Structure database (LMSD)

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LM IDLMGP20020013
Common NamePE(P-18:0/20:4(6E,8Z,11Z,14Z)(5OH[S]))
Systematic Name1-O-(1Z-octadecenyl)-2-(5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-
3-phosphoethanolamine
Synonyms18:0p/5-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)52929795
InChIKeyNZGVLVQVZFXVAT-JAFOANHRSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C43H78NO8P/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-37-49-39-42(4
0-51-53(47,48)50-38-36-44)52-43(46)35-32-34-41(45)33-30-28-26-24-22-20-16-14-12-
10-8-6-4-2/h12,14,20,22,26,28,30-31,33,37,41-42,45H,3-11,13,15-19,21,23-25,27,29
,32,34-36,38-40,44H2,1-2H3,(H,47,48)/b14-12-,22-20-,28-26-,33-30+,37-31-/t41-,42
-/m1/s1
SMILESCCCCC/C=C\C/C=C\C/C=C\C=C\[C@@H](O)CCCC(=O)O[C@@H](COP(O)(=O)OCCN)CO/C=C\CCCCCCC
CCCCCCCCC
StatusActive
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.

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