Structure Database (LMSD)
Common Name
CL(1'-[18:2(9Z,11E)(13OOH)/18:2(9Z,12Z)],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
LMGP20030001
Formula
Exact Mass
Calculate m/z
1480.962061
Sum Composition
Status
Active
No other lipid differing only in stereochemistry/bond geometry found
3D model of CL(1'-[18:2(9Z,11E)(13OOH)/18:2(9Z,12Z)],3'- [18:2(9Z,12Z)/18:2(9Z,12Z)])
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
synthetic construct
(#32630)
Cardiolipin: characterization of distinct oxidized molecular species.,
J Lipid Res, 2011
J Lipid Res, 2011
Pubmed ID:
20858593
DOI:
10.1194/jlr.M010520
String Representations
InChiKey (Click to copy)
FXMDXAUMXVVVOP-BFMZYDRASA-N
InChi (Click to copy)
InChI=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)67-61-55-50-44-39-36-33-30-27-24-21-18-15-11-7-3)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,5-18,25-27,34-45,47-50,52-56,58-62,64-73H2,1-4H3,(H,88,89)(H,90,91)/b22-19-,23-20-,24-21-,31-28-,32-29-,33-30-,51-46-,63-57+/t74-,75?,76+,77+/m0/s1
SMILES (Click to copy)
P(OC[C@]([H])(OC(CCCCCCC/C=C\C/C=C\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
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
102
Rings
0
Aromatic Rings
0
Rotatable Bonds
79
Van der Waals Molecular Volume
1584.85
Topological Polar Surface Area
266.41
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
19
logP
25.61
Molar Refractivity
416.04
Admin
Created at
-
Updated at
8th Nov 2024
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.
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.