Showing metabocard for CL(10:0/10:0/10:0/10:0) (MMDBc0056467)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:49:45 UTC
Update Date2022-08-14 02:47:32 UTC
MiMeDB IDMMDBc0056467
Metabolite Identification
Common NameCL(10:0/10:0/10:0/10:0)
DescriptionCL(10:0/10:0/10:0/10:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(10:0/10:0/10:0/10:0) contains one decanoyl chain at the C1 position, one decanoyl chain at the C2 position, one decanoyl chain at the C3 position, and one decanoyl chain at the C4 position. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 19 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f09201a4200>

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3D MOL for #<Metabolite:0x00007f09201a4200>

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3D SDF for #<Metabolite:0x00007f09201a4200>

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3D-SDF for #<Metabolite:0x00007f09201a4200>

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PDB for #<Metabolite:0x00007f09201a4200>

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3D PDB for #<Metabolite:0x00007f09201a4200>

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SMILES for #<Metabolite:0x00007f09201a4200>

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INCHI for #<Metabolite:0x00007f09201a4200>

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Synonyms
ValueSource
1'-[1,2-Dianimal fats-rac-glycero-3-phospho],3'-[1,2-dianimal fats-rac-glycero-3-phospho]-glycerolHMDB
1'-[1,2-Didecanoic acid-rac-glycero-3-phospho],3'-[1,2-didecanoic acid-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(10:0/10:0/10:0/10:0)HMDB
CL(40:0)HMDB
CL(1'-[10:0/10:0],3'-[10:0/10:0])HMDB
Cardiolipin(40:0)HMDB
CL(10:0/10:0/10:0/10:0)Lipid Annotator
Chemical FormulaC49H94O17P2
Average Molecular Weight1017.222
Monoisotopic Molecular Weight1016.596625563
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C49H94O17P2/c1-5-9-13-17-21-25-29-33-46(51)59-39-44(65-48(53)35-31-27-23-19-15-11-7-3)41-63-67(55,56)61-37-43(50)38-62-68(57,58)64-42-45(66-49(54)36-32-28-24-20-16-12-8-4)40-60-47(52)34-30-26-22-18-14-10-6-2/h43-45,50H,5-42H2,1-4H3,(H,55,56)(H,57,58)/t44-,45-/m1/s1
InChI KeyCPAOCZJKWGUOKZ-GSFSDPDBSA-N