Structure Database (LMSD)

Common Name
8,11,14-Eicosatriynoic acid
Systematic Name
8,11,14-Eicosatriynoic acid
Synonyms
LM ID
LMFA01030692
Formula
C20H28O2
Exact Mass
Calculate m/z
300.20893
Sum Composition
FA 20:6
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

8,11,14-Eicosatriynoic acid is an inhibitor of prostaglandin and leukotriene biosynthesis as well as arachidonic acid induced platelet aggregation.1 It inhibits cyclooxygenase (IC50 = 14 µM), human 12-lipoxygenase (IC50 = 0.46 µM), 5-lipoxygenase (IC50 = 25 µM) and the actions of slow-reacting substance of anaphylaxis (SRS-A) (IC50 = 10 µM).2,3

This information has been provided by Cayman Chemical

References

1. Sun, F.F., McGuire, J.C., Morton, D.R., et al. Inhibition of platelet arachidonic acid 12-lipoxygenase by acetylenic acid compounds. Prostaglandins 21(2), 333-343 (1981).
2. Goetz, J.M., Sprecher, H., Cornwell, D.G., et al. Inhibition of prostaglandin biosynthesis by triynoic acids. Prostaglandins 12(2), 187-192 (1976).
3. Jakschik, B.A., DiSantis, D.M., Sankarappa, S.K., et al. Modulation of leukotriene formation by various acetylenic acids. Leukotrienes and Other Lipoxygenase Products 127-135 (1982).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Inhibition of prostaglandin biosynthesis by triynoic acids.,
Prostaglandins, 1976
Pubmed ID: 959584

String Representations

InChiKey (Click to copy)
QLLIWTBTVOPGCM-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14-19H2,1H3,(H,21,22)
SMILES (Click to copy)
C(CCCCCCC#CCC#CCC#CCCCCC)(=O)O

Other Databases

LIPIDAT ID
3501
CHEBI ID
192957
PubChem CID
9543604
Cayman ID
10007900

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 353.66
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.78
Molar Refractivity 92.04

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Created at
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Updated at
5th Mar 2025