You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB11929
Name2-MLCL(16:0/16:0/16:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-MLCL(16:0/16:0/16:0/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-MLCL(16:0/16:0/16:0/0:0) may be a unique S.cerevisiae (yeast) metabolite. 2-MLCL(16:0/16:0/16:0/0:0) participates in a number of enzymatic reactions, within yeast. In particular, 2-MLCL(16:0/16:0/16:0/0:0) can be converted into CL(10:0/14:0/15:0/29:0) through the action of the enzyme transacylase TAZ1P. Furthermore, 2-MLCL(16:0/16:0/16:0/0:0) can be converted into CL(10:0/14:0/15:0/29:0); which is mediated by the enzyme transacylase TAZ1P. Furthermore, 2-MLCL(16:0/16:0/16:0/0:0) can be converted into CL(10:0/20:1(13Z)/10:0/20:1(13Z)) through its interaction with the enzyme transacylase TAZ1P. Furthermore, 2-MLCL(16:0/16:0/16:0/0:0) can be converted into CL(10:0/20:1(13Z)/10:0/20:1(13Z)); which is mediated by the enzyme transacylase TAZ1P. Furthermore, 2-MLCL(16:0/16:0/16:0/0:0) can be converted into CL(10:0/22:1(11Z)/10:0/22:1(11Z)); which is mediated by the enzyme transacylase TAZ1P. Finally, 2-MLCL(16:0/16:0/16:0/0:0) can be converted into CL(10:0/22:1(11Z)/10:0/22:1(11Z)); which is catalyzed by the enzyme transacylase TAZ1P. In yeast, 2-MLCL(16:0/16:0/16:0/0:0) is involved in several metabolic pathways, some of which include cardiolipin biosynthesis CL(10:0/14:0/15:0/29:0) pathway, cardiolipin biosynthesis CL(10:0/20:1(13Z)/10:0/20:1(13Z)) pathway, cardiolipin biosynthesis CL(10:0/22:1(11Z)/10:0/22:1(11Z)) pathway, cardiolipin biosynthesis CL(10:0/24:1(9Z)/10:0/24:1(9Z)) pathway, cardiolipin biosynthesis CL(10:0/25:1(9Z)/10:0/25:1(9Z)) pathway, cardiolipin biosynthesis CL(10:0/26:1(11Z)/10:0/26:1(11Z)) pathway, cardiolipin biosynthesis CL(12:0/18:0/12:0/18:0) pathway, cardiolipin biosynthesis CL(12:0/23:1(11Z)/12:0/23:1(11Z)) pathway, and cardiolipin biosynthesis CL(12:0/24:1(11Z)/12:0/24:1(11Z)) pathway.
Structure
Thumb
SynonymsNot Available
CAS numberNot Available
WeightAverage: 1115.455
Monoisotopic: 1114.742561522
InChI KeyVGERFNNSKBECLU-SAMNPIAGSA-N
InChIInChI=1S/C57H112O16P2/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-55(60)67-46-52(58)47-69-74(63,64)70-48-53(59)49-71-75(65,66)72-51-54(73-57(62)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)50-68-56(61)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h52-54,58-59H,4-51H2,1-3H3,(H,63,64)(H,65,66)/t52-,53-,54-/m1/s1
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy][(2R)-3-({[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional IUPAC Name(2R)-2,3-bis(hexadecanoyloxy)propoxy((2R)-3-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
Chemical FormulaC57H112O16P2
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP8.16ALOGPS
logP16.79ChemAxon
logS-6.7ALOGPS
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 Count62ChemAxon
Refractivity296.51 m³·mol⁻¹ChemAxon
Polarizability132.56 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(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))PW007898 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
2-MLCL(16:0/16:0/16:0/0:0)CL(10:0/10:0/14:1(11Z)/26:0)
2-MLCL(16:0/16:0/16:0/0:0)CL(10:0/10:0/14:1(11Z)/26:1(11Z))
2-MLCL(16:0/16:0/16:0/0:0)CL(10:0/10:0/14:1(11Z)/26:1(9Z))
2-MLCL(16:0/16:0/16:0/0:0)CL(10:0/10:0/14:1(11Z)/28:0)
2-MLCL(16:0/16:0/16:0/0:0)CL(10:0/10:0/14:1(11Z)/28:1(11Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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