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81246-84-6 | 2-Oxiranebutanoic acid,3-(2,5,8-tetradecatrien-1-yl)-
CAS No: 81246-84-6 Catalog No: AG004Z50 MDL No:
Product Description
Catalog Number:
AG004Z50
Chemical Name:
2-Oxiranebutanoic acid,3-(2,5,8-tetradecatrien-1-yl)-
CAS Number:
81246-84-6
Molecular Formula:
C20H32O3
Molecular Weight:
320.4663
IUPAC Name:
4-(3-tetradeca-2,5,8-trienyloxiran-2-yl)butanoic acid
InChI:
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)
InChI Key:
VBQNSZQZRAGRIX-UHFFFAOYSA-N
SMILES:
CCCCC/C=C\C/C=C\C/C=C\CC1OC1CCCC(=O)O
Properties
Complexity:
396
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
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:
3
XLogP3:
5.5
Literature
| Title | Journal |
|---|---|
| 5,6-EET is released upon neuronal activity and induces mechanical pain hypersensitivity via TRPA1 on central afferent terminals. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20120502 |
| Paraoxonase1 deficiency in mice is associated with hypotension and increased levels of 5,6-epoxyeicosatrienoic acid. | Atherosclerosis 20120501 |
| A cytochrome P450-derived epoxygenated metabolite of anandamide is a potent cannabinoid receptor 2-selective agonist. | Molecular pharmacology 20090401 |
| Role of cytochrome P450-dependent transient receptor potential V4 activation in flow-induced vasodilatation. | Cardiovascular research 20081201 |
| Arachidonic acid metabolites inhibit the stimulatory effect of angiotensin II in renal proximal tubules. | Hypertension research : official journal of the Japanese Society of Hypertension 20081201 |
| Transient receptor potential vanilloid 4 mediates protease activated receptor 2-induced sensitization of colonic afferent nerves and visceral hyperalgesia. | American journal of physiology. Gastrointestinal and liver physiology 20080501 |
| Cyclooxygenase (COX)-1 and COX-2 participate in 5,6-epoxyeicosatrienoic acid-induced contraction of rabbit intralobar pulmonary arteries. | The Journal of pharmacology and experimental therapeutics 20070501 |
| Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. | The Journal of pharmacology and experimental therapeutics 20070501 |
| Determinants of 4 alpha-phorbol sensitivity in transmembrane domains 3 and 4 of the cation channel TRPV4. | The Journal of biological chemistry 20070427 |
| Acute tissue-type plasminogen activator release in human microvascular endothelial cells: the roles of Galphaq, PLC-beta, IP3 and 5,6-epoxyeicosatrienoic acid. | Thrombosis and haemostasis 20070201 |
| 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 |
| Chiral resolution of the epoxyeicosatrienoic acids, arachidonic acid epoxygenase metabolites. | Analytical biochemistry 20060501 |
| Glial cells dilate and constrict blood vessels: a mechanism of neurovascular coupling. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20060315 |
| A role for 5,6-epoxyeicosatrienoic acid in calcium entry by de novo conformational coupling in human platelets. | The Journal of physiology 20060115 |
| Modulation of the Ca2 permeable cation channel TRPV4 by cytochrome P450 epoxygenases in vascular endothelium. | Circulation research 20051028 |
| 5,6-EET-induced contraction of intralobar pulmonary arteries depends on the activation of Rho-kinase. | Journal of applied physiology (Bethesda, Md. : 1985) 20051001 |
| Cytochrome P450/NADPH-dependent biosynthesis of 5,6-trans-epoxyeicosatrienoic acid from 5,6-trans-arachidonic acid. | The Biochemical journal 20050915 |
| 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 |
| Stereospecific synthesis and mass spectrometry of 5,6-trans-epoxy-8Z,11Z,14Z-eicosatrienoic acid. | Bioorganic & medicinal chemistry letters 20050615 |
| Stable 5,6-epoxyeicosatrienoic acid analog relaxes coronary arteries through potassium channel activation. | Hypertension (Dallas, Tex. : 1979) 20050401 |
| 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 |
| Identification of 5,6-trans-epoxyeicosatrienoic acid in the phospholipids of red blood cells. | The Journal of biological chemistry 20040827 |
| 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 |
| 5,6-epoxyeicosatrienoic acid mediates the enhanced renal vasodilation to arachidonic acid in the SHR. | Hypertension (Dallas, Tex. : 1979) 20031001 |
| 14,15-epoxyeicosa-5(Z)-enoic-mSI: a 14,15- and 5,6-EET antagonist in bovine coronary arteries. | Hypertension (Dallas, Tex. : 1979) 20031001 |
| Differential effects of 5,6-EET on segmental pulmonary vasoactivity in the rabbit. | American journal of physiology. Heart and circulatory physiology 20030601 |
| HETEs/EETs in renal glomerular and epithelial cell functions. | Current opinion in pharmacology 20030401 |
| The regulation of arachidonic acid metabolism in human first trimester trophoblast by cyclic AMP. | Prostaglandins & other lipid mediators 20030401 |
| Cerebral capillary endothelial cell mitogenesis and morphogenesis induced by astrocytic epoxyeicosatrienoic Acid. | Stroke 20021201 |
| Suppression of cortical functional hyperemia to vibrissal stimulation in the rat by epoxygenase inhibitors. | American journal of physiology. Heart and circulatory physiology 20021101 |
| Role of 5,6-epoxyeicosatrienoic acid in the regulation of newborn piglet pulmonary vascular tone. | American journal of physiology. Lung cellular and molecular physiology 20020801 |
| The production of progesterone and 5,6-epoxyeicosatrienoic acid by human granulosa cells. | The Journal of steroid biochemistry and molecular biology 20020801 |
| 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 |
| Calcium influx factor from cytochrome P-450 metabolism and secretion-like coupling mechanisms for capacitative calcium entry in corneal endothelial cells. | The Journal of biological chemistry 20020510 |
| 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 |
| Stereospecific synthesis of trans-arachidonic acids. | Bioorganic & medicinal chemistry letters 20010917 |
| Nitric oxide synthase activity in neutrophils from patients with localized aggressive periodontitis. | Journal of periodontology 20010801 |
| Mediation of EDHF-induced reduction of smooth muscle [Ca(2+)](i) and arteriolar dilation by K(+) channels, 5,6-EET, and gap junctions. | Microcirculation (New York, N.Y. : 1994) 20010801 |
| Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids. | The Journal of biological chemistry 20010511 |
| Gap junction-dependent increases in smooth muscle cAMP underpin the EDHF phenomenon in rabbit arteries. | Biochemical and biophysical research communications 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 |
| The lung HETEs (and EETs) up. | American journal of physiology. Heart and circulatory physiology 20010101 |
| Dual regulation of the cerebral microvasculature by epoxyeicosatrienoic acids. | Trends in cardiovascular medicine 20010101 |
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