Structure database (LMSD)

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LM IDLMGP20050032
Common NameOHODiA-PI
Systematic Name1-(9Z-octadecenoyl)-2-(5-hydroxy-7-carboxy-6E-heptenoyl)-sn-glycero-3-phospho-
(1'-myo-inositol)
Synonyms-
Exact Mass
768.3697 (neutral)    Calculate m/z:
FormulaC35H61O16P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 26:3;O3
PubChem CID134812449
InChIKeyXPIBHMKPQNUICW-YOIMPFALSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C35H61O16P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-28(39)48-23-26(50-29(40)20-17-18-25(36)21-22-27(37)38)24-49-52(46,47)51-35-33(44)31(42)30(41)32(43)34(35)45/h9-10,21-22,25-26,30-36,41-45H,2-8,11-20,23-24H2,1H3,(H,37,38)(H,46,47)/b10-9-,22-21+/t25?,26-,30-,31-,32+,33-,34-,35-/m1/s1
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SMILES
[C@]([H])(OC(CCCC(O)/C=C/C(=O)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
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms52Rings1Aromatic Rings0Rotatable Bonds31
 van der Waals
Molecular Volume
748.97Topological Polar
Surface Area
267.04Hydrogen
Bond Donors
8Hydrogen
Bond Acceptors
16
 logP6.00Molar
Refractivity
192.55    
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.