Structure Database (LMSD)

Common Name
5,8,11,14-Eicosatetraynoic acid
Systematic Name
5,8,11,14-Eicosatetraynoic acid
Synonyms
LM ID
LMFA01030691
Formula
C20H24O2
Exact Mass
Calculate m/z
296.17763
Sum Composition
FA 20:8
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

5,8,11,14-Eicosatetraynoic Acid (ETYA) is a nonspecific inhibitor of cyclooxygenases and lipoxygenases.1 ETYA inhibits human platelet 12-LO and COX-1 with IC50 values of 4 µM and 8 µM, respectively.1 ETYA is a PPAR ligand which activates PPARα and PPARγ chimeras at concentrations of 10 µM.2

This information has been provided by Cayman Chemical

References

1. Hammarström, S. Selective inhibition of platelet n-8 lipoxygenase by 5,8,11-eicosatriynoic acid. Biochim. Biophys. Acta 487(3), 517-519 (1977).
2. Kliewer, S.A., Lenhard, J.M., Willson, T.M., et al. A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiation. Cell 83(5), 813-819 (1995).

Reactions

Filter by species:
ⓘ 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.
Click on an edge to display the reaction(s).
Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Selective inhibition of platelet n-8 lipoxygenase by 5,8,11-eicosatriynoic acid.,
Biochim Biophys Acta, 1977
Pubmed ID: 406933

String Representations

InChiKey (Click to copy)
MGLDCXPLYOWQRP-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
SMILES (Click to copy)
C(CCCC#CCC#CCC#CCC#CCCCCC)(=O)O

Other Databases

LIPIDAT ID
3500
CHEBI ID
94483
PubChem CID
1780
Cayman ID
90120
PDB ID
ITY
GuidePharm ID
2669

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 348.38
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.01
Molar Refractivity 90.58

Admin

Created at
-
Updated at
28th Mar 2025