Identification
YMDB IDYMDB11913
Name2-MLCL(10:0/15:0/22:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(10:0/15:0/22:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(10:0/15:0/22:0/0:0) contains one chain of decanoic acid at the C1 position, one chain of pentadecanoic acid at the C2 position, one chain of docosanoic acid at the C3 position, one chain of at the C4 position. MLCL is present in eukaryotes as part of the metabolic cycle of mitochondrial lipids. Removal of one acyl chain from a cardiolipin results in generation of monolysocardiolipin (MLCL). MLCL has been used as an inter­mediate in the synthesis of spin-labeled CL to study the interaction of CL with mitochondrial enzymes. Because a role for MLCL has been suggested in apoptosis, this molecule has been used to study its interaction with various enzymes involved in lipid remodeling and apoptosis. There are two species of monolysocardiolipins, 1-MLCL which is missing a fatty acid in position R1 the and 2-MLCL which is missing a fatty acid in position R4.
Structure
Thumb
SynonymsNot Available
CAS numberNot Available
WeightAverage: 1101.428
Monoisotopic: 1100.726911458
InChI KeyRGGMLYICJQEETC-IKCSEEPVSA-N
InChIInChI=1S/C56H110O16P2/c1-4-7-10-13-16-18-20-22-23-24-25-26-27-28-30-31-34-37-39-42-54(59)66-45-51(57)46-68-73(62,63)69-47-52(58)48-70-74(64,65)71-50-53(49-67-55(60)43-40-36-33-15-12-9-6-3)72-56(61)44-41-38-35-32-29-21-19-17-14-11-8-5-2/h51-53,57-58H,4-50H2,1-3H3,(H,62,63)(H,64,65)/t51-,52-,53-/m1/s1
IUPAC Name[(2R)-3-(decanoyloxy)-2-(pentadecanoyloxy)propoxy][(2R)-3-({[(2R)-3-(docosanoyloxy)-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-3-(decanoyloxy)-2-(pentadecanoyloxy)propoxy((2R)-3-{[(2R)-3-(docosanoyloxy)-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC56H110O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP8.09ALOGPS
logP16.35ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area230.88 ŲChemAxon
Rotatable Bond Count61ChemAxon
Refractivity291.91 m³·mol⁻¹ChemAxon
Polarizability130.69 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(10:0/15:0/22:0/23:1(11Z))PW004880 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/15:0/22:0/23:1(9Z))PW004881 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/15:0/22:0/25:0)PW004882 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/15:0/22:0/25:1(11Z))PW004883 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/15:0/22:0/25:1(9Z))PW004884 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(10:0/15:0/22:0/0:0)CL(10:0/15:0/22:0/23:1(11Z))
2-MLCL(10:0/15:0/22:0/0:0)CL(10:0/15:0/22:0/23:1(9Z))
2-MLCL(10:0/15:0/22:0/0:0)CL(10:0/15:0/22:0/25:0)
2-MLCL(10:0/15:0/22:0/0:0)CL(10:0/15:0/22:0/25:1(11Z))
2-MLCL(10:0/15:0/22:0/0:0)CL(10:0/15:0/22:0/25:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kcr-9678263342-e338a40ae0e06261c870JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0561-9488576422-2b7bf0e43e34180bd54dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbb-7398361200-78640a92502277d2ac16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-4938111120-e6298a7f70f2b732cebbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00g0-8928111000-a65e9366e12b66d60f22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9232110000-8cdaca7283f667d42911JSpectraViewer
References
References:
  • Baile MG, Lu YW, Claypool SM. (2014). "The topology and regulation of cardiolipin biosynthesis and remodeling in yeast." Chem Phys Lipids. 2014 Apr;179:25-31. doi: 10.1016/j.chemphyslip.2013.10.008. Epub 2013 Nov 1.24184646
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