1-MLCL(0:0/15:0/18:0/22:0) (YMDB11706)

Identification
YMDB IDYMDB11706
Name1-MLCL(0:0/15:0/18:0/22:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-MLCL(0:0/15:0/18:0/22:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/15:0/18:0/22:0) contains one chain of at the C1 position, one chain of pentadecanoic acid at the C2 position, one chain of octadecanoic acid at the C3 position, one chain of docosanoic 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: 1213.644
Monoisotopic: 1212.852111973
InChI KeyHZVYVBAIVKBJIX-ZSGYRCJPSA-N
InChIInChI=1S/C64H126O16P2/c1-4-7-10-13-16-19-22-25-27-28-29-30-32-34-37-40-43-46-49-52-64(69)80-61(56-74-62(67)50-47-44-41-38-36-33-31-26-23-20-17-14-11-8-5-2)58-78-82(72,73)76-55-59(66)54-75-81(70,71)77-57-60(53-65)79-63(68)51-48-45-42-39-35-24-21-18-15-12-9-6-3/h59-61,65-66H,4-58H2,1-3H3,(H,70,71)(H,72,73)/t59-,60+,61+/m0/s1
IUPAC Name[(2R)-2-(docosanoyloxy)-3-(octadecanoyloxy)propoxy][(2S)-2-hydroxy-3-({hydroxy[(2R)-3-hydroxy-2-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional IUPAC Name(2R)-2-(docosanoyloxy)-3-(octadecanoyloxy)propoxy((2S)-2-hydroxy-3-{[hydroxy((2R)-3-hydroxy-2-(pentadecanoyloxy)propoxy)phosphoryl]oxy}propoxy)phosphinic acid
Chemical FormulaC64H126O16P2
SMILES[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
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 Solubility9.6e-05 g/LALOGPS
logP8.7ALOGPS
logP19.9ChemAxon
logS-7.1ALOGPS
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 Count69ChemAxon
Refractivity328.72 m³·mol⁻¹ChemAxon
Polarizability147.01 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(15:0/15:0/18:0/22:0)PW011454 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
CL(15:0/15:0/18:0/22:0) → 1-MLCL(0:0/15:0/18:0/22:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0092-0593103034-38b8b8de2cf83169acb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1594111134-a02d9bbdef943e33fe88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054k-4395303120-e508431df2c90a710327JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01c3-0192000012-638ef4c1548845de87afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-7193010100-59547a3c2e4a6d9db9adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9052000100-d3baf952f1e210bcf369JSpectraViewer
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