U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ARACHIDONIC ACID

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-

HIDE SMILES / InChI

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

PubMed

PubMed

TitleDatePubMed
Butylated hydroxyanisole specifically inhibits tumor necrosis factor-induced cytotoxicity and growth enhancement.
1992 Jul
Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin.
2001 Dec 15
Arachidonic acid-induced inhibition of Ca2+ channel currents in retinal glial (Müller) cells.
2001 Nov
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.
2002 Apr 19
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.
2002 Jan
LTRPC2 Ca2+-permeable channel activated by changes in redox status confers susceptibility to cell death.
2002 Jan
Antioxidant and pro-oxidant effects of a manganese porphyrin complex against CYP2E1-dependent toxicity.
2002 Jul 1
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
Induction of MnSOD gene by arachidonic acid is mediated by reactive oxygen species and p38 MAPK signaling pathway in human HepG2 hepatoma cells.
2002 Jun 1
Leukotriene B4 production in human mononuclear phagocytes is modulated by interleukin-4-induced 15-lipoxygenase.
2002 Mar
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
Celecoxib reduces skin damage after radiation: selective reduction of chemokine and receptor mRNA expression in irradiated skin but not in irradiated mammary tumor.
2003 Aug
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes.
2003 Feb
Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line.
2003 Feb 1
Metallothionein 2A induction by zinc protects HEPG2 cells against CYP2E1-dependent toxicity.
2003 Feb 15
Genetic variation in cyclooxygenase 1: effects on response to aspirin.
2003 Jan
PGE(2) is generated by specific COX-2 activity and increases VEGF production in COX-2-expressing human pancreatic cancer cells.
2003 Jul 11
Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells.
2003 Jun 6
Effect of the lipid peroxidation product acrolein on tau phosphorylation in neural cells.
2003 Mar 15
Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants.
2003 Nov
Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology.
2003 Oct
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
Heme oxygenase-1 protects HepG2 cells against cytochrome P450 2E1-dependent toxicity.
2004 Feb 1
Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis.
2004 Jan
Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.
2004 Mar 25
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation.
2005
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.
2005 Apr 8
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
Angiotensin II-induced Akt activation through the epidermal growth factor receptor in vascular smooth muscle cells is mediated by phospholipid metabolites derived by activation of phospholipase D.
2005 Mar
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
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
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
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
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
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 Dec 15 15:17:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:51 GMT 2023
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 Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
NCI_THESAURUS C2563
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 90915-0
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
NCI_THESAURUS C68357
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 88994-9
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 1889-5
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 90909-3
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 88996-4
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 90916-8
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 35168-4
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 35411-8
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 75110-7
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
Code System Code Type Description
CHEBI
15843
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
DAILYMED
27YG812J1I
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
CHEBI
36306
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-033-4
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
RXCUI
1368625
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
ALTERNATIVE
MESH
D016718
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
NCI_THESAURUS
C282
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
SMS_ID
100000088503
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID4040420
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
PUBCHEM
444899
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
DRUG BANK
DB04557
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
WIKIPEDIA
ARACHIDONIC ACID
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
RXCUI
1368624
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m2024
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY Merck Index
CAS
506-32-1
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
FDA UNII
27YG812J1I
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
EVMPD
SUB21901
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
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