Structure Database (LMSD)
Common Name
10-hydroxy-12Z-octadecenoic acid
Systematic Name
10-hydroxy-12Z-octadecenoic acid
Synonyms
- 12(Z)-10-HOME
3D model of 10-hydroxy-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-hydroxy-12(Z)-Octadecenoic acid is a racemic mixture of 10(R)-hydroxy-12(Z)-octadecenoic acid and 10(S)-hydroxy-12(Z)-octadecenoic acid. 10(S)-hydroxy-12(Z)-Octadecenoic acid, also known as HYA™, is a gut microbiome metabolite of linoleic acid that is formed by conjugated linoleic acid hydrase (CLA-HY) as an intermediate in CLA biosynthesis.1,2 10(S)-hydroxy-12(Z)-Octadecenoic acid (30 µM) inhibits LPS-induced nitric oxide (NO) production, ERK phosphorylation, and increases in inducible NO synthase (iNOS) levels in BV-2 microglia cells.3 It reduces TNF-α, NO2, and IL-10 levels in LPS-stimulated and -unstimulated isolated dendritic bone marrow cells when used at a concentration of 100 µM.4 10(S)-hydroxy-12(Z)-Octadecenoic acid (100 µM) decreases LPS-induced maturation of the dendritic cell population within isolated mouse bone marrow cells. It induces calcium mobilization in HEK293 cells expressing the human free fatty acid receptor GPR40 or GPR120 (EC50s = 7.51 and 8.1 µM, respectively).5 In vivo, 10(S)-hydroxy-12(Z)-octadecenoic acid (1 g/kg) increases GLP-1 release and reduces body weight in a mouse model of high-fat diet-induced obesity.
This information has been provided by Cayman Chemical
References
2. Bergamo, P., Luongo, D., Miyamoto, J., et al. Immunomodulatory activity of a gut microbial metabolite of dietary linoleic acid, 10-hydroxy-cis-12-octadecenoic acid, associated with improved antioxidant/detoxifying defences. J. Funct. Foods 11, 192-202 (2014).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Mortierella alpina
(#64518)
Mortierellomycetes
(#2212732)
Polyunsaturated fatty acids production and transformation by Mortierella alpina and anaerobic bacteria,
Eur J Lipid Sci, 2012
Eur J Lipid Sci, 2012
String Representations
InChiKey (Click to copy)
WVYIZGMCLSGZGG-FLIBITNWSA-N
InChi (Click to copy)
InChI=1S/C18H34O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h8,11,17,19H,2-7,9-10,12-16H2,1H3,(H,20,21)/b11-8-
SMILES (Click to copy)
C(C(C/C=C\CCCCC)O)CCCCCCCC(O)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
341.05
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
5.37
Molar Refractivity
88.99
Admin
Created at
-
Updated at
5th Jan 2023