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
Endogenous prostaglandin formation in the field-stimulated guinea-pig vas deferens: comparison of the inhibitory effects of indomethacin and NS-398.
1999 Dec
Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression.
1999 Jun
Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells.
2000 Dec
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
2000 Jun 20
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.
2000 Sep 15
Prostaglandin levels in stimulated macrophages are controlled by phospholipase A2-activating protein and by activation of phospholipase C and D.
2001 Feb 23
Acute effects of the cys-leukotriene-1 receptor antagonist, montelukast, on experimental colitis in rats.
2001 Oct 19
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
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
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
Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes.
2003 Feb
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
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
2004 Aug
Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance?
2004 Jul
Glucuronidation of oxidized fatty acids and prostaglandins B1 and E2 by human hepatic and recombinant UDP-glucuronosyltransferases.
2004 Sep
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation.
2005
Increase in heme oxygenase-1 levels ameliorates renovascular hypertension.
2005 Dec
Fenamates and diltiazem modulate lipid-sensitive mechano-gated 2P domain K(+) channels.
2005 Dec
COX-2 inhibitors and metabolism of essential fatty acids.
2005 Jul
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
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
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
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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