Structure database (LMSD)

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LM IDLMGP20050037
Common NamePI(16:0/18:3;O)
Systematic Name1-hexadecanoyl-2-(9-[1'E,3'Z-dien-1'-yloxy]-non-8E-enoyl)-sn-glycero-3-phospho-
(1'-myo-inositol)
Synonyms1-palmitoyl-2-colneleoyl-sn-glycero-3-phospho-(1'-myo-inositol)
Exact Mass
848.5051 (neutral)    Calculate m/z:
FormulaC43H77O14P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 34:3;O
PubChem CID-
InChIKeyZMCQLOBWCOXULW-XLFUREKFSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C43H77O14P/c1-3-5-7-9-11-12-13-14-15-16-17-21-25-29-36(44)54-33-35(34-55-58(51,52)57-43-41(49)39(47)38(46)40(48)42(43)50)56-37(45)30-26-22-18-20-24-28-32-53-31-27-23-19-10-8-6-4-2/h19,23,27-28,31-32,35,38-43,46-50H,3-18,20-22,24-26,29-30,33-34H2,1-2H3,(H,51,52)/b23-19-,31-27+,32-28+/t35-,38-,39-,40+,41-,42-,43-/m1/s1
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SMILES
[C@]([H])(OC(CCCCCC/C=C/O/C=C/C=C\CCCCC)=O)(COP(=O)(O)O[C@@H]1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O)O)O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms58Rings1Aromatic Rings0Rotatable Bonds38
 van der Waals
Molecular Volume
869.79Topological Polar
Surface Area
218.74Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
14
 logP10.51Molar
Refractivity
226.61    
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.