Structure database (LMSD)

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LM IDLMGP10050019
Common NamePA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
Systematic Name1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phosphate
SynonymsLPA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); LPA(22:6)
Exact Mass
482.2433 (neutral)    Calculate m/z:
FormulaC25H39O7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassMonoacylglycerophosphates [GP1005]
PubChem CID52929753
SWISSLIPIDS IDSLM:000020648
InChIKeyUWHSPTWBPTXYMF-DOYOFOADSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C25H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)
31-22-24(26)23-32-33(28,29)30/h3-4,6-7,9-10,12-13,15-16,18-19,24,26H,2,5,8,11,14
,17,20-23H2,1H3,(H2,28,29,30)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-/t24-/m1/s1
SMILES[C@](COP(=O)(O)O)([H])(O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
StatusActive
ReferencesImproved method for the quantification of lysophospholipids
including enol ether species by liquid chromatography-tandem mass spectrometry
James G. Bollinger, Hiromi Ii, Martin Sadilek, and Michael H. Gelb
J. Lipid Res. 010 51:(2) 440-447
Calculated physicochemical properties (?):
 Heavy Atoms33Rings0Aromatic Rings0Rotatable Bonds20
 van der Waals
Molecular Volume
503.94Topological Polar
Surface Area
113.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP6.67Molar
Refractivity
133.63    
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.