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Identification
YMDB IDYMDB00428
Name(S)-2-acetyl-2-hydroxybutanoate
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 the action of 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 through the action of 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
  • (S)-2-Aceto-2-hydroxybutanoate
  • (S)-2-acetyl-2-hydroxybutyrate
  • (S)-2-Hydroxy-2-ethyl-3-oxobutanoate
  • (S)-2-Acetyl-2-hydroxybutyric acid
  • (S)-2-Hydroxy-2-ethyl-3-oxobutanoic acid
  • (2S)-2-Ethyl-2-hydroxy-3-oxobutanoate
  • (2S)-2-Ethyl-2-hydroxy-3-oxobutanoic acid
  • 2S-Acetyl-2-hydroxy-butanoate
  • (S)-2-Aceto-2-hydroxy-butyrate
  • 2-Aceto-2-hydroxybutyric acid
  • 2-Ethyl-2-hydroxy-3-oxobutanoic acid
  • Acetohydroxybutyric acid
  • alpha-Aceto-alpha-hydroxybutyric acid
  • alpha-Acetohydroxybutyric acid
  • α-Aceto-α-hydroxybutyric acid
  • α-Acetohydroxybutyric acid
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
SMILESCC[C@](O)(C(C)=O)C(O)=O
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
StateNot Available
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 PathwaysNot Available
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB ReactionsNot Available
KEGG Reactions
Pyruvic acid + hydron + 2-Ketobutyric acidCarbon dioxide + (S)-2-acetyl-2-hydroxybutanoate
NADPH + hydron + (S)-2-acetyl-2-hydroxybutanoateNADP + (R)-2,3-Dihydroxy-3-methylvalerate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-4a32387e4d1a3c2518e2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9260000000-03d854f5c6e2c1cd66ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-58139948a2d318b20cd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-7900000000-5d95d041962e4d0c29c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9400000000-54a124cdee1ab9c9f382JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-c26fd82bd80ef12ed78aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-79a2c717c39914d90709JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-14cfb3f09136a8d1b1fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0900000000-e31b2e7070d5d06bb420JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kam-9200000000-8e85855717b408d3368eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0a3fed2352239366e095JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kal-9600000000-fd5ff61bfd773a3d7ff1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-775b97d756977d989ad0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9000000000-287791e86291cbac2749JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Cullin, C., Baudin-Baillieu, A., Guillemet, E., Ozier-Kalogeropoulos, O. (1996). "Functional analysis of YCL09C: evidence for a role as the regulatory subunit of acetolactate synthase." Yeast 12:1511-1518.8972574
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27681
HMDB IDHMDB0006900
Pubchem Compound ID21145135
Kegg IDC06006
ChemSpider ID389708
FOODB IDFDB024147
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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 magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ILV2
Uniprot ID:
P07342
Molecular weight:
74936.29688
Reactions
2 pyruvate → 2-acetolactate + CO(2).