Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMFA03000011
Common Name5S-HETE di-endoperoxide
Systematic Name5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid
Synonyms-
Exact Mass
402.2254 (neutral)    Calculate m/z:
FormulaC20H34O8
CategoryFatty Acyls [FA]
Main ClassEicosanoids [FA03]
Sub ClassOther Eicosanoids [FA0300]
Alternative ClassesUnsaturated fatty acids[FA0103], Hydroxy fatty acids[FA0105], Carbocyclic fatty acids[FA0114]
PubChem CID52921873
InChIKeyDOXGUXRZAOCYPM-IPIAXWAYSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C20H34O8/c1-2-3-4-6-14(21)9-11-16-18-13-19(28-27-18)17(26-25-16)12-10-1
5(22)7-5-8-20(23)24/h10,12,14-19,21-22H,2-9,11,13H2,1H3,(H,23,24)/b12-10+/t14-,1
5-,16-,17-,18+,19-/m0/s1
SMILES[C@@H]12OO[C@@H]([C@H](CC[C@@H](O)CCCCC)OO[C@H]1/C=C/[C@@H](O)CCCC(=O)O)C2
StatusActive
ReferencesConvergence of the 5-LOX and COX-2 pathways:
heme-catalyzed cleavage of the 5S-HETE-derived di-endoperoxide into aldehyde fragments.
Griesser M, Boeglin WE, Suzuki T, Schneider C.
J Lipid Res. 2009 Dec;50(12):2455-62
Calculated physicochemical properties (?):
 Heavy Atoms28Rings2Aromatic Rings0Rotatable Bonds13
 van der Waals
Molecular Volume
394.88Topological Polar
Surface Area
122.96Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP4.39Molar
Refractivity
103.20