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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

2013
589
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 1.2 µM [IC50]
Agonist
2752
 1.6 µM [IC50]
Agonist
2752
 3.1 µM [IC50]
Inhibitor
8504
 602.56 nM [IC50]
Inhibitor
8504
 1071.0 nM [IC50]
Binding Agent
1076
 180.0 nM [Kd]
Substrate
661
PubMed

PubMed

TitleDatePubMed
Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element.
2007-03
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.
2006-11-25
Arachidonic acid-induced gene expression in colon cancer cells.
2006-10
Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques.
2006-08-09
Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers.
2006-08
Induction of CYP1A and cyp2-mediated arachidonic acid epoxygenation and suppression of 20-hydroxyeicosatetraenoic acid by imidazole derivatives including the aromatase inhibitor vorozole.
2006-08
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.
2006-07
Mechanism of induction of muscle protein degradation by angiotensin II.
2006-07
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.
2006-06-27
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.
2006-06
Cytoglobin overexpression protects against damage-induced fibrosis.
2006-06
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?
2006-05
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006-05
How dietary arachidonic- and docosahexaenoic- acid rich oils differentially affect the murine hepatic transcriptome.
2006-04-20
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.
2006-03
Nongenomic action of progesterone inhibits oxytocin-induced phosphoinositide hydrolysis and prostaglandin F2alpha secretion in the ovine endometrium.
2006-02
[Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques].
2006-01-14
Nitric oxide alters arachidonic acid turnover in brain cortex synaptoneurosomes.
2006-01
Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial.
2005-12
Increase in heme oxygenase-1 levels ameliorates renovascular hypertension.
2005-12
Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention.
2005-12
Fenamates and diltiazem modulate lipid-sensitive mechano-gated 2P domain K(+) channels.
2005-12
Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha.
2005-11
Late-gestation rat myometrial cells express multiple isoforms of phospholipase A2 that mediate PCB 50-induced release of arachidonic acid with coincident prostaglandin production.
2005-11
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005-10-28
Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin.
2005-10
Vasoactive prostanoids are generated from arachidonic acid by COX-1 and COX-2 in the mouse.
2005-10
Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells.
2005-09
A Thrombelastograph whole blood assay for clinical monitoring of NSAID-insensitive transcellular platelet activation by arachidonic acid.
2005-07
COX-2 inhibitors and metabolism of essential fatty acids.
2005-07
Fatty acids and expression of adipokines.
2005-05-30
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.
2005-04-08
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.
2005-03
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation.
2005
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004-12
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004-10
Glucuronidation of oxidized fatty acids and prostaglandins B1 and E2 by human hepatic and recombinant UDP-glucuronosyltransferases.
2004-09
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
2004-08
Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1.
2004-08
In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG).
2004-08
Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance?
2004-07
The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney.
2004-07
2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells.
2004-04
Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.
2004-03-25
Heme oxygenase-1 protects HepG2 cells against cytochrome P450 2E1-dependent toxicity.
2004-02-01
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
Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants.
2003-11
Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology.
2003-10
Butylated hydroxyanisole specifically inhibits tumor necrosis factor-induced cytotoxicity and growth enhancement.
1992-07
Patents

Patents

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2
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8
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2
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12
JP2000069987A
2
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2
JP2000143524A
2
JP2000217596A
2
JP2000247884A
2
JP2000270885A
12
JP2000290178A
12
JP2000512663A
47
JP2001031566A
7
JP2001128642A
6
JP2001172176A
5
JP2001187791A
2
JP2001206876A
2
JP2001233778A
2
JP2001245687A
5
JP2001245688A
2
JP2001278797A
2
JP2001316387A
2
JP2001342143A
2
JP2001505882A
2
JP2001505915A
2
JP2001519700A
7
JP2001527506A
2
JP2002145777A
2
JP2002291464A
2
JP2002316937A
2
JP2002325558A
2
JP2002360184A
2
JP2002514229A
11
JP2002532687A
6
JP2002536308A
4
JP2002543230A
2
JP2003048831A
2
JP2003238401A
2
JP2003277259A
7
JP2003505427A
2
JP2003508487A
10
JP2003509485A
2
JP2003520788A
4
JP2003522787A
13
JP2003524586A
8
JP2003533978A
6
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
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SALT/SOLVATE -> PARENT
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METABOLIC ENZYME -> SUBSTRATE
COX-1
METABOLIC ENZYME -> SUBSTRATE
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NCATS
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