Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP10050043
Common NameLPA(0:0/18:0)
Systematic Name[(2R)-3-hydroxy-2-(octadecanoyloxy)propoxy]phosphonic acid
Synonyms-
Exact Mass
438.2746 (neutral)    Calculate m/z:
FormulaC21H43O7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassMonoacylglycerophosphates [GP1005]
PubChem Compound ID (CID)53478600
METABOLOMICS ID-
KEGG IDC00416
HMDB IDHMDB07850
YMDB ID-
CHEBI ID-
InChIKeyRPAOEHFOGLEBTJ-HXUWFJFHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C21H43O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)
19-27-29(24,25)26/h20,22H,2-19H2,1H3,(H2,24,25,26)/t20-/m1/s1
SMILESCCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP(O)(O)=O)CO
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms29Rings0Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
450.58Topological Polar
Surface Area
113.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.46Molar
Refractivity
115.73    
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.

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