Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20020015
Common NamePE(P-18:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)(14OH))
Systematic Name1-O-(1Z-octadecenyl)-2-(14-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoyl)-sn-
Synonyms18:0p/14-HDOHE-PE; PE(40:6(OH)); PE(18:0_22:6(OH))
Exact Mass
791.5465 (neutral)    Calculate m/z:
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
AbbrevPE O-40:7;O
Abbrev ChainsPE 18:0_22:6;O
PubChem CID52929797
CHEBI ID138547
InChIKeyJLRGEXVZRFPGSD-DZAZWCTESA-N  Show lipids differing only in stereochemistry/bond geometry
Click to highlight InChI
Click to highlight SMILES
ReferencesMorgan, LT, Thomas, CP, Kuhn, H and O'Donnell, VB. (2010)
Thrombin activated human platelets acutely generate oxidized docosahexanoic acid-containing phospholipids
via 12-lipoxygenase.
Biochem J. 431, 141-148
Calculated physicochemical properties (?):
 Heavy Atoms55Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
867.09Topological 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.