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 Compound ID (CID)52929798
InChIKeyFXMDXAUMXVVVOP-BFMZYDRASA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=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)67-61-55-50-44-39-36-33-30-27-24-2
1-18-15-11-7-3)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,5-18,25-27,34-45,47-50,52-56,58-62,64-7
3H2,1-4H3,(H,88,89)(H,90,91)/b22-19-,23-20-,24-21-,31-28-,32-29-,33-30-,51-46-,6
3-57+/t74-,75?,76+,77+/m0/s1
SMILESCCCCCC(/C=C/C=C\CCCCCCCC(=O)OC[C@@H](COP(O)(=O)OC[C@H](O)COP(O)(=O)OC[C@H](COC(=
O)CCCCCCC/C=C\C/C=C\CCCCC)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)OC(=O)CCCCCCC/C=C\C/C=C\
CCCCC)OO
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.

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