Structure database (LMSD)

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LM IDLMGP02010960
Common NamePE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))
Systematic Name1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-glycero-
3-phosphoethanolamine
SynonymsPE(42:8); PE(20:4_22:4)
Exact Mass
815.5465 (neutral)    Calculate m/z:
FormulaC47H78NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassDiacylglycerophosphoethanolamines [GP0201]
PubChem CID52924661
HMDB IDHMDB0009405
SWISSLIPIDS IDSLM:000033147
InChIKeyIAMDYOOTWAQMME-DVRHFKRZSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C47H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-47(50)56-45(44-55-57(51,52)54-42-41-48)43-53-46(49)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,22,24-25,27-28,30-31,33,45H,3-10,15-16,21,23,26,29,32,34-44,48H2,1-2H3,(H,51,52)/b13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t45-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCN)([H])(OC(CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms57Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
896.41Topological Polar
Surface Area
134.38Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP14.20Molar
Refractivity
240.00    
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.