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Showing metabocard for 2-Ketobutyric acid (HMDB0000005)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (21) Show 21 proteinsXML
enzymes (21) Show 21 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:11:34 UTC
HMDB IDHMDB0000005
Secondary Accession Numbers
  • HMDB00005
  • HMDB0006544
  • HMDB06544
Metabolite Identification
Common Name2-Ketobutyric acid
Description2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, 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 substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. It is also one of the degradation products of threonine. It can be converted into propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted into succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle. More specifically, 2-ketobutyric acid is a product of the lysis of cystathionine.
Structure
Data?1582752107
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000005 (2-Ketobutyric acid)

      
  Mrv1652305261923542D          

  7  6  0  0  0  0            999 V2000
    2.4602    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000005 (2-Ketobutyric acid)

Download
3D SDF for HMDB0000005 (2-Ketobutyric acid)
      
  Mrv1652305201900222D          

  7  6  0  0  0  0            999 V2000
    2.4602    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000005

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.1994455800129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxobutanoic acid

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
0.7664098003333332

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1869864284881544

> <JCHEM_PKA_STRONGEST_BASIC>
-9.650960797412663

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
22.616600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0000005 (2-Ketobutyric acid)
58
  -OEChem-10221910553D

 13 12  0     0  0  0  0  0  0999 V2000
   -0.3863   -1.4867   -0.0143 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404   -0.7885    0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.4245   -0.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    0.7615    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090    0.1263    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316   -0.2747    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1805    0.2377    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179    1.3870   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164    1.3878    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -0.5023   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -0.5036    0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.8985    0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -0.4906   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <PUBCHEM_COMPOUND_CID>
58

> <PUBCHEM_CONFORMER_RMSD>
0.4

> <PUBCHEM_CONFORMER_DIVERSEORDER>
1
4
2
3

> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
7
1 -0.57
13 0.5
2 -0.65
3 -0.57
4 0.06
6 0.51
7 0.72

> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
2

> <PUBCHEM_PHARMACOPHORE_FEATURES>
5
1 1 acceptor
1 2 acceptor
1 3 acceptor
1 5 hydrophobe
3 2 3 7 anion

> <PUBCHEM_HEAVY_ATOM_COUNT>
7

> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
0

> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_DEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0

> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0

> <PUBCHEM_COMPONENT_COUNT>
1

> <PUBCHEM_CACTVS_TAUTO_COUNT>
2

> <PUBCHEM_CONFORMER_ID>
0000003A00000001

> <PUBCHEM_MMFF94_ENERGY>
5.6256

> <PUBCHEM_FEATURE_SELFOVERLAP>
25.441

> <PUBCHEM_SHAPE_FINGERPRINT>
20096714 4 18410292527365276113
21040471 1 18338797926230442441
24536 1 18266162014977872972
29004967 10 18338238137388742922
5084963 1 18272367547015116361
5460574 1 9223225252131621481

> <PUBCHEM_SHAPE_MULTIPOLES>
126.45
3.01
1.25
0.57
1.14
0.05
0
-0.22
0.01
-0.33
-0.01
0.05
-0.01
-0.01

> <PUBCHEM_SHAPE_SELFOVERLAP>
237.141

> <PUBCHEM_SHAPE_VOLUME>
78.5

> <PUBCHEM_COORDINATE_TYPE>
2
5
10

$$$$

Download
PDB for HMDB0000005 (2-Ketobutyric acid)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       4.592   0.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.258   1.719   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.925   0.949   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.925  -0.591   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.591   1.719   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.742   0.949   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.591   3.259   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

Download
3D PDB for HMDB0000005 (2-Ketobutyric acid)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CCC(=O)C(O)=O/file?format=sdf&g... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       2.738   0.112   0.000  1.00  0.00           C  
HETATM    2  C   UNL     1       1.374   0.804   0.000  1.00  0.00           C  
HETATM    3  C   UNL     1       0.283  -0.236   0.000  1.00  0.00           C  
HETATM    4  O   UNL     1       0.568  -1.410   0.000  1.00  0.00           O  
HETATM    5  C   UNL     1      -1.147   0.184   0.000  1.00  0.00           C  
HETATM    6  O   UNL     1      -2.121  -0.745   0.000  1.00  0.00           O  
HETATM    7  O   UNL     1      -1.433   1.362   0.000  1.00  0.00           O  
HETATM    8  H   UNL     1       2.830  -0.510   0.890  1.00  0.00           H  
HETATM    9  H   UNL     1       2.830  -0.510  -0.890  1.00  0.00           H  
HETATM   10  H   UNL     1       3.527   0.865   0.000  1.00  0.00           H  
HETATM   11  H   UNL     1       1.282   1.427   0.890  1.00  0.00           H  
HETATM   12  H   UNL     1       1.282   1.427  -0.890  1.00  0.00           H  
HETATM   13  H   UNL     1      -3.034  -0.424   0.000  1.00  0.00           H  
CONECT    1    2    8    9   10                                       
CONECT    2    1    3   11   12                                       
CONECT    3    2    4    4    5                                       
CONECT    4    3    3                                                 
CONECT    5    3    6    7    7                                       
CONECT    6    5   13                                                 
CONECT    7    5    5                                                 
CONECT    8    1                                                      
CONECT    9    1                                                      
CONECT   10    1                                                      
CONECT   11    2                                                      
CONECT   12    2                                                      
CONECT   13    6                                                      
MASTER        0    0    0    0    0    0    0    0   13    0   13    0
END

Download
SMILES for HMDB0000005 (2-Ketobutyric acid)
CCC(=O)C(O)=O
Download
INCHI for HMDB0000005 (2-Ketobutyric acid)
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Ketobutanoic acidChEBI
2-Oxobutyric acidChEBI
3-Methyl pyruvic acidChEBI
alpha-KetobutyrateChEBI
alpha-Ketobutyric acidChEBI
alpha-oxo-N-Butyric acidChEBI
2-OxobutyrateKegg
2-Oxobutanoic acidKegg
2-KetobutanoateGenerator
3-Methyl pyruvateGenerator
a-KetobutyrateGenerator
a-Ketobutyric acidGenerator
Α-ketobutyrateGenerator
Α-ketobutyric acidGenerator
a-oxo-N-ButyrateGenerator
a-oxo-N-Butyric acidGenerator
alpha-oxo-N-ButyrateGenerator
Α-oxo-N-butyrateGenerator
Α-oxo-N-butyric acidGenerator
2-OxobutanoateGenerator
2-KetobutyrateGenerator
2-oxo-ButanoateHMDB
2-oxo-Butanoic acidHMDB
2-oxo-ButyrateHMDB
2-oxo-Butyric acidHMDB
2-oxo-N-ButyrateHMDB
2-oxo-N-Butyric acidHMDB
3-MethylpyruvateHMDB
3-Methylpyruvic acidHMDB
a-Keto-N-butyrateHMDB
a-Keto-N-butyric acidHMDB
a-OxobutyrateHMDB
a-Oxobutyric acidHMDB
alpha-Keto-N-butyrateHMDB
alpha-Keto-N-butyric acidHMDB
alpha-Ketobutric acidHMDB
alpha-OxobutyrateHMDB
alpha-Oxobutyric acidHMDB
Methyl-pyruvateHMDB
Methyl-pyruvic acidHMDB
Propionyl-formateHMDB
Propionyl-formic acidHMDB
alpha-Ketobutyric acid, sodium saltHMDB
2-Ketobutyric acidChEBI
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
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
Role
Industrial application:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility119 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available121.34231661259  
DarkChem[M-H]-PredictedNot Available114.49731661259  
AllCCS[M+H]+PredictedNot Available126.28832859911  
AllCCS[M-H]-PredictedNot Available123.11832859911  
Retention Indices
Underivatized
Not Available
Derivatized
DerivativeValueReference
2-Ketobutyric acid,1TMS,#11013.7316https://arxiv.org/abs/1905.12712
2-Ketobutyric acid,1TMS,#21091.1218https://arxiv.org/abs/1905.12712
2-Ketobutyric acid,1TBDMS,#11240.5403https://arxiv.org/abs/1905.12712
2-Ketobutyric acid,1TBDMS,#21332.4362https://arxiv.org/abs/1905.12712
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eea2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9200000000-3b3816ffee57712159042014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-6910000000-5b264d5f7e53f3e80b122014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-6950000000-db7f6a0f03a8cce59bae2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ftb-0920000000-a6c93d8761ef15f7f7d42017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0920000000-406fe70e72dbd9c3f2742017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eea2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9200000000-3b3816ffee57712159042017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-6910000000-5b264d5f7e53f3e80b122017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-6950000000-db7f6a0f03a8cce59bae2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-8900000000-97bab6630de4df095a7f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-0ebb2354fe3f935fe1772017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-32269ef3ef778c482f992016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adi-9200000000-f92941e9f326d8ccf3e42017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-9000000000-f5c68a892dfb4ae632ed2021-09-05View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4d2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b552012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b872012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdede2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdede2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0pb9-9600000000-b10635fbec5572d4d0842020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9100000000-4c5e7d24dca6677e15702020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-ded44cfcbe7960954fdf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-1b350be7438b08f1946a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-056r-9000000000-172a175b8b9ebfd5529f2020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f1272015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0f2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06d2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c92015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072c2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e32015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0a4i-9000000000-aced8e004436190f07b72021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0a4i-9000000000-a3d7ddf227bd6aa91a542021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0pb9-9700000000-503296025148ec3143832021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0a4i-9000000000-933b567955b5de5b17442021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0006-9000000000-7d9db52021fefc87a8552021-09-09View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-04View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
    • 

  • Cerebrospinal Fluid (CSF)
    • 

  • Saliva
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.33 +/- 5.00 uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified9.4 (3.4-15.4) uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified8.6 (6.0-11.2) uMChildren (1-13 years old)BothNormal  details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
Cerebrospinal Fluid (CSF)Detected and Quantified4.8 (3.4-6.2) uMChildren (1-13 years old)BothNormal  details
SalivaDetected and Quantified0.0412 +/- 0.214 uMAdult (>18 years old)Male
 
Normal
    • Sugimoto et al. (...
  details
SalivaDetected and Quantified2.62 +/- 4.13 uMAdult (>18 years old)Not Specified
 
Normal
    • Sugimoto et al. (...
  details
SalivaDetected and Quantified4.06 +/- 8.39 uMAdult (>18 years old)Female
 
Normal
    • Sugimoto et al. (...
  details
SalivaDetected and Quantified4.12 +/- 4.41 uMAdult (>18 years old)Not Specified
 
Normal
    • Sugimoto et al. (...
  details
UrineDetected and Quantified0.39 (0.05-2.2) umol/mmol creatinineAdult (>18 years old)MaleNormal  details
UrineDetected and Quantified0.13 (0.04-0.51) umol/mmol creatinineAdult (>18 years old)FemaleNormal  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
UrineDetected and Quantified9.476 +/- 6.626 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
 
Normal
    • Mordechai, Hien, ...
  details
UrineDetected and Quantified2.9 (0.7-5.4) umol/mmol creatinineAdult (>18 years old)Both
 
Normal		  details
UrineDetected and Quantified2.6 (1.1-4.1)  umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
UrineDetected and Quantified0-50 umol/mmol creatinineNewborn (0-30 days old)Both
 
Normal		  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.564 +/- 7.802 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
 
Eosinophilic esophagitis
    • Mordechai, Hien, ...
  details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1.  (). Mordechai, Hien, and David S. Wishart. . 
Associated OMIM IDs
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  
Food Biomarker OntologyNot Available
VMH ID2OBUT  
MarkerDB IDNot Available
References
Synthesis ReferenceFigge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl.  (2006), 31pp.  
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sprague CL, Elfarra AA: Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. Drug Metab Dispos. 2003 Aug;31(8):986-92. [PubMed:12867486  ] 
  2. Yaegaki K, Sanada K: Biochemical and clinical factors influencing oral malodor in periodontal patients. J Periodontol. 1992 Sep;63(9):783-9. [PubMed:1474480  ] 
  3. Yaegaki K, Sanada K: Effects of a two-phase oil-water mouthwash on halitosis. Clin Prev Dent. 1992 Jan-Feb;14(1):5-9. [PubMed:1499240  ] 
  4. Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. [PubMed:3918815  ] 
  Only showing the first  10 proteins. There  are 21 proteins in total. 
Show all enzymes and transporters
Enzymes
  Enzyme Details
1. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.

Gene Name:
PDHB
Uniprot ID:
P11177  
Molecular weight:
39233.1
References
  1. Paxton R, Scislowski PW, Davis EJ, Harris RA: Role of branched-chain 2-oxo acid dehydrogenase and pyruvate dehydrogenase in 2-oxobutyrate metabolism. Biochem J. 1986 Mar 1;234(2):295-303. [PubMed:3718468  ] 
  Enzyme Details
2. Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.

Gene Name:
PDHA1
Uniprot ID:
P08559  
Molecular weight:
43295.255
References
  1. Paxton R, Scislowski PW, Davis EJ, Harris RA: Role of branched-chain 2-oxo acid dehydrogenase and pyruvate dehydrogenase in 2-oxobutyrate metabolism. Biochem J. 1986 Mar 1;234(2):295-303. [PubMed:3718468  ] 
  Enzyme Details
3. Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.

Gene Name:
PDHA2
Uniprot ID:
P29803  
Molecular weight:
42932.855
References
  1. Paxton R, Scislowski PW, Davis EJ, Harris RA: Role of branched-chain 2-oxo acid dehydrogenase and pyruvate dehydrogenase in 2-oxobutyrate metabolism. Biochem J. 1986 Mar 1;234(2):295-303. [PubMed:3718468  ] 
  Enzyme Details
4. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Involved in catalytic activity
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:
P21953  
Molecular weight:
43122.065
  Enzyme Details
5. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
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:
P12694  
Molecular weight:
50470.58
  Enzyme Details
6. 2-oxoglutarate dehydrogenase, mitochondrial
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).

Gene Name:
OGDH
Uniprot ID:
Q02218  
Molecular weight:
48179.59
  Enzyme Details
7. Cystathionine gamma-lyase
General function:
Involved in pyridoxal phosphate binding
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.

Gene Name:
CTH
Uniprot ID:
P32929  
Molecular weight:
41259.91
Reactions
L-Cystathionine + Water → L-Cysteine + Ammonia + 2-Ketobutyric aciddetails
Selenomethionine + Water → Methaneselenol + Ammonia + 2-Ketobutyric aciddetails
Selenocystathionine + Water → Selenocysteine + Ammonia + 2-Ketobutyric aciddetails
  Enzyme Details
8. L-serine dehydratase/L-threonine deaminase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
SDS
Uniprot ID:
P20132  
Molecular weight:
34625.105
Reactions
L-Threonine → 2-Ketobutyric acid + Ammoniadetails
  Enzyme Details
9. L-lactate dehydrogenase A-like 6A
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.

Gene Name:
LDHAL6A
Uniprot ID:
Q6ZMR3  
Molecular weight:
36507.015
Reactions
2-Hydroxybutyric acid + NAD → 2-Ketobutyric acid + NADH + Hydrogen Iondetails
  Enzyme Details
10. Urocanate hydratase
General function:
Involved in urocanate hydratase activity
Specific function:
Not Available
Gene Name:
UROC1
Uniprot ID:
Q96N76  
Molecular weight:
80911.275
  Only showing the first  10 proteins. There  are 21 proteins in total. 
Show all enzymes and transporters