1-MLCL(0:0/16:0/18:0/20:0) (YMDB11691)

Identification
YMDB IDYMDB11691
Name1-MLCL(0:0/16:0/18:0/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-MLCL(0:0/16:0/18:0/20:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/16:0/18:0/20:0) contains one chain of at the C1 position, one chain of hexadecanoic acid at the C2 position, one chain of octadecanoic acid at the C3 position, one chain of eicosanoic 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: 1199.617
Monoisotopic: 1198.836461909
InChI KeyGVAYODWDOLOHLH-IFKAMHRBSA-N
InChIInChI=1S/C63H124O16P2/c1-4-7-10-13-16-19-22-25-27-28-30-33-36-39-42-45-48-51-63(68)79-60(55-73-61(66)49-46-43-40-37-34-32-29-26-23-20-17-14-11-8-5-2)57-77-81(71,72)75-54-58(65)53-74-80(69,70)76-56-59(52-64)78-62(67)50-47-44-41-38-35-31-24-21-18-15-12-9-6-3/h58-60,64-65H,4-57H2,1-3H3,(H,69,70)(H,71,72)/t58-,59+,60+/m0/s1
IUPAC Name[(2S)-3-({[(2R)-2-(hexadecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2-(hexadecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-(icosanoyloxy)-3-(octadecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC63H124O16P2
SMILES[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00011 g/LALOGPS
logP8.62ALOGPS
logP19.46ChemAxon
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 Count68ChemAxon
Refractivity324.12 m³·mol⁻¹ChemAxon
Polarizability144.72 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(10:0/16:0/18:0/20:0)PW005224 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:0/18:0/20:0)PW007216 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/16:0/18:0/20:0)PW009011 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(11Z)/16:0/18:0/20:0)PW010018 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/16:0/18:0/20:0)PW011044 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CL(10:0/16:0/18:0/20:0) → 1-MLCL(0:0/16:0/18:0/20:0)
CL(12:0/16:0/18:0/20:0) → 1-MLCL(0:0/16:0/18:0/20:0)
CL(14:0/16:0/18:0/20:0) → 1-MLCL(0:0/16:0/18:0/20:0)
CL(14:1(11Z)/16:0/18:0/20:0) → 1-MLCL(0:0/16:0/18:0/20:0)
CL(14:1(9Z)/16:0/18:0/20:0) → 1-MLCL(0:0/16:0/18:0/20:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lj-0792104124-833e8b8cd1b9e19febf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lj-0392011221-086e826ba6d778e3c40aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08i9-4296302300-64518f049f7b863f0545JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07d0-0292000012-7501d52bce5e3309e78eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-7191210110-af2a1a396263558ca25fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9061000100-ab996ff3cc7920a63df9JSpectraViewer
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