , Yamanashi H , Boeglin WE , Graves JP , DeGraff LM , Lih FB , Zeldin DC , Brash AR |
| Ref : Journal of Biological Chemistry , 296 :100198 , 2021 |
| Abstract : |
| PubMedSearch : Edin_2021_J.Biol.Chem_296_100198 |
| PubMedID: 33334892 |
| Gene_locus related to this paper: human-EPHX3 , mouse-ephx3 |
| Title : The oxidized linoleic acid metabolite 12,13-DiHOME mediates thermal hyperalgesia during inflammatory pain - Zimmer_2018_Biochim.Biophys.Acta_1863_669 |
| Author(s) : Zimmer B , Angioni C , Osthues T , Toewe A , Thomas D , Pierre SC , Geisslinger G , Scholich K , Sisignano M |
| Ref : Biochimica & Biophysica Acta , 1863 :669 , 2018 |
| Abstract : |
| PubMedSearch : Zimmer_2018_Biochim.Biophys.Acta_1863_669 |
| PubMedID: 29625231 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : The oxidized linoleic acid metabolite 12,13-DiHOME mediates thermal hyperalgesia during inflammatory pain - Zimmer_2018_Biochim.Biophys.Acta_1863_669 |
| Author(s) : Zimmer B , Angioni C , Osthues T , Toewe A , Thomas D , Pierre SC , Geisslinger G , Scholich K , Sisignano M |
| Ref : Biochimica & Biophysica Acta , 1863 :669 , 2018 |
| Abstract : |
| PubMedSearch : Zimmer_2018_Biochim.Biophys.Acta_1863_669 |
| PubMedID: 29625231 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : The oxidized linoleic acid metabolite 12,13-DiHOME mediates thermal hyperalgesia during inflammatory pain - Zimmer_2018_Biochim.Biophys.Acta_1863_669 |
| Author(s) : Zimmer B , Angioni C , Osthues T , Toewe A , Thomas D , Pierre SC , Geisslinger G , Scholich K , Sisignano M |
| Ref : Biochimica & Biophysica Acta , 1863 :669 , 2018 |
| Abstract : |
| PubMedSearch : Zimmer_2018_Biochim.Biophys.Acta_1863_669 |
| PubMedID: 29625231 |
| 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 : 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 : 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 : Development of a semi-automated LC\/MS\/MS method for the simultaneous quantitation of 14,15-epoxyeicosatrienoic acid, 14,15-dihydroxyeicosatrienoic acid, leukotoxin and leukotoxin diol in human plasma as biomarkers of soluble epoxide hydrolase activity in vivo - Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2487 |
| Author(s) : Zhu P , Peck B , Licea-Perez H , Callahan JF , Booth-Genthe C |
| Ref : Journal of Chromatography B Analyt Technol Biomed Life Sciences , 879 :2487 , 2011 |
| Abstract : |
| PubMedSearch : Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2487 |
| PubMedID: 21798825 |
| Title : Development of a semi-automated LC\/MS\/MS method for the simultaneous quantitation of 14,15-epoxyeicosatrienoic acid, 14,15-dihydroxyeicosatrienoic acid, leukotoxin and leukotoxin diol in human plasma as biomarkers of soluble epoxide hydrolase activity in vivo - Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2487 |
| Author(s) : Zhu P , Peck B , Licea-Perez H , Callahan JF , Booth-Genthe C |
| Ref : Journal of Chromatography B Analyt Technol Biomed Life Sciences , 879 :2487 , 2011 |
| Abstract : |
| PubMedSearch : Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2487 |
| PubMedID: 21798825 |
| Title : Development of a semi-automated LC\/MS\/MS method for the simultaneous quantitation of 14,15-epoxyeicosatrienoic acid, 14,15-dihydroxyeicosatrienoic acid, leukotoxin and leukotoxin diol in human plasma as biomarkers of soluble epoxide hydrolase activity in vivo - Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2487 |
| Author(s) : Zhu P , Peck B , Licea-Perez H , Callahan JF , Booth-Genthe C |
| Ref : Journal of Chromatography B Analyt Technol Biomed Life Sciences , 879 :2487 , 2011 |
| Abstract : |
| PubMedSearch : Zhu_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2487 |
| PubMedID: 21798825 |