Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP02060006
Common Name1-hexadecanoyl-sn--glycero-3-phospho-D-myo-inositol
Systematic Name(2R)-2-hydroxy-3-[(hydroxy{[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-
pentahydroxycyclohexyl]oxy}phosphoryl)oxy]propyl hexadecanoate
Synonyms1-hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol);1-palmitoyl-sn--glycero-
3-phospho-D-myo-inositol;PI(16:0/0:0)
Exact Mass
572.2962 (neutral)    Calculate m/z:
FormulaC25H49O12P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoinositols [GP06]
Sub ClassMonoacylglycerophosphoinositols [GP0605]
PubChem CID71296207
HMDB IDHMDB0061695
CHEBI ID73218
InChIKeyUOXRPRZMAROFPH-OAOCPRPWSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C25H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)35-16-18(26)17-36
-38(33,34)37-25-23(31)21(29)20(28)22(30)24(25)32/h18,20-26,28-32H,2-17H2,1H3,(H,
33,34)/t18-,20-,21-,22+,23-,24-,25-/m1/s1
SMILES[C@@H]1(O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@H]1OP(O)(=O)OC[C@H](O)COC(=O)CCC
CCCCCCCCCCCC
MS SpectraView MoNA MS spectra     
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms38Rings1Aromatic Rings0Rotatable Bonds22
 van der Waals
Molecular Volume
551.37Topological Polar
Surface Area
203.44Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP4.44Molar
Refractivity
142.39    
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.