Structure database (LMSD)

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LM IDLMGP02010975
Common NamePE(20:5(5Z,8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z))
Systematic Name1-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-(6Z,9Z,12Z-octadecatrienoyl)-glycero-
3-phosphoethanolamine
SynonymsPE(38:8); PE(18:3_20:5)
Exact Mass
759.4839 (neutral)    Calculate m/z:
FormulaC43H70NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub ClassDiacylglycerophosphoethanolamines [GP0201]
PubChem CID52924676
HMDB IDHMDB0009457
SWISSLIPIDS IDSLM:000033064
InChIKeyMBBQSNLOZALUSQ-TUYAJEPASA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C43H70NO8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44)52-43(46)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26-29,41H,3-4,6,8-10,15-16,20,24-25,30-40,44H2,1-2H3,(H,47,48)/b7-5-,13-11-,14-12-,19-17-,21-18-,23-22-,28-26-,29-27-/t41-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCN)([H])(OC(CCCC/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms53Rings0Aromatic Rings0Rotatable Bonds37
 van der Waals
Molecular Volume
827.21Topological Polar
Surface Area
134.38Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP12.64Molar
Refractivity
221.53    
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.