Structure Database (LMSD)

Common Name
(+/-)9(10)-EpOME-d4
Systematic Name
(+/-)9(10)-epoxy-12Z-octadecenoic 9,10,12,13-d4 acid
Synonyms
  • Coronaric acid-d4
  • leukotoxin-d4
  • (+/-)9,10-EODE-d4
LM ID
LMFA02000457
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

(±)9,10-EpOME-d4 is intended for use as an internal standard for the quantification of (±)9(10)-EpOME by GC- or LC-MS. (±)9(10)-EpOME is the 9,10-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst.1 It has been recovered from the lungs of hyperoxic rats and from humans with acute respiratory distress syndrome.2 Mitochondrial dysfunction is the main feature of (±)9(10)-EpOME cytotoxicity, which may be due to the diol metabolites as well as the parent epoxide.3,4

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. Ozawa, T., Hayakawa, M., Takamura, T., et al. Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia. Biochem. Biophys. Res. Commun. 134(3), 1071-1078 (1986).
3. Kosaka, K., Suzuki, K., Hayakawa, M., et al. Leukotoxin, a linoleate epoxide: Its implication in the late death of patients with extensive burns. Mol. Cell. Biochem. 139(2), 141-148 (1994).
4. Moran, J.H., Weise, R., Schnellmann, R.G., et al. Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol. Appl. Pharmacol. 146(1), 53-59 (1997).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
FBUKMFOXMZRGRB-LRVICGPYSA-N
InChi (Click to copy)
InChI=1S/C18H32O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)/b10-7-/i7D,10D,16D,17D
SMILES (Click to copy)
C(CCCCCCCC1([2H])OC1([2H])C/C(/[2H])=C(/[2H])\CCCCC)(=O)O

Other Databases

Cayman ID
10009995

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

Admin

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