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Details

Stereochemistry ACHIRAL
Molecular Formula C20H32O2
Molecular Weight 304.4676
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ARACHIDONIC ACID

SMILES

CCCCC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\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-

HIDE SMILES / InChI

Molecular Formula C20H32O2
Molecular Weight 304.4676
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Butylated hydroxyanisole specifically inhibits tumor necrosis factor-induced cytotoxicity and growth enhancement.
1992 Jul
Antiallergic effects of H1-receptor antagonists.
2000
Targeted disruption of the leukotriene B(4) receptor in mice reveals its role in inflammation and platelet-activating factor-induced anaphylaxis.
2000 Aug 7
Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells.
2000 Dec
Prostaglandin levels in stimulated macrophages are controlled by phospholipase A2-activating protein and by activation of phospholipase C and D.
2001 Feb 23
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
Evidence for the presence of phospholipid hydroperoxide glutathione peroxidase in human platelets: implications for its involvement in the regulatory network of the 12-lipoxygenase pathway of arachidonic acid metabolism.
2001 Jan 1
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components.
2001 Jun
Direct activation of an inwardly rectifying potassium channel by arachidonic acid.
2001 May
Arachidonic acid-induced inhibition of Ca2+ channel currents in retinal glial (Müller) cells.
2001 Nov
p38 MAP kinase mediates stress-induced leukotriene synthesis in a human B-lymphocyte cell line.
2001 Nov
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.
2002 Jan
Cytosolic phospholipase A2 (cPLA2) regulation of human monocyte NADPH oxidase activity. cPLA2 affects translocation but not phosphorylation of p67(phox) and p47(phox).
2002 Jul 12
Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole.
2002 Nov
On the interaction of specific prostaglandin H synthase-2 inhibitors with prostaglandin H synthase-1.
2002 Oct 25
Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line.
2003 Feb 1
Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation.
2003 Sep
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
2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells.
2004 Apr
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
2004 Aug
In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG).
2004 Aug
The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney.
2004 Jul
Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial.
2005 Dec
Increase in heme oxygenase-1 levels ameliorates renovascular hypertension.
2005 Dec
Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention.
2005 Dec
Fenamates and diltiazem modulate lipid-sensitive mechano-gated 2P domain K(+) channels.
2005 Dec
A Thrombelastograph whole blood assay for clinical monitoring of NSAID-insensitive transcellular platelet activation by arachidonic acid.
2005 Jul
Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha.
2005 Nov
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
Vasoactive prostanoids are generated from arachidonic acid by COX-1 and COX-2 in the mouse.
2005 Oct
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005 Oct 28
How dietary arachidonic- and docosahexaenoic- acid rich oils differentially affect the murine hepatic transcriptome.
2006 Apr 20
Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers.
2006 Aug
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
Nongenomic action of progesterone inhibits oxytocin-induced phosphoinositide hydrolysis and prostaglandin F2alpha secretion in the ovine endometrium.
2006 Feb
Nitric oxide alters arachidonic acid turnover in brain cortex synaptoneurosomes.
2006 Jan
[Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques].
2006 Jan-Apr
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.
2006 Jul
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
Cytoglobin overexpression protects against damage-induced fibrosis.
2006 Jun
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
High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome.
2006 Mar
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
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006 May
Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques.
2006 May-Aug
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.
2006 Nov 25
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 Fri Jun 25 23:03:38 UTC 2021
Edited
by admin
on Fri Jun 25 23:03:38 UTC 2021
Record UNII
27YG812J1I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARACHIDONIC ACID
INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
ARACHIDONIC ACID [INCI]
Common Name English
(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAENOIC ACID
Systematic Name English
ARACHIDONIC ACID [MART.]
Common Name English
ARACHIDONATE
Common Name English
ARACHIDONIC ACID [MI]
Common Name English
ARACHIDONIC ACID [WHO-DD]
Common Name English
ARA
Common Name English
Classification Tree Code System Code
DSLD 1467 (Number of products:46)
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
NCI_THESAURUS C2563
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 90915-0
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
NCI_THESAURUS C68357
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 88994-9
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 1889-5
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 90909-3
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 88996-4
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 90916-8
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 35168-4
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 35411-8
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
LOINC 75110-7
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
208-033-4
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
RXCUI
1368625
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
ALTERNATIVE
MESH
D016718
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
NCI_THESAURUS
C282
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
EPA CompTox
506-32-1
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
PUBCHEM
444899
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
DRUG BANK
DB04557
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
WIKIPEDIA
ARACHIDONIC ACID
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
RXCUI
1368624
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M2024
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY Merck Index
CAS
506-32-1
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
FDA UNII
27YG812J1I
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
EVMPD
SUB21901
Created by admin on Fri Jun 25 23:03:38 UTC 2021 , Edited by admin on Fri Jun 25 23:03:38 UTC 2021
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
Durkee Industrial Foods, Cleveland, Ohio(average value).
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE