Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20020010
Common NamePE(P-18:0/20:4(5Z,8Z,11Z,13E)(15OH[S]))
Systematic Name1-O-(1Z-octadecenyl)-2-(15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-
3-phosphoethanolamine
Synonyms18:0p/15-HETE-PE
Exact Mass
767.5465 (neutral)    Calculate m/z:
FormulaC43H78NO8P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem Compound ID (CID)52929792
InChIKeyQDGWOVQOWNWSKX-PGVAFJLHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H78NO8P/c1-3-5-7-8-9-10-11-12-13-14-15-19-22-25-28-32-37-49-39-42(40
-51-53(47,48)50-38-36-44)52-43(46)35-31-27-24-21-18-16-17-20-23-26-30-34-41(45)3
3-29-6-4-2/h16-17,21,23-24,26,30,32,34,37,41-42,45H,3-15,18-20,22,25,27-29,31,33
,35-36,38-40,44H2,1-2H3,(H,47,48)/b17-16-,24-21-,26-23-,34-30+,37-32-/t41-,42+/m
0/s1
SMILESCCCCCCCCCCCCCCCC/C=C\OC[C@@H](COP(O)(=O)OCCN)OC(=O)CCC/C=C\C/C=C\C/C=C\C=C\[C@H]
(O)CCCCC
StatusActive
ReferencesMaskrey, B.H., Bermudez-Fajardo, A., Morgan, A., Stewart-Jones, E., Dioszeghy, V., Taylor, G.W.,
Baker, P.R.S., Coles, B., Coffey, M.J., Kuhn, H., and O'Donnell, V.B. (2007)
Activated platelets and monocytes generate four hydroxy phosphatidylethanolamines via lipoxygenase
J Biol Chem 282, 20151-20163
Calculated physicochemical properties (?):
 Heavy Atoms53Rings0Aromatic Rings0Rotatable Bonds40
 van der Waals
Molecular Volume
837.77Topological Polar
Surface Area
137.54Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP13.39Molar
Refractivity
223.33    
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.

logo LIPID MAPS is funded by a Wellcome Trust.