Structure database (LMSD)

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LM IDLMGP20050025
Common NameOKOHA-PI
Systematic Name1-(9Z-octadecenoyl)-2-(4,7-dioxo-5E-heptenoyl)-sn-glycero-3-phospho-(1'-myo-
inositol)
Synonyms-
Exact Mass
736.3435 (neutral)    Calculate m/z:
FormulaC34H57O15P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 25:4;O2
PubChem CID134812442
InChIKeyVKIRESWKTTXAND-QBWBRGFYSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C34H57O15P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-27(37)46-23-26(48-28(38)21-20-25(36)18-17-22-35)24-47-50(44,45)49-34-32(42)30(40)29(39)31(41)33(34)43/h9-10,17-18,22,26,29-34,39-43H,2-8,11-16,19-21,23-24H2,1H3,(H,44,45)/b10-9-,18-17+/t26-,29-,30-,31+,32-,33-,34-/m1/s1
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SMILES
[C@]([H])(OC(CCC(=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
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms50Rings1Aromatic Rings0Rotatable Bonds30
 van der Waals
Molecular Volume
720.24Topological Polar
Surface Area
243.65Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
15
 logP5.65Molar
Refractivity
184.85    
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.