Structure Database (LMSD)
Common Name
9-OxoODE
Systematic Name
9-oxo-10E,12E-octadecadienoic acid
Synonyms
- 10(E),12(E)-9-oxo-ODE
3D model of 9-OxoODE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
9-oxo-10(E),12(E)-Octadecadienoic acid (9-oxo ODA) is a natural agonist, abundant in tomatoes, that activates PPARα at 10-20 µM.1 It is produced from conjugated linoleic acid, which is also known to be a PPARα agonist.1,2 9-oxo ODA increases the expression of genes regulated by PPARα in primary mouse hepatocytes, altering lipid metabolism.1
This information has been provided by Cayman Chemical
References
1. Kim, Y.I., Hirai, S., Takahashi, H., et al. 9-oxo-10(E),12(E)-octadecadienoic acid derived from tomato is a potent PPAR α agonist to decrease triglyceride accumulation in mouse primary hepatocytes. Mol. Nutr. Food Res. 55(4), 585-593 (2010).
2. Moya-Camarena, S.Y., Heuvel, J.P.V., Blanchard, S.G., et al. Conjugated linoleic acid is a potent naturally occurring ligand and activator of PPARα. J. Lipid Res. 40(8), 1426-1433 (1999).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Dimorphotheca sinuata
(#112408)
Magnoliopsida
(#3398)
Chromatographic analysis of seed oils. II. fatty acid composition of dimorphotheca oil,
J AOCS, 1964
J AOCS, 1964
DOI:
10.1007/BF02673484
Solanum lycopersicum
(#4081)
Magnoliopsida
(#3398)
9-oxo-10(E),12(E)-Octadecadienoic acid derived from tomato is a potent PPAR α agonist to decrease triglyceride accumulation in mouse primary hepatocytes.,
Mol Nutr Food Res, 2011
Mol Nutr Food Res, 2011
Pubmed ID:
21462326
String Representations
InChiKey (Click to copy)
LUZSWWYKKLTDHU-SIGMCMEVSA-N
InChi (Click to copy)
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11+
SMILES (Click to copy)
C(=C/C=C/CCCCC)\C(=O)CCCCCCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
335.77
Topological Polar Surface Area
54.37
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
5.06
Molar Refractivity
87.38
Admin
Created at
-
Updated at
15th Nov 2024