Structure database (LMSD)

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LM IDLMGP20030003
Common NameCL(1'-[18:2(8E,13E)(10OOH,12OOH)/18:2(9Z,12Z)],3'- [18:2(9Z,12Z)/18:2(9Z,12Z)])
Systematic Name1'-[1-(10,12-dihydroperoxy-8E,13E-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 CID52929800
InChIKeyPUDIRAHAAMVVDQ-IBZOWKQCSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C81H142O21P2/c1-5-9-13-17-20-23-26-29-32-35-38-41-44-50-56-62-78(83)93-69-76(99-80(85)64-58-52-45-42-39-36-33-30-27-24-21-18-14-10-6-2)71-97-103(89,90)95-67-73(82)68-96-104(91,92)98-72-77(100-81(86)65-59-53-46-43-40-37-34-31-28-25-22-19-15-11-7-3)70-94-79(84)63-57-51-48-47-49-55-61-75(102-88)66-74(101-87)60-54-16-12-8-4/h20-25,29-34,54-55,60-61,73-77,82,87-88H,5-19,26-28,35-53,56-59,62-72H2,1-4H3,(H,89,90)(H,91,92)/b23-20-,24-21-,25-22-,32-29-,33-30-,34-31-,60-54+,61-55+/t73-,74?,75?,76+,77+/m0/s1
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SMILES
P(OC[C@]([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)COC(CCCCCC/C=C/C(OO)CC(OO)/C=C/CCCC)=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.