Structure database (LMSD)

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LM IDLMGP20020002
Common NamePE(18:0/20:4(5Z,8Z,11Z,13E)(15OH[S]))
Systematic Name1-octadecanoyl-2-(15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoyl)-sn-glycero-3-
phosphoethanolamine
Synonyms18:0/15-HETE-PE
Exact Mass
783.5414 (neutral)    Calculate m/z:
FormulaC43H78NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
PubChem Compound ID (CID)52929784
InChIKeyICSHQSNRXGUFHT-AQLFUWFLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H78NO9P/c1-3-5-7-8-9-10-11-12-13-14-17-20-23-26-30-34-42(46)50-38-41
(39-52-54(48,49)51-37-36-44)53-43(47)35-31-27-24-21-18-15-16-19-22-25-29-33-40(4
5)32-28-6-4-2/h15-16,21-22,24-25,29,33,40-41,45H,3-14,17-20,23,26-28,30-32,34-39
,44H2,1-2H3,(H,48,49)/b16-15-,24-21-,25-22-,33-29+/t40-,41+/m0/s1
SMILESCCCCCCCCCCCCCCCCCC(=O)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 Atoms54Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
846.56Topological Polar
Surface Area
154.61Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP12.79Molar
Refractivity
223.81    
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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