Structure database (LMSD)

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LM IDLMGP02030003
Common NamePE(P-18:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-
phosphoethanolamine
Synonyms5,8,11,14-Eicosatetraenoic acid, 1-[[[(2-aminoethoxy)
hydroxyphosphinyl]oxy]methyl]-2-(1-octadecenyloxy)ethyl ester, [R-(all-Z)]-;
PE(P-18:0/20:4); PE(P-38:4); PE(P-18:0/20:4)
Exact Mass
751.5516 (neutral)    Calculate m/z:
FormulaC43H78NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub Class1-(1Z-alkenyl),2-acylglycerophosphoethanolamines [GP0203]
LIPIDAT ID9525
PubChem CID9547058
HMDB IDHMDB0005779
SWISSLIPIDS IDSLM:000050523
InChIKeyURPXXNCTXCOATD-FXMFQVEGSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C43H78NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,35,38,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-34,36-37,39-41,44H2,1-2H3,(H,46,47)/b13-11-,19-17-,24-22-,30-28-,38-35-/t42-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCN)([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO/C=C\CCCCCCCCCCCCCCCC
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MS StandardView lipid standard
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms52Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
828.98Topological Polar
Surface Area
117.31Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
7
 logP14.13Molar
Refractivity
221.42    
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.