Structure database (LMSD)

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LM IDLMGP20020014
Common NamePE(P-16:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)(14OH))
Systematic Name1-O-(1Z-hexadecenyl)-2-(14-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoyl)-sn-
glycero-3-phosphoethanolamine
Synonyms16:0p/14-HDOHE-PE; PE(38:6(OH)); PE(16:0_22:6(OH))
Exact Mass
763.5152 (neutral)    Calculate m/z:
FormulaC43H74NO8P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem CID52929796
InChIKeyQHFOWXSGAYXXMA-GBCDHVKLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H74NO8P/c1-3-5-7-9-11-12-13-14-15-18-21-24-28-32-37-49-39-42(40-51-5
3(47,48)50-38-36-44)52-43(46)35-31-27-23-20-17-16-19-22-26-30-34-41(45)33-29-25-
10-8-6-4-2/h6,8,16-17,22-23,25-27,29-30,32,34,37,41-42,45H,3-5,7,9-15,18-21,24,2
8,31,33,35-36,38-40,44H2,1-2H3,(H,47,48)/b8-6-,17-16-,26-22-,27-23-,29-25-,34-30
+,37-32-/t41?,42-/m1/s1
SMILES[C@](COP(=O)(O)OCCN)([H])(OC(CC/C=C\C/C=C\C/C=C\C=C\C(O)C/C=C\C/C=C\CC)=O)CO/C=C
\CCCCCCCCCCCCCC
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 Atoms53Rings0Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
832.49Topological Polar
Surface Area
137.54Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP12.94Molar
Refractivity
223.14    
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.