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81246-85-7 | (+)8,9-Epoxyeicosa-8z,11z,14z trienoic acid
CAS No: 81246-85-7 Catalog No: AG005F37 MDL No:MFCD00065840
Product Description
Catalog Number:
AG005F37
Chemical Name:
(+)8,9-Epoxyeicosa-8z,11z,14z trienoic acid
CAS Number:
81246-85-7
Molecular Formula:
C20H32O3
Molecular Weight:
320.4663
MDL Number:
MFCD00065840
IUPAC Name:
(E)-7-[3-[(2E,5E)-undeca-2,5-dienyl]oxiran-2-yl]hept-5-enoic acid
InChI:
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6+,12-9+,13-10+
InChI Key:
DBWQSCSXHFNTMO-QPZDSRGTSA-N
SMILES:
CCCCC/C=C/C/C=C/CC1OC1C/C=C/CCCC(=O)O
Properties
Complexity:
396
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
3
Exact Mass:
320.235g/mol
Formal Charge:
0
Heavy Atom Count:
23
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
320.473g/mol
Monoisotopic Mass:
320.235g/mol
Rotatable Bond Count:
14
Topological Polar Surface Area:
49.8A^2
Undefined Atom Stereocenter Count:
2
Undefined Bond Stereocenter Count:
0
XLogP3:
5.4
Literature
| Title | Journal |
|---|---|
| Beyond detoxification: a role for mouse mEH in the hepatic metabolism of endogenous lipids. | Archives of toxicology 20170101 |
| Targeting of splice variants of human cytochrome P450 2C8 (CYP2C8) to mitochondria and their role in arachidonic acid metabolism and respiratory dysfunction. | The Journal of biological chemistry 20141024 |
| A soluble epoxide hydrolase inhibitor--8-HUDE increases pulmonary vasoconstriction through inhibition of K(ATP) channels. | Pulmonary pharmacology & therapeutics 20120201 |
| 8,9-Epoxyeicosatrienoic acid inhibits antibody production of B lymphocytes in mice. | PloS one 20120101 |
| Effects of cytochrome P-450 metabolites of arachidonic acid on the epithelial sodium channel (ENaC). | American journal of physiology. Renal physiology 20110901 |
| Increases in plasma trans-EETs and blood pressure reduction in spontaneously hypertensive rats. | American journal of physiology. Heart and circulatory physiology 20110601 |
| Soluble epoxide hydrolase limits mechanical hyperalgesia during inflammation. | Molecular pain 20110101 |
| 8,9-Epoxyeicosatrienoic acid analog protects pulmonary artery smooth muscle cells from apoptosis via ROCK pathway. | Experimental cell research 20100815 |
| Inhibition of soluble epoxide hydrolase enhances the anti-inflammatory effects of aspirin and 5-lipoxygenase activation protein inhibitor in a murine model. | Biochemical pharmacology 20100315 |
| Rapid, simultaneous quantitation of mono and dioxygenated metabolites of arachidonic acid in human CSF and rat brain. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091201 |
| 8,9-Epoxyeicosatrienoic acid protects the glomerular filtration barrier. | Prostaglandins & other lipid mediators 20090601 |
| [Promotive effects of epoxyeicosatrienoic acids (EETs) on proliferation of tumor cells]. | Ai zheng = Aizheng = Chinese journal of cancer 20081101 |
| Cytochrome P450 (CYP) 2J2 gene transfection attenuates MMP-9 via inhibition of NF-kappabeta in hyperhomocysteinemia. | Journal of cellular physiology 20080601 |
| Determinants of 4 alpha-phorbol sensitivity in transmembrane domains 3 and 4 of the cation channel TRPV4. | The Journal of biological chemistry 20070427 |
| Mechanisms by which epoxyeicosatrienoic acids (EETs) elicit cardioprotection in rat hearts. | Journal of molecular and cellular cardiology 20070301 |
| Regulation of endothelial nitric-oxide synthase activity through phosphorylation in response to epoxyeicosatrienoic acids. | Prostaglandins & other lipid mediators 20070101 |
| Rat mesenteric arterial dilator response to 11,12-epoxyeicosatrienoic acid is mediated by activating heme oxygenase. | American journal of physiology. Heart and circulatory physiology 20061001 |
| Inhibition of ATP binding to the carboxyl terminus of Kir6.2 by epoxyeicosatrienoic acids. | Biochimica et biophysica acta 20060901 |
| Chiral resolution of the epoxyeicosatrienoic acids, arachidonic acid epoxygenase metabolites. | Analytical biochemistry 20060501 |
| Modulation of the Ca2 permeable cation channel TRPV4 by cytochrome P450 epoxygenases in vascular endothelium. | Circulation research 20051028 |
| Effects of epoxyeicosatrienoic acids on levels of eNOS phosphorylation and relevant signaling transduction pathways involved. | Science in China. Series C, Life sciences 20051001 |
| Chick chorioallantoic membrane as an in vivo model to study vasoreactivity: characterization of development-dependent hyperemia induced by epoxyeicosatrienoic acids (EETs). | The anatomical record. Part A, Discoveries in molecular, cellular, and evolutionary biology 20050801 |
| Characterization of 5,6- and 8,9-epoxyeicosatrienoic acids (5,6- and 8,9-EET) as potent in vivo angiogenic lipids. | The Journal of biological chemistry 20050722 |
| Molecular determinants of cardiac K(ATP) channel activation by epoxyeicosatrienoic acids. | The Journal of biological chemistry 20050513 |
| Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoids. | Archives of biochemistry and biophysics 20050115 |
| Activation of rat mesenteric arterial KATP channels by 11,12-epoxyeicosatrienoic acid. | American journal of physiology. Heart and circulatory physiology 20050101 |
| Membrane-potential-dependent inhibition of platelet adhesion to endothelial cells by epoxyeicosatrienoic acids. | Arteriosclerosis, thrombosis, and vascular biology 20040301 |
| Role of EETs in regulation of endothelial permeability in rat lung. | American journal of physiology. Lung cellular and molecular physiology 20040201 |
| Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR). | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030401 |
| Mediation of arachidonic acid metabolite(s) produced by endothelial cytochrome P-450 3A4 in monkey arterial relaxation. | Hypertension research : official journal of the Japanese Society of Hypertension 20030301 |
| Cerebral capillary endothelial cell mitogenesis and morphogenesis induced by astrocytic epoxyeicosatrienoic Acid. | Stroke 20021201 |
| 14,15-Epoxyeicosa-5(Z)-enoic acid: a selective epoxyeicosatrienoic acid antagonist that inhibits endothelium-dependent hyperpolarization and relaxation in coronary arteries. | Circulation research 20020517 |
| Functional reconstitution of an eicosanoid-modulated Cl- channel from bovine tracheal smooth muscle. | American journal of physiology. Cell physiology 20020301 |
| Development of enzyme immunoassays for 5,6-, 8,9-, 11,12-, and 14,15- EETs and the corresponding DHETs. | Advances in experimental medicine and biology 20020101 |
| Activation of ATP-sensitive K(+) channels by epoxyeicosatrienoic acids in rat cardiac ventricular myocytes. | The Journal of physiology 20011215 |
| Stereospecific synthesis of trans-arachidonic acids. | Bioorganic & medicinal chemistry letters 20010917 |
| EET homologs potently dilate coronary microvessels and activate BK(Ca) channels. | American journal of physiology. Heart and circulatory physiology 20010601 |
| Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids. | The Journal of biological chemistry 20010511 |
| EETs relax airway smooth muscle via an EpDHF effect: BK(Ca) channel activation and hyperpolarization. | American journal of physiology. Lung cellular and molecular physiology 20010501 |
| Enhanced renal microvascular reactivity to angiotensin II in hypertension is ameliorated by the sulfonimide analog of 11,12-epoxyeicosatrienoic acid. | Journal of hypertension 20010501 |
| Epoxyeicosatrienoic acid-mediated renal vasodilation to arachidonic acid is enhanced in SHR. | Hypertension (Dallas, Tex. : 1979) 20010301 |
| Dual regulation of the cerebral microvasculature by epoxyeicosatrienoic acids. | Trends in cardiovascular medicine 20010101 |
| Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. | Circulation research 20001124 |
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