Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP03050010
Common NamePS(16:1(9Z)/0:0)
Systematic Name1-(9Z-hexadecenoyl)-glycero-3-phosphoserine
SynonymsLPS(16:1(9Z)/0:0); LPS(16:1)
Exact Mass
495.2597 (neutral)    Calculate m/z:
FormulaC22H42NO9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub ClassMonoacylglycerophosphoserines [GP0305]
PubChem CID52926278
SWISSLIPIDS IDSLM:000030076
InChIKeyXSJRZJQMAINRKX-KGMDJONISA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C22H42NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(25)30-16-19(24)17-31
-33(28,29)32-18-20(23)22(26)27/h7-8,19-20,24H,2-6,9-18,23H2,1H3,(H,26,27)(H,28,2
9)/b8-7-/t19-,20+/m1/s1
SMILESC(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(O)COC(CCCCCCC/C=C\CCCCCC)=O)(=O)O
MS SpectraView MoNA MS spectra      Predict MS/MS spectrum (Neg. mode)
StatusActive
ReferencesImproved method for the quantification of lysophospholipids
including enol ether species by liquid chromatography-tandem mass spectrometry
James G. Bollinger, Hiromi Ii, Martin Sadilek, and Michael H. Gelb
J. Lipid Res. 010 51:(2) 440-447
Calculated physicochemical properties (?):
 Heavy Atoms33Rings0Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
491.18Topological Polar
Surface Area
165.61Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
9
 logP5.29Molar
Refractivity
126.88    
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.