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2-Ketobutyric acid (YMDB00071)

Identification
YMDB IDYMDB00071
Name2-Ketobutyric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Ketobutyric acid, also known as alpha-ketobutyrate or a-oxo-N-butyrate, 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. 2-Ketobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Ketobutyric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Ketobutanoate
  • 2-Ketobutanoic acid
  • 2-ketobutyrate
  • 2-ketobutyric acid
  • 2-Oxo-Butanoate
  • 2-Oxo-Butanoic acid
  • 2-oxo-Butyrate
  • 2-oxo-Butyric acid
  • 2-Oxo-n-butyrate
  • 2-Oxo-n-butyric acid
  • 2-Oxobutanoate
  • 2-Oxobutanoic acid
  • 2-Oxobutyrate
  • 2-Oxobutyric acid
  • 3-Methylpyruvate
  • 3-Methylpyruvic acid
  • a-keto-n-Butyrate
  • a-keto-n-Butyric acid
  • a-Ketobutyrate
  • a-Ketobutyric acid
  • a-Oxo-n-butyrate
  • a-Oxo-n-butyric acid
  • a-Oxobutyrate
  • a-Oxobutyric acid
  • alpha-Keto-n-butyrate
  • alpha-Keto-n-butyric acid
  • alpha-Ketobutric acid
  • alpha-Ketobutyrate
  • alpha-Ketobutyric acid
  • alpha-Oxo-n-butyrate
  • alpha-Oxo-n-butyric acid
  • alpha-Oxobutyrate
  • alpha-Oxobutyric acid
  • Butanoic acid, 2-oxo-
  • Butyric acid, 2-oxo-
  • Formic acid, propionyl-
  • Ketobutyrate
  • methyl-Pyruvate
  • methyl-Pyruvic acid
  • Oxobutyrate
  • propionyl-formate
  • propionyl-formic acid
  • Pyruvic acid, methyl-
  • 3-Methyl pyruvic acid
  • 3-Methyl pyruvate
  • Α-ketobutyrate
  • Α-ketobutyric acid
  • Α-oxo-N-butyrate
  • Α-oxo-N-butyric acid
  • alpha-Ketobutyric acid, sodium salt
CAS number600-18-0
WeightAverage: 102.0886
Monoisotopic: 102.031694058
InChI KeyTYEYBOSBBBHJIV-UHFFFAOYSA-N
InChIInChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
IUPAC Name2-oxobutanoic acid
Traditional IUPAC Name2-oxobutanoic acid
Chemical FormulaC4H6O3
SMILES[H]OC(=O)C(=O)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
  • Short-chain keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point33°C
Experimental Properties
PropertyValueReference
Water Solubility119 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility79.2 g/LALOGPS
logP0.07ALOGPS
logP0.77ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.62 m³·mol⁻¹ChemAxon
Polarizability9.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BrownFDB030356
CaramelFDB030356
CreamyFDB030356
LactonicFDB030356
SweetFDB030356
SMPDB Pathways
Cysteine MetabolismPW002383 ThumbThumb?image type=greyscaleThumb?image type=simple
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
Selenocompound metabolismPW002472 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
isoleucine biosynthesisPW002476 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Glycine, serine and threonine metabolismec00260 Map00260
Propanoate metabolismec00640 Map00640
Selenocompound metabolismec00450 Map00450
Sulfur metabolismec00920 Map00920
SMPDB Reactions
water + L-Cystathionine → Ammonium + L-Cysteine + 2-Ketobutyric acid
4-Methylthio-2-oxobutanoate + L-Phenylalanine → L-Methionine + 2-Ketobutyric acid
2-Ketobutyric acid + hydron + Pyruvic acid → Carbon dioxide + (S)-2-Aceto-2-hydroxybutanoic acid
Selenomethionine + water → methylselenol + Ammonia + 2-Ketobutyric acid
KEGG Reactions
Pyruvic acid + hydron + 2-Ketobutyric acid → Carbon dioxide + (S)-2-acetyl-2-hydroxybutanoate
NAD + 2-hydroxybutyric acid ↔ NADH + hydron + 2-Ketobutyric acid
NAD + Coenzyme A + 2-Ketobutyric acid → NADH + propionyl-CoA + Carbon dioxide
L-Cystathionine + water → L-Cysteine + Ammonium + 2-Ketobutyric acid
L-Threonine → Ammonium + 2-Ketobutyric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eeaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9200000000-3b3816ffee5771215904JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-6910000000-5b264d5f7e53f3e80b12JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-6950000000-db7f6a0f03a8cce59baeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ftb-0920000000-a6c93d8761ef15f7f7d4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0920000000-406fe70e72dbd9c3f274JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eeaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9200000000-3b3816ffee5771215904JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-6910000000-5b264d5f7e53f3e80b12JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-6950000000-db7f6a0f03a8cce59baeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-8900000000-97bab6630de4df095a7fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-0ebb2354fe3f935fe177JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-32269ef3ef778c482f99JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adi-9200000000-f92941e9f326d8ccf3e4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b55JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0pb9-9600000000-b10635fbec5572d4d084JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9100000000-4c5e7d24dca6677e1570JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-ded44cfcbe7960954fdfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-1b350be7438b08f1946aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-056r-9000000000-172a175b8b9ebfd5529fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f127JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-aced8e004436190f07b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a3d7ddf227bd6aa91a54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9700000000-503296025148ec314383JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-933b567955b5de5b1744JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7d9db52021fefc87a855JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Yamagata, S., Yasugahira, T., Okuda, Y., Iwama, T. (2003). "Conversion of the aminocrotonate intermediate limits the rate of gamma-elimination reaction catalyzed by L-cystathionine gamma-lyase of the yeast Saccharomyces cerevisiae." J Biochem 134:607-613.14607989
  • 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:Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp.
External Links:
ResourceLink
CHEBI ID30831
HMDB IDHMDB00005
Pubchem Compound ID58
Kegg IDC00109
ChemSpider ID57
FOODB IDFDB030356
WikipediaAlpha-ketobutyric_acid
BioCyc ID2-OXOBUTANOATE

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. Putative cystathionine gamma-synthase YML082W
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q04533
Molecular weight:
74312.70313
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
Protein Details
3. Cystathionine gamma-lyase
General function:
Involved in pyridoxal phosphate binding
Specific function:
L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Gene Name:
CYS3
Uniprot ID:
P31373
Molecular weight:
42541.69922
Reactions
L-cystathionine + H(2)O → L-cysteine + NH(3) + 2-oxobutanoate.
Protein Details
4. Threonine dehydratase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
L-threonine = 2-oxobutanoate + NH(3)
Gene Name:
ILV1
Uniprot ID:
P00927
Molecular weight:
63830.69922
Reactions
L-threonine → 2-oxobutanoate + NH(3).
Protein Details
5. Catabolic L-serine/threonine dehydratase
General function:
Involved in catalytic activity
Specific function:
L-serine = pyruvate + NH(3)
Gene Name:
CHA1
Uniprot ID:
P25379
Molecular weight:
39301.0
Reactions
L-serine → pyruvate + NH(3).
L-threonine → 2-oxobutanoate + NH(3).
Protein Details
6. Aromatic amino acid aminotransferase 2
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
ARO9
Uniprot ID:
P38840
Molecular weight:
58527.0
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
Protein Details
7. 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).