Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20020010
Common NamePE(P-18:0/20:4(5Z,8Z,11Z,13E)(15OH[S]))
Systematic Name1-O-(1Z-octadecenyl)-2-(15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-
Synonyms18:0p/15-HETE-PE; PE(P-40:4(OH)); PE(P-18:0/20:4(OH))
Exact Mass
767.5465 (neutral)    Calculate m/z:
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
AbbrevPE O-38:5;O
Abbrev ChainsPE P-18:0/20:4;O
PubChem CID52929792
InChIKeyQDGWOVQOWNWSKX-PGVAFJLHSA-N  Show lipids differing only in stereochemistry/bond geometry
Click to highlight InChI
Click to highlight SMILES
ReferencesMaskrey, B.H., Bermudez-Fajardo, A., Morgan, A., Stewart-Jones, E., Dioszeghy, V., Taylor, G.W.,
Baker, P.R.S., Coles, B., Coffey, M.J., Kuhn, H., and O'Donnell, V.B. (2007)
Activated platelets and monocytes generate four hydroxy phosphatidylethanolamines via lipoxygenase
J Biol Chem 282, 20151-20163
Calculated physicochemical properties (?):
 Heavy Atoms53Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
837.77Topological Polar
Surface Area
Bond Donors
Bond Acceptors
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.