Structure database (LMSD)

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LM IDLMGP04060003
Common NamePG(O-16:0/0:0)
Systematic Name1-hexadecyl-glycero-3-phospho-(1'-sn-glycerol)
SynonymsLPG(O-16:0)
Exact Mass
470.3009 (neutral)    Calculate m/z:
FormulaC22H47O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerols [GP04]
Sub ClassMonoalkylglycerophosphoglycerols [GP0406]
AbbrevLPG O-16:0
Abbrev ChainsLPG O-16:0
PubChem CID11540059
SWISSLIPIDS IDSLM:000504556
InChIKeyNSJPSUNAUBAKMH-FCHUYYIVSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C22H47O8P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-28-18-22(25)20-30-31(26,27)29-19-21(24)17-23/h21-25H,2-20H2,1H3,(H,26,27)/t21-,22+/m0/s1
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SMILES
[C@]([H])(O)(COP(=O)(O)OC[C@@]([H])(O)CO)COCCCCCCCCCCCCCCCC
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StatusActive (generated by computational methods)
Calculated physicochemical properties (?):
 Heavy Atoms31Rings0Aromatic Rings0Rotatable Bonds24
 van der Waals
Molecular Volume
479.31Topological Polar
Surface Area
125.68Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
8
 logP6.50Molar
Refractivity
125.30    
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.