Structure database (LMSD)

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LM IDLMGP20030001
Common NameCL(1'-[18:2(9Z,11E)(13OOH)/18:2(9Z,12Z)],3'- [18:2(9Z,12Z)/18:2(9Z,12Z)])
Systematic Name1'-[1-(13-hydroperoxy-9Z,11E-octadienoyl),2-(9Z,12Z-octadienoyl)-sn-glycero-3-
phospho],3'-[1,2-di-(9Z,12Z-octadienoyl)-sn-glycero-3-phospho]-sn-glycerol
Synonyms-
Exact Mass
1480.9621 (neutral)    Calculate m/z:
FormulaC81H142O19P2
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized Cardiolipins [GP2003]
PubChem CID52929798
InChIKeyFXMDXAUMXVVVOP-BFMZYDRASA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C81H142O19P2/c1-5-9-13-16-19-22-25-28-31-34-37-42-47-52-58-64-78(83)92-70-76(98-80(85)66-60-54-49-43-38-35-32-29-26-23-20-17-14-10-6-2)72-96-101(88,89)94-68-74(82)69-95-102(90,91)97-73-77(99-81(86)67-61-55-50-44-39-36-33-30-27-24-21-18-15-11-7-3)71-93-79(84)65-59-53-48-45-40-41-46-51-57-63-75(100-87)62-56-12-8-4/h19-24,28-33,46,51,57,63,74-77,82,87H,5-18,25-27,34-45,47-50,52-56,58-62,64-73H2,1-4H3,(H,88,89)(H,90,91)/b22-19-,23-20-,24-21-,31-28-,32-29-,33-30-,51-46-,63-57+/t74-,75?,76+,77+/m0/s1
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SMILES
P(OC[C@]([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)COC(CCCCCCC/C=C\C=C\C(OO)CCCCC)=O)(O)(OC[C@](O)([H])COP(OC[C@]([H])(OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)COC(=O)CCCCCCC/C=C\C/C=C\CCCCC)(O)=O)=O
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StatusActive
ReferencesCardiolipin: characterization of distinct oxidized molecular species
Junhwan Kim, Paul E. Minkler, Robert G. Salomon, Vernon E. Anderson, and Charles L. Hoppel
J. Lipid Res. 2011 52:(1) 125-135
Calculated physicochemical properties (?):
 Heavy Atoms102Rings0Aromatic Rings0Rotatable Bonds79
 van der Waals
Molecular Volume
1584.85Topological Polar
Surface Area
266.41Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
19
 logP25.61Molar
Refractivity
416.04    
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.