Structure database (LMSD)

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LM IDLMGP04050017
Common NamePG(22:4(7Z,10Z,13Z,16Z)/0:0)
Systematic Name1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-glycero-3-phospho-(1'-sn-glycerol)
SynonymsLPG(22:4(7Z,10Z,13Z,16Z)/0:0); LPG(22:4)
Exact Mass
560.3114 (neutral)    Calculate m/z:
FormulaC28H49O9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerols [GP04]
Sub ClassMonoacylglycerophosphoglycerols [GP0405]
PubChem CID52927440
SWISSLIPIDS IDSLM:000043093
InChIKeyGTUVDMUYRYBFAU-INRKLGSDSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C28H49O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-28(32)
35-23-27(31)25-37-38(33,34)36-24-26(30)22-29/h6-7,9-10,12-13,15-16,26-27,29-31H,
2-5,8,11,14,17-25H2,1H3,(H,33,34)/b7-6-,10-9-,13-12-,16-15-/t26-,27+/m0/s1
SMILES[H][C@](O)(CO)COP(OC[C@]([H])(O)COC(CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)(=O)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 Atoms38Rings0Aromatic Rings0Rotatable Bonds26
 van der Waals
Molecular Volume
578.70Topological Polar
Surface Area
142.75Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
9
 logP7.19Molar
Refractivity
152.27    
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.