Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20010009
Common NamePKHdiA-PC
Systematic Name1-hexadecanoyl-2-(4-oxo-6-carboxy-5E-hexenoyl)-sn-glycero-3-phosphocholine
Synonyms1-palmitoyl-2-(4-oxo-6-carboxy-5E-hexenoyl)-sn-glycero-3-phosphocholine
Exact Mass
649.3591 (neutral)    Calculate m/z:
FormulaC31H56NO11P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphocholines [GP2001]
PubChem CID134812280
InChIKeyLIXQARDWJRUJFM-HFRCXCCNSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C31H56NO11P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-30(36)40-25-28(26-4
2-44(38,39)41-24-23-32(2,3)4)43-31(37)22-20-27(33)19-21-29(34)35/h19,21,28H,5-18
,20,22-26H2,1-4H3,(H-,34,35,38,39)/b21-19+/t28-/m1/s1
SMILES[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(OC(CCC(=O)/C=C/C(=O)O)=O)COC(CCCCCCCCCCCC
CCC)=O
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 Atoms44Rings0Aromatic Rings0Rotatable Bonds31
 van der Waals
Molecular Volume
659.18Topological Polar
Surface Area
165.56Hydrogen
Bond Donors
1Hydrogen
Bond Acceptors
12
 logP6.55Molar
Refractivity
167.05    
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.