Structure database (LMSD)

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LM IDLMGP20050010
Common NamePKOHA-PI
Systematic Name1-hexadecanoyl-2-(4,7-dioxo-5E-heptenoyl)-sn-glycero-3-phospho-(1'-myo-
inositol)
Synonyms1-palmitoyl-2-(4,7-dioxo-5E-heptenoyl)-sn-glycero-3-phospho-(1'-myo-inositol)
Exact Mass
710.3279 (neutral)    Calculate m/z:
FormulaC32H55O15P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
PubChem CID134812427
InChIKeyFZKZEOQHTJPIQC-QWGFUZRMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C32H55O15P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-25(35)44-21-24(46-26(36)19-18-23(34)16-15-20-33)22-45-48(42,43)47-32-30(40)28(38)27(37)29(39)31(32)41/h15-16,20,24,27-32,37-41H,2-14,17-19,21-22H2,1H3,(H,42,43)/b16-15+/t24-,27?,28-,29?,30?,31?,32-/m1/s1
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SMILES
[C@]([H])(OC(CCC(=O)/C=C/C(=O)[H])=O)(COP(=O)(O)O[C@@H]1C(O)[C@H](O)C(O)C(O)C1O)COC(CCCCCCCCCCCCCCC)=O
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StatusActive
ReferencesOxidized Phospholipids as Endogenous Pattern Recognition Ligands in Innate Immunity. Stanley L. Hazen. The Journal of Biological Chemistry. Volume 283, Issue 23, June 2008, pp. 15527-15531. DOI 10.1074/jbc.R700054200.

http://www.jbc.org/content/283/23/15527.full.pdf
Calculated physicochemical properties (?):
 Heavy Atoms48Rings1Aromatic Rings0Rotatable Bonds29
 van der Waals
Molecular Volume
688.28Topological Polar
Surface Area
243.65Hydrogen
Bond Donors
6Hydrogen
Bond Acceptors
15
 logP5.09Molar
Refractivity
175.71    
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.