Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20070002
Common NamePKODA-PA
Systematic Name1-hexadecanoyl-2-(9,12-dioxo-10E-dodecenoyl)-sn-glycero-3-phosphate
Synonyms1-palmitoyl-2-(9,12-dioxo-10E-dodecenoyl)-sn-glycero-3-phosphate
Exact Mass
618.3533 (neutral)    Calculate m/z:
FormulaC31H55O10P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoglycerols [GP2007]
PubChem CID134812491
InChIKeyAJQOBMGMWBFKNV-BXKMJNKPSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C31H55O10P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-23-30(34)39-26-29(27-40-42
(36,37)38)41-31(35)24-19-16-13-14-17-21-28(33)22-20-25-32/h20,22,25,29H,2-19,21,
23-24,26-27H2,1H3,(H2,36,37,38)/b22-20+/t29-/m1/s1
SMILES[C@](COP(=O)(O)O)([H])(OC(CCCCCCCC(=O)/C=C/C([H])=O)=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 Atoms42Rings0Aromatic Rings0Rotatable Bonds32
 van der Waals
Molecular Volume
639.39Topological Polar
Surface Area
153.50Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
10
 logP8.28Molar
Refractivity
162.89    
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.