Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP06060003
Common NamePI(O-16:0/0:0)
Systematic Name1-hexadecyl-glycero-3-phospho-(1'-myo-inositol)
SynonymsLPI(O-16:0)
Exact Mass
558.3169 (neutral)    Calculate m/z:
FormulaC25H51O11P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoalkylglycerophosphoinositols [GP0606]
PubChem CID52928630
SWISSLIPIDS IDSLM:000055174
InChIKeyFFAHVVKFSPSLDR-FRXBKMHMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C25H51O11P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-34-17-19(26)18-35-37
(32,33)36-25-23(30)21(28)20(27)22(29)24(25)31/h19-31H,2-18H2,1H3,(H,32,33)/t19-,
20?,21-,22?,23?,24?,25-/m1/s1
SMILES[C@]([H])(O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)COCCCCCCCCCCCCCCCC
StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms37Rings1Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
545.22Topological Polar
Surface Area
186.37Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
11
 logP5.20Molar
Refractivity
142.74    
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.