Structure Database (LMSD)

HO 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(9Z,11E)(13OOH)/18:2(9Z,11E)(13OOH)],3'- [18:2(9Z,12Z)/18:2(9Z,12Z)])
Systematic Name
1'-[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
LM ID
LMGP20030002
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)
ZIHSFBWBYJWYGW-IFZFSJJHSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
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

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
52929799

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.