Structure database (LMSD)Return to Databases Overview
|Main Class||Oxidized glycerophospholipids [GP20]|
|Sub Class||Oxidized glycerophosphocholines [GP2001]|
|InChIKey||PEZXEQJZQAVYCZ-NLMPBQEBSA-N Show lipids differing only in stereochemistry/bond geometry|
InChI=1S/C32H58NO11P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-31(37)41-26-29(27-43-45(39,40)42-25-24-33(2,3)4)44-32(38)21-18-19-28(34)22-23-30(35)36/h22-23,29H,5-21,24-27H2,1-4H3,(H-,35,36,39,40)/b23-22+/t29-/m1/s1Click to highlight InChI
[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCCCCCCCCCC)=OClick to highlight SMILES
|References||Oxidized Phospholipids as Endogenous Pattern Recognition Ligands in Innate Immunity. Stanley L. Hazen. The Journal of Biological Chemistry. Volume 283, Issue 23, June 2008, pp. 15527-15531. DOI 10.1074/jbc.R700054200.|
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.