Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMFA03000014
Common Name8R,9S-cis-epoxy-10S-hydroxy-eicosa-11Z,14Z-dienoic acid.
Systematic Name8R,9S-epoxy-10S-hydroxy-11Z,14Z-eicosadienoic acid.
Synonyms8R,9S-epoxy-10S-hydroxy-eicosa-11Z,14Z-dienoic acid.
Exact Mass
338.2457 (neutral)    Calculate m/z:
FormulaC20H34O4
CategoryFatty Acyls [FA]
Main ClassEicosanoids [FA03]
Sub ClassOther Eicosanoids [FA0300]
Alternative ClassesUnsaturated fatty acids[FA0103], Hydroxy fatty acids[FA0105], Epoxy fatty acids[FA0107]
PubChem CID56935877
InChIKeyOSJHGFZWDLQFAS-GPTLMNHHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-11-14-17(21)20-18(24-20)15-12-9-10-13-16-19(2
2)23/h6-7,11,14,17-18,20-21H,2-5,8-10,12-13,15-16H2,1H3,(H,22,23)/b7-6-,14-11-/t
17-,18+,20-/m0/s1
SMILESC(O)(=O)CCCCCC[C@H]1O[C@H]1[C@@H](O)/C=C\C/C=C\CCCCC
StatusActive
References8R-Lipoxygenase-catalyzed synthesis of a prominent cis-epoxyalcohol from dihomo-gamma-linolenic acid:
a distinctive transformation compared with S-lipoxygenases
Jing Jin, William E. Boeglin, Jin K. Cha and Alan R. Brash.
J. Lipid Res. 53, 292-299 (2012)
Calculated physicochemical properties (?):
 Heavy Atoms24Rings1Aromatic Rings0Rotatable Bonds15
 van der Waals
Molecular Volume
369.44Topological Polar
Surface Area
70.06Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
4
 logP5.48Molar
Refractivity
98.58