Structure database (LMSD)

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LM IDLMGP20050018
Common NamePON-PI
Systematic Name1-hexadecanoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phospho-(1'-myo-inositol)
Synonyms1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phospho-(1'-myo-inositol)
Exact Mass
726.3955 (neutral)    Calculate m/z:
FormulaC34H63O14P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
AbbrevPI 25:1;O
PubChem CID134812435
InChIKeyJMGBOXZEBZUNQD-YMVZDVTASA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C34H63O14P/c1-2-3-4-5-6-7-8-9-10-11-12-15-18-21-27(36)45-24-26(47-28(37)22-19-16-13-14-17-20-23-35)25-46-49(43,44)48-34-32(41)30(39)29(38)31(40)33(34)42/h23,26,29-34,38-42H,2-22,24-25H2,1H3,(H,43,44)/t26-,29-,30-,31+,32-,33-,34-/m1/s1
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SMILES
[C@]([H])(OC(CCCCCCCC([H])=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(CCCCCCCCCCCCCCC)=O
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms49Rings1Aromatic Rings0Rotatable Bonds32
 van der Waals
Molecular Volume
719.37Topological Polar
Surface Area
226.58Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
14
 logP6.92Molar
Refractivity
184.64    
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.