Arachidonic acidAA

PUFA20:4Ω-6

  Overview

Stats

PUFA
Type
20
Carbons
4
Double bonds
3
Bis-allylic sites
304.47
Weight · g/mol
-49.5 °C
Melting point
C20H32O2
Formula

Also known as

IUPAC (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Synonyms

  At a Glance

Key Points

A key precursor of leukotrienes, prostaglandins and thromboxanes (eicosanoid signaling).

Source

Conditionally essential. Primarily from meat; also in fungi and fish & seafood. Also made by the body.

Type

Long-chain polyunsaturated fatty acid with 20 carbons and four cis double bonds, an omega-6 fatty acid. Its multiple bis-allylic sites make it prone to oxidation.

Identification

  Synonyms

Common Name Arachidonic acid
IUPAC Name (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional Name —
Other Synonyms
  • 5Z,8Z,11Z,14Z-icosatetraenoic acid
  • Arachidonate
  • cis-5,8,11,14-Eicosatetraenoic acid
  • (all-Z)-5,8,11,14-Eicosatetraenoic acid
  • all-cis-5,8,11,14-eicosatetraenoic acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030001
Lipid Bank DFA0213
Swiss Lipids 000000296
PlantFA ID —
Food & Nutrition
FooDB FDB011872
INFOODS —
Chemistry / Compounds
PubChem CID 444899
CAS 506-32-1
ChEBI 15843
ChEMBL CHEMBL15594
ChemSpider 392692
InChIKey —
ZINC ID ZINC000004474696
NIKKAJI ID J12.228I
PDBe ACD
UCI (UniChem) 274717
SureChEMBL 16162
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0001043
METLIN 193
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS10446
BioCyc/MetaCyc ARACHIDONIC_ACID
MetaNetX ID MNXM135
BiGG ID 1586189
KEGG C00219
KNApSAcK C00000388
Reactome ID —
Drugs & Pharmacology
DrugBank DB04557
DrugCentral —
BindingDB 22319
Guide to Pharm 2391
Probes & Drugs —
Clinical & Medical
SNOMED-CT —
MeSH D016718
NCIt Code C282
Regulatory
NIH UNII (USA) 27YG812J1I
FDA SRS (USA) 27YG812J1I
NHPID (Canada) —
DTXSID (USA) DTXSID4040420
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-666-529
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:4 (3)

Other fatty acids sharing the 20:4 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Arachidonic acid
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
 5Z,8Z,11Z,14Z —
444899
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Description —
Origin Details

No origin information recorded.
Positional (2)
Eicosatetraenoic acid
(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoic acid
 8Z,11Z,14Z,17Z —
11722594
Category —
Conjugation Type Isolated
SMILES CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Juniperonic Acid
(5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid
 5Z,11Z,14Z,17Z —
5312543
Category Non-Methylene-Interrupted Omega-3 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C\C=C/CCCC\C=C/CCCC(=O)O
Description A non-methylene-interrupted omega-3 polyunsaturated fatty acid with a characteristic Δ5 olefin, found in gymnosperm seeds and investigated for anti-proliferative and eicosanoid-modulating activity.
Origin Details
Origin Source Type Details
Gymnosperm Seeds Natural Present in seeds of Juniperus, Podocarpus, Ginkgo, and Taxus species as the C20 product of gymnosperm Δ5-desaturase acting on eicosatrienoic intermediates.

Chemical Properties

Name(s):
Common Name Arachidonic acid
Abbreviation AA
Simple Notation 20:4
Notation 20:4(n-6)
IUPAC Name (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Structure:
Molecular C20H32O2
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Cis / Trans cis
E-Z 5Z,8Z,11Z,14Z
Physical:
Weight 304.47 g/mol
Melting Point -49.5 °C
Reactivity
Double Bonds 4
Bis-Allylic Carbons 3 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 137 ATP