Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20070013
Common NamePON-PA
Systematic Name1-hexadecanoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphate
Synonyms1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphate
Exact Mass
564.3427 (neutral)    Calculate m/z:
FormulaC28H53O9P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoglycerols [GP2007]
PubChem CID101391787
InChIKeyDQLZFJTVJNXVFN-AREMUKBSSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C28H53O9P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-21-27(30)35-24-26(25-36-38(
32,33)34)37-28(31)22-19-16-13-14-17-20-23-29/h23,26H,2-22,24-25H2,1H3,(H2,32,33,
34)/t26-/m1/s1
SMILES[C@](COP(=O)(O)O)([H])(OC(CCCCCCCC(=O)[H])=O)COC(CCCCCCCCCCCCCCC)=O
MS Spectra-     
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 Atoms38Rings0Aromatic Rings0Rotatable Bonds30
 van der Waals
Molecular Volume
583.98Topological Polar
Surface Area
136.43Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
9
 logP8.16Molar
Refractivity
148.75    
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.