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Identification
YMDB IDYMDB11820
Name2-MLCL(10:0/16:0/18:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(10:0/16:0/18:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(10:0/16:0/18:0/0:0) contains one chain of decanoic acid at the C1 position, one chain of hexadecanoic acid at the C2 position, one chain of octadecanoic 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 1059.347
Monoisotopic: 1058.679961265
InChI KeyUXXXPAKQQMPSLT-KXSRAAHWSA-N
InChIInChI=1S/C53H104O16P2/c1-4-7-10-13-16-18-20-22-23-25-26-28-31-34-36-39-51(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)40-37-33-30-15-12-9-6-3)69-53(58)41-38-35-32-29-27-24-21-19-17-14-11-8-5-2/h48-50,54-55H,4-47H2,1-3H3,(H,59,60)(H,61,62)/t48-,49-,50-/m1/s1
IUPAC NameNot Available
Traditional IUPAC NameNot Available
Chemical FormulaC53H104O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
ChargeNot Available
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted PropertiesNot Available
Biological Properties
Cellular Locations
  • Mitochondrion membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(10:0/16:0/18:0/18:1(11Z))PW005222 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/16:0/18:0/18:1(9Z))PW005223 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/16:0/18:0/20:1(11Z))PW005225 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/16:0/18:0/20:1(13Z))PW005226 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/16:0/18:0/22:1(11Z))PW005228 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(10:0/16:0/18:0/0:0)CL(10:0/16:0/18:0/18:1(11Z))
2-MLCL(10:0/16:0/18:0/0:0)CL(10:0/16:0/18:0/18:1(9Z))
2-MLCL(10:0/16:0/18:0/0:0)CL(10:0/16:0/18:0/20:1(11Z))
2-MLCL(10:0/16:0/18:0/0:0)CL(10:0/16:0/18:0/20:1(13Z))
2-MLCL(10:0/16:0/18:0/0:0)CL(10:0/16:0/18:0/22:1(11Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052o-8393413140-dab92812f0a39f5ac8faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-5292431210-a54923526546aa3adbd6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5295311100-eb3a63dc22c01cbb3e76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-107i-3690110110-4dfed2e4109350cc8f6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00c0-7790120000-74b39a054f06d50d1cbaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9250110000-841f87eed915a9b69961JSpectraViewer
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