Showing metabocard for 2-Ketobutyric acid (BMDB0000005)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
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Record Information
Version1.0
Creation Date2016-09-30 22:07:17 UTC
Update Date2020-05-21 16:29:03 UTC
BMDB IDBMDB0000005
Secondary Accession Numbers
  • BMDB00005
Metabolite Identification
Common Name2-Ketobutyric acid
Description2-Ketobutyric acid, also known as 2-ketobutyric acid 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Ketobutyric acid exists in all living species, ranging from bacteria to humans. 2-Ketobutyric acid participates in a number of enzymatic reactions, within cattle. In particular, 2-Ketobutyric acid can be biosynthesized from L-threonine; which is mediated by the enzyme L-serine dehydratase/l-threonine deaminase. In addition, 2-Ketobutyric acid and coenzyme A can be converted into propionyl-CoA through its interaction with the enzyme branched-chain alpha-keto dehydrogenase complex. In cattle, 2-ketobutyric acid is involved in the metabolic pathway called the threonine and 2-ketobutyric acid degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name2-oxobutanoic acid
Traditional Name2-oxobutanoic acid
CAS Registry Number600-18-0
SMILES
CCC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
InChI KeyTYEYBOSBBBHJIV-UHFFFAOYSA-N
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility119 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eeaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9200000000-3b3816ffee5771215904View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-6910000000-5b264d5f7e53f3e80b12View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-6950000000-db7f6a0f03a8cce59baeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ftb-0920000000-a6c93d8761ef15f7f7d4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0920000000-406fe70e72dbd9c3f274View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eeaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9200000000-3b3816ffee5771215904View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-6910000000-5b264d5f7e53f3e80b12View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-6950000000-db7f6a0f03a8cce59baeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-8900000000-97bab6630de4df095a7fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-0ebb2354fe3f935fe177View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-32269ef3ef778c482f99View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adi-9200000000-f92941e9f326d8ccf3e4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0pb9-9600000000-b10635fbec5572d4d084View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9100000000-4c5e7d24dca6677e1570View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-ded44cfcbe7960954fdfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-1b350be7438b08f1946aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-056r-9000000000-172a175b8b9ebfd5529fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-aced8e004436190f07b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a3d7ddf227bd6aa91a54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9700000000-503296025148ec314383View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-933b567955b5de5b1744View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7d9db52021fefc87a855View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000005
DrugBank IDDB04553
Phenol Explorer Compound IDNot Available
FooDB IDFDB030356
KNApSAcK IDC00019675
Chemspider ID57
KEGG Compound IDC00109
BioCyc ID2-OXOBUTANOATE
BiGG ID33889
Wikipedia LinkAlpha-Ketobutyric_acid
METLIN IDNot Available
PubChem Compound58
PDB IDNot Available
ChEBI ID30831
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. L-serine dehydratase/L-threonine deaminase
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
SDS
Uniprot ID:
Q0VCW4
Molecular weight:
34441.0
Reactions
L-Threonine → 2-Ketobutyric acid + Ammoniadetails
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Energy production and conversion
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P11178
Molecular weight:
51678.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADHdetails
Enzyme Details
3. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Energy production and conversion
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21839
Molecular weight:
42935.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADHdetails
Enzyme Details
4. Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial
General function:
Energy production and conversion
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3). Within this complex, the catalytic function of this enzyme is to accept, and to transfer to coenzyme A, acyl groups that are generated by the branched-chain alpha-keto acid decarboxylase component.
Gene Name:
DBT
Uniprot ID:
P11181
Molecular weight:
53410.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADHdetails
Enzyme Details
5. Cystathionine gamma-lyase
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function (By similarity).
Gene Name:
CTH
Uniprot ID:
Q58DW2
Molecular weight:
44406.0
Reactions
Selenocystathionine + Water → Selenocysteine + Ammonia + 2-Ketobutyric aciddetails
L-Cystathionine + Water → L-Cysteine + 2-Ketobutyric acid + Ammoniadetails
L-Cystathionine + Water → L-Cysteine + 2-Ketobutyric aciddetails
Enzyme Details
6. Dihydrolipoyl dehydrogenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
DLD
Uniprot ID:
F1N206
Molecular weight:
54187.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADHdetails