2-MLCL(14:0/16:0/16:1(9Z)/0:0) (YMDB11896)

Identification
YMDB IDYMDB11896
Name2-MLCL(14:0/16:0/16:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(14:0/16:0/16:1(9Z)/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(14:0/16:0/16:1(9Z)/0:0) contains one chain of tetradecanoic acid at the C1 position, one chain of hexadecanoic acid at the C2 position, one chain of (9Z-hexadecenoyl) 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: 1085.385
Monoisotopic: 1084.695611329
InChI KeyKXOMILXCDYOEPO-RKJNGQHZSA-N
InChIInChI=1S/C55H106O16P2/c1-4-7-10-13-16-19-22-24-27-30-32-35-38-41-53(58)65-44-50(56)45-67-72(61,62)68-46-51(57)47-69-73(63,64)70-49-52(48-66-54(59)42-39-36-33-29-26-21-18-15-12-9-6-3)71-55(60)43-40-37-34-31-28-25-23-20-17-14-11-8-5-2/h19,22,50-52,56-57H,4-18,20-21,23-49H2,1-3H3,(H,61,62)(H,63,64)/b22-19-/t50-,51-,52-/m1/s1
IUPAC Name[(2R)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name(2R)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propoxy)phosphinic acid
Chemical FormulaC55H106O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)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
  • 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 Solubility0.00033 g/LALOGPS
logP7.99ALOGPS
logP15.54ChemAxon
logS-6.5ALOGPS
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 Count59ChemAxon
Refractivity288.42 m³·mol⁻¹ChemAxon
Polarizability126.58 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(14:0/14:0/16:0/16:1(9Z))PW008155 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/16:0/16:1(9Z)/16:1(11Z))PW008991 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/16:0/16:1(9Z)/16:1(9Z))PW008992 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/16:0/16:1(9Z)/18:0)PW008993 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(14:0/16:0/16:1(9Z)/18:1(11Z))PW008994 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(14:0/16:0/16:1(9Z)/0:0) → CL(14:0/14:0/16:0/16:1(9Z))
2-MLCL(14:0/16:0/16:1(9Z)/0:0) → CL(14:0/16:0/16:1(9Z)/16:1(11Z))
2-MLCL(14:0/16:0/16:1(9Z)/0:0) → CL(14:0/16:0/16:1(9Z)/16:1(9Z))
2-MLCL(14:0/16:0/16:1(9Z)/0:0) → CL(14:0/16:0/16:1(9Z)/18:0)
2-MLCL(14:0/16:0/16:1(9Z)/0:0) → CL(14:0/16:0/16:1(9Z)/18:1(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, Negativesplash10-0kdr-2090000020-8b718e70e3fdae018179JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4090000000-dc2ba2da5635807edfa7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9060001000-a91e2ee6e8173538d420JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029i-7092222050-17aab6e3b8684caf4301JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-4193132130-554b4799df5e79c96d26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vr-4293312000-8ea88ce4ee1b3d05beeeJSpectraViewer
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