Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP03050027
Common NamePS(20:5(5Z,8Z,11Z,14Z,17Z)/0:0)
Systematic Name1-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-glycero-3-phosphoserine
Synonyms-
Exact Mass
543.2597 (neutral)    Calculate m/z:
FormulaC26H42NO9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub ClassMonoacylglycerophosphoserines [GP0305]
PubChem CID52926295
SWISSLIPIDS IDSLM:000030056
InChIKeyGXWJRGLFYSTLKU-AQFYTDKMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C26H42NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(29)34-20
-23(28)21-35-37(32,33)36-22-24(27)26(30)31/h3-4,6-7,9-10,12-13,15-16,23-24,28H,2
,5,8,11,14,17-22,27H2,1H3,(H,30,31)(H,32,33)/b4-3-,7-6-,10-9-,13-12-,16-15-/t23-
,24+/m1/s1
SMILESC(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
)(=O)O
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms37Rings0Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
549.82Topological Polar
Surface Area
165.61Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
9
 logP5.96Molar
Refractivity
144.97    
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.