Identification
YMDB IDYMDB11806
Name2-MLCL(10:0/10:0/23:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(10:0/10:0/23:1(9Z)/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(10:0/10:0/23:1(9Z)/0:0) contains two chains of decanoic acid at the C1 and C2 positions, one chain of 9Z-tricosanoic 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: 1043.304
Monoisotopic: 1042.648661136
InChI KeyXGINZWXFWINMFR-IZRHKEMGSA-N
InChIInChI=1S/C52H100O16P2/c1-4-7-10-13-16-17-18-19-20-21-22-23-24-25-26-27-28-31-33-35-38-50(55)62-41-47(53)42-64-69(58,59)65-43-48(54)44-66-70(60,61)67-46-49(68-52(57)40-37-34-30-15-12-9-6-3)45-63-51(56)39-36-32-29-14-11-8-5-2/h24-25,47-49,53-54H,4-23,26-46H2,1-3H3,(H,58,59)(H,60,61)/b25-24-/t47-,48-,49-/m1/s1
IUPAC Name[(2R)-2,3-bis(decanoyloxy)propoxy][(2R)-2-hydroxy-3-({hydroxy[(2R)-2-hydroxy-3-[(9Z)-tricos-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis(decanoyloxy)propoxy((2R)-2-hydroxy-3-{[hydroxy((2R)-2-hydroxy-3-[(9Z)-tricos-9-enoyloxy]propoxy)phosphoryl]oxy}propoxy)phosphinic acid
Chemical FormulaC52H100O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCC\C=C/CCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
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
  • 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 Solubility0.00049 g/LALOGPS
logP7.75ALOGPS
logP14.21ChemAxon
logS-6.3ALOGPS
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 Count56ChemAxon
Refractivity274.62 m³·mol⁻¹ChemAxon
Polarizability120.18 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(10:0/10:0/23:1(9Z)/25:0)PW003701 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/23:1(9Z)/25:1(11Z))PW003702 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/23:1(9Z)/25:1(9Z))PW003703 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/23:1(9Z)/27:0)PW003704 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/23:1(9Z)/27:1(11Z))PW003705 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(10:0/10:0/23:1(9Z)/0:0)CL(10:0/10:0/23:1(9Z)/25:0)
2-MLCL(10:0/10:0/23:1(9Z)/0:0)CL(10:0/10:0/23:1(9Z)/25:1(11Z))
2-MLCL(10:0/10:0/23:1(9Z)/0:0)CL(10:0/10:0/23:1(9Z)/25:1(9Z))
2-MLCL(10:0/10:0/23:1(9Z)/0:0)CL(10:0/10:0/23:1(9Z)/27:0)
2-MLCL(10:0/10:0/23:1(9Z)/0:0)CL(10:0/10:0/23:1(9Z)/27:1(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, Positivesplash10-05dl-9315353060-1829c40782641eab2329JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adr-9547887250-99ff6bdfca0c7b451a5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-8279772000-58568f179809c412d9f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-4809112020-4083e55ce8dc16435f12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0umi-7809112000-3920164cddb2c6d1bb14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9222200000-e6308d47e0f049acbd96JSpectraViewer
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