2-MLCL(15:0/15:0/26:0/0:0) (YMDB12045)

Identification
YMDB IDYMDB12045
Name2-MLCL(15:0/15:0/26:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(15:0/15:0/26:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(15:0/15:0/26:0/0:0) contains two chains of pentadecanoic acid at the C1 and C2 positions, one chain of hexacosanoic 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: 1227.671
Monoisotopic: 1226.867762038
InChI KeyWHSDIZKJHWWSES-DLAFNDBQSA-N
InChIInChI=1S/C65H128O16P2/c1-4-7-10-13-16-19-22-25-26-27-28-29-30-31-32-33-34-35-38-40-42-45-48-51-63(68)75-54-60(66)55-77-82(71,72)78-56-61(67)57-79-83(73,74)80-59-62(81-65(70)53-50-47-44-41-37-24-21-18-15-12-9-6-3)58-76-64(69)52-49-46-43-39-36-23-20-17-14-11-8-5-2/h60-62,66-67H,4-59H2,1-3H3,(H,71,72)(H,73,74)/t60-,61-,62-/m1/s1
IUPAC Name[(2R)-2,3-bis(pentadecanoyloxy)propoxy][(2R)-3-({[(2R)-3-(hexacosanoyloxy)-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis(pentadecanoyloxy)propoxy((2R)-3-{[(2R)-3-(hexacosanoyloxy)-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC65H128O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.2e-05 g/LALOGPS
logP8.8ALOGPS
logP20.35ChemAxon
logS-7.1ALOGPS
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 Count70ChemAxon
Refractivity333.32 m³·mol⁻¹ChemAxon
Polarizability148.97 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(10:0/15:0/15:0/26:0)PW004763 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/15:0/15:0/26:0)PW006815 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/15:0/15:0/26:0)PW008688 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(11Z)/15:0/15:0/26:0)PW009700 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/15:0/15:0/26:0)PW010720 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(15:0/15:0/26:0/0:0) → CL(10:0/15:0/15:0/26:0)
2-MLCL(15:0/15:0/26:0/0:0) → CL(12:0/15:0/15:0/26:0)
2-MLCL(15:0/15:0/26:0/0:0) → CL(14:0/15:0/15:0/26:0)
2-MLCL(15:0/15:0/26:0/0:0) → CL(14:1(11Z)/15:0/15:0/26:0)
2-MLCL(15:0/15:0/26:0/0:0) → CL(14:1(9Z)/15:0/15:0/26:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-1092223214-e486b36912188334f734JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-2093246302-dac9652b743e113a7478JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6292646200-d3ab19313700e45818fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00bd-1096011011-fb859a050a07cd0eb0feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-7189021100-eb22d1218ef2cf8de1e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9042011000-c78810f4756d223ea283JSpectraViewer
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