U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin.
2001 Dec 15
Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components.
2001 Jun
Vasopressin-stimulated Ca2+ spiking in vascular smooth muscle cells involves phospholipase D.
2001 Jun
Stimulative effect of cadmium on prostaglandin E2 production in primary mouse osteoblastic cells.
2001 Mar
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
Acute effects of the cys-leukotriene-1 receptor antagonist, montelukast, on experimental colitis in rats.
2001 Oct 19
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
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.
2003 Aug 30
Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line.
2003 Feb 1
Genetic variation in cyclooxygenase 1: effects on response to aspirin.
2003 Jan
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
Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease.
2003 Oct
The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers.
2004
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
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
Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance?
2004 Jul
The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney.
2004 Jul
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation.
2005
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
COX-2 inhibitors and metabolism of essential fatty acids.
2005 Jul
Fatty acids and expression of adipokines.
2005 May 30
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
Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin.
2005 Oct
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
Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells.
2005 Sep
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
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 Mon Mar 31 17:53:15 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:15 GMT 2025
Record UNII
27YG812J1I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARA
Preferred Name English
ARACHIDONIC ACID
INCI   MART.   MI   WHO-DD  
INCI  
Official 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
Classification Tree Code System Code
DSLD 1467 (Number of products:46)
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
NCI_THESAURUS C2563
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 90915-0
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
NCI_THESAURUS C68357
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 88994-9
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 1889-5
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 90909-3
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 88996-4
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 90916-8
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 35168-4
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 35411-8
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
LOINC 75110-7
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
Code System Code Type Description
CHEBI
15843
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
DAILYMED
27YG812J1I
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
CHEBI
36306
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-033-4
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
RXCUI
1368625
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
ALTERNATIVE
MESH
D016718
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
NCI_THESAURUS
C282
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
SMS_ID
100000088503
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID4040420
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
PUBCHEM
444899
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
DRUG BANK
DB04557
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
WIKIPEDIA
ARACHIDONIC ACID
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
RXCUI
1368624
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m2024
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY Merck Index
CAS
506-32-1
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
FDA UNII
27YG812J1I
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
EVMPD
SUB21901
Created by admin on Mon Mar 31 17:53:15 GMT 2025 , Edited by admin on Mon Mar 31 17:53:15 GMT 2025
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
Durkee Industrial Foods, Cleveland, Ohio(average value).
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
MAJOR
METABOLITE ACTIVE -> PARENT