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CL(12:0/20:0/12:0/20:0) (YMDB06473)

Identification
YMDB IDYMDB06473
NameCL(12:0/20:0/12:0/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCL(12:0/20:0/12:0/20:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(12:0/20:0/12:0/20:0) contains two chains of dodecanoic acid at the C1 and C3 positions, two chains of eicosanoic acid at the C2 and C4 positions. 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 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. 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
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS numberNot Available
WeightAverage: 1353.87
Monoisotopic: 1352.972227108
InChI KeyRFSRKUCXJZIMAB-ULKDXPJMSA-N
InChIInChI=1S/C73H142O17P2/c1-5-9-13-17-21-25-27-29-31-33-35-37-39-43-47-51-55-59-72(77)89-68(63-83-70(75)57-53-49-45-41-23-19-15-11-7-3)65-87-91(79,80)85-61-67(74)62-86-92(81,82)88-66-69(64-84-71(76)58-54-50-46-42-24-20-16-12-8-4)90-73(78)60-56-52-48-44-40-38-36-34-32-30-28-26-22-18-14-10-6-2/h67-69,74H,5-66H2,1-4H3,(H,79,80)(H,81,82)/t68-,69-/m1/s1
IUPAC Name[(2R)-3-(dodecanoyloxy)-2-(icosanoyloxy)propoxy][3-({[(2R)-3-(dodecanoyloxy)-2-(icosanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-3-(dodecanoyloxy)-2-(icosanoyloxy)propoxy(3-{[(2R)-3-(dodecanoyloxy)-2-(icosanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC73H142O17P2
SMILES[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentCardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.7e-05 g/LALOGPS
logP8.85ALOGPS
logP23.71ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 ŲChemAxon
Rotatable Bond Count78ChemAxon
Refractivity370.1 m³·mol⁻¹ChemAxon
Polarizability163.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(12:0/20:0/12:0/20:0)PW008035 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PG(12:0/20:0) + CDP-DG(12:0/20:0) → Cytidine monophosphate + hydron + CL(12:0/20:0/12:0/20:0)
CL(12:0/20:0/12:0/20:0) → 1-MLCL(0:0/16:0/16:0/16:0)
2-MLCL(16:0/16:0/16:0/0:0) → CL(12:0/20:0/12:0/20:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pk-0609360000-8d123760d55c0e74c62bJSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Cardiolipin synthase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol
Gene Name:
CRD1
Uniprot ID:
Q07560
Molecular weight:
32019.30078
Reactions
2 Phosphatidylglycerol → diphosphatidylglycerol + glycerol.