1-MLCL(0:0/12:0/14:0/22:0) (YMDB11601)

Identification
YMDB IDYMDB11601
Name1-MLCL(0:0/12:0/14:0/22:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-MLCL(0:0/12:0/14:0/22:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/12:0/14:0/22:0) contains one chain of at the C1 position, one chain of dodecanoic acid at the C2 position, one chain of tetradecanoic acid at the C3 position, one chain of docosanoic 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: 1115.455
Monoisotopic: 1114.742561522
InChI KeyRQOZIZBVYRJADK-OXYMOTDNSA-N
InChIInChI=1S/C57H112O16P2/c1-4-7-10-13-16-19-21-22-23-24-25-26-27-28-30-33-36-39-42-45-57(62)73-54(49-67-55(60)43-40-37-34-32-29-20-17-14-11-8-5-2)51-71-75(65,66)69-48-52(59)47-68-74(63,64)70-50-53(46-58)72-56(61)44-41-38-35-31-18-15-12-9-6-3/h52-54,58-59H,4-51H2,1-3H3,(H,63,64)(H,65,66)/t52-,53+,54+/m0/s1
IUPAC Name[(2R)-2-(docosanoyloxy)-3-(tetradecanoyloxy)propoxy][(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2-(docosanoyloxy)-3-(tetradecanoyloxy)propoxy((2S)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC57H112O16P2
SMILES[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP8.17ALOGPS
logP16.79ChemAxon
logS-6.7ALOGPS
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 Count62ChemAxon
Refractivity296.51 m³·mol⁻¹ChemAxon
Polarizability132.27 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(10:0/12:0/14:0/22:0)PW003749 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/14:0/22:0)PW005887 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/14:0/22:0/22:0)PW006338 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/14:0/22:0/22:1(11Z))PW006339 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/14:0/22:0/22:1(9Z))PW006340 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CL(16:0/16:0/16:0/16:0) → 1-MLCL(0:0/12:0/14:0/22:0)
CL(10:0/12:0/14:0/22:0) → 1-MLCL(0:0/12:0/14:0/22:0)
CL(12:0/12:0/14:0/22:0) → 1-MLCL(0:0/12:0/14:0/22:0)
CL(12:0/14:0/22:0/22:0) → 1-MLCL(0:0/12:0/14:0/22:0)
CL(12:0/14:0/22:0/22:1(11Z)) → 1-MLCL(0:0/12:0/14:0/22:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07it-9785233533-d8182fa31086ddf9a7e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059t-7986403533-cff1b9131fa5320bdddeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6592212300-2bf497f71238c010bd74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-072j-2694000212-66373bce0d9c3f87b8d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9274110110-aa15279adfac012970d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9142000000-46c31eed6b2532acb176JSpectraViewer
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