2-MLCL(16:0/16:0/22:0/0:0) (YMDB12012)

Identification
YMDB IDYMDB12012
Name2-MLCL(16:0/16:0/22:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(16:0/16:0/22:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(16:0/16:0/22:0/0:0) contains two chains of hexadecanoic acid at the C1 and C2 positions, one chain of docosanoic acid at the C3 position, 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: 1199.617
Monoisotopic: 1198.836461909
InChI KeyPFAIFWVJMVHASE-UPMPAGDASA-N
InChIInChI=1S/C63H124O16P2/c1-4-7-10-13-16-19-22-25-26-27-28-29-30-33-35-37-40-43-46-49-61(66)73-52-58(64)53-75-80(69,70)76-54-59(65)55-77-81(71,72)78-57-60(79-63(68)51-48-45-42-39-36-32-24-21-18-15-12-9-6-3)56-74-62(67)50-47-44-41-38-34-31-23-20-17-14-11-8-5-2/h58-60,64-65H,4-57H2,1-3H3,(H,69,70)(H,71,72)/t58-,59-,60-/m1/s1
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy][(2R)-3-({[(2R)-3-(docosanoyloxy)-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis(hexadecanoyloxy)propoxy((2R)-3-{[(2R)-3-(docosanoyloxy)-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC63H124O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
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
logP8.66ALOGPS
logP19.46ChemAxon
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 Count68ChemAxon
Refractivity324.12 m³·mol⁻¹ChemAxon
Polarizability144.75 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(10:0/16:0/16:0/22:0)PW005170 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:0/16:0/22:0)PW007161 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/16:0/16:0/22:0)PW008965 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/16:0/16:0/22:0)PW010998 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:0)PW012408 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(16:0/16:0/22:0/0:0) → CL(10:0/16:0/16:0/22:0)
2-MLCL(16:0/16:0/22:0/0:0) → CL(12:0/16:0/16:0/22:0)
2-MLCL(16:0/16:0/22:0/0:0) → CL(14:0/16:0/16:0/22:0)
2-MLCL(16:0/16:0/22:0/0:0) → CL(14:1(9Z)/16:0/16:0/22:0)
2-MLCL(16:0/16:0/22:0/0:0) → CL(16:0/16:0/16:0/22:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8d-0956044127-a4d74c06ac30cbddfde3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1697256234-c0cd4b23b6746e38adb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k92-6279163010-8509dded9dcf30793463JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-1398102012-b460782e1d6a4d40845cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0550-7198102000-cc8b1eb9e61cc921a20eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9042101000-ff86191d1387ca6f313cJSpectraViewer
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