Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMGP20050031
Common NameOHOOA-PI
Systematic Name1-(9Z-octadecenoyl)-2-(5-hydroxy-8-oxo-6E-octenoyl)-sn-glycero-3-phospho-(1'-
myo-inositol)
Synonyms-
Exact Mass
752.3748 (neutral)    Calculate m/z:
FormulaC35H61O15P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 26:3;O2
PubChem CID134812448
InChIKeyJEECOQISAZFYNQ-VAWFODACSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C35H61O15P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21-28(38)47-24-27(49-29(39)22-17-19-26(37)20-18-23-36)25-48-51(45,46)50-35-33(43)31(41)30(40)32(42)34(35)44/h9-10,18,20,23,26-27,30-35,37,40-44H,2-8,11-17,19,21-22,24-25H2,1H3,(H,45,46)/b10-9-,20-18+/t26?,27-,30-,31-,32+,33-,34-,35-/m1/s1
Click to highlight InChI
SMILES
[C@]([H])(OC(CCCC(O)/C=C/C=O)=O)(COP(=O)(O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)COC(CCCCCCC/C=C\CCCCCCCC)=O
Click to highlight SMILES
StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms51Rings1Aromatic Rings0Rotatable Bonds31
 van der Waals
Molecular Volume
740.18Topological Polar
Surface Area
246.81Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
15
 logP6.12Molar
Refractivity
190.98    
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.