Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H32O2 |
Molecular Weight | 304.4669 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI
InChIKey=YZXBAPSDXZZRGB-DOFZRALJSA-N
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
Molecular Formula | C20H32O2 |
Molecular Weight | 304.4669 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Optical Activity | NONE |
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL239 |
1.2 µM [IC50] | ||
Target ID: CHEMBL235 |
1.6 µM [IC50] | ||
Target ID: CHEMBL3979 |
3.1 µM [IC50] | ||
Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415 |
602.56 nM [IC50] | ||
Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415 |
1071.0 nM [IC50] | ||
Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12036355 |
180.0 nM [Kd] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12444669 |
PubMed
Title | Date | PubMed |
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Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin. | 2001 Dec 15 |
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Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components. | 2001 Jun |
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Vasopressin-stimulated Ca2+ spiking in vascular smooth muscle cells involves phospholipase D. | 2001 Jun |
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Stimulative effect of cadmium on prostaglandin E2 production in primary mouse osteoblastic cells. | 2001 Mar |
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Arachidonic acid-induced inhibition of Ca2+ channel currents in retinal glial (Müller) cells. | 2001 Nov |
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p38 MAP kinase mediates stress-induced leukotriene synthesis in a human B-lymphocyte cell line. | 2001 Nov |
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Acute effects of the cys-leukotriene-1 receptor antagonist, montelukast, on experimental colitis in rats. | 2001 Oct 19 |
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TRA-418, a novel compound having both thromboxane A(2) receptor antagonistic and prostaglandin I(2) receptor agonistic activities: its antiplatelet effects in human and animal platelets. | 2003 Aug |
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Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts. | 2003 Aug 30 |
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Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line. | 2003 Feb 1 |
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Genetic variation in cyclooxygenase 1: effects on response to aspirin. | 2003 Jan |
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Effect of the lipid peroxidation product acrolein on tau phosphorylation in neural cells. | 2003 Mar 15 |
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Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants. | 2003 Nov |
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Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. | 2003 Oct |
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Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease. | 2003 Oct |
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The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers. | 2004 |
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Effects of d-003, a new substance purified from sugar cane wax, on platelet aggregation and plasma levels of arachidonic acid metabolites in healthy volunteers. | 2004 |
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2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells. | 2004 Apr |
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In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG). | 2004 Aug |
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Heme oxygenase-1 protects HepG2 cells against cytochrome P450 2E1-dependent toxicity. | 2004 Feb 1 |
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Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis. | 2004 Jan |
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Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance? | 2004 Jul |
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The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney. | 2004 Jul |
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Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
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Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation. | 2005 |
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Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention. | 2005 Dec |
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Fenamates and diltiazem modulate lipid-sensitive mechano-gated 2P domain K(+) channels. | 2005 Dec |
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A Thrombelastograph whole blood assay for clinical monitoring of NSAID-insensitive transcellular platelet activation by arachidonic acid. | 2005 Jul |
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COX-2 inhibitors and metabolism of essential fatty acids. | 2005 Jul |
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Fatty acids and expression of adipokines. | 2005 May 30 |
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Late-gestation rat myometrial cells express multiple isoforms of phospholipase A2 that mediate PCB 50-induced release of arachidonic acid with coincident prostaglandin production. | 2005 Nov |
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Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin. | 2005 Oct |
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Vasoactive prostanoids are generated from arachidonic acid by COX-1 and COX-2 in the mouse. | 2005 Oct |
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Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005 Oct 28 |
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Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells. | 2005 Sep |
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How dietary arachidonic- and docosahexaenoic- acid rich oils differentially affect the murine hepatic transcriptome. | 2006 Apr 20 |
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Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers. | 2006 Aug |
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Induction of CYP1A and cyp2-mediated arachidonic acid epoxygenation and suppression of 20-hydroxyeicosatetraenoic acid by imidazole derivatives including the aromatase inhibitor vorozole. | 2006 Aug |
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Nongenomic action of progesterone inhibits oxytocin-induced phosphoinositide hydrolysis and prostaglandin F2alpha secretion in the ovine endometrium. | 2006 Feb |
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Nitric oxide alters arachidonic acid turnover in brain cortex synaptoneurosomes. | 2006 Jan |
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[Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques]. | 2006 Jan-Apr |
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Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. | 2006 Jul |
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Mechanism of induction of muscle protein degradation by angiotensin II. | 2006 Jul |
|
Protective effects of a standard extract of Mangifera indica L. (VIMANG) against mouse ear edemas and its inhibition of eicosanoid production in J774 murine macrophages. | 2006 Jun |
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Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance. | 2006 Jun 27 |
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Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? | 2006 May |
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Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques. | 2006 May-Aug |
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The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006 Nov 25 |
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Arachidonic acid-induced gene expression in colon cancer cells. | 2006 Oct |
|
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 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:53:15 GMT 2025
by
admin
on
Mon Mar 31 17:53:15 GMT 2025
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Record UNII |
27YG812J1I
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Record Status |
Validated (UNII)
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Record Version |
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Preferred Name | English | ||
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Official Name | English | ||
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Systematic Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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DSLD |
1467 (Number of products:46)
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NCI_THESAURUS |
C2563
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LOINC |
90915-0
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NCI_THESAURUS |
C68357
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LOINC |
88994-9
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LOINC |
1889-5
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LOINC |
90909-3
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LOINC |
88996-4
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LOINC |
90916-8
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LOINC |
35168-4
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LOINC |
35411-8
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LOINC |
75110-7
Created by
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Code System | Code | Type | Description | ||
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15843
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PRIMARY | |||
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27YG812J1I
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36306
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208-033-4
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1368625
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ALTERNATIVE | |||
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D016718
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PRIMARY | |||
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C282
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PRIMARY | |||
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100000088503
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DTXSID4040420
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444899
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DB04557
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ARACHIDONIC ACID
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1368624
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PRIMARY | RxNorm | ||
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m2024
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PRIMARY | Merck Index | ||
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506-32-1
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27YG812J1I
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SUB21901
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PRIMARY |
Related Record | Type | Details | ||
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LIPID -> FATTY ACID |
Durkee Industrial Foods, Cleveland, Ohio(average value).
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
MAJOR
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METABOLITE ACTIVE -> PARENT |
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