Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02050023
Common NamePE(22:1(11Z)/0:0)
Systematic Name1-(11Z-docosenoyl)-glycero-3-phosphoethanolamine
SynonymsLPE(22:1)
Exact Mass
535.3638 (neutral)    Calculate m/z:
FormulaC27H54NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoacylglycerophosphoethanolamines [GP0205]
PubChem CID52925142
InChIKeyYIRCYBYHGSZKPX-XCMWCYMESA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C27H54NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(30
)33-24-26(29)25-35-36(31,32)34-23-22-28/h11-12,26,29H,2-10,13-25,28H2,1H3,(H,31,
32)/b12-11-/t26-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCCCCC/C=C\CCCCCCCCCC)=O
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms36Rings0Aromatic Rings0Rotatable Bonds28
 van der Waals
Molecular Volume
562.74Topological Polar
Surface Area
128.31Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP8.18Molar
Refractivity
148.00    
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.