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)
SynonymsLPI(20:3)
Exact Mass
622.3118 (neutral)    Calculate m/z:
FormulaC29H51O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoacylglycerophosphoinositols [GP0605]
AbbrevLPI 20:3
Abbrev ChainsLPI 20:3
PubChem CID52928616
SWISSLIPIDS IDSLM:000043018
InChIKeyLBUGPTQSMSJVAG-HHLOBWNLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=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
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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(CCCCCC/C=C\C/C=C\C/C=C\CCCCC)=O
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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.