Structure Database (LMSD)

Common Name
alpha-eleostearic acid
Systematic Name
9Z,11E,13E-octadecatrienoic acid
Synonyms
  • cis-9, trans-11, trans-13-octadecatrienoic acid
  • C18:3n-5,7,9
  • alpha-eleostearinic acid
  • Margarolic acid
  • cis-Eleostearic acid
LM ID
LMFA01030147
Formula
C18H30O2
Exact Mass
Calculate m/z
278.224581
Sum Composition
FA 18:3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

9(Z),11(E),13(E)-Octadecatrienoic Acid (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil.1 α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats.2 It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ.1 In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 µM.2 It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 µM for different isoforms of the enzymes.3

This information has been provided by Cayman Chemical

References

2. Tsuzuki, T., Tokuyama, Y., Igarashi, M., et al. Tumor growth suppression by a α-eleostearic acid, linolenic acid isomer with a conjugated triene system, via lipid peroxidation. Carcinogenesis 25(8), 1417-1425 (2004).
3. Mizushina, Y., Tsuzuki, T., Eitsuka, T., et al. Inhibitory action of conjugated C18-fatty acids on DNA polymerases and DNA topoisomerases. Lipids 39(10), 977-983 (2004).
1. Yasui, Y., Hosokawa, M., Sahara, T., et al. Bitter gourd seed fatty acid rich in 9c,11t,13t-conjugated linolenic acid induces apoptosis and up-regulates the GADD45, p53 and PPARγ in human colon cancer caco-2 cells. Prostaglandins Leukot. Essent. Fatty Acids 73(2), 113-119 (2005).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
CUXYLFPMQMFGPL-WPOADVJFSA-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
eleostearic acid
KEGG ID
C08315
CHEBI ID
10275
LIPIDBANK ID
DFA0186
PubChem CID
5281115
PlantFA ID
10109
Cayman ID
10008349

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

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Created at
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Updated at
25th Apr 2022