2-MLCL(12:0/20:0/20:0/0:0) (YMDB11975)

Identification
YMDB IDYMDB11975
Name2-MLCL(12:0/20:0/20:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(12:0/20:0/20:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(12:0/20:0/20:0/0:0) contains one chain of dodecanoic acid at the C1 position, two chains of eicosanoic acid at the C2 and C3 positions, 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
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS numberNot Available
WeightAverage: 1171.563
Monoisotopic: 1170.80516178
InChI KeyYCDDKPOCFVFLHL-IPCNJRPSSA-N
InChIInChI=1S/C61H120O16P2/c1-4-7-10-13-16-19-21-23-25-27-29-31-33-36-39-41-44-47-59(64)71-50-56(62)51-73-78(67,68)74-52-57(63)53-75-79(69,70)76-55-58(54-72-60(65)48-45-42-38-35-18-15-12-9-6-3)77-61(66)49-46-43-40-37-34-32-30-28-26-24-22-20-17-14-11-8-5-2/h56-58,62-63H,4-55H2,1-3H3,(H,67,68)(H,69,70)/t56-,57-,58-/m1/s1
IUPAC Name[(2R)-3-(dodecanoyloxy)-2-(icosanoyloxy)propoxy][(2R)-2-hydroxy-3-({hydroxy[(2R)-2-hydroxy-3-(icosanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional IUPAC Name(2R)-3-(dodecanoyloxy)-2-(icosanoyloxy)propoxy((2R)-2-hydroxy-3-{[hydroxy((2R)-2-hydroxy-3-(icosanoyloxy)propoxy)phosphoryl]oxy}propoxy)phosphinic acid
Chemical FormulaC61H120O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00013 g/LALOGPS
logP8.54ALOGPS
logP18.57ChemAxon
logS-7ALOGPS
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 Count66ChemAxon
Refractivity314.91 m³·mol⁻¹ChemAxon
Polarizability141.39 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(10:0/12:0/20:0/20:0)PW003896 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:0/20:0/20:0)PW008036 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:0/20:0/20:1(11Z))PW008037 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/20:0/20:0/20:1(13Z))PW008038 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(12:0/20:0/20:0/0:0) → CL(10:0/12:0/20:0/20:0)
2-MLCL(12:0/20:0/20:0/0:0) → CL(12:0/20:0/20:0/20:0)
2-MLCL(12:0/20:0/20:0/0:0) → CL(12:0/20:0/20:0/20:1(11Z))
2-MLCL(12:0/20:0/20:0/0:0) → CL(12:0/20:0/20:0/20:1(13Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zmi-0943042161-56ffb5aac2838b350f7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfs-1973246261-9531dd50d44421cad36bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-6497163120-924dc4c6cf3acb4c4fb0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pn-0934001020-dd86197902f1d7b2ce31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-6935202010-9c694f41636c0f4574a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ta-9232101000-59922f0376ff6d6bfeddJSpectraViewer
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