Structure database (LMSD)Return to Databases Overview
|Main Class||Oxidized glycerophospholipids [GP20]|
|Sub Class||Oxidized glycerophosphoethanolamines [GP2002]|
|InChIKey||KHCDOGCXPPEYDV-MQGJRLHQSA-N Show lipids differing only in stereochemistry/bond geometry|
1S/C32H60NO10P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-20-23-31(36)40-27-29(28-42-44(38,39)41-26-25-33)43-32(37)24-21-18-15-16-19-22-30(34)35/h9-10,29H,2-8,11-28,33H2,1H3,(H,34,35)(H,38,39)/b10-9-/t29-/m1/s1Click to highlight InChI
[C@](COP(=O)(O)OCCN)([H])(OC(CCCCCCCC(=O)O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=OClick to highlight SMILES
|References||A Novel Family of Atherogenic Oxidized Phospholipids Promotes Macrophage Foam Cell Formation via the Scavenger Receptor CD36 and Is Enriched in Atherosclerotic Lesions. Eugene A. Podrez, Eugenia Poliakov, Zhongzhou Shen, Renliang Zhang, Yijun Deng, Mingjiang Sun, Paula J. Finton, Lian Shan, Maria Febbraio, David P. Hajjar, Roy L. Silverstein, Henry F. Hoff, Robert G. Salomon, and Stanley L. Hazen. The Journal of Biological Chemistry. Volume 277, Issue 41, October 2002, pp. 38517-38523. DOI 10.1074/jbc.M205924200 http://www.jbc.org/content/277/41/38517|
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.