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Showing metabocard for 2-Oxo-4-methylthiobutanoic acid (HMDB0001553)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-11 16:42:54 UTC
HMDB IDHMDB0001553
Secondary Accession Numbers
  • HMDB0013210
  • HMDB01553
  • HMDB13210
Metabolite Identification
Common Name2-Oxo-4-methylthiobutanoic acid
Description2-oxo-4-methylthiobutanoate, also known as 2-keto-4-methylthiobutyric acid, 2-keto-4-methylthiobutyrate or 4-(methylsulfanyl)-2-oxobutanoic acid, is a member of the class of compounds known as thia- fatty acids. Thia-fatty acids are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Thus, 2-oxo-4-methylthiobutanoate is a fatty acid lipid molecule. 2-oxo-4-methylthiobutanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-oxo-4-methylthiobutanoate can be synthesized from L-methionine and butyric acid. 2-oxo-4-methylthiobutanoate can also be synthesized into S-adenosyl-4-methylthio-2-oxobutanoic acid. 2-oxo-4-methylthiobutanoate can be found in a number of food items such as cloves, highbush blueberries, common beets, and cashew nuts. 2-oxo-4-methylthiobutanoate can be found in urine. Within the cell, 2-oxo-4-methylthiobutanoate is primarily located in the cytoplasm and in the membrane. 2-oxo-4-methylthiobutanoate has been found in all living species, from bacteria to humans. In humans, 2-oxo-4-methylthiobutanoate is found to be involved in several metabolic disorders, some of those are S-adenosylhomocysteine (SAH) hydrolase deficiency, methylenetetrahydrofolate reductase deficiency (MTHFRD), methionine adenosyltransferase deficiency, and glycine N-methyltransferase deficiency. 4-Methylthio-2-oxobutanoic acid is the direct precursor of methional, which is a potent inducer of apoptosis in a BAF3 murine lymphoid cell line which is interleukin-3 (IL3)-dependent (PMID: 7848263 ).
Structure
Data?1589215374
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)


  Mrv0541 02231216042D          

  9  8  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
Download

3D MOL for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

Download
3D SDF for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

  Mrv0541 02231216042D          

  9  8  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001553

> <DATABASE_NAME>
hmdb

> <SMILES>
CSCCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)

> <INCHI_KEY>
SXFSQZDSUWACKX-UHFFFAOYSA-N

> <FORMULA>
C5H8O3S

> <MOLECULAR_WEIGHT>
148.18

> <EXACT_MASS>
148.019414812

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.212411248449214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(methylsulfanyl)-2-oxobutanoic acid

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
1.1240172496666667

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.823095177292476

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.303792429217063

> <JCHEM_PKA_STRONGEST_BASIC>
-9.673901775734686

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
35.0709

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxo-4-thiomethylbutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)
https://cactus.nci.nih.gov/chemical/structure/CSCCC(=O)C(O)=O/file?format=sdf...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:16})
 17 16  0  0  0  0  0  0  0  0999 V2000
    4.0999   -0.5951   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567    0.6242    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2666   -0.4104   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250    0.4838   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2129   -0.3759   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124   -1.5794   -0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.2597   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6669   -0.5080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622    1.4681   -0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0596   -0.0783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236   -1.2197    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236   -1.2197   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612   -1.0397   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612   -1.0397    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304    1.1130    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304    1.1130   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189   -0.0506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 17  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       4.620   2.667   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

Download
3D PDB for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CSCCC(=O)C(O)=O/file?format=sdf... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       4.100  -0.595   0.000  1.00  0.00           C  
HETATM    2  S   UNL     1       2.757   0.624   0.000  1.00  0.00           S  
HETATM    3  C   UNL     1       1.267  -0.410   0.000  1.00  0.00           C  
HETATM    4  C   UNL     1       0.025   0.484   0.000  1.00  0.00           C  
HETATM    5  C   UNL     1      -1.213  -0.376   0.000  1.00  0.00           C  
HETATM    6  O   UNL     1      -1.112  -1.579   0.000  1.00  0.00           O  
HETATM    7  C   UNL     1      -2.561   0.260   0.000  1.00  0.00           C  
HETATM    8  O   UNL     1      -3.667  -0.508   0.000  1.00  0.00           O  
HETATM    9  O   UNL     1      -2.662   1.468   0.000  1.00  0.00           O  
HETATM   10  H   UNL     1       5.060  -0.078   0.000  1.00  0.00           H  
HETATM   11  H   UNL     1       4.024  -1.220   0.890  1.00  0.00           H  
HETATM   12  H   UNL     1       4.024  -1.220  -0.890  1.00  0.00           H  
HETATM   13  H   UNL     1       1.261  -1.040  -0.890  1.00  0.00           H  
HETATM   14  H   UNL     1       1.261  -1.040   0.890  1.00  0.00           H  
HETATM   15  H   UNL     1       0.030   1.113   0.890  1.00  0.00           H  
HETATM   16  H   UNL     1       0.030   1.113  -0.890  1.00  0.00           H  
HETATM   17  H   UNL     1      -4.519  -0.051   0.000  1.00  0.00           H  
CONECT    1    2   10   11   12                                       
CONECT    2    1    3                                                 
CONECT    3    2    4   13   14                                       
CONECT    4    3    5   15   16                                       
CONECT    5    4    6    6    7                                       
CONECT    6    5    5                                                 
CONECT    7    5    8    9    9                                       
CONECT    8    7   17                                                 
CONECT    9    7    7                                                 
CONECT   10    1                                                      
CONECT   11    1                                                      
CONECT   12    1                                                      
CONECT   13    3                                                      
CONECT   14    3                                                      
CONECT   15    4                                                      
CONECT   16    4                                                      
CONECT   17    8                                                      
MASTER        0    0    0    0    0    0    0    0   17    0   17    0
END

Download
SMILES for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)
CSCCC(=O)C(O)=O
Download
INCHI for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)
InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Keto-4-methylthiobutyric acidChEBI
2-oxo-4-MethylthiobutanoateChEBI
2-OxomethionineChEBI
4-(METHYLsulfanyl)-2-oxobutanoIC ACIDChEBI
4-Methylthio-2-oxobutanoateChEBI
alpha-oxo-gamma-Methylthiobutyric acidChEBI
4-(Methylsulfanyl)-2-oxobutanoateKegg
2-Keto-4-methylthiobutyrateGenerator
4-(METHYLsulphanyl)-2-oxobutanoateGenerator
4-(METHYLsulphanyl)-2-oxobutanoic acidGenerator
4-Methylthio-2-oxobutanoic acidGenerator
a-oxo-g-MethylthiobutyrateGenerator
a-oxo-g-Methylthiobutyric acidGenerator
alpha-oxo-gamma-MethylthiobutyrateGenerator
Α-oxo-γ-methylthiobutyrateGenerator
Α-oxo-γ-methylthiobutyric acidGenerator
2-KetomethiobutyrateHMDB
4-Methylthio-2-ketobutanoateHMDB
4-Methylthio-2-ketobutanoic acidHMDB
4-Methylthio-2-ketobutyrateHMDB
4-Methylthio-2-oxobutyrateHMDB
alpha-Keto-methiolbutyric acidHMDB
Keto-4-methylthiobutyrateHMDB
KetomethiobutyrateHMDB
Ketomethiobutyric acidHMDB
KMTBHMDB
MethylthiobutyrateHMDB
Methylthiobutyric acidHMDB
2-Keto-4-methylthiobutanoic acidHMDB
2-Keto-4-thiomethylbutyrateHMDB
2-oxo-4-Thiomethylbutyric acidHMDB
alpha-Keto-gamma-methiolbutyrateHMDB
alpha-KetomethionineHMDB
alpha-OxomethionineHMDB
2-Keto-4-methylthiobutyric acid, monosodium saltHMDB
2-Ketothiomethylbutyric acidHMDB
4-Methylthio-2-oxobutyric acidHMDB
S-Methyl-alpha-ketobutyric acidHMDB
2-Keto-4-methylthiobutyric acid, calcium saltHMDB
4-Methylthio-2-ketobutyric acidHMDB
gamma-Methiol-keto-butyric acidHMDB
4-Methylmercapto-2-oxobutyrateHMDB
2-oxo-4-Methylthiobutanoic acidKEGG
Chemical FormulaC5H8O3S
Average Molecular Weight148.18
Monoisotopic Molecular Weight148.019414812
IUPAC Name4-(methylsulfanyl)-2-oxobutanoic acid
Traditional Name2-oxo-4-thiomethylbutyric acid
CAS Registry Number583-92-6
SMILES
CSCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeySXFSQZDSUWACKX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentThia fatty acids  
Alternative Parents
Substituents
  • Short-chain keto acid
    • 

  • Thia fatty acid
    • 

  • Alpha-keto acid
    • 

  • Keto acid
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Dialkylthioether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Sulfenyl compound
    • 

  • Thioether
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organosulfur compound
    • 

  • Organic oxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
Role
Biological role:
Industrial application:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.44 g/LALOGPS
logP-0.07ALOGPS
logP1.12ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.07 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0f79-9620000000-a37f1649aaa00fe355f62014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0uyr-7940000000-be5c411217da093f2c8a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-9620000000-a37f1649aaa00fe355f62017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uyr-7940000000-be5c411217da093f2c8a2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9200000000-1471d6fe57ac965a873d2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4j-9400000000-16ddd3b5c053991fac9a2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0gvp-9300000000-20b6937ce0fd75fa1a652021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0a6t-0900000000-ed86a80611ad68e921e22020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-9000000000-9b1238b1c990e180a4762020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0002-9000000000-a0fb6b922f7482546f1f2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-1900000000-f3facf4268a57538266c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-2900000000-71e4f52b95b529acc1a32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-5900000000-c6325fbf5479dbaa355c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-7900000000-bccb79b226dccd29e36f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9700000000-8e6b66c2a5dd967a95392020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9500000000-dee1d47be79038a62ac82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9200000000-184f804af473361e56d42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-9f652bc59797907a90e82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9100000000-2924be77506cc359576f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-ac83262a096530d8343f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-12841f2d918636eb3ba82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0002-9000000000-beb5b9021683b7e71f412020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-a7b6fa585a128c4bbf252020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-0900000000-5d4054fa9cdf6414108d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-0900000000-70154862c61d3d6ece442020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0f8a-1900000000-ed36a40a48bf904312f42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0zir-9700000000-7bbe813aa31ceba0b5252015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0a6r-9100000000-89ba14ad10b374e8daab2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0002-9200000000-b9179ec180a89222c1472015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0002-9100000000-63d77e1e6b7bea5353fe2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0002-9000000000-31b5d7804293c55c928e2015-05-27View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
    • 

  • Extracellular
    • 

  • Membrane
Biospecimen Locations
  • Feces
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
UrineDetected and Quantified0.02 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
  details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02238  
Phenol Explorer Compound IDNot Available
FooDB IDFDB030353  
KNApSAcK IDC00007474  
Chemspider ID460  
KEGG Compound IDC01180  
BioCyc IDCPD-479  
BiGG ID228408  
Wikipedia LinkNot Available
METLIN ID6319  
PubChem Compound473  
PDB IDNot Available
ChEBI ID33574  
Food Biomarker OntologyNot Available
VMH ID2KMB  
MarkerDB IDNot Available
References
Synthesis ReferenceBrodelius, P.; Hagerdal, B.; Mosbach, K.  Immobilized whole cells of the yeast Trigonopsis variabilis containing D-amino acid oxidase for the production of a-keto acids.    Enzyme Engineering  (1980),  5  383-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Martensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9. [PubMed:3706736  ] 
  2. Quash G, Roch AM, Chantepie J, Michal Y, Fournet G, Dumontet C: Methional derived from 4-methylthio-2-oxobutanoate is a cellular mediator of apoptosis in BAF3 lymphoid cells. Biochem J. 1995 Feb 1;305 ( Pt 3):1017-25. [PubMed:7848263  ] 
Enzymes
  Enzyme Details
1. Tyrosine aminotransferase
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.

Gene Name:
TAT
Uniprot ID:
P17735  
Molecular weight:
50398.895
Reactions
2-Oxo-4-methylthiobutanoic acid + L-Glutamic acid → L-Methionine + Oxoglutaric aciddetails
  Enzyme Details
2. Kynurenine--oxoglutarate transaminase 1
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.

Gene Name:
CCBL1
Uniprot ID:
Q16773  
Molecular weight:
47874.765
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
  Enzyme Details
3. L-amino-acid oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).

Gene Name:
IL4I1
Uniprot ID:
Q96RQ9  
Molecular weight:
65327.26
Reactions
L-Methionine + Water + Oxygen → 2-Oxo-4-methylthiobutanoic acid + Ammonia + Hydrogen peroxidedetails
  Enzyme Details
4. Kynurenine--oxoglutarate transaminase 3
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).

Gene Name:
CCBL2
Uniprot ID:
Q6YP21  
Molecular weight:
51399.855
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
  Enzyme Details
5. 1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase
General function:
Involved in metal ion binding
Specific function:
Catalyzes the formation of formate and 2-keto-4-methylthiobutyrate (KMTB) from 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene). Also down-regulates cell migration mediated by MMP14. Necessary for hepatitis C virus replication in an otherwise non-permissive cell line.

Gene Name:
ADI1
Uniprot ID:
Q9BV57  
Molecular weight:
21498.23
Reactions
1,2-Dihydroxy-3-keto-5-methylthiopentene + Oxygen → 2-Oxo-4-methylthiobutanoic acid + Formic aciddetails