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34450-18-5 | 17-Octadecynoic Acid
CAS No: 34450-18-5 Catalog No: AG0032O5 MDL No:MFCD00077382
Product Description
Catalog Number:
AG0032O5
Chemical Name:
17-Octadecynoic Acid
CAS Number:
34450-18-5
Molecular Formula:
C18H32O2
Molecular Weight:
280.4455
MDL Number:
MFCD00077382
IUPAC Name:
octadec-17-ynoic acid
InChI:
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1H,3-17H2,(H,19,20)
InChI Key:
DZIILFGADWDKMF-UHFFFAOYSA-N
SMILES:
C#CCCCCCCCCCCCCCCCC(=O)O
Properties
Complexity:
262
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
280.24g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
280.452g/mol
Monoisotopic Mass:
280.24g/mol
Rotatable Bond Count:
15
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.1
Literature
| Title | Journal |
|---|---|
| 2-Alkynoic fatty acids inhibit topoisomerase IB from Leishmania donovani. | Bioorganic & medicinal chemistry letters 20121001 |
| Bioorthogonal proteomics of 15-hexadecynyloxyacetic acid chemical reporter reveals preferential targeting of fatty acid modified proteins and biosynthetic enzymes. | Bioorganic & medicinal chemistry 20120115 |
| DHHC5 protein palmitoylates flotillin-2 and is rapidly degraded on induction of neuronal differentiation in cultured cells. | The Journal of biological chemistry 20120102 |
| 17-Octadecynoic acid improves contractile response to angiotensin II by releasing vasocontrictor prostaglandins. | Prostaglandins & other lipid mediators 20120101 |
| Global profiling of dynamic protein palmitoylation. | Nature methods 20120101 |
| Arachidonic acid inhibits Na⁺-K⁺-ATPase via cytochrome P-450, lipoxygenase and protein kinase C-dependent pathways in sheep pulmonary artery. | Vascular pharmacology 20120101 |
| iPLA2β overexpression in smooth muscle exacerbates angiotensin II-induced hypertension and vascular remodeling. | PloS one 20120101 |
| Proteomic analysis of S-acylated proteins in human B cells reveals palmitoylation of the immune regulators CD20 and CD23. | PloS one 20120101 |
| P-450-dependent epoxygenase pathway of arachidonic acid is involved in myeloma-induced angiogenesis of endothelial cells. | Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20111001 |
| Species differences in intestinal metabolic activities of cytochrome P450 isoforms between cynomolgus monkeys and humans. | Drug metabolism and pharmacokinetics 20110601 |
| Contribution of Ras farnesyl transferase, MAP kinase and cytochrome P-450 metabolites to endothelin-1 induced hypertension. | Bosnian journal of basic medical sciences 20110501 |
| Lipid-cell interactions in human monocytes investigated by doubly-resonant coherent anti-Stokes Raman scattering microscopy. | Journal of biomedical optics 20110201 |
| The role of palmitoylation in signalling, cellular trafficking and plasma membrane localization of protease-activated receptor-2. | PloS one 20110101 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Onset of pulmonary ventilation in fetal sheep produces pial arteriolar constriction dependent on cytochrome p450 omega-hydroxylase activity. | Journal of applied physiology (Bethesda, Md. : 1985) 20100801 |
| Protease-activated receptor 2 and bradykinin-mediated vasodilation in the cerebral arteries of stroke-prone rats. | Peptides 20100201 |
| CYP-omega-hydroxylation-dependent metabolites of arachidonic acid inhibit the basolateral 10 pS chloride channel in the rat thick ascending limb. | Kidney international 20091001 |
| Large-scale profiling of protein palmitoylation in mammalian cells. | Nature methods 20090201 |
| Cytochrome P450 omega-hydroxylase inhibition reduces cardiomyocyte apoptosis via activation of ERK1/2 signaling in rat myocardial ischemia-reperfusion. | European journal of pharmacology 20081031 |
| Antiangiogenic effect of inhibitors of cytochrome P450 on rats with glioblastoma multiforme. | Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20080801 |
| 20-Hydroxyeicosatetraenoic acid inhibits the apoptotic responses in pulmonary artery smooth muscle cells. | European journal of pharmacology 20080624 |
| Endothelial dysfunction and improvement of the angiotensin II-reactivity in hypercholesterolemic rabbits: role of cyclooxygenase metabolites. | European journal of pharmacology 20080202 |
| Cytosolic phospholipase A2 and arachidonic acid metabolites modulate ventilator-induced permeability increases in isolated mouse lungs. | Journal of applied physiology (Bethesda, Md. : 1985) 20080201 |
| Role of 20-HETE in the hypoxia-induced activation of Ca2+-activated K+ channel currents in rat cerebral arterial muscle cells. | American journal of physiology. Heart and circulatory physiology 20080101 |
| Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine. | Drug metabolism and disposition: the biological fate of chemicals 20071101 |
| Role of 20-HETE in D1/D2 dopamine receptor synergism resulting in the inhibition of Na+-K+-ATPase activity in the proximal tubule. | American journal of physiology. Renal physiology 20070501 |
| High dietary salt reduces the contribution of 20-HETE to arteriolar oxygen responsiveness in skeletal muscle. | American journal of physiology. Heart and circulatory physiology 20070301 |
| Vascular dysfunction in type 2 diabetic TallyHo mice: role for an increase in the contribution of PGH2/TxA2 receptor activation and cytochrome p450 products. | Canadian journal of physiology and pharmacology 20070101 |
| Pharmacological characteristics of endothelium-derived hyperpolarizing factor-mediated relaxation of small mesenteric arteries from db/db mice. | European journal of pharmacology 20061203 |
| Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth. | Journal of lipid research 20061201 |
| CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime]. | Drug metabolism and disposition: the biological fate of chemicals 20061201 |
| Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid. | FEBS letters 20060710 |
| Omega-oxidation of very long-chain fatty acids in human liver microsomes. Implications for X-linked adrenoleukodystrophy. | The Journal of biological chemistry 20060512 |
| ROS-sensitive cytochrome P450 activity maintains endothelial dilatation in ageing but is transitory in dyslipidaemic mice. | British journal of pharmacology 20060401 |
| Regulation of potassium channels in coronary smooth muscle by adenoviral expression of cytochrome P-450 epoxygenase. | American journal of physiology. Heart and circulatory physiology 20060101 |
| Transfection of cytochrome P4504B1 into the cornea increases angiogenic activity of the limbal vessels. | The Journal of pharmacology and experimental therapeutics 20051001 |
| Effects of epoxyeicosatrienoic acids on levels of eNOS phosphorylation and relevant signaling transduction pathways involved. | Science in China. Series C, Life sciences 20051001 |
| Enhanced release of endothelium-derived hyperpolarizing factor in small coronary arteries from rats with congestive heart failure. | Clinical and experimental pharmacology & physiology 20050801 |
| Mediators involved in decreasing peripheral vascular resistance with carbachol in the rat hind limb perfusion model. | Journal of pharmacological sciences 20050701 |
| Comparison of muscarinic receptor- and beta-adrenoceptor-mediated vasorelaxation between euthyroid and acute hyperthyroid rats. | Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20050701 |
| Angiotensin II-induced Akt activation is mediated by metabolites of arachidonic acid generated by CaMKII-stimulated Ca2(+)-dependent phospholipase A2. | American journal of physiology. Heart and circulatory physiology 20050501 |
| Evidence for two enzymatic pathways for omega-oxidation of docosanoic acid in rat liver microsomes. | Journal of lipid research 20050501 |
| The synthesis of 20-HETE in small porcine coronary arteries antagonizes EDHF-mediated relaxation. | Cardiovascular research 20050201 |
| Redundant signaling mechanisms contribute to the vasodilatory response of the afferent arteriole to proteinase-activated receptor-2. | American journal of physiology. Renal physiology 20050101 |
| Role of hydrogen peroxide in ACh-induced dilation of human submucosal intestinal microvessels. | American journal of physiology. Heart and circulatory physiology 20050101 |
| Involvement of NO and EDHF in flow-induced vasodilation in isolated hamster cremasteric arterioles. | Journal of vascular research 20050101 |
| Cytochrome P450 omega-hydroxylase inhibition reduces infarct size during reperfusion via the sarcolemmal KATP channel. | Journal of molecular and cellular cardiology 20041201 |
| Design and synthesis of 1-(4-benzoylphenyl)imidazole derivatives as new potent 20-HETE synthase inhibitors. | Bioorganic & medicinal chemistry letters 20041101 |
| Inhibition of cytochrome P450omega-hydroxylase: a novel endogenous cardioprotective pathway. | Circulation research 20041015 |
| Arachidonic acid relaxes human pulmonary arteries through K+ channels and nitric oxide pathways. | European journal of pharmacology 20041006 |
| Changes in renal haemodynamics induced by indomethacin in the rat involve cytochrome P450 arachidonic acid-dependent epoxygenases. | Clinical and experimental pharmacology & physiology 20041001 |
| Essential role of EDHF in the initiation and maintenance of adrenergic vasomotion in rat mesenteric arteries. | American journal of physiology. Heart and circulatory physiology 20040801 |
| Activation of Na+-independent Mg2+ efflux by 20-hydroxyeicosatetraenoic acid in rat renal epithelial cells. | The Japanese journal of physiology 20040801 |
| P2Y purine receptor responses and expression in the pulmonary circulation of juvenile rabbits. | American journal of physiology. Heart and circulatory physiology 20040701 |
| Acute hyperthyroidism alters adrenoceptor- and muscarinic receptor-mediated responses in isolated rat renal and femoral arteries. | European journal of pharmacology 20040616 |
| Cytochrome P-450 metabolites in endothelin-stimulated cardiac hormone secretion. | American journal of physiology. Regulatory, integrative and comparative physiology 20040501 |
| Distinct roles for protease-activated receptors 1 and 2 in vasomotor modulation in rat superior mesenteric artery. | Cardiovascular research 20040301 |
| Role of EETs in regulation of endothelial permeability in rat lung. | American journal of physiology. Lung cellular and molecular physiology 20040201 |
| Bidirectional regulation of renal cortical Na+,K+-ATPase by protein kinase C. | Acta biochimica Polonica 20040101 |
| Arachidonic acid-activated Na+-dependent Mg2+ efflux in rat renal epithelial cells. | Biochimica et biophysica acta 20031203 |
| Cytochrome P-450 metabolites but not NO, PGI2, and H2O2 contribute to ACh-induced hyperpolarization of pressurized canine coronary microvessels. | American journal of physiology. Heart and circulatory physiology 20031101 |
| Arachidonic acid metabolites contribute to the irreversible depolarization induced by in vitro ischemia. | Journal of neurophysiology 20031101 |
| Determinants of renal afferent arteriolar actions of bradykinin: evidence that multiple pathways mediate responses attributed to EDHF. | American journal of physiology. Renal physiology 20030901 |
| Adrenomedullin-induced endothelium-dependent relaxation in porcine ciliary arteries. | Investigative ophthalmology & visual science 20030901 |
| Dopamine D1 receptor-dependent inhibition of NaCl transport in the rat thick ascending limb: mechanism of action. | European journal of pharmacology 20030725 |
| Cytochrome p-450 epoxygenase products contribute to attenuated vasoconstriction after chronic hypoxia. | American journal of physiology. Heart and circulatory physiology 20030701 |
| Electron spin resonance detection of hydrogen peroxide as an endothelium-derived hyperpolarizing factor in porcine coronary microvessels. | Arteriosclerosis, thrombosis, and vascular biology 20030701 |
| Nitric oxide decreases renal medullary Na+, K+-ATPase activity through cyclic GMP-protein kinase G dependent mechanism. | Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20030601 |
| Effects of H2O2 on membrane potential of smooth muscle cells in rabbit mesenteric resistance artery. | European journal of pharmacology 20030319 |
| Mechanisms of hydrogen-peroxide-induced biphasic response in rat mesenteric artery. | British journal of pharmacology 20030301 |
| An endothelium-derived factor modulates purinergic neurotransmission to mesenteric arterial smooth muscle of hamster. | European journal of pharmacology 20030214 |
| Endothelium-derived hyperpolarizing factor in human internal mammary artery is 11,12-epoxyeicosatrienoic acid and causes relaxation by activating smooth muscle BK(Ca) channels. | Circulation 20030211 |
| Norepinephrine-induced stimulation of p38 mitogen-activated protein kinase is mediated by arachidonic acid metabolites generated by activation of cytosolic phospholipase A(2) in vascular smooth muscle cells. | The Journal of pharmacology and experimental therapeutics 20030201 |
| Regulation of renal Na(+),K(+)-ATPase and ouabain-sensitive H(+),K(+)-ATPase by the cyclic AMP-protein kinase A signal transduction pathway. | Acta biochimica Polonica 20030101 |
| Acute decrease of cerebrocortical microflow and lack of carbon dioxide reactivity following subarachnoid haemorrhage in the rat. | Acta neurochirurgica. Supplement 20030101 |
| Oxidant stress-induced increase in myogenic activation of skeletal muscle resistance arteries in obese Zucker rats. | American journal of physiology. Heart and circulatory physiology 20021201 |
| Nitric oxide contributes to 20-HETE-induced relaxation of pulmonary arteries. | Journal of applied physiology (Bethesda, Md. : 1985) 20021001 |
| EDHF, but not NO or prostaglandins, is critical to evoke a conducted dilation upon ACh in hamster arterioles. | American journal of physiology. Heart and circulatory physiology 20020901 |
| 20-HETE pathway antagonists inhibit rat small mesenteric artery tone. | Microvascular research 20020901 |
| Role of 20-hydroxyeicosatetraenoic acid in the renal and vasoconstrictor actions of angiotensin II. | American journal of physiology. Regulatory, integrative and comparative physiology 20020701 |
| 20-HETE contributes to the acute fall in cerebral blood flow after subarachnoid hemorrhage in the rat. | American journal of physiology. Heart and circulatory physiology 20020401 |
| Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes. | The Journal of pharmacology and experimental therapeutics 20020101 |
| Multiple mechanisms of vascular smooth muscle relaxation by the activation of proteinase-activated receptor 2 in mouse mesenteric arterioles. | British journal of pharmacology 20020101 |
| Differential effect of cytochrome P-450 omega-hydroxylase inhibition on O2-induced constriction of arterioles in SHR with early and established hypertension. | Microcirculation (New York, N.Y. : 1994) 20011201 |
| Initial and sustained phases of myogenic response of rat mesenteric small arteries. | American journal of physiology. Heart and circulatory physiology 20011101 |
| Role of prostanoids and 20-HETE in mediating oxygen-induced constriction of skeletal muscle resistance arteries. | Microvascular research 20011101 |
| Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels. | British journal of pharmacology 20011101 |
| Expressed CYP4A4 metabolism of prostaglandin E(1) and arachidonic acid. | Archives of biochemistry and biophysics 20010915 |
| Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles. | Hypertension research : official journal of the Japanese Society of Hypertension 20010901 |
| Further investigations into the endothelium-dependent hyperpolarizing effects of bradykinin and substance P in porcine coronary artery. | British journal of pharmacology 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 the phosphatidylinositol 3-kinase-Akt/protein kinase B signaling pathway in arachidonic acid-stimulated human myeloid and endothelial cells: involvement of the ErbB receptor family. | The Journal of biological chemistry 20010720 |
| Activation of cardiac afferents by arachidonic acid: relative contributions of metabolic pathways. | American journal of physiology. Heart and circulatory physiology 20010701 |
| Arachidonic acid directly activates members of the mitogen-activated protein kinase superfamily in rabbit proximal tubule cells. | Kidney international 20010601 |
| Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels. | Circulation 20010417 |
| Cytochrome P-450 omega-hydroxylase: a potential O(2) sensor in rat arterioles and skeletal muscle cells. | American journal of physiology. Heart and circulatory physiology 20010401 |
| Altered mechanisms underlying hypoxic dilation of skeletal muscle resistance arteries of hypertensive versus normotensive Dahl rats. | Microcirculation (New York, N.Y. : 1994) 20010401 |
| Triple-bonded unsaturated fatty acids are redox active compounds. | Lipids 20010401 |
| EDHF contributes to strain-related differences in pulmonary arterial relaxation in rats. | American journal of physiology. Lung cellular and molecular physiology 20010301 |
| 20-HETE modulates myogenic response of skeletal muscle resistance arteries from hypertensive Dahl-SS rats. | American journal of physiology. Heart and circulatory physiology 20010301 |
| Bradykinin attenuates the [Ca(2+)](i) response to angiotensin II of renal juxtamedullary efferent arterioles via an EDHF. | British journal of pharmacology 20010201 |
| Role of 20-HETE in mediating the effect of dietary K intake on the apical K channels in the mTAL. | American journal of physiology. Renal physiology 20010201 |
| 20-HETE contributes to myogenic activation of skeletal muscle resistance arteries in Brown Norway and Sprague-Dawley rats. | Microcirculation (New York, N.Y. : 1994) 20010201 |
| Relative contributions of cyclooxygenase- and cytochrome P450 omega-hydroxylase-dependent pathways to hypoxic dilation of skeletal muscle resistance arteries. | Journal of vascular research 20010101 |
| Leukotriene B4 omega-hydroxylase in human polymorphonuclear leukocytes. Suicidal inactivation by acetylenic fatty acids. | The Journal of biological chemistry 19851025 |
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