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]
PubChem CID134812449
InChIKeyXPIBHMKPQNUICW-INDIHPSHSA-N  Show lipids differing only in stereochemistry/bond geometry
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]1C(O)[C@H](O)C(O)C(O)C1O)COC(CCCCCCC/C=C\CCCCCCCC)=O
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StatusActive
ReferencesA Novel Family of Atherogenic Oxidized Phospholipids Promotes Macrophage Foam Cell Formation via the Scavenger Receptor CD36 and Is Enriched in Atherosclerotic Lesions. Eugene A. Podrez, Eugenia Poliakov, Zhongzhou Shen, Renliang Zhang, Yijun Deng, Mingjiang Sun, Paula J. Finton, Lian Shan, Maria Febbraio, David P. Hajjar, Roy L. Silverstein, Henry F. Hoff, Robert G. Salomon, and Stanley L. Hazen. The Journal of Biological Chemistry. Volume 277, Issue 41, October 2002, pp. 38517-38523. DOI 10.1074/jbc.M205924200 http://www.jbc.org/content/277/41/38517
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.