Structure Database (LMSD)

Common Name
Punicic acid
Systematic Name
9Z,11E,13Z-octadecatrienoic acid
Synonyms
  • Trichosanic acid
  • cis-9, trans-11, cis-13-octadecatrienoic acid
  • C18:3n-5,7,9
  • Trichosanoic acid
  • Punicinic acid
LM ID
LMFA01030146
Formula
C18H30O2
Exact Mass
Calculate m/z
278.224581
Sum Composition
FA 18:3
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

9(Z),11(E),13(Z)-Octadecatrienoic acid is an ω-5 long-chain polyunsaturated fatty acid and an isomer of 9(E),11(E),13(E)-octadecatrienoic acid and of conjugated linoleic acids.1 It has been found as a major component in pomegranate seed oil, making up approximately 65% of the fatty acid content.2 9(Z),11(E),13(Z)-Octadecatrienoic acid binds to the ligand-dependent transactivation domain (AF2) of PPARγ (IC50 = 2.5 µM) and increases PPARα and PPARγ activity in 3T3-L1 cells in a reporter assay.1

This information has been provided by Cayman Chemical

References

1. Schubert, S.Y., Lansky, E.P., and Neeman, I. Antioxidant and eicosanoid enzyme inhibition properties of pomegranate seed oil and fermented juice flavonoids. J. Ethnopharmacol. 66(1), 11-17 (1999).
2. Hontecillas, R., O'Shea, M., Einerhand, A., et al. Activation of PPARγ and α by punicic acid ameliorates glucose tolerance and suppresses obesity-related inflammation. J. Am. Coll. Nutr. 28(2), 184-195 (2009).

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
Punica granatum (#22663)
Magnoliopsida (#3398)
Lipids. Part VI. Total synthesis of α- and β-elæostearic and punicic (trichosanic) acid,
J Chem Soc, 1957

String Representations

InChiKey (Click to copy)
CUXYLFPMQMFGPL-BGDVVUGTSA-N
InChi (Click to copy)
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5-,8-7+,10-9-
SMILES (Click to copy)
C(CCCCCCC(=O)O)/C=C\C=C\C=C/CCCC

Other Databases

Wikipedia
Punicic acid
KEGG ID
C08364
CHEBI ID
8638
LIPIDBANK ID
DFA0185
PubChem CID
5281126
PlantFA ID
10110
Cayman ID
26057

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 326.98
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.66
Molar Refractivity 86.90

Admin

Created at
-
Updated at
2nd Jan 2025