Structure database (LMSD)

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LM IDLMGP20020011
Common NamePE(P-16:0/20:4(6E,8Z,11Z,14Z)(5OH[S]))
Systematic Name1-O-(1Z-hexadecenyl)-2-(5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-
3-phosphoethanolamine
Synonyms16:0p/5-HETE-PE; PE(P-38:4(OH)); PE(P-16:0/20:4(OH))
Exact Mass
739.5152 (neutral)    Calculate m/z:
FormulaC41H74NO8P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem CID52929793
InChIKeyUJUOJVKUPIFXHE-BMFLBSJVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C41H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-35-47-37-40(38-49-5
1(45,46)48-36-34-42)50-41(44)33-30-32-39(43)31-28-26-24-22-20-18-16-14-12-10-8-6
-4-2/h12,14,18,20,24,26,28-29,31,35,39-40,43H,3-11,13,15-17,19,21-23,25,27,30,32
-34,36-38,42H2,1-2H3,(H,45,46)/b14-12-,20-18-,26-24-,31-28+,35-29-/t39-,40-/m1/s
1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCCC)=O)CO/C=C\CCC
CCCCCCCCCCC
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms51Rings0Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
803.17Topological Polar
Surface Area
137.54Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP12.61Molar
Refractivity
214.09    
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.