Structure Database (LMSD)

Common Name
17-octadecynoic acid
Systematic Name
17-octadecynoic acid
Synonyms
  • 17-ODYA
LM ID
LMFA01030575
Formula
C18H32O2
Exact Mass
Calculate m/z
280.240231
Sum Composition
FA 18:2
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]
Octadecanoids [FA02]

Biological Context

17-Octadecynoic Acid (17-ODYA) is a fatty acid alkyne. It is a suicide inhibitor of leukotriene B4 20-hydroxylase and renal CYP450 ω-hydroxylase.1,2 17-ODYA (10 µM) completely inhibits the bradykinin-dependent transport of sodium chloride in rat TALH cells.2 It has been used as a click chemistry probe for labeling palmitoylation substrates in vitro.3 It has also been used to study the formation of lipid droplets in live THP-1 macrophages and C. elegans.4

This information has been provided by Cayman Chemical

References

1. Wei, L., Hu, F., Shen, Y., et al. Live-cell imaging of alkyne-tagged small biomolecules by stimulated Raman scattering. Nat. Methods 11(4), 410-412 (2014).
2. Martin, B.R., and Cravatt, B.F. Large-scale profiling of protein palmitoylation in mammalian cells. Nat. Methods 6(2), 135-138 (2009).
3. Grider, J.S., Falcone, J.C., Kilpatrick, E.L., et al. P450 arachidonate metabolites mediate bradykinin-dependent inhibition of NaCl transport in the rat thick ascending limb. Can. J. Physiol. Pharmacol. 75(2), 91-96 (1997).
4. Shak, S., Reich, N.O., Goldstein, I.M., et al. Leukotriene B4 ω-hydroxylase in human polymorphonuclear leukocytes. Suicidal inactivation by acetylenic fatty acids. J. Biol. Chem. 260:24, 13023-13028 (1985).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Epoxyeicosatrienoic acids, potassium channel blockers and endothelium-dependent hyperpolarization in the guinea-pig carotid artery.,
Br J Pharmacol, 1998
Pubmed ID: 9504399

String Representations

InChiKey (Click to copy)
DZIILFGADWDKMF-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1H,3-17H2,(H,19,20)
SMILES (Click to copy)
C(CCCCCCCCCCCCCCCC#C)(=O)O

Other Databases

LIPIDAT ID
5820
CHEBI ID
142447
PubChem CID
1449
Cayman ID
90270
GuidePharm ID
8851

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 329.62
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.56
Molar Refractivity 85.72

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Created at
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Updated at
28th Mar 2025