Structure Database (LMSD)

OH O HO O O O HO O P O HO H H O O O O OH O O P H O O O O
Common Name
CL(1'-[18:2(8E,13E)(10OOH,12OOH)/18:2(9Z,12Z)],3'- [18:2(9Z,12Z)/18:2(9Z,12Z)])
Systematic Name
1'-[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
LM ID
LMGP20030003
Formula
C81H142O21P2
Exact Mass
Calculate m/z
1512.951891
Sum Composition
CL 72:8;O4
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Glycerophospholipids [GP]
Oxidized glycerophospholipids [GP20]
Oxidized Cardiolipins [GP2003]

String Representations

InChiKey (Click to copy)
PUDIRAHAAMVVDQ-IBZOWKQCSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Cardiolipin: characterization of distinct oxidized molecular species.,
J Lipid Res, 2011
Pubmed ID: 20858593

Other Databases

PubChem CID
52929800

Calculated Physicochemical Properties

Heavy Atoms 104
Rings 0
Aromatic Rings 0
Rotatable Bonds 80
Van der Waals Molecular Volume 1602.43
Topological Polar Surface Area 295.87
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 21
logP 25.54
Molar Refractivity 419.30

Admin

Created at
-
Updated at
25th Apr 2022
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.