Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP06050021
Common NamePI(20:3(8Z,11Z,14Z)/0:0)
Systematic Name1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phospho-(1'-myo-inositol)
Synonyms-
Exact Mass
622.3118 (neutral)    Calculate m/z:
FormulaC29H51O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoacylglycerophosphoinositols [GP0605]
PubChem CID52928616
SWISSLIPIDS IDSLM:000043018
InChIKeyLBUGPTQSMSJVAG-HHLOBWNLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C29H51O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(31)39-20
-22(30)21-40-42(37,38)41-29-27(35)25(33)24(32)26(34)28(29)36/h6-7,9-10,12-13,22,
24-30,32-36H,2-5,8,11,14-21H2,1H3,(H,37,38)/b7-6-,10-9-,13-12-/t22-,24?,25-,26?,
27?,28?,29-/m1/s1
SMILES[C@]([H])(O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)COC(CCCCCC/C=C\C/C=C\C/C=
C\CCCCC)=O
MS Spectra-      Predict MS/MS spectrum (Neg. mode)
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms42Rings1Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
612.65Topological Polar
Surface Area
203.44Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP5.33Molar
Refractivity
160.57    
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.