Structure Database (LMSD)

Common Name
Arachidonic acid
Systematic Name
5Z,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
  • 5Z,8Z,11Z,14Z-icosatetraenoic acid
  • AA
  • Arachidonate
  • cis-5,8,11,14-Eicosatetraenoic acid
  • (all-Z)-5,8,11,14-Eicosatetraenoic acid
  • all-cis-5,8,11,14-Eicosatetraenoic acid
LM ID
LMFA01030001
Formula
C20H32O2
Exact Mass
Calculate m/z
304.24023
Sum Composition
FA 20:4
Status
Curated
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View ion mobility data

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

Arachidonic acid is an essential fatty acid and a precursor for all prostaglandins, thromboxanes, and leukotrienes. Virtually all cellular arachidonic acid is esterified in membrane phospholipids where its presence is tightly regulated through multiple interconnected pathways.1 Free arachidonic acid is a transient, critical substrate for the biosynthesis of eicosanoid second messengers. Receptor-stimulated release, metabolism, and re-uptake of free arachidonate are all important aspects of cell signaling and inflammation.2

This information has been provided by Cayman Chemical

References

1. Burgoyne, R.D., and Morgan, A. The control of free arachidonic acid levels. Trends Biochem. Sci. 15(10), 365-366 (1990).
2. Nixon, A.B., Greene, D.G., and Wykle, R.L. Comparison of acceptor and donor substrates in the CoA-independent transacylase reaction in human neutrophils. Biochim. Biophys. Acta 1300(3), 187-196 (1996).

Reactions

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ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
YZXBAPSDXZZRGB-DOFZRALJSA-N
InChi (Click to copy)
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-
SMILES (Click to copy)
C(O)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC

Other Databases

Wikipedia
Arachidonic acid
KEGG ID
C00219
HMDB ID
HMDB0001043
CHEBI ID
15843
LIPIDBANK ID
DFA0213
PubChem CID
444899
PlantFA ID
10144
SwissLipids ID
SLM:000000296
Cayman ID
90010
PDB ID
ACD
GuidePharm ID
2391

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 358.94
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.22
Molar Refractivity 96.04

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Created at
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Updated at
25th Apr 2022