Structure database (LMSD)

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LM IDLMGP20030002
Common NameCL(1'-[18:2(9Z,11E)(13OOH)/18:2(9Z,11E)(13OOH)],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
1512.9519 (neutral)    Calculate m/z:
FormulaC81H142O21P2
CategoryGlycerophospholipids [GP]
Main ClassOxidized glycerophospholipids [GP20]
Sub ClassOxidized Cardiolipins [GP2003]
PubChem CID52929799
InChIKeyZIHSFBWBYJWYGW-IFZFSJJHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C81H142O21P2/c1-5-9-13-15-17-19-21-23-25-27-29-35-41-47-55-63-78(83)93-69-76(99-80(85)65-57-49-43-36-30-28-26-24-22-20-18-16-14-10-6-2)71-97-103(89,90)95-67-73(82)68-96-104(91,92)98-72-77(100-81(86)66-58-50-44-38-32-34-40-46-54-62-75(102-88)60-52-12-8-4)70-94-79(84)64-56-48-42-37-31-33-39-45-53-61-74(101-87)59-51-11-7-3/h17-20,23-26,39-40,45-46,53-54,61-62,73-77,82,87-88H,5-16,21-22,27-38,41-44,47-52,55-60,63-72H2,1-4H3,(H,89,90)(H,91,92)/b19-17-,20-18-,25-23-,26-24-,45-39-,46-40-,61-53+,62-54+/t73-,74?,75?,76+,77+/m0/s1
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SMILES
P(OC[C@]([H])(OC(CCCCCCC/C=C\C=C\C(OO)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 Atoms104Rings0Aromatic Rings0Rotatable Bonds80
 van der Waals
Molecular Volume
1602.43Topological Polar
Surface Area
295.87Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
21
 logP25.54Molar
Refractivity
419.30    
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.