Structure Database (LMSD)

Common Name
12S,13R-EpOME
Systematic Name
12S,13R-epoxy-9Z-octadecenoic acid
Synonyms
  • (9Z)-(12S,13R)-12,13-Epoxyoctadecenoic acid
  • Vernolic acid
LM ID
LMFA02000282
Formula
C18H32O3
Exact Mass
Calculate m/z
296.235145
Sum Composition
FA 18:2;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

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 is the 12,13-cis epoxide form of linoleic acid .1,2 It is formed primarily via linoleic acid metabolism by the cytochrome P450 (CYP) isoforms CYP2J2, CYP2C8, and CYP2C9, however, CYP1A1 can contribute to (±)12(13)-EpOME production when pharmacologically induced.2 (±)12(13)-EpOME (500 µM) induces mitochondrial dysfunction and cell death in renal proximal tubule epithelial cells.

This information has been provided by Cayman Chemical

References

1. Hayakawa, M., Sugiyama, S., Takamura, T., et al. Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoate. Biochem. Biophys. Res. Commun. 137(1), 424-430 (1986).
2. 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Baccharoides anthelmintica (#759864)
Magnoliopsida (#3398)
Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) seed oil,
J Chem Soc, 1954

String Representations

InChiKey (Click to copy)
CCPPLLJZDQAOHD-GJGKEFFFSA-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-/t16-,17+/m1/s1
SMILES (Click to copy)
C(CCCCCCC/C=C\C[C@@H]1O[C@@H]1CCCCC)(=O)O

Other Databases

KEGG ID
C08368
CHEBI ID
27706
PubChem CID
6449780
PlantFA ID
10337
Cayman ID
52450

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings 0
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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Updated at
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