Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP10050040
Common Name1-(18-mercaptooctadecanoyl)-sn-glycerol 3-phosphate
Systematic Name(2R)-2-hydroxy-3-(phosphonooxy)propyl 18-sulfanyloctadecanoate
Synonyms1-(18-mercaptooctadecanoyl) lysophosphatidic acid;1-(18-mercaptooctadecanoyl)-
2-lyso-sn-glycerol 3-phosphatidic acid;1-(18-mercaptooctadecanoyl)glycerol 3-
phosphate;1-O-(18-mercaptooctadecanoyl)-sn-glycerol 3-phosphate
Exact Mass
470.2467 (neutral)    Calculate m/z:
FormulaC21H43O7PS
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassMonoacylglycerophosphates [GP1005]
PubChem CID53477643
CHEBI ID62835
InChIKeyBHYDDPWHIAPIOG-HXUWFJFHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C21H43O7PS/c22-20(19-28-29(24,25)26)18-27-21(23)16-14-12-10-8-6-4-2-1-3
-5-7-9-11-13-15-17-30/h20,22,30H,1-19H2,(H2,24,25,26)/t20-/m1/s1
SMILESC(=O)(OC[C@@H](O)COP(O)(O)=O)CCCCCCCCCCCCCCCCCS
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms30Rings0Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
469.09Topological Polar
Surface Area
113.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.65Molar
Refractivity
124.39    
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.