Structure Database (LMSD)
Common Name
10-keto-12Z-octadecenoic acid
Systematic Name
10-oxo-12Z-octadecenoic acid
Synonyms
- 10-oxo-12-cis-octadecenoic acid
- 12(Z)-10KOME
3D model of 10-keto-12Z-octadecenoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
10-oxo-12(Z)-Octadecenoic acid is a metabolite of linoleic acid and an activator of transient receptor potential vanilloid 1 (TRPV1).1,2 It is formed from linoleic acid by conjugated linoleic acid dehydrogenase (CLA-DH) via a 10-hydroxy-12(Z)-octadecenoic acid intermediate and can also be produced from linoleic acid by gut microbiota.1 10-oxo-12(Z)-Octadecenoic acid (100 µM) selectively increases calcium levels in HEK293 cells expressing TRPV1 over those expressing TRPV2, TRPV3, TRPV4, and TRP melastatin 8 (TRPM8).2 It also induces inward currents in HEK293 cells expressing TRPV1, an effect that can be blocked by the TRPV1 antagonist capsazepine . Dietary administration of 10-oxo-12(Z)-octadecenoic acid (0.1% w/w) reduces weight gain and adipose tissue weight and increases the expression of the gene encoding mitochondrial uncoupling protein 1 (Ucp1) in wild-type, but not Trpv1 knockout, mice fed a high-fat diet. It also decreases plasma glucose and triglyceride levels in diabetic KKAy mice fed a high-fat diet.
This information has been provided by Cayman Chemical
References
1. Kim, M., Furuzono, T., Yamakuni, K., et al. 10-oxo-12(Z)-octadecenoic acid, a linoleic acid metabolite produced by gut lactic acid bacteria, enhances energy metabolism by activation of TRPV1. FASEB J. 3(11), 5036-5048 (2017).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Flavobacterium sp.
(#239)
Flavobacteriia
(#117743)
Conversion of linoleic acid to 10-hydroxy-12(Z)-octadecenoic acid byFlavobacterium sp. (NRRL B-14859),
J Am Oil Chem Soc, 1994
J Am Oil Chem Soc, 1994
DOI:
10.1007/BF02542264
String Representations
InChiKey (Click to copy)
IEQLMTRAAYQDSD-FLIBITNWSA-N
InChi (Click to copy)
InChI=1S/C18H32O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h8,11H,2-7,9-10,12-16H2,1H3,(H,20,21)/b11-8-
SMILES (Click to copy)
C(CCCCCCCCC(=O)C/C=C\CCCCC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
338.41
Topological Polar Surface Area
54.37
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
5.29
Molar Refractivity
87.48
Admin
Created at
-
Updated at
5th Jan 2023