Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02050029
Common NamePE(18:3(9Z,12Z,15Z)/0:0)
Systematic Name1-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphoethanolamine
SynonymsLPE(18:3)
Exact Mass
475.2699 (neutral)    Calculate m/z:
FormulaC23H42NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoacylglycerophosphoethanolamines [GP0205]
PubChem CID52925148
HMDB IDHMDB0011509
SWISSLIPIDS IDSLM:000030154
InChIKeyNTBBASCGALPTDC-WOBXFXBNSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C23H42NO7P/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/h3-4,6-7,9-10,22,25H,2,5,8,11-21,24H2,1H3,(H,27,28)/
b4-3-,7-6-,10-9-/t22-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCCC/C=C\C/C=C\C/C=C\CC)=O
MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms32Rings0Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
488.26Topological Polar
Surface Area
128.31Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.17Molar
Refractivity
129.35    
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.