Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H34O2 |
| Molecular Weight | 282.4614 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C\CCCCCCCC(O)=O
InChI
InChIKey=ZQPPMHVWECSIRJ-MDZDMXLPSA-N
InChI=1S/C18H34O2/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)/b10-9+
| 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 |
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Target ID: CHEMBL612542 |
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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 |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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PubMed
| Title | Date | PubMed |
|---|---|---|
| Fatty acids and derivatives as antimicrobial agents. | 1972 Jul |
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| Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses. | 1980 Dec |
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| Effects of acute lung injury and anesthesia on left ventricular mechanics. | 1986 Dec |
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| Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies. | 1991 Oct |
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| Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes. | 1995 Dec 1 |
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| Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat. | 1998 |
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| Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. | 1999 Jan |
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| Significance of fatty acids in pregnancy-induced immunosuppression. | 1999 Jul |
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| Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man. | 2000 |
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| Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
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| Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
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| The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. | 2001 Jan |
|
| Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
|
| Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. | 2001 Jul |
|
| Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. | 2001 Jun |
|
| Bezafibrate attenuates the overexpression of plasminogen activator inhibitor-1 messenger RNA by a combination of mono-unsaturated fatty acid and insulin in hepG2 cells. | 2001 Mar 9 |
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| Regulation of uncoupling protein-2 mRNA in L6 myotubules: II: Thyroid hormone amplifies stimulation of uncoupling protein-2 gene by thiazolidinediones and other peroxisome proliferator-activated receptor ligands in L6 myotubules: evidence for a priming effect. | 2002 Nov |
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| Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells. | 2003 Dec |
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| A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
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| Endogenous phospholipase D2 localizes to the plasma membrane of RBL-2H3 mast cells and can be distinguished from ADP ribosylation factor-stimulated phospholipase D1 activity by its specific sensitivity to oleic acid. | 2003 Jan 15 |
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| Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme. | 2003 Jun |
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| Decreasing IRS-2 expression in pancreatic beta-cells (INS-1) promotes apoptosis, which can be compensated for by introduction of IRS-4 expression. | 2003 Nov 14 |
|
| Stearoyl-CoA desaturase 1 gene expression is necessary for fructose-mediated induction of lipogenic gene expression by sterol regulatory element-binding protein-1c-dependent and -independent mechanisms. | 2004 Jun 11 |
|
| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
|
| COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers. | 2004 Sep-Oct |
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| Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. | 2005 Dec |
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| Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
|
| Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation. | 2005 Mar |
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| Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein. | 2005 Oct 1 |
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| Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005 Oct 28 |
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| 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 |
|
| PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver. | 2006 May |
|
| 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 |
|
| Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. | 2007 Mar |
|
| [Effects of recruitment maneuvers in prone position for pulmonary or extra-pulmonary acute respiratory distress syndrome on hemodynamics in dog]. | 2008 Jun |
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| 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 |
|
| Glucosamine-induced endoplasmic reticulum stress attenuates apolipoprotein B100 synthesis via PERK signaling. | 2009 Sep |
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| Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion. | 2010 Feb |
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| Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells. | 2011 Jun |
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| New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors. | 2012 Nov |
|
| Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line. | 2012 Oct 15 |
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| Changes in mitochondrial carriers exhibit stress-specific signatures in INS-1Eβ-cells exposed to glucose versus fatty acids. | 2013 |
|
| 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 |
|
| 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 |
|
| PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells. | 2014 Apr 1 |
|
| The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH. | 2015 Oct |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 21:31:55 GMT 2023
by
admin
on
Fri Dec 15 21:31:55 GMT 2023
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| Record UNII |
4837010H8C
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C68405
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NCI_THESAURUS |
C68440
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300000047596
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ELAIDIC ACID
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204-006-6
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DTXSID8058619
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m4851
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C68363
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4837010H8C
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C011459
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26988
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112-79-8
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637517
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27997
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
