File:Arachidonic_acid.svg · Wikimedia Commons · See Wikimedia Commons
arachidonic acid
Sign in to saveAlso known as all-cis-5,8,11,14-eicosatetraenoic acid, cis-Delta(5,8,11,14)-eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid, AA, ARA, Arachidonate, cis-D5,8,11,14-Eicosatetraenoic acid, 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid
chemical compound
OverviewAI-generated
Arachidonic acid is a chemical compound with the IUPAC name (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid. Its chemical formula is C₂₀H₃₂O₂, and it has a mass of 304.24. The substance exhibits a density of 0.922, a melting point of -49.5, and a flash point of 113. Its pKa value is 4.752.
The compound has an xlogp of 6.3 and a topological polar surface area (tpsa) of 37.3. It contains one hydrogen bond donor and two hydrogen bond acceptors, with a charge of 0. The canonical SMILES representation is CCCCCC=CCC=CCC=CCC=CCCCC(=O)O, while the isomeric SMILES is CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O.
Literature references for arachidonic acid number 51,763. The subject is referenced by 1,085 other encyclopedia articles.
Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
In the Vinony graph
Vinony's link graph records 1,085 inbound references to arachidonic acid, and connects out to hepoxilin, phospholipids and cell signaling.
Vinony files it under Alkenoic acids, Arachidonyl compounds and Chembox having GHS data.
Vinony links it to 45 Wikipedia language editions.
Chemical data
- Formula
- C20H32O2
- Molecular weight
- 304.5 g/mol
- IUPAC name
- (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
- SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
- InChIKey
- YZXBAPSDXZZRGB-DOFZRALJSA-N
- XLogP
- 6.3
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
51,763 papers- Arachidonic Acid Derivatives and Neuroinflammation.CNS & neurological disorders drug targets · 2022
- Role of arachidonic acid-derived eicosanoids in intestinal innate immunity.Critical reviews in food science and nutrition · 2021
- Arachidonic Acid Mediators and their Role in Neurological Disease.CNS & neurological disorders drug targets · 2022
- Regulation of arachidonic acid oxidation and metabolism by lipid electrophiles.Prostaglandins & other lipid mediators · 2021
- Intake of arachidonic acid-containing lipids in adult humans: dietary surveys and clinical trials.Lipids in health and disease · 2019
via PubMed
Wikidata facts
- Subclass of
- eicosatetraenoic acid
- Has part
- hydrogen
- Mass
- 304.24
Show 9 more facts
- found in taxon
- Epilobium dodonaei
- canonical SMILES
- CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
- chemical formula
- C₂₀H₃₂O₂
- isomeric SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
- density
- 0.922
- melting point
- -49.5
- flash point
- 113
- pKa
- 4.752
- Commons category
- Arachidonic acid
Sources (7)
via Wikidata · CC0
~12 min read
Encyclopedic overview
Names
Preferred IUPAC name (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid
Excerpted from Wikipedia’s “arachidonic acid” article, available under the CC BY-SA 4.0 licence.