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Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP03070003
Common NamePS(P-16:0/0:0)
Systematic Name1-(1Z-hexadecenyl)-glycero-3-phosphoserine
SynonymsLPS(P-16:0)
Exact Mass
481.2805 (neutral)    Calculate m/z:
FormulaC22H44NO8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoserines [GP03]
Sub Class1Z-alkenylglycerophosphoserines [GP0307]
AbbrevLPS O-16:1
Abbrev ChainsLPS P-16:0
PubChem CID52926306
SWISSLIPIDS IDSLM:000052258
InChIKeyNHHCXOCBELHLLQ-GOEKCXRKSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C22H44NO8P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-29-17-20(24)18-30-32(27,28)31-19-21(23)22(25)26/h15-16,20-21,24H,2-14,17-19,23H2,1H3,(H,25,26)(H,27,28)/b16-15-/t20-,21+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(O)CO/C=C\CCCCCCCCCCCCCC)(=O)O
Click to highlight SMILES
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms32Rings0Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
485.03Topological Polar
Surface Area
148.54Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
8
 logP6.11Molar
Refractivity
126.49    
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.