2-MLCL(14:1(9Z)/15:0/15:0/0:0) (YMDB11839)

Identification
YMDB IDYMDB11839
Name2-MLCL(14:1(9Z)/15:0/15:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(14:1(9Z)/15:0/15:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(14:1(9Z)/15:0/15:0/0:0) contains one chain of (9Z-tetradecenoyl) at the C1 position, two chains of pentadecanoic acid at the C2 and C3 positions, 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: 1057.331
Monoisotopic: 1056.6643112
InChI KeyQJYKPNKKVZYVKG-KAKWWVIKSA-N
InChIInChI=1S/C53H102O16P2/c1-4-7-10-13-16-19-22-25-28-30-33-36-39-51(56)63-42-48(54)43-65-70(59,60)66-44-49(55)45-67-71(61,62)68-47-50(46-64-52(57)40-37-34-31-27-24-21-18-15-12-9-6-3)69-53(58)41-38-35-32-29-26-23-20-17-14-11-8-5-2/h15,18,48-50,54-55H,4-14,16-17,19-47H2,1-3H3,(H,59,60)(H,61,62)/b18-15-/t48-,49-,50-/m1/s1
IUPAC Name[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-hydroxy-3-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-(pentadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name(2R)-2-hydroxy-3-{[hydroxy((2R)-2-hydroxy-3-(pentadecanoyloxy)propoxy)phosphoryl]oxy}propoxy((2R)-2-(pentadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propoxy)phosphinic acid
Chemical FormulaC53H102O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00044 g/LALOGPS
logP7.79ALOGPS
logP14.65ChemAxon
logS-6.4ALOGPS
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 Count57ChemAxon
Refractivity279.22 m³·mol⁻¹ChemAxon
Polarizability122.81 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(14:1(9Z)/15:0/15:0/16:1(11Z))PW010706 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/15:0/15:0/18:1(11Z))PW010709 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/15:0/15:0/18:1(9Z))PW010710 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/15:0/15:0/20:1(11Z))PW010712 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/15:0/15:0/20:1(13Z))PW010713 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(14:1(9Z)/15:0/15:0/0:0) → CL(14:1(9Z)/15:0/15:0/16:1(11Z))
2-MLCL(14:1(9Z)/15:0/15:0/0:0) → CL(14:1(9Z)/15:0/15:0/18:1(11Z))
2-MLCL(14:1(9Z)/15:0/15:0/0:0) → CL(14:1(9Z)/15:0/15:0/18:1(9Z))
2-MLCL(14:1(9Z)/15:0/15:0/0:0) → CL(14:1(9Z)/15:0/15:0/20:1(11Z))
2-MLCL(14:1(9Z)/15:0/15:0/0:0) → CL(14:1(9Z)/15:0/15:0/20:1(13Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap0-7090231060-023c9a1ba07fb008f44fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-4190241130-6a221d8291afb7b02731JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053s-3390212110-82c43fbf462e701b172fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0adl-2090000020-395f036dcf9356b99cddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4191010000-4dfde71df45df15321efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9071010000-198bfd7ef8381b6610e9JSpectraViewer
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