Structure database (LMSD)

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LM IDLMGP06050010
Common NamePI(18:2(9Z,12Z)/0:0)
Systematic Name1-(9Z,12Z-octadecadienoyl)-glycero-3-phospho-(1'-myo-inositol)
SynonymsLPI(18:2(9Z,12Z)/0:0); LPI(18:2)
Exact Mass
596.2962 (neutral)    Calculate m/z:
FormulaC27H49O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoacylglycerophosphoinositols [GP0605]
PubChem CID52928605
SWISSLIPIDS IDSLM:000043024
InChIKeySAHCQBPGXQFTRA-VJGPZIHTSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C27H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(29)37-18-20(28)19-38-40(35,36)39-27-25(33)23(31)22(30)24(32)26(27)34/h6-7,9-10,20,22-28,30-34H,2-5,8,11-19H2,1H3,(H,35,36)/b7-6-,10-9-/t20-,22?,23-,24?,25?,26?,27-/m1/s1
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SMILES
[C@]([H])(O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)COC(CCCCCCC/C=C\C/C=C\CCCCC)=O
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MS SpectraView MoNA 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 Atoms40Rings1Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
580.69Topological Polar
Surface Area
203.44Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP4.77Molar
Refractivity
151.43    
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.