Structure database (LMSD)

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LM IDLMGP20020015
Common NamePE(P-18:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)(14OH))
Systematic Name1-O-(1Z-octadecenyl)-2-(14-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoyl)-sn-
glycero-3-phosphoethanolamine
Synonyms18:0p/14-HDOHE-PE
Exact Mass
791.5465 (neutral)    Calculate m/z:
FormulaC45H78NO8P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem Compound ID (CID)52929797
InChIKeyJLRGEXVZRFPGSD-DZAZWCTESA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C45H78NO8P/c1-3-5-7-9-11-12-13-14-15-16-17-20-23-26-30-34-39-51-41-44(4
2-53-55(49,50)52-40-38-46)54-45(48)37-33-29-25-22-19-18-21-24-28-32-36-43(47)35-
31-27-10-8-6-4-2/h6,8,18-19,24-25,27-29,31-32,34,36,39,43-44,47H,3-5,7,9-17,20-2
3,26,30,33,35,37-38,40-42,46H2,1-2H3,(H,49,50)/b8-6-,19-18-,28-24-,29-25-,31-27-
,36-32+,39-34-/t43?,44-/m1/s1
SMILESCCCCCCCCCCCCCCCC/C=C\OC[C@@H](COP(O)(=O)OCCN)OC(=O)CC/C=C\C/C=C\C/C=C\C=C\C(O)C/
C=C\C/C=C\CC
StatusActive
ReferencesMorgan, LT, Thomas, CP, Kuhn, H and O'Donnell, VB. (2010)
Thrombin activated human platelets acutely generate oxidized docosahexanoic acid-containing phospholipids
via 12-lipoxygenase.
Biochem J. 431, 141-148
Calculated physicochemical properties (?):
 Heavy Atoms55Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
867.09Topological Polar
Surface Area
137.54Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP13.72Molar
Refractivity
232.37    
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.

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