Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02050036
Common NameLysoPE(0:0/16:0)
Systematic Name(2-aminoethoxy)[(2R)-2-(hexadecanoyloxy)-3-hydroxypropoxy]phosphinic acid
Synonyms-
Exact Mass
453.2855 (neutral)    Calculate m/z:
FormulaC21H44NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoacylglycerophosphoethanolamines [GP0205]
PubChem Compound ID (CID)53480922
HMDB IDHMDB11473
InChIKeyCKPBBEOJHAPPBT-HXUWFJFHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)29-20(18-23)19-28
-30(25,26)27-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
SMILESCCCCCCCCCCCCCCCC(=O)O[C@@H](COP(O)(=O)OCCN)CO
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms30Rings0Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
461.58Topological Polar
Surface Area
128.31Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.06Molar
Refractivity
120.40    
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.

logo LIPID MAPS is funded by a Wellcome Trust.