Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02050011
Common NamePE(18:2(9Z,12Z)/0:0)
Systematic Name1-(9Z,12Z-octadecadienoyl)-glycero-3-phosphoethanolamine
SynonymsLPE(18:2(9Z,12Z)/0:0); LPE(18:2)
Exact Mass
477.2855 (neutral)    Calculate m/z:
FormulaC23H44NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoacylglycerophosphoethanolamines [GP0205]
PubChem CID52925130
HMDB IDHMDB0011507
SWISSLIPIDS IDSLM:000030156
InChIKeyDBHKHNGBVGWQJE-USWSLJGRSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C23H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25
)21-31-32(27,28)30-19-18-24/h6-7,9-10,22,25H,2-5,8,11-21,24H2,1H3,(H,27,28)/b7-6
-,10-9-/t22-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCCC/C=C\C/C=C\CCCCC)=O
MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
StatusActive
ReferencesImproved method for the quantification of lysophospholipids
including enol ether species by liquid chromatography-tandem mass spectrometry
James G. Bollinger, Hiromi Ii, Martin Sadilek, and Michael H. Gelb
J. Lipid Res. 010 51:(2) 440-447
Calculated physicochemical properties (?):
 Heavy Atoms32Rings0Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
490.90Topological Polar
Surface Area
128.31Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.39Molar
Refractivity
129.44    
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.