1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0) (YMDB11524)

Identification
YMDB IDYMDB11524
Name1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0) contains one chain of at the C1 position, two chains of (9Z-tetradecenoyl) at the C2 and C3 positions, one chain of hexadecanoic acid 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: 1055.315
Monoisotopic: 1054.648661136
InChI KeyAYTAIRLUJFTNPU-CMYXBTSXSA-N
InChIInChI=1S/C53H100O16P2/c1-4-7-10-13-16-19-22-23-26-29-32-35-38-41-53(58)69-50(45-63-51(56)39-36-33-30-27-24-20-17-14-11-8-5-2)47-67-71(61,62)65-44-48(55)43-64-70(59,60)66-46-49(42-54)68-52(57)40-37-34-31-28-25-21-18-15-12-9-6-3/h14-15,17-18,48-50,54-55H,4-13,16,19-47H2,1-3H3,(H,59,60)(H,61,62)/b17-14-,18-15-/t48-,49+,50+/m0/s1
IUPAC Name[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propoxy][(2S)-2-hydroxy-3-({hydroxy[(2R)-3-hydroxy-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional IUPAC Name(2R)-2-(hexadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propoxy((2S)-2-hydroxy-3-{[hydroxy((2R)-3-hydroxy-2-[(9Z)-tetradec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxy)phosphinic acid
Chemical FormulaC53H100O16P2
SMILES[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCC\C=C/CCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCCCCCCCCCC
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
  • Primary alcohol
  • 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 Solubility0.00051 g/LALOGPS
logP7.74ALOGPS
logP14.29ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area230.88 ŲChemAxon
Rotatable Bond Count56ChemAxon
Refractivity280.34 m³·mol⁻¹ChemAxon
Polarizability121.11 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)/14:1(9Z)/16:0/16:1(11Z))PW010589 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/14:1(9Z)/16:0/18:0)PW010591 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/14:1(9Z)/16:0/18:1(11Z))PW010592 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/14:1(9Z)/16:0/18:1(9Z))PW010593 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:1(9Z)/14:1(9Z)/16:0/20:0)PW010594 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CL(14:1(9Z)/14:1(9Z)/16:0/16:1(11Z)) → 1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0)
CL(14:1(9Z)/14:1(9Z)/16:0/18:0) → 1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0)
CL(14:1(9Z)/14:1(9Z)/16:0/18:1(11Z)) → 1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0)
CL(14:1(9Z)/14:1(9Z)/16:0/18:1(9Z)) → 1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0)
CL(14:1(9Z)/14:1(9Z)/16:0/20:0) → 1-MLCL(0:0/14:1(9Z)/14:1(9Z)/16:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-7090132250-13c325bffc0910892ae8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-4291132320-c3ca463c9d966bdbf3e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05a9-5290222000-16017bb411556e74207bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056s-4091021240-2e8fb352ed35e1015aefJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9043031110-c9ecb3abf6efd9a67bf9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9052010000-718067db895aa4b593bcJSpectraViewer
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