Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP06070002
Common NamePI(P-18:0/0:0)
Systematic Name1-(1Z-octadecenyl)-glycero-3-phospho-(1'-myo-inositol)
SynonymsLPI(P-18:0)
Exact Mass
584.3326 (neutral)    Calculate m/z:
FormulaC27H53O11P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub Class1Z-alkenylglycerophosphoinositols [GP0607]
PubChem CID52928632
SWISSLIPIDS IDSLM:000055194
InChIKeyVQWOKPHLVOSHNB-YCWCZIDBSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C27H53O11P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-36-19-21(28)20
-37-39(34,35)38-27-25(32)23(30)22(29)24(31)26(27)33/h17-18,21-33H,2-16,19-20H2,1
H3,(H,34,35)/b18-17-/t21-,22?,23-,24?,25?,26?,27-/m1/s1
SMILES[C@]([H])(O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)CO/C=C\CCCCCCCCCCCCCCCC
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms39Rings1Aromatic Rings0Rotatable Bonds23
 van der Waals
Molecular Volume
577.18Topological Polar
Surface Area
186.37Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
11
 logP5.81Molar
Refractivity
151.14    
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.