Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20030002
Common NameCL(1'-[18:2(9Z,11E)(13OOH)/18:2(9Z,11E)(13OOH)],3'- [18:2(9Z,12Z)/18:2(9Z,12Z)
Systematic Name1'-[1-(13-hydroperoxy-9Z,11E-octadienoyl),2-(9Z,12Z-octadienoyl)-sn-glycero-3-
Exact Mass
1512.9519 (neutral)    Calculate m/z:
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized Cardiolipins [GP2003]
PubChem CID52929799
InChIKeyZIHSFBWBYJWYGW-IFZFSJJHSA-N  Show lipids differing only in stereochemistry/bond geometry
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ReferencesCardiolipin: characterization of distinct oxidized molecular species
Junhwan Kim, Paul E. Minkler, Robert G. Salomon, Vernon E. Anderson, and Charles L. Hoppel
J. Lipid Res. 2011 52:(1) 125-135
Calculated physicochemical properties (?):
 Heavy Atoms104Rings0Aromatic Rings0Rotatable Bonds80
 van der Waals
Molecular Volume
1602.43Topological 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.