Structure database (LMSD)

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LM IDLMGP20050012
Common NamePKHdiA-PI
Systematic Name1-hexadecanoyl-2-(4-oxo-6-carboxy-5E-hexenoyl)-sn-glycero-3-phospho-(1'-myo-
inositol)
Synonyms1-palmitoyl-2-(4-oxo-6-carboxy-5E-hexenoyl)-sn-glycero-3-phospho-(1'-myo-
inositol)
Exact Mass
726.3228 (neutral)    Calculate m/z:
FormulaC32H55O16P
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized glycerophosphoinositols [GP2005]
PubChem CID134812429
InChIKeyTTZZKCXTZNSTCZ-ZUPXOCPDSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C32H55O16P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-25(36)45-20-23(47-26(37)19-17-22(33)16-18-24(34)35)21-46-49(43,44)48-32-30(41)28(39)27(38)29(40)31(32)42/h16,18,23,27-32,38-42H,2-15,17,19-21H2,1H3,(H,34,35)(H,43,44)/b18-16+/t23-,27?,28-,29?,30?,31?,32-/m1/s1
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SMILES
[C@]([H])(OC(CCC(=O)/C=C/C(=O)O)=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 Atoms49Rings1Aromatic Rings0Rotatable Bonds29
 van der Waals
Molecular Volume
697.07Topological Polar
Surface Area
263.88Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
16
 logP4.98Molar
Refractivity
177.28    
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.