1-MLCL(0:0/12:0/16:0/20:0) (YMDB11602)

Identification
YMDB IDYMDB11602
Name1-MLCL(0:0/12:0/16:0/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-MLCL(0:0/12:0/16:0/20:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/12:0/16:0/20:0) contains one chain of at the C1 position, one chain of dodecanoic acid at the C2 position, one chain of hexadecanoic 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: 1115.455
Monoisotopic: 1114.742561522
InChI KeyWLIBCAUROPTCLI-OXYMOTDNSA-N
InChIInChI=1S/C57H112O16P2/c1-4-7-10-13-16-19-21-23-24-25-26-28-30-33-36-39-42-45-57(62)73-54(49-67-55(60)43-40-37-34-32-29-27-22-20-17-14-11-8-5-2)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[(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-(icosanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name(2S)-3-{[(2R)-2-(dodecanoyloxy)-3-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-(icosanoyloxy)propoxy)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)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphoglycerophosphoglycerols. These are glycerophospholipids that contain three glycerol moieties sequentially linked to each other with a phosphate group. They include cardiolipins.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentGlycerophosphoglycerophosphoglycerols
Alternative Parents
Substituents
  • Glycerophosphoglycerophosphoglycerol
  • Tricarboxylic acid or derivatives
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
Polarizability132.2 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(10:0/12:0/16:0/20:0)PW003807 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/16:0/20:0)PW005954 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:0/20:0/20:1(11Z))PW007257 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:0/20:0/20:1(13Z))PW007258 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:0/20:0/22:0)PW007259 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CL(16:0/16:0/16:0/16:0) → 1-MLCL(0:0/12:0/16:0/20:0)
CL(10:0/12:0/16:0/20:0) → 1-MLCL(0:0/12:0/16:0/20:0)
CL(12:0/12:0/16:0/20:0) → 1-MLCL(0:0/12:0/16:0/20:0)
CL(12:0/16:0/20:0/20:1(11Z)) → 1-MLCL(0:0/12:0/16:0/20:0)
CL(12:0/16:0/20:0/20:1(13Z)) → 1-MLCL(0:0/12:0/16:0/20:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-6590114252-83b7cb833d6c466028e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4490202141-aa08086ebd87bfd6ff7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-5391102300-e39eaf5dab21c95d5750JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08g1-2593000031-90eeb7dcd41023b5ae24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9183110110-163aca7e8f1ec09088b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9142000000-02915ad5d092c42a1877JSpectraViewer
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