Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20020040
Common NameOKOHA-PE
Systematic Name1-(9Z-octadecenoyl)-2-(4,7-dioxo-5E-heptenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms-
Exact Mass
617.3329 (neutral)    Calculate m/z:
FormulaC30H52NO10P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem CID134812370
InChIKeyYKOVBCROVCVQHT-BJPYDILMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI1S/C30H52NO10P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-29(34)38-25-28(26-40-4
2(36,37)39-24-22-31)41-30(35)21-20-27(33)18-17-23-32/h9-10,17-18,23,28H,2-8,11-1
6,19-22,24-26,31H2,1H3,(H,36,37)/b10-9-,18-17+/t28-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CCC(=O)/C=C/C=O)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O
StatusActive
ReferencesA 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
Calculated physicochemical properties (?):
 Heavy Atoms42Rings0Aromatic Rings0Rotatable Bonds31
 van der Waals
Molecular Volume
630.45Topological Polar
Surface Area
168.52Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
11
 logP7.27Molar
Refractivity
162.85    
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.