Structure database (LMSD)

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LM IDLMGP10050016
Common NamePA(16:1(9Z)/0:0)
Systematic Name1-(9Z-hexadecenoyl)-glycero-3-phosphate
SynonymsLPA(16:1(9Z)/0:0); LPA(16:1)
Exact Mass
408.2277 (neutral)    Calculate m/z:
FormulaC19H37O7P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphates [GP10]
Sub ClassMonoacylglycerophosphates [GP1005]
PubChem CID52929751
HMDB IDHMDB0062323
SWISSLIPIDS IDSLM:000020666
InChIKeyGLGQZYWTNAOWHT-JTHGQSKGSA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-
27(22,23)24/h7-8,18,20H,2-6,9-17H2,1H3,(H2,22,23,24)/b8-7-/t18-/m1/s1
SMILES[C@](COP(=O)(O)O)([H])(O)COC(CCCCCCC/C=C\CCCCCC)=O
StatusActive
ReferencesImproved method for the quantification of lysophospholipids
including enol ether species by liquid chromatography-tandem mass spectrometry
James G. Bollinger, Hiromi Ii, Martin Sadilek, and Michael H. Gelb
J. Lipid Res. 010 51:(2) 440-447
Calculated physicochemical properties (?):
 Heavy Atoms27Rings0Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
413.34Topological Polar
Surface Area
113.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
7
 logP5.45Molar
Refractivity
106.40    
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.