Structure database (LMSD)

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LM IDLMGP06050012
Common NamePI(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)
Systematic Name1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phospho-(1'-myo-inositol)
SynonymsLPI(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); LPI(22:6)
Exact Mass
644.2962 (neutral)    Calculate m/z:
FormulaC31H49O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoacylglycerophosphoinositols [GP0605]
PubChem CID52928607
SWISSLIPIDS IDSLM:000043003
InChIKeyCAPHXUZAFHNJAV-GMXJNWCBSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C31H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(33
)41-22-24(32)23-42-44(39,40)43-31-29(37)27(35)26(34)28(36)30(31)38/h3-4,6-7,9-10
,12-13,15-16,18-19,24,26-32,34-38H,2,5,8,11,14,17,20-23H2,1H3,(H,39,40)/b4-3-,7-
6-,10-9-,13-12-,16-15-,19-18-/t24-,26?,27-,28?,29?,30?,31-/m1/s1
SMILES[C@]([H])(O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)COC(CC/C=C\C/C=C\C/C=C\C/
C=C\C/C=C\C/C=C\CC)=O
MS Spectra-      Predict MS/MS spectrum (Neg. mode)
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 Atoms44Rings1Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
639.33Topological Polar
Surface Area
203.44Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP5.43Molar
Refractivity
169.53    
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.