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
Exact Mass
Calculate m/z
278.224581
Sum Composition
Status
Curated

Classification

Biological Context

α-Eleostearic acid (α-ESA), also known as 9(Z),11(E),13(E)-octadecatrienoic acid, is a conjugated polyunsaturated fatty acid and peroxisome proliferator-activated receptor γ (PPARγ) agonist that has been found in tung tree seed oil.1,2 It is converted to 9(Z),11(E)-conjugated linoleic acid by the cytochrome P450 (CYP) isoform CYP4F13 in rats.3 α-ESA (10 µM) activates PPARγ transcriptional activity in a reporter assay using RAW 264.7 cells.1 It is an inhibitor of DNA polymerase α, -β, -γ, -Δ, and -ε (IC50s = 10.7, 13.4, 10.6, 14, and 22 µM, respectively) and topoisomerase I and -II (IC50s = 20 and 5 µM, respectively).4 α-ESA reduces the viability of, and induces apoptosis in, MCF-7 breast cancer cells in a concentration-dependent manner.5 It induces ferroptosis in MDA-MB-231 breast cancer cells, increasing lipid peroxidation when used at concentrations of 50 and 100 µM and inducing cell death when used at concentrations ranging from 10 to 40 µM.2 These effects are dependent on long-chain acyl-CoA synthetase 1 (ACSL1) and can be blocked by ferrostatin-1. Dietary administration of α-ESA reduces clinical signs of disease in a model of inflammatory bowel disease (IBD) induced by dextran sodium sulfate in PPARγ-expressing, but not PPARγ-knockout, mice.1

This information has been provided by Cayman Chemical

References

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
KEGG ID
CHEBI ID
LIPIDBANK ID
DFA0186
PubChem CID
PlantFA ID
Cayman ID

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