Structure database (LMSD)

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LM IDLMGP02020020
Common NamePE(O-16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Systematic Name1-hexadecyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-
phosphoethanolamine
SynonymsPE(16:0e/22:6)
Exact Mass
749.5359 (neutral)    Calculate m/z:
FormulaC43H76NO7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoethanolamines [GP02]
Sub Class1-alkyl,2-acylglycerophosphoethanolamines [GP0202]
PubChem Compound ID (CID)22833649
InChIKeyJJMPYAHUHHQAJB-FYOCAXJLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H76NO7P/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-26-28-30-32-34-36-4
3(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-18-16-14-12-10-
8-6-4-2/h5,7,11,13,17,19,21-22,24,26,30,32,42H,3-4,6,8-10,12,14-16,18,20,23,25,2
7-29,31,33-41,44H2,1-2H3,(H,46,47)/b7-5-,13-11-,19-17-,22-21-,26-24-,32-30-/t42-
/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CC/C=CC/C=CC/C=CC/C=CC/C=CC/C=CCC)=O)COCCCCCCCCCCCC
CCCC
StatusActive
ReferencesQuantitative analysis of phospholipids containing arachidonate and
docosahexaenoate chains in microdissected regions of mouse brain
Paul H. Axelsen and Robert C. Murphy
J. Lipid Res. 2010 51:(3) 660-671
Calculated physicochemical properties (?):
 Heavy Atoms52Rings0Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
826.34Topological Polar
Surface Area
117.31Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
7
 logP13.85Molar
Refractivity
222.07    
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.