Structure Database (LMSD)

Common Name
9S,10R-epoxy-stearic acid
Systematic Name
9S,10R-epoxy-octadecanoic acid
Synonyms
LM ID
LMFA02000001
Formula
C18H34O3
Exact Mass
Calculate m/z
298.250796
Sum Composition
FA 18:1;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]
Epoxy fatty acids [FA0107]

Biological Context

cis-9,10-Epoxyoctadecanoic acid is an epoxy fatty acid. It is an oxidation product of oleic acid formed by the cytochrome P450 (CYP) isoforms CYP2C and CYP3A.1 It has been found in the fungus P. carinii isolated from the lungs of rats in a model of P. carinii-induced pneumonia.2 cis-9,10-Epoxyoctadecanoic acid has also been found in human plasma, and plasma levels are decreased in patients with impaired liver function.1

This information has been provided by Cayman Chemical

References

1. Kaneshiro, E.S., Ellis, J.E., Guo, Z., et al. Characterizations of neutral lipid fatty acids and cis-9,10-epoxy octadecanoic acid in Pneumocystis carinii carinii. Infect. Immun. 64, 4105-4114 (1996).
2. Thum, T., Batkai, S., Malinski, P.G., et al. Measurement and diagnostic use of hepatic cytochrome P450 metabolism of oleic acid in liver disease. Liver Int. 30(8), 1181-1188 (2010).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Pneumocystis carinii (#4754)
Pneumocystomycetes (#147553)
Characterizations of neutral lipid fatty acids and cis-9,10-epoxy octadecanoic acid in Pneumocystis carinii carinii.,
Infect Immun, 1996
Pubmed ID: 8926076

String Representations

InChiKey (Click to copy)
IMYZYCNQZDBZBQ-SJORKVTESA-N
InChi (Click to copy)
InChI=1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)/t16-,17+/m1/s1
SMILES (Click to copy)
C(CCCCCCC[C@@H]1O[C@@H]1CCCCCCCC)(=O)O

Other Databases

CHEBI ID
138262
PubChem CID
119250
Cayman ID
36442

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 331.33
Topological Polar Surface Area 49.83
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.89
Molar Refractivity 87.63

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Created at
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Updated at
15th Apr 2025