Bovine Metabolome Database: Showing metabocard for 2-Ketobutyric acid (BMDB0000005)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:07:17 UTC

Update Date

2020-05-21 16:29:03 UTC

BMDB ID

BMDB0000005

Secondary Accession Numbers

BMDB00005

Metabolite Identification

Common Name

2-Ketobutyric acid

Description

2-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Ketobutanoic acid	ChEBI
2-Oxobutyric acid	ChEBI
3-Methyl pyruvic acid	ChEBI
alpha-Ketobutyrate	ChEBI
alpha-Ketobutyric acid	ChEBI
alpha-oxo-N-Butyric acid	ChEBI
2-Oxobutyrate	Kegg
2-Oxobutanoic acid	Kegg
2-Ketobutanoate	Generator
3-Methyl pyruvate	Generator
a-Ketobutyrate	Generator
a-Ketobutyric acid	Generator
Α-ketobutyrate	Generator
Α-ketobutyric acid	Generator
a-oxo-N-Butyrate	Generator
a-oxo-N-Butyric acid	Generator
alpha-oxo-N-Butyrate	Generator
Α-oxo-N-butyrate	Generator
Α-oxo-N-butyric acid	Generator
2-Oxobutanoate	Generator
2-Ketobutyrate	Generator
2-oxo-Butanoate	HMDB
2-oxo-Butanoic acid	HMDB
2-oxo-Butyrate	HMDB
2-oxo-Butyric acid	HMDB
2-oxo-N-Butyrate	HMDB
2-oxo-N-Butyric acid	HMDB
3-Methylpyruvate	HMDB
3-Methylpyruvic acid	HMDB
a-Keto-N-butyrate	HMDB
a-Keto-N-butyric acid	HMDB
a-Oxobutyrate	HMDB
a-Oxobutyric acid	HMDB
alpha-Keto-N-butyrate	HMDB
alpha-Keto-N-butyric acid	HMDB
alpha-Ketobutric acid	HMDB
alpha-Oxobutyrate	HMDB
alpha-Oxobutyric acid	HMDB
Methyl-pyruvate	HMDB
Methyl-pyruvic acid	HMDB
Propionyl-formate	HMDB
Propionyl-formic acid	HMDB
alpha-Ketobutyric acid, sodium salt	HMDB
2-Ketobutyric acid	ChEBI

Chemical Formula

C₄H₆O₃

Average Molecular Weight

102.0886

Monoisotopic Molecular Weight

102.031694058

IUPAC Name

2-oxobutanoic acid

Traditional Name

2-oxobutanoic acid

CAS Registry Number

600-18-0

SMILES

CCC(=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)

InChI Key

TYEYBOSBBBHJIV-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-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 Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:30831 )
short-chain fatty acid (CHEBI:30831 )
Oxo fatty acids (C00109 )
Oxo fatty acids (LMFA01060002 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	33 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	119 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.07	ALOGPS
logP	0.77	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.62 m³·mol⁻¹	ChemAxon
Polarizability	9.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014s-1910000000-d01bcd7b41fdcc634eea	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9200000000-3b3816ffee5771215904	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-6910000000-5b264d5f7e53f3e80b12	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-6950000000-db7f6a0f03a8cce59bae	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ftb-0920000000-a6c93d8761ef15f7f7d4	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-0920000000-406fe70e72dbd9c3f274	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014s-1910000000-d01bcd7b41fdcc634eea	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9200000000-3b3816ffee5771215904	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-6910000000-5b264d5f7e53f3e80b12	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-6950000000-db7f6a0f03a8cce59bae	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-8900000000-97bab6630de4df095a7f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9200000000-0ebb2354fe3f935fe177	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-32269ef3ef778c482f99	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0adi-9200000000-f92941e9f326d8ccf3e4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-9600000000-53ebb7164f74d7d92a4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0zfr-5900000000-1db864754705beb79b55	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0udi-9800000000-5ba5b9ede5b1bc389b87	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-0pb9-9600000000-b10635fbec5572d4d084	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0a4i-9100000000-4c5e7d24dca6677e1570	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0a4i-9000000000-ded44cfcbe7960954fdf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0a4i-9000000000-1b350be7438b08f1946a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-056r-9000000000-172a175b8b9ebfd5529f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-9400000000-0061f4635858d851f127	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-b943445194fb5f8e3a0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-bc5920b9bd140be6b06d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f7dfb4554f0b9e1499c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-9200000000-e54106ad5bf45a9f072c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7bbba57578cf720974e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-aced8e004436190f07b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a3d7ddf227bd6aa91a54	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9700000000-503296025148ec314383	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-933b567955b5de5b1744	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7d9db52021fefc87a855	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Liver
Mammary Gland
Semen

Pathways

Name	SMPDB/Pathwhiz	KEGG
Selenoamino Acid Metabolism		Not Available
Homocysteine Degradation		Not Available
Glycine and Serine Metabolism		Not Available
Propanoate Metabolism		Not Available
Methionine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31533629	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000005

DrugBank ID

DB04553

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030356

KNApSAcK ID

C00019675

Chemspider ID

KEGG Compound ID

C00109

BioCyc ID

2-OXOBUTANOATE

BiGG ID

33889

Wikipedia Link

Alpha-Ketobutyric_acid

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

30831

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not 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 + Ammonia	details

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 + NADH	details

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 + NADH	details

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 + NADH	details

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 acid	details
L-Cystathionine + Water → L-Cysteine + 2-Ketobutyric acid + Ammonia	details
L-Cystathionine + Water → L-Cysteine + 2-Ketobutyric acid	details

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 + NADH	details

Showing metabocard for 2-Ketobutyric acid (BMDB0000005)

Structure for BMDB0000005 (2-Ketobutyric acid)

Enzymes

Reactions

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