Structure database (LMSD)

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LM IDLMGP02010096
Common NamePE(16:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-
phosphoethanolamine
Synonyms5,8,11,14-Eicosatetraenoic acid, 1-[[[(2-aminoethoxy)
hydroxyphosphinyl]oxy]methyl]-2-[(1-oxohexadecyl)oxy]ethyl ester, [R-(all-Z)]-
; PE(16:0/20:4)
Exact Mass
739.5152 (neutral)    Calculate m/z:
FormulaC41H74NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassDiacylglycerophosphoethanolamines [GP0201]
LIPIDAT ID7234
PubChem Compound ID (CID)9546800
HMDB IDHMDB08937
InChIKeyDRIVXEVMDWCWLI-CAQMIEAISA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C41H74NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-41(44)5
0-39(38-49-51(45,46)48-36-35-42)37-47-40(43)33-31-29-27-25-23-21-16-14-12-10-8-6
-4-2/h11,13,17-18,20,22,26,28,39H,3-10,12,14-16,19,21,23-25,27,29-38,42H2,1-2H3,
(H,45,46)/b13-11-,18-17-,22-20-,28-26-/t39-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CCC/C=CC/C=CC/C=CC/C=CCCCCC)=O)COC(CCCCCCCCCCCCCCC)
=O
MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms51Rings0Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
803.17Topological Polar
Surface Area
134.38Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP12.76Molar
Refractivity
212.67    
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.