Structure Database (LMSD)

Common Name
10-hydroxy-12Z-octadecenoic acid
Systematic Name
10-hydroxy-12Z-octadecenoic acid
Synonyms
  • 12(Z)-10-HOME
LM ID
LMFA02000345
Formula
Exact Mass
Calculate m/z
298.250795
Sum Composition
Status
Curated

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

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

CHEBI ID
PubChem CID
Cayman ID

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

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Created at
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Updated at
5th Jan 2023