Structure database (LMSD)

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LM IDLMGP20020028
Common NamePON-PE
Systematic Name1-hexadecanoyl-2-(9-oxo-nonanoyl)-sn-glycero-phosphoethanolamine
Synonyms1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-phosphoethanolamine
Exact Mass
607.3849 (neutral)    Calculate m/z:
FormulaC30H58NO9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoethanolamines [GP2002]
AbbrevPE 25:1;O
PubChem CID134812359
InChIKeyMVAIWYVEWHAGGD-MUUNZHRXSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C30H58NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-21-29(33)37-26-28(27-39-41(35,36)38-25-23-31)40-30(34)22-19-16-13-14-17-20-24-32/h24,28H,2-23,25-27,31H2,1H3,(H,35,36)/t28-/m1/s1
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SMILES
[C@](COP(=O)(O)OCCN)([H])(OC(CCCCCCCC([H])=O)=O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
ReferencesOxidized Phospholipids as Endogenous Pattern Recognition Ligands in Innate Immunity. Stanley L. Hazen. The Journal of Biological Chemistry. Volume 283, Issue 23, June 2008, pp. 15527-15531. DOI 10.1074/jbc.R700054200.

http://www.jbc.org/content/283/23/15527.full.pdf
Calculated physicochemical properties (?):
 Heavy Atoms41Rings0Aromatic Rings0Rotatable Bonds33
 van der Waals
Molecular Volume
629.58Topological Polar
Surface Area
151.45Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
10
 logP8.54Molar
Refractivity
162.65    
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.