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

Details

Stereochemistry ACHIRAL
Molecular Formula C20H31O2.Na
Molecular Weight 326.4487
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ARACHIDONIC ACID, SODIUM SALT

SMILES

[Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O

InChI

InChIKey=DDMGAAYEUNWXSI-XVSDJDOKSA-M
InChI=1S/C20H32O2.Na/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);/q;+1/p-1/b7-6-,10-9-,13-12-,16-15-;

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H31O2
Molecular Weight 303.4589
Charge -1
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
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
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
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.
2003 Aug 30
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
Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease.
2003 Oct
Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation.
2003 Sep
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
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
2004 Aug
Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1.
2004 Aug
In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG).
2004 Aug
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
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
Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.
2004 Mar 25
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
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
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.
2005 Apr 8
Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial.
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
COX-2 inhibitors and metabolism of essential fatty acids.
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
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
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
[Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques].
2006 Jan-Apr
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
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 Thu Jul 06 14:11:36 UTC 2023
Edited
by admin
on Thu Jul 06 14:11:36 UTC 2023
Record UNII
SGR9XN5UVM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARACHIDONIC ACID, SODIUM SALT
Common Name English
5,8,11,14-EICOSATETRAENOIC ACID, SODIUM SALT, (ALL-Z)-
Common Name English
Code System Code Type Description
FDA UNII
SGR9XN5UVM
Created by admin on Thu Jul 06 14:11:37 UTC 2023 , Edited by admin on Thu Jul 06 14:11:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID001047683
Created by admin on Thu Jul 06 14:11:37 UTC 2023 , Edited by admin on Thu Jul 06 14:11:37 UTC 2023
PRIMARY
PUBCHEM
23675453
Created by admin on Thu Jul 06 14:11:37 UTC 2023 , Edited by admin on Thu Jul 06 14:11:37 UTC 2023
PRIMARY
CAS
6610-25-9
Created by admin on Thu Jul 06 14:11:37 UTC 2023 , Edited by admin on Thu Jul 06 14:11:37 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE