1-MLCL(0:0/12:0/15:0/25:0) (YMDB11650)

Identification
YMDB IDYMDB11650
Name1-MLCL(0:0/12:0/15:0/25:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-MLCL(0:0/12:0/15:0/25:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/12:0/15:0/25:0) contains one chain of at the C1 position, one chain of dodecanoic acid at the C2 position, one chain of pentadecanoic acid at the C3 position, one chain of pentacosanoic acid 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 KeyBXMGEQYOSOTVEP-FOCARYSPSA-N
InChIInChI=1S/C61H120O16P2/c1-4-7-10-13-16-19-21-23-24-25-26-27-28-29-30-31-32-34-37-40-43-46-49-61(66)77-58(53-71-59(64)47-44-41-38-36-33-22-20-17-14-11-8-5-2)55-75-79(69,70)73-52-56(63)51-72-78(67,68)74-54-57(50-62)76-60(65)48-45-42-39-35-18-15-12-9-6-3/h56-58,62-63H,4-55H2,1-3H3,(H,67,68)(H,69,70)/t56-,57+,58+/m0/s1
IUPAC Name[(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(pentacosanoyloxy)-3-(pentadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-(pentacosanoyloxy)-3-(pentadecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC61H120O16P2
SMILES[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCCCCC
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
logP8.5ALOGPS
logP18.57ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area230.88 ŲChemAxon
Rotatable Bond Count66ChemAxon
Refractivity314.91 m³·mol⁻¹ChemAxon
Polarizability140.95 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(10:0/12:0/15:0/25:0)PW003782 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/15:0/25:0)PW005928 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CL(16:0/16:0/16:0/16:0) → 1-MLCL(0:0/12:0/15:0/25:0)
CL(10:0/12:0/15:0/25:0) → 1-MLCL(0:0/12:0/15:0/25:0)
CL(12:0/12:0/15:0/25:0) → 1-MLCL(0:0/12:0/15:0/25:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v59-0953112214-6dfafde3f804db14b505JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-100u-1955201313-72f2d3c3580a27f8442fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5793203120-a3746d52f18b2c4e303bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ry-0895000213-1ada18dd070fc10175c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9484020101-777599f40ecef9428f3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9143000100-abf48aa9715e41de4928JSpectraViewer
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