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Identification
YMDB IDYMDB01064
Name(S)-malate(2-)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description(S)-malate(2-), also known as L-malate or (S)-malic acid, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom (S)-malate(2-) is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-malate(2-) may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (S)-Malate
  • (S)-Malic acid
  • (S)-Malic acid(2-)
  • L-Malate
  • L-Malic acid
CAS numberNot Available
WeightAverage: 132.0716
Monoisotopic: 132.005873238
InChI KeyBJEPYKJPYRNKOW-REOHCLBHSA-L
InChIInChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/p-2/t2-/m0/s1
IUPAC Name(2S)-2-hydroxybutanedioate
Traditional IUPAC NameL-malate
Chemical FormulaC4H4O5
SMILESO[C@@H](CC([O-])=O)C([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge-2
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility826 g/LALOGPS
logP-0.93ALOGPS
logP-1.1ChemAxon
logS0.69ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area100.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.55 m³·mol⁻¹ChemAxon
Polarizability10.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyruvate metabolismec00620 Map00620
SMPDB ReactionsNot Available
KEGG Reactions
Fumaric acid + water(S)-malate(2-)
NAD + (S)-malate(2-)NADH + hydron + Oxalacetic acid
Glyoxylic acid + Acetyl-CoA + waterhydron + Coenzyme A + (S)-malate(2-)
NAD + (S)-malate(2-)NADH + Pyruvic acid + Carbon dioxide
NADP + (S)-malate(2-)Pyruvic acid + Carbon dioxide + NADPH
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Kunze, M., Kragler, F., Binder, M., Hartig, A., Gurvitz, A. (2002). "Targeting of malate synthase 1 to the peroxisomes of Saccharomyces cerevisiae cells depends on growth on oleic acid medium." Eur J Biochem 269:915-922.11846793
  • Przybyla-Zawislak, B., Gadde, D. M., Ducharme, K., McCammon, M. T. (1999). "Genetic and biochemical interactions involving tricarboxylic acid cycle (TCA) function using a collection of mutants defective in all TCA cycle genes." Genetics 152:153-166.10224250
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15589
HMDB IDNot Available
Pubchem Compound ID5459792
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDMAL