Structure Database (LMSD)

Common Name
(+/-)10-hydroxy-12Z-octadecenoic acid-d5
Systematic Name
10-hydroxyoctadec-12Z-enoic-17,17,18,18,18-d5 acid
Synonyms
  • 12(Z)-10-HOME-d5
LM ID
LMFA02000458
Formula
C18H29D5O3
Exact Mass
Calculate m/z
303.282179
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View spectra on LIPID MAPS Standard Spectra DB

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Other Octadecanoids [FA0200]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]
Unsaturated fatty acids [FA0103]

Biological Context

(±)-10-hydroxy-12(Z)-Octadecenoic acid-d5 is intended for use as an internal standard for the quantification of (±)-10-hydroxy-12(Z)-octadecenoic acid by GC- or LC-MS. (±)-10-hydroxy-12(Z)-Octadecenoic acid is an oxylipin and a metabolite of linoleic acid. 1 It is formed from linoleic acid by conjugated linoleic acid-hydrase (CLA-HY) as an intermediate in CLA biosynthesis and can also be produced from linoleic acid by gut microbiota. (±)-10-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.2 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.3 (±)-10-hydroxy-12(Z)-Octadecenoic acid (100 µM) decreases LPS-induced maturation of dendritic cells in isolated mouse bone marrow cells.

This information has been provided by Cayman Chemical

References

1. Kishino, S., Takeuchi, M., Park, S.-B., et al. Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Proc. Natl. Acad. Sci. USA 110(44), 17808-17813 (2013).
2. Ikeguchi, S., Izumi, Y., Kitamura, N., et al. Inhibitory effect of the gut microbial linoleic acid metabolites, 10-oxo-trans-11-octadecenoic acid and 10-hydroxy-cis-12-octadecenoic acid, on BV-2 microglial cell activation. J. Pharmacol. Sci. 138(1), 9-15 (2018).
3. 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
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
WVYIZGMCLSGZGG-PJKSMEJXSA-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-/i1D3,2D2
SMILES (Click to copy)
C(C(C/C=C\CCCC([2H])([2H])C([2H])([2H])[2H])O)CCCCCCCC(O)=O

Other Databases

PubChem CID
168322700
Cayman ID
37282

Calculated Physicochemical Properties

Heavy Atoms 21
Rings
Aromatic Rings
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
3rd Dec 2024
Updated at
5th Dec 2024