Structure Database (LMSD)

Common Name
13-tetradecynoic acid
Systematic Name
13-tetradecynoic acid
Synonyms
  • 13-alkyne Myristic Acid
LM ID
LMFA01030594
Formula
C14H24O2
Exact Mass
Calculate m/z
224.17763
Sum Composition
FA 14:2
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]

Biological Context

Myristic acid is a 14-carbon saturated (14:0) fatty acid. In vivo, it is commonly added covalently to the N-terminus of proteins in a co-translational process termed N-myristoylation.1 The sirtuin SIRT6 removes this acyl group from myristoylated TNF-α, enhancing secretion.2 Myristic acid alkyne is a form of this myristic acid with an ω-terminal alkyne. Such terminal alkyne groups can be used in linking reactions, known as click chemistry, characterized by high dependability and specificity of azide-alkyne bioconjugation reactions.3,4

This information has been provided by Cayman Chemical

References

1. Jiang, H., Khan, S., Wang, Y., et al. SIRT6 regulates TNF-α secretion through hydrolysis of long-chain fatty acyl lysine. Nature 496(7443), 110-113 (2013).
2. Lutz, J.-F., and Zarafshani, Z. Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry. Adv. Drug Deliv. Rev. 60(9), 958-970 (2008).
3. Kolb, H.C., and Sharpless, K.B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 8(24), 1128-1137 (2003).
4. Farazi, T.A., Waksman, G., and Gordon, J.I. The biology and enzymology of protein N-myristoylation. J. Biol. Chem. 276(43), 39501-39504 (2001).

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
synthetic construct (#32630)
Synthesised for 'click' chemistry

String Representations

InChiKey (Click to copy)
JNXXRQLAAJXERE-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h1H,3-13H2,(H,15,16)
SMILES (Click to copy)
C(CCCCCCCCCCCC#C)(=O)O

Other Databases

LIPIDAT ID
6470
CHEBI ID
196053
PubChem CID
5312715
Cayman ID
13267

Calculated Physicochemical Properties

Heavy Atoms 16
Rings 0
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 260.42
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.00
Molar Refractivity 67.26

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Created at
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Updated at
7th Jan 2025