Structure database (LMSD)

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LM IDLMGP20020003
Common NamePE(16:0/22:6(54Z,7Z,10Z,12E,16Z,19Z)(14OH))
Systematic Name1-hexadecanoyl-2-(14-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoyl)-sn-glycero-
3-phosphoethanolamine
Synonyms16:0/14-HDOHE-PE
Exact Mass
779.5101 (neutral)    Calculate m/z:
FormulaC43H74NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem Compound ID (CID)52929785
InChIKeyHHJJTYMYHYKVOT-LPUIUFANSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H74NO9P/c1-3-5-7-9-11-12-13-14-15-19-22-26-30-34-42(46)50-38-41(39-5
2-54(48,49)51-37-36-44)53-43(47)35-31-27-23-20-17-16-18-21-25-29-33-40(45)32-28-
24-10-8-6-4-2/h6,8,16-17,21,23-25,27-29,33,40-41,45H,3-5,7,9-15,18-20,22,26,30-3
2,34-39,44H2,1-2H3,(H,48,49)/b8-6-,17-16-,25-21-,27-23-,28-24-,33-29+/t40?,41-/m
1/s1
SMILESCCCCCCCCCCCCCCCC(=O)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 Atoms54Rings0Aromatic Rings0Rotatable Bonds39
 van der Waals
Molecular Volume
841.28Topological Polar
Surface Area
154.61Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP12.35Molar
Refractivity
223.62    
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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