(S)-2-Acetolactate (YMDB00177)

Identification
YMDB IDYMDB00177
Name(S)-2-Acetolactate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-2-Acetolactate, also known as b-dyn a, 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-Acetolactate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-2-Acetolactate exists in all living species, ranging from bacteria to humans. Within yeast, (S)-2-acetolactate participates in a number of enzymatic reactions. In particular, (S)-2-acetolactate can be biosynthesized from pyruvic acid through its interaction with the enzyme acetolactate synthase / acetohydroxybutanoate synthase. In addition, (S)-2-acetolactate can be biosynthesized from pyruvic acid through its interaction with the enzyme acetohydroxybutanoate synthase / acetolactate synthase. In yeast, (S)-2-acetolactate is involved in the metabolic pathway called valine biosynthesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (S)-2-Hydroxy-2-methyl-3-oxobutanoate
  • (S)-2-Hydroxy-2-methyl-3-oxobutanoic acid
  • (2S)-2-Hydroxy-2-methyl-3-oxobutanoate
  • (2S)-2-Hydroxy-2-methyl-3-oxobutanoic acid
  • (S)-2-Acetolactic acid
  • 13-Biotinyl-lys-dynorphin a amide (1-13)
  • b-DYN a
  • (S)-alpha-Acetolactic acid
  • (S)-α-Acetolactic acid
  • 2-Acetolactic acid
  • 2-Hydroxy-2-methyl-3-oxobutanoic acid
  • Acetolactic acid
CAS numberNot Available
WeightAverage: 132.1146
Monoisotopic: 132.042258744
InChI KeyNMDWGEGFJUBKLB-YFKPBYRVSA-N
InChIInChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1
IUPAC Name(2S)-2-hydroxy-2-methyl-3-oxobutanoic acid
Traditional IUPAC Nameacetolactic acid
Chemical FormulaC5H8O4
SMILES[H]OC(=O)[C@@](O[H])(C(=O)C([H])([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
  • Methyl-branched fatty 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 Solubility286 g/LALOGPS
logP-0.65ALOGPS
logP-0.28ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.59 m³·mol⁻¹ChemAxon
Polarizability11.81 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
Valine BiosynthesisPW002474 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB Reactions
(S)-2-Acetolactate + hydron + NADPH → NADP + (R)-2,3-Dihydroxy-isovalerate
Pyruvic acid + hydron → Carbon dioxide + (S)-2-Acetolactate
Pyruvic acid + hydron → Carbon dioxide + (S)-2-Acetolactate
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0c1fe460a2ec8a1a255dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0303-9780000000-ed6c7b366835f2a4a9c0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-5900000000-a14af8bd96fdcce5e84fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015l-9400000000-53c1f10a4a9b63a25574JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-9000000000-03c96ef4ce31ab174fddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9700000000-641c507686f1b0493bdeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-cd68c82882667330e329JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-9000000000-f0530bd3c4f32baa697cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9300000000-0c998add67e750d36bc4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9200000000-3e8a380405cb5b02d1d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-aeeb164d9240ff735bc5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ke-9200000000-c8b983df55a14da2898aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-79267be0bc618dc8018fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-cd1679ff8fbd31e9b90fJSpectraViewer
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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18409
HMDB IDHMDB06855
Pubchem Compound ID22
Kegg IDC06010
ChemSpider ID389710
FOODB IDFDB024120
WikipediaAcetolactic_acid
BioCyc IDNot Available

Enzymes

Protein Details
1. Pyruvate decarboxylase isozyme 3
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.
Protein Details
2. Ketol-acid reductoisomerase, mitochondrial
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.
Protein Details
3. Acetolactate synthase catalytic subunit, mitochondrial
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).
Protein Details
4. 2-dehydropantoate 2-reductase
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.