Structure database (LMSD)

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LM IDLMGP20020004
Common NamePE(18:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)(14OH))
Systematic Name1-octadecanoyl-2-(14-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoyl)-sn-glycero-
3-phosphoethanolamine
Synonyms18:0/14-HDOHE-PE; PE(40:6(OH)); PE(18:0_22:6(OH))
Exact Mass
807.5414 (neutral)    Calculate m/z:
FormulaC45H78NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
AbbrevPE 40:6;O
Abbrev ChainsPE 18:0_22:6;O
PubChem CID52929786
InChIKeyWTJFOADFPCHAKT-BDGBNODMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C45H78NO9P/c1-3-5-7-9-11-12-13-14-15-16-17-21-24-28-32-36-44(48)52-40-43(41-54-56(50,51)53-39-38-46)55-45(49)37-33-29-25-22-19-18-20-23-27-31-35-42(47)34-30-26-10-8-6-4-2/h6,8,18-19,23,25-27,29-31,35,42-43,47H,3-5,7,9-17,20-22,24,28,32-34,36-41,46H2,1-2H3,(H,50,51)/b8-6-,19-18-,27-23-,29-25-,30-26-,35-31+/t42?,43-/m1/s1
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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)COC(CCCCCCCCCCCCCCCCC)=O
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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 Atoms56Rings0Aromatic Rings0Rotatable Bonds41
 van der Waals
Molecular Volume
875.88Topological Polar
Surface Area
154.61Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP13.13Molar
Refractivity
232.86    
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.