Structure Database (LMSD)

Common Name
(+/-)12(13)-EpOME-d4
Systematic Name
(+/-)12(13)-epoxy-9Z-octadecenoic-9,10,12,13-d4 acid
Synonyms
  • Vernolic acid-d4
  • isoleukotoxin-d4
  • (+/-)12,13-EODE-d4
LM ID
LMFA02000456
Formula
C18H28D4O3
Exact Mass
Calculate m/z
300.260252
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]
Unsaturated fatty acids [FA0103]
Epoxy fatty acids [FA0107]

Biological Context

(±)12(13)-EpOME-d4 is intended for use as an internal standard for the quantification of 12(13)-EpOME by GC- or LC-MS. 12(13)-EpOME is an epoxide formed primarily via metabolism of linoleic acid by the cytochrome P450 (CYP) isoforms CYP2J2, CYP2C8, and CYP2C9, however, CYP1A1 can contribute to 12(13)-EpOME production when pharmacologically induced.1 12(S),13(R)-EpOME and 12(R),13(S)-EpOME are produced at equal proportions from linoleic acid by peroxygenase, whereas CYP450-mediated metabolism of linoleic acid exclusively produces 12(S),13(R)-EpOME, in E. lagascae microsomes.2

This information has been provided by Cayman Chemical

References

1. Hildreth, K., Kodani, S.D., Hammock, B.D., et al. Cytochrome P450-derived linoleic acid metabolites EpOMEs and DiHOMEs: A review of recent studies. J. Nutr. Biochem. 19, 108484 (2020).
2. Blee, E., Ståhl, U., Schuber, F., et al. Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae. Biochem. Biophys. Res. Commun. 197(2), 778-784 (1993).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
CCPPLLJZDQAOHD-LZHWIENRSA-N
InChi (Click to copy)
InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/i8D,11D,16D,17D
SMILES (Click to copy)
C(CCCCCCC/C(/[2H])=C(/[2H])\CC1([2H])OC1([2H])CCCCC)(=O)O

Other Databases

Cayman ID
10009996

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings
Rotatable Bonds 14
Van der Waals Molecular Volume 328.69
Topological Polar Surface Area 49.83
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.67
Molar Refractivity 87.54

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Created at
3rd Dec 2024
Updated at
5th Dec 2024