Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H33O2.H4N |
| Molecular Weight | 299.4919 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[NH4+].CCCCCCCC\C=C/CCCCCCCC([O-])=O
InChI
InChIKey=WFXRJNDIBXZNJK-KVVVOXFISA-N
InChI=1S/C18H34O2.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h9-10H,2-8,11-17H2,1H3,(H,19,20);1H3/b10-9-;
| Molecular Formula | H3N |
| Molecular Weight | 17.0305 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C18H34O2 |
| Molecular Weight | 282.4614 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Elaidic acid is the 9-trans isomer of oleic acid. It is a monounsaturated trans-fatty acid, which can be found in partially hydrogenated cooking oils. It was revealed, that elaidic acid inhibits HHT and HETE formation in human platelets incubated with arachidonic acid. Also was shown, that trans oleic acid increased plasma CETP activity, which increases low-density lipoprotein (LDL) cholesterol and decreases high-density lipoprotein (HDL).
CNS Activity
Curator's Comment: It was demonstrated that the 18 carbon-monocarboxylic fatty acids, linoleic acid with two cis-double bonds entered brain, whereas oleic acid, with one cis-double bond, did not enter brain. It was concluded the entry of essential fatty acids into brain is accomplished in a highly selective and discrete manner
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4822 |
61.31 µM [IC50] | ||
Target ID: CHEMBL3455 |
|||
Target ID: CHEMBL612542 |
|||
Target ID: CHEMBL2083 |
185.0 nM [Ki] | ||
Target ID: P11597 Gene ID: 1071.0 Gene Symbol: CETP Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
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PubMed
| Title | Date | PubMed |
|---|---|---|
| Fatty acids and derivatives as antimicrobial agents. | 1972 Jul |
|
| Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses. | 1980 Dec |
|
| Effect of sodium nitroprusside on cardiovascular function and pulmonary shunt in canine oleic acid pulmonary edema. | 1981 Nov |
|
| Effects of hydralazine on cardiopulmonary function in canine low-pressure pulmonary edema. | 1983 Sep |
|
| Effects of acute lung injury and anesthesia on left ventricular mechanics. | 1986 Dec |
|
| Induction of fatty acid binding protein by peroxisome proliferators in primary hepatocyte cultures and its relationship to the induction of peroxisomal beta-oxidation. | 1990 Apr 23 |
|
| Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies. | 1991 Oct |
|
| Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. | 1994 Sep 30 |
|
| Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage. | 1996 Nov |
|
| Effects of beta-adrenoceptor subtype stimulation on obese gene messenger ribonucleic acid and on leptin secretion in mouse brown adipocytes differentiated in culture. | 1997 Feb |
|
| Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat. | 1998 |
|
| Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. | 2005 Dec |
|
| Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein. | 2005 Oct 1 |
|
| High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
|
| Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells. | 2006 Aug |
|
| Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids. | 2006 Mar |
|
| Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men. | 2007 Apr |
|
| Intake of fish oil, oleic acid, folic acid, and vitamins B-6 and E for 1 year decreases plasma C-reactive protein and reduces coronary heart disease risk factors in male patients in a cardiac rehabilitation program. | 2007 Feb |
|
| Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia. | 2008 Apr |
|
| Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes. | 2008 Jan |
|
| Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids. | 2008 Jul |
|
| [Effects of recruitment maneuvers in prone position for pulmonary or extra-pulmonary acute respiratory distress syndrome on hemodynamics in dog]. | 2008 Jun |
|
| Regulation of fat-stimulated neurotensin secretion in healthy subjects. | 2008 May |
|
| A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine. | 2008 May |
|
| PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression. | 2008 May 19 |
|
| Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus. | 2008 Sep |
|
| Glucosamine-induced endoplasmic reticulum stress attenuates apolipoprotein B100 synthesis via PERK signaling. | 2009 Sep |
|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010 Aug |
|
| Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion. | 2010 Feb |
|
| Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells. | 2011 Jun |
|
| PKC activation by resveratrol derivatives with unsaturated aliphatic chain. | 2012 |
|
| Differential signaling by splice variants of the human free fatty acid receptor GPR120. | 2012 May |
|
| New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors. | 2012 Nov |
|
| Oleic acid decreases BCRP mediated efflux of mitoxantrone in Caco-2 cell monolayers. | 2012 Oct |
|
| Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line. | 2012 Oct 15 |
|
| Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells. | 2012 Sep |
|
| Changes in mitochondrial carriers exhibit stress-specific signatures in INS-1Eβ-cells exposed to glucose versus fatty acids. | 2013 |
|
| Sophocarpine alleviates hepatocyte steatosis through activating AMPK signaling pathway. | 2013 Apr |
|
| Amelioration by chicory seed extract of diabetes- and oleic acid-induced non-alcoholic fatty liver disease (NAFLD)/non-alcoholic steatohepatitis (NASH) via modulation of PPARα and SREBP-1. | 2013 Aug |
|
| Extra virgin olive oil potentiates the effects of aromatase inhibitors via glutathione depletion in estrogen receptor-positive human breast cancer (MCF-7) cells. | 2013 Dec |
|
| Increased autoimmune responses against auto-epitopes modified by oxidative and nitrosative damage in depression: implications for the pathways to chronic depression and neuroprogression. | 2013 Jul |
|
| Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice. | 2013 Jul 5 |
|
| Quercetin ameliorate insulin resistance and up-regulates cellular antioxidants during oleic acid induced hepatic steatosis in HepG2 cells. | 2013 Mar |
|
| Gustducin couples fatty acid receptors to GLP-1 release in colon. | 2013 Mar 15 |
|
| PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells. | 2014 Apr 1 |
|
| Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal. | 2014 Dec 5 |
|
| Monascin and ankaflavin act as natural AMPK activators with PPARα agonist activity to down-regulate nonalcoholic steatohepatitis in high-fat diet-fed C57BL/6 mice. | 2014 Feb |
|
| Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ. | 2014 Sep 15 |
|
| The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH. | 2015 Oct |
|
| Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets. | 2015 Sep 18 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:51:26 GMT 2023
by
admin
on
Fri Dec 15 18:51:26 GMT 2023
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| Record UNII |
EH7L6J9LHN
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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Official Name | English | ||
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| Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
31703
Created by
admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
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EH7L6J9LHN
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208-873-1
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6435897
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544-60-5
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DTXSID50878372
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m1802
Created by
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
