Structure database (LMSD)

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LM IDLMGP02050022
Common NamePE(20:3(8Z,11Z,14Z)/0:0)
Systematic Name1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphoethanolamine
SynonymsLPE(20:3)
Exact Mass
503.3012 (neutral)    Calculate m/z:
FormulaC25H46NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassMonoacylglycerophosphoethanolamines [GP0205]
PubChem CID52925141
HMDB IDHMDB0011516
SWISSLIPIDS IDSLM:000030150
InChIKeyRNWSKZCVPICGIX-XQCPFYKGSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C25H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22
-24(27)23-33-34(29,30)32-21-20-26/h6-7,9-10,12-13,24,27H,2-5,8,11,14-23,26H2,1H3
,(H,29,30)/b7-6-,10-9-,13-12-/t24-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(O)COC(CCCCCC/C=C\C/C=C\C/C=C\CCCCC)=O
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms34Rings0Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
522.86Topological Polar
Surface Area
128.31Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.95Molar
Refractivity
138.58    
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.