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149301-79-1

149301-79-1 | 6,9,12,15-Heneicosatetraen-2-one, 1,1,1-trifluoro-, (6Z,9Z,12Z,15Z)-

CAS No: 149301-79-1 Catalog No: AG001LK2 MDL No:MFCD00236427

Product Description

Catalog Number:
AG001LK2
Chemical Name:
6,9,12,15-Heneicosatetraen-2-one, 1,1,1-trifluoro-, (6Z,9Z,12Z,15Z)-
CAS Number:
149301-79-1
Molecular Formula:
C21H31F3O
Molecular Weight:
356.4654
MDL Number:
MFCD00236427
IUPAC Name:
(6Z,9Z,12Z,15Z)-1,1,1-trifluorohenicosa-6,9,12,15-tetraen-2-one
InChI:
InChI=1S/C21H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(25)21(22,23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI Key:
PLWROONZUDKYKG-DOFZRALJSA-N
SMILES:
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F
UNII:
00XIW1CR0F

Properties

Complexity:
443  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
4  
Exact Mass:
356.233g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
356.473g/mol
Monoisotopic Mass:
356.233g/mol
Rotatable Bond Count:
14  
Topological Polar Surface Area:
17.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.6  

Literature

Title Journal
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Inhibition of cytosolic phospholipase A(2) alpha protects against focal ischemic brain damage in mice. Brain research 20120830
Involvement of protein kinase A activation and phospholipase A(2) inhibition in the adenosine-activated basolateral 50 pS K(+) channels in the thick ascending limb of the rat kidney. Sheng li xue bao : [Acta physiologica Sinica] 20120825
Cysteinyl leukotrienes mediate the response of submucosal ganglia from rat colon to bradykinin. European journal of pharmacology 20120415
Stimulation of Ca2+-sensing receptor inhibits the basolateral 50-pS K channels in the thick ascending limb of rat kidney. Biochimica et biophysica acta 20120201
Arachidonyl trifluoromethyl ketone ameliorates experimental autoimmune encephalomyelitis via blocking peroxynitrite formation in mouse spinal cord white matter. Experimental neurology 20110901
Cytosolic phospholipase A2 as a molecular target for the radiosensitization of ovarian cancer. Cancer letters 20110528
Stimulation of A(₂a) adenosine receptor abolishes the inhibitory effect of arachidonic acid on the basolateral 50-pS K channel in the thick ascending limb. American journal of physiology. Renal physiology 20110401
Structure-activity relationship studies on 1-(5-carboxyindol-1-yl)-propan-2-one inhibitors of human cytosolic phospholipase A2α: variation of the activated ketone moiety. Bioorganic & medicinal chemistry letters 20110315
Delayed production of arachidonic acid contributes to the delay of proteinase-activated receptor-1 (PAR1)-triggered prostaglandin E2 release in rat gastric epithelial RGM1 cells. Journal of cellular biochemistry 20110301
COX-2 inhibition and inhibition of cytosolic phospholipase A2 increase CD36 expression and foam cell formation in THP-1 cells. Lipids 20110201
Peroxisome proliferation activation receptor alpha modulation of Ca2+-regulated exocytosis via arachidonic acid in guinea-pig antral mucous cells. Experimental physiology 20100801
TLR4-dependent induction of vascular adhesion molecule-1 in rheumatoid arthritis synovial fibroblasts: Roles of cytosolic phospholipase A(2)alpha/cyclooxygenase-2. Journal of cellular physiology 20100501
Evidence for de novo synthesis of lysophosphatidic acid in the spinal cord through phospholipase A2 and autotaxin in nerve injury-induced neuropathic pain. The Journal of pharmacology and experimental therapeutics 20100501
Nanomolar vitamin E alpha-tocotrienol inhibits glutamate-induced activation of phospholipase A2 and causes neuroprotection. Journal of neurochemistry 20100301
1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A(2)alpha and fatty acid amide hydrolase. Bioorganic & medicinal chemistry 20100115
Cytosolic phospholipase A2alpha mediates Pseudomonas aeruginosa LPS-induced airway constriction of CFTR -/- mice. Respiratory research 20100101
Mechanism underlying endothelium-dependent relaxation by 2-methylthio-ADP in monkey cerebral artery. Journal of pharmacological sciences 20100101
Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors. Journal of medicinal chemistry 20091210
Group IVA phospholipase A(2) activity may mediate prostaglandin F(2alpha)-induced luteal regression in pseudopregnant rats. Prostaglandins & other lipid mediators 20091201
Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors. Journal of medicinal chemistry 20091126
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Characterization of the pattern of the nongenomic signaling pathway through which TCDD-induces early inflammatory responses in U937 human macrophages. Chemosphere 20090301
Cytosolic phospholipase A2: targeting cancer through the tumor vasculature. Clinical cancer research : an official journal of the American Association for Cancer Research 20090301
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Initial and extended inflammatory messages of the nongenomic signaling pathway of the TCDD-activated Ah receptor in U937 macrophages. Archives of biochemistry and biophysics 20081215
Ca2+-independent PLA2 controls endothelial store-operated Ca2+ entry and vascular tone in intact aorta. American journal of physiology. Heart and circulatory physiology 20081201
Simultaneous stimulation of spinal NK1 and NMDA receptors produces LPC which undergoes ATX-mediated conversion to LPA, an initiator of neuropathic pain. Journal of neurochemistry 20081201
Inhibition of cyclooxygenases 1 and 2 by the phospholipase-blocker, arachidonyl trifluoromethyl ketone. British journal of pharmacology 20081101
Phospholipase A2 reduction ameliorates cognitive deficits in a mouse model of Alzheimer's disease. Nature neuroscience 20081101
Identification and functional characterization of adipose-specific phospholipase A2 (AdPLA). The Journal of biological chemistry 20080912
[Suppression of cell proliferation by inhibitors to redox signaling in human lens epithelial cells]. [Zhonghua yan ke za zhi] Chinese journal of ophthalmology 20080701
Tumour necrosis factor alpha upregulates platelet CD40L in patients with heart failure. Cardiovascular research 20080601
Activation of cytosolic phospholipase A2 and fatty acid transacylase is essential but not sufficient for thrombin-induced smooth muscle cell proliferation. American journal of physiology. Cell physiology 20080601
Cytochrome P-450 metabolites of 2-arachidonoylglycerol play a role in Ca2+-induced relaxation of rat mesenteric arteries. American journal of physiology. Heart and circulatory physiology 20080501
Cytosolic phospholipase A2 and arachidonic acid metabolites modulate ventilator-induced permeability increases in isolated mouse lungs. Journal of applied physiology (Bethesda, Md. : 1985) 20080201
Evidence that PAR2-triggered prostaglandin E2 (PGE2) formation involves the ERK-cytosolic phospholipase A2-COX-1-microsomal PGE synthase-1 cascade in human lung epithelial cells. Cell biochemistry and function 20080101
Arachidonic acid as a retrograde signal controlling growth and dynamics of retinotectal arbors. Developmental neurobiology 20080101
STAT5 mediates PAF-induced NADPH oxidase NOX5-S expression in Barrett's esophageal adenocarcinoma cells. American journal of physiology. Gastrointestinal and liver physiology 20080101
Involvement of cPLA2 inhibition in dexamethasone-induced thymocyte apoptosis. International journal of immunopathology and pharmacology 20080101
Role of phospholipase A2 (group I secreted) in the genesis of basal tone in the internal anal sphincter smooth muscle. American journal of physiology. Gastrointestinal and liver physiology 20071101
Arachidonic acid signaling is involved in the mechanism of imidazoline-induced KATP channel-independent stimulation of insulin secretion. Cellular and molecular life sciences : CMLS 20071101
A novel role of group VIB calcium-independent phospholipase A2 (iPLA2gamma) in the inducible expression of group IIA secretory PLA2 in rat fibroblastic cells. The Journal of biological chemistry 20070713
Apoptosis is mediated by cytosolic phospholipase A2 during simulated ischaemia/reperfusion-induced injury in neonatal cardiac myocytes. Prostaglandins, leukotrienes, and essential fatty acids 20070701
Regulation of luteal prostaglandin F(2 alpha) production and its relevance to cell death: an in vitro study using rat dispersed luteal cells. Prostaglandins & other lipid mediators 20070601
1-(5-Carboxy- and 5-carbamoylindol-1-yl)propan-2-ones as inhibitors of human cytosolic phospholipase A2alpha: bioisosteric replacement of the carboxylic acid and carboxamide moiety. Bioorganic & medicinal chemistry 20070415
Effects of arachidonate metabolism inhibitors on basal and human chorionic gonadotropin-stimulated progesterone secretion by rat corpus luteum cells in vitro. Prostaglandins & other lipid mediators 20070201
Lysophosphatidylcholine induces inflammatory activation of human coronary artery smooth muscle cells. Molecular and cellular biochemistry 20070101
Cytosolic PLA2 in zymogen granule fusion and amylase release: inhibition of GTP-induced fusion by arachidonyl trifluoromethyl ketone points to cPLA2 in G-protein-mediated secretory vesicle fusion. Journal of biochemistry 20070101
The role of arachidonic acid and its metabolites in insulin secretion from human islets of langerhans. Diabetes 20070101
Amyloid beta enhances cytosolic phospholipase A2 level and arachidonic acid release via nitric oxide in APP-transfected PC12 cells. Acta biochimica Polonica 20070101
Phospholipase A2 activation regulates cytotoxicity of methylmercury in vascular endothelial cells. International journal of toxicology 20070101
Cytosolic phospholipase A alpha modulates NMDA neurotoxicity in mouse hippocampal cultures. The European journal of neuroscience 20061201
Effects of pyrrophenone, an inhibitor of group IVA phospholipase A2, on eicosanoid and PAF biosynthesis in human neutrophils. British journal of pharmacology 20061001
Pro-atherogenic effect of interleukin-4 in endothelial cells: modulation of oxidative stress, nitric oxide and monocyte chemoattractant protein-1 expression. Atherosclerosis 20060801
Cytosolic phospholipase A2 inhibition attenuates ischemia-reperfusion injury in an isolated rat lung model. Transplantation 20060627
Targeting cytosolic phospholipase A2 by arachidonyl trifluoromethyl ketone prevents chronic inflammation in mice. European journal of pharmacology 20060613
Lysophosphatidic acid is constitutively produced by human peritoneal mesothelial cells and enhances adhesion, migration, and invasion of ovarian cancer cells. Cancer research 20060315
Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor. British journal of pharmacology 20060301
Homeodomain-interacting protein kinase-2 restrains cytosolic phospholipase A2-dependent prostaglandin E2 generation in human colorectal cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20060201
The cellular mechanisms by which adenosine evokes release of nitric oxide from rat aortic endothelium. The Journal of physiology 20060101
Enhancement of Ca2+-regulated exocytosis by indomethacin in guinea-pig antral mucous cells: arachidonic acid accumulation. Experimental physiology 20060101
A novel role for calcium-independent phospholipase A in alpha-amino-3-hydroxy-5-methylisoxazole-propionate receptor regulation during long-term potentiation. The European journal of neuroscience 20060101
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Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine. Journal of immunology (Baltimore, Md. : 1950) 20050915
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Leptin rapidly activates PPARs in C2C12 muscle cells. Biochemical and biophysical research communications 20050708
Vitamin C inhibits platelet expression of CD40 ligand. Free radical biology & medicine 20050615
Activation of BK channels in GH3 cells by a c-PLA2-dependent G-protein signaling pathway. Journal of neurophysiology 20050601
Clara cell secretory protein and phospholipase A2 activity modulate acute ventilator-induced lung injury in mice. Journal of applied physiology (Bethesda, Md. : 1985) 20050401
Oxidant-mediated activation of cytosolic phospholipase a(2) in pulmonary endothelium: role of protein kinase C alpha and a pertussis toxin-sensitive protein. Endothelium : journal of endothelial cell research 20050101
Group IIA secretory phospholipase A2 is a unique 12/15-lipoxygenase-regulated gene in cytokine-stimulated rat fibroblastic 3Y1 cells. Biochimica et biophysica acta 20041108
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Mitochondrial dysfunction is a primary event in renal cell oxalate toxicity. Kidney international 20041101
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gp91phox-dependent expression of platelet CD40 ligand. Circulation 20040907
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Identifying pathways involved in leptin-dependent aggregation of human platelets. International journal of obesity and related metabolic disorders : journal of the International Association for the Study of Obesity 20040801
Comparison of cellular mechanisms underlying histamine release from rat mast cells induced by ionic and nonionic radiographic contrast media. Investigative radiology 20040801
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Cytosolic and mitochondrial ROS in staurosporine-induced retinal cell apoptosis. Free radical biology & medicine 20031201
Prostacyclin production in rat aortic smooth muscle cells: role of protein kinase C, phospholipase D and cyclooxygenase-2 expression. Cardiovascular research 20031101
Phospholipase A2 plays an important role in myelin breakdown and phagocytosis during Wallerian degeneration. Molecular and cellular neurosciences 20031101
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Endothelial NADPH oxidase: mechanism of activation by low-density lipoprotein. Endothelium : journal of endothelial cell research 20030101
Peroxynitrite stimulates the activity of cytosolic phospholipase A2 in U937 cells: the extent of arachidonic acid formation regulates the balance between cell survival or death. Cell death and differentiation 20021201
Essential role of Ca2+ -dependent phospholipase A2 in estradiol-induced lysosome activation. American journal of physiology. Cell physiology 20021101
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Role of p38 MAPK in the regulation of apoptosis signaling induced by TNF-alpha in differentiated PC12 cells. Journal of biochemistry and molecular biology 20020531
Voltage independence of vasomotion in isolated irideal arterioles of the rat. The Journal of physiology 20020401
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Possible implication of Golgi-nucleating function for the centrosome. Biochemical and biophysical research communications 20020301
4-Bromophenacyl bromide induces Ca2+ influx in human gingival fibroblasts. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20020301
Mechanisms of glutamate release in the rat spinal cord slices during metabolic inhibition. Journal of neurotrauma 20020201
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The central role of thromboxane and platelet activating factor receptors in ex vivo regulation of endotoxin-induced monocyte tissue factor activity in human whole blood. Journal of endotoxin research 20020101
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The Ca2+-sensing receptor activates cytosolic phospholipase A2 via a Gqalpha -dependent ERK-independent pathway. The Journal of biological chemistry 20010427
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Signal transduction pathways for activation of extracellular signal-regulated kinase by arachidonic acid in rat neutrophils. Journal of leukocyte biology 20010401
Stimulative effect of cadmium on prostaglandin E2 production in primary mouse osteoblastic cells. Calcified tissue international 20010301
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