Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP10050033
Common NamePA(20:5(5Z,8Z,11Z,14Z,17Z)/0:0)
Systematic Name1-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-glycero-3-phosphate
SynonymsLPA(20:5)
Exact Mass
456.2277 (neutral)    Calculate m/z:
FormulaC23H37O7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassMonoacylglycerophosphates [GP1005]
PubChem CID52929765
SWISSLIPIDS IDSLM:000020650
InChIKeyDKFJPTBTSHHMCQ-MWRKSYAASA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C23H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-
22(24)21-30-31(26,27)28/h3-4,6-7,9-10,12-13,15-16,22,24H,2,5,8,11,14,17-21H2,1H3
,(H2,26,27,28)/b4-3-,7-6-,10-9-,13-12-,16-15-/t22-/m1/s1
SMILES[C@](COP(=O)(O)O)([H])(O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms31Rings0Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
471.98Topological Polar
Surface Area
113.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.12Molar
Refractivity
124.49    
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.