2-MLCL(12:0/12:0/16:1(9Z)/0:0) (YMDB11774)

Identification
YMDB IDYMDB11774
Name2-MLCL(12:0/12:0/16:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(12:0/12:0/16:1(9Z)/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(12:0/12:0/16:1(9Z)/0:0) contains two chains of dodecanoic acid at the C1 and C2 positions, 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: 1001.223
Monoisotopic: 1000.601710943
InChI KeyGOIRKTZBWOCXNG-WAHIVQMQSA-N
InChIInChI=1S/C49H94O16P2/c1-4-7-10-13-16-19-20-21-22-25-27-29-32-35-47(52)59-38-44(50)39-61-66(55,56)62-40-45(51)41-63-67(57,58)64-43-46(65-49(54)37-34-31-28-24-18-15-12-9-6-3)42-60-48(53)36-33-30-26-23-17-14-11-8-5-2/h19-20,44-46,50-51H,4-18,21-43H2,1-3H3,(H,55,56)(H,57,58)/b20-19-/t44-,45-,46-/m1/s1
IUPAC Name[(2R)-2,3-bis(dodecanoyloxy)propoxy][(2R)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis(dodecanoyloxy)propoxy((2R)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC49H94O16P2
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)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
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 Solubility0.00081 g/LALOGPS
logP7.29ALOGPS
logP12.87ChemAxon
logS-6.1ALOGPS
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 Count53ChemAxon
Refractivity260.82 m³·mol⁻¹ChemAxon
Polarizability113.75 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(12:0/12:0/16:1(9Z)/20:0)PW005986 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/16:1(9Z)/20:1(11Z))PW005987 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/16:1(9Z)/20:1(13Z))PW005988 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/16:1(9Z)/22:0)PW005989 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/12:0/16:1(9Z)/22:1(11Z))PW005990 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(12:0/12:0/16:1(9Z)/0:0) → CL(12:0/12:0/16:1(9Z)/20:0)
2-MLCL(12:0/12:0/16:1(9Z)/0:0) → CL(12:0/12:0/16:1(9Z)/20:1(11Z))
2-MLCL(12:0/12:0/16:1(9Z)/0:0) → CL(12:0/12:0/16:1(9Z)/20:1(13Z))
2-MLCL(12:0/12:0/16:1(9Z)/0:0) → CL(12:0/12:0/16:1(9Z)/22:0)
2-MLCL(12:0/12:0/16:1(9Z)/0:0) → CL(12:0/12:0/16:1(9Z)/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, Positivesplash10-0f89-4575661489-4ca195d7626a7d6d4c1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-1777592156-aa04508fc26df48a11c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-4497540102-a45af3f443dca52ab8fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f7t-0890020213-051ca1387c5d1509f31dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fca-7981120000-a97446b2c402cfe10b56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9241010000-fb35df6e78aa33cf84d2JSpectraViewer
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