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Identification
YMDB IDYMDB00039
Name(S)-2-Aceto-2-hydroxybutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-2-Aceto-2-hydroxybutanoic acid, also known as (S)-2-hydroxy-2-ethyl-3-oxobutanoate or (S)-2-acetyl-2-hydroxybutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms (S)-2-Aceto-2-hydroxybutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-2-Aceto-2-hydroxybutanoic acid exists in all living species, ranging from bacteria to humans. Within yeast, (S)-2-aceto-2-hydroxybutanoic acid participates in a number of enzymatic reactions. In particular, (S)-2-aceto-2-hydroxybutanoic acid can be biosynthesized from 2-ketobutyric acid and pyruvic acid through its interaction with the enzymes acetohydroxybutanoate synthase / acetolactate synthase, acetohydroxybutanoate synthase / acetolactate synthase 2, and acetolactate synthase / acetohydroxybutanoate synthase 3. In addition, (S)-2-aceto-2-hydroxybutanoic acid can be converted into (R) 2,3-dihydroxy-3-methylvalerate; which is mediated by the enzyme acetohydroxy acid isomeroreductase. In yeast, (S)-2-aceto-2-hydroxybutanoic acid is involved in the metabolic pathway called isoleucine biosynthesis pathway.
Structure
Thumb
Synonyms
  • (2S)-2-ethyl-2-hydroxy-3-oxobutanoate
  • (2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
  • (S)-2-Aceto-2-hydroxybutanoate
  • (S)-2-Aceto-2-hydroxybutanoic acid
  • (S)-2-Acetyl-2-hydroxybutyrate
  • (S)-2-Acetyl-2-hydroxybutyric acid
  • (S)-2-Hydroxy-2-ethyl-3-oxobutanoate
  • (S)-2-Hydroxy-2-ethyl-3-oxobutanoic acid
  • 2S-Acetyl-2-hydroxy-butanoate
CAS numberNot Available
WeightAverage: 146.1412
Monoisotopic: 146.057908808
InChI KeyVUQLHQFKACOHNZ-LURJTMIESA-N
InChIInChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1
IUPAC Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
Traditional IUPAC Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
Chemical FormulaC6H10O4
SMILES[H]OC(=O)[C@@](O[H])(C(=O)C([H])([H])[H])C([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain keto acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Acyloin
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility259 g/LALOGPS
logP-0.58ALOGPS
logP0.24ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.11 m³·mol⁻¹ChemAxon
Polarizability13.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
isoleucine biosynthesisPW002476 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB Reactions
(S)-2-Aceto-2-hydroxybutanoic acid + NADPH + hydronNADP + (R)-2,3-Dihydroxy-3-methylvalerate
2-Ketobutyric acid + hydron + Pyruvic acidCarbon dioxide + (S)-2-Aceto-2-hydroxybutanoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27681
HMDB IDHMDB06900
Pubchem Compound ID8279
Kegg IDC06006
ChemSpider ID389708
FOODB IDFDB024147
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Minor of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins. The expression level of this protein in the presence of fermentable carbon sources is so low that it can not compensate for the other two pyruvate decarboxylases to sustain fermentation
Gene Name:
PDC6
Uniprot ID:
P26263
Molecular weight:
61579.89844
Reactions
A 2-oxo acid → an aldehyde + CO(2).
3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2).
Phenylpyruvate → phenylacetaldehyde + CO(2).
Pyruvate → Acetaldehyde + CO(2).
A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2).
An aldehyde + an aldehyde → A 2-hydroxy ketone.
General function:
Involved in oxidoreductase activity
Specific function:
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:
ILV5
Uniprot ID:
P06168
Molecular weight:
44368.10156
Reactions
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) → (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH.
(2R,3R)-2,3-dihydroxy-3-methylpentanoate + NADP(+) → (S)-2-hydroxy-2-ethyl-3-oxobutanoate + NADPH.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of ketopantoate into pantoic acid
Gene Name:
PAN5
Uniprot ID:
P38787
Molecular weight:
42820.89844
Reactions
(R)-pantoate + NADP(+) → 2-dehydropantoate + NADPH.