Structure database (LMSD)

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LM IDLMGP01030016
Common NamePE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Systematic Name1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-
sn-glycero-3-phosphoethanolamine
SynonymsPE(22:4/22:6); PE(44:10); PE(22:4_22:6)
Exact Mass
839.5465 (neutral)    Calculate m/z:
FormulaC49H78NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphocholines [GP01]
Sub Class1-(1Z-alkenyl),2-acylglycerophosphocholines [GP0103]
PubChem CID52923868
HMDB IDHMDB0009605
SWISSLIPIDS IDSLM:000033769
InChIKeyAKHBLRYFRJWEOC-JUIVBTPUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C49H78NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-4
8(51)55-45-47(46-57-59(53,54)56-44-43-50)58-49(52)42-40-38-36-34-32-30-28-26-24-
22-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,23-26,29-32,36,38,47H,3-5,7,9-10,1
5-16,21-22,27-28,33-35,37,39-46,50H2,1-2H3,(H,53,54)/b8-6-,13-11-,14-12-,19-17-,
20-18-,25-23-,26-24-,31-29-,32-30-,38-36-/t47-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COC(CCCC
C/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
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 Atoms59Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
925.73Topological Polar
Surface Area
134.38Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
8
 logP14.53Molar
Refractivity
249.05    
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.