Structure database (LMSD)

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LM IDLMGP03050013
Common NamePS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
Systematic Name1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phosphoserine
SynonymsLPS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); LPS(22:6)
Exact Mass
569.2754 (neutral)    Calculate m/z:
FormulaC28H44NO9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub ClassMonoacylglycerophosphoserines [GP0305]
PubChem CID52926281
SWISSLIPIDS IDSLM:000030054
InChIKeyFZUFCKYWYUGORZ-SLSDLOGTSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C28H44NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(31
)36-22-25(30)23-37-39(34,35)38-24-26(29)28(32)33/h3-4,6-7,9-10,12-13,15-16,18-19
,25-26,30H,2,5,8,11,14,17,20-24,29H2,1H3,(H,32,33)(H,34,35)/b4-3-,7-6-,10-9-,13-
12-,16-15-,19-18-/t25-,26+/m1/s1
SMILESC(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\
CC)=O)(=O)O
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 Atoms39Rings0Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
581.78Topological Polar
Surface Area
165.61Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
9
 logP6.51Molar
Refractivity
154.11    
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.