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

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enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:47 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?1676999747
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

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


  Mrv1652309042000242D          

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

HMDB0001553
     RDKit          3D
2-Oxo-4-methylthiobutanoic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    3.6581   -0.1397    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.3887   -0.7817 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466    0.0188    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -0.1559   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    0.1814    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.5549    1.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0544    0.0947   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1890   -0.2761   -1.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1907    0.3976    0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725    0.0852   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484   -1.0539    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    0.6783    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1049    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -0.6022    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -1.2024   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    0.5024   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655    1.2734    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)


  Mrv1652309042000242D          

  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_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.212411248449321

> <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

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

HMDB0001553
     RDKit          3D
2-Oxo-4-methylthiobutanoic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    3.6581   -0.1397    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.3887   -0.7817 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466    0.0188    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -0.1559   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    0.1814    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.5549    1.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0544    0.0947   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1890   -0.2761   -1.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1907    0.3976    0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725    0.0852   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484   -1.0539    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    0.6783    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1049    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -0.6022    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -1.2024   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    0.5024   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655    1.2734    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         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
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3D PDB for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

COMPND    HMDB0001553
HETATM    1  C1  UNL     1       3.658  -0.140   0.299  1.00  0.00           C  
HETATM    2  S1  UNL     1       2.222  -0.389  -0.782  1.00  0.00           S  
HETATM    3  C2  UNL     1       0.747   0.019   0.192  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.518  -0.156  -0.619  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.710   0.181   0.193  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.594   0.555   1.389  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.054   0.095  -0.358  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.189  -0.276  -1.550  1.00  0.00           O  
HETATM    9  O3  UNL     1      -4.191   0.398   0.357  1.00  0.00           O  
HETATM   10  H1  UNL     1       4.572   0.085  -0.307  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.848  -1.054   0.921  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.417   0.678   1.002  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.820   1.105   0.427  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.693  -0.602   1.104  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.566  -1.202  -0.981  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.488   0.502  -1.502  1.00  0.00           H  
HETATM   17  H8  UNL     1      -4.666   1.273   0.215  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   17
END
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SMILES for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

CSCCC(=O)C(O)=O
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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 NMR AssignmentsView 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.39231661259
DarkChem[M-H]-126.80531661259
AllCCS[M+H]+131.93532859911
AllCCS[M-H]-133.52932859911
DeepCCS[M+H]+131.04530932474
DeepCCS[M-H]-128.2830932474
DeepCCS[M-2H]-164.72630932474
DeepCCS[M+Na]+139.52530932474
AllCCS[M+H]+131.932859911
AllCCS[M+H-H2O]+128.032859911
AllCCS[M+NH4]+135.632859911
AllCCS[M+Na]+136.732859911
AllCCS[M-H]-133.532859911
AllCCS[M+Na-2H]-136.232859911
AllCCS[M+HCOO]-139.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.62 minutes32390414
Predicted by Siyang on May 30, 202210.6611 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.58 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid59.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1384.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid363.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid102.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid244.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid101.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid341.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid473.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)130.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid851.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid303.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid956.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid267.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid330.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate439.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA284.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water122.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Oxo-4-methylthiobutanoic acidCSCCC(=O)C(O)=O2267.1Standard polar33892256
2-Oxo-4-methylthiobutanoic acidCSCCC(=O)C(O)=O1323.8Standard non polar33892256
2-Oxo-4-methylthiobutanoic acidCSCCC(=O)C(O)=O1245.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Oxo-4-methylthiobutanoic acid,1TMS,isomer #1CSCCC(=O)C(=O)O[Si](C)(C)C1362.1Semi standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,1TMS,isomer #2CSCC=C(O[Si](C)(C)C)C(=O)O1461.5Semi standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,2TMS,isomer #1CSCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1505.4Semi standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,2TMS,isomer #1CSCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1466.5Standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,2TMS,isomer #1CSCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1638.6Standard polar33892256
2-Oxo-4-methylthiobutanoic acid,1TBDMS,isomer #1CSCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C1609.3Semi standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,1TBDMS,isomer #2CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O1699.0Semi standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,2TBDMS,isomer #1CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1972.1Semi standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,2TBDMS,isomer #1CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1880.3Standard non polar33892256
2-Oxo-4-methylthiobutanoic acid,2TBDMS,isomer #1CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1910.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (1 MEOX; 1 TMS)splash10-0f79-9620000000-a37f1649aaa00fe355f62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (1 MEOX; 1 TMS)splash10-0uyr-7940000000-be5c411217da093f2c8a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (Non-derivatized)splash10-0f79-9620000000-a37f1649aaa00fe355f62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (Non-derivatized)splash10-0uyr-7940000000-be5c411217da093f2c8a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9200000000-1471d6fe57ac965a873d2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0g4j-9400000000-16ddd3b5c053991fac9a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxo-4-methylthiobutanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid LC-ESI-QTOF 35V, positive-QTOFsplash10-0a6t-0900000000-ed86a80611ad68e921e22020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid LC-ESI-QFT , negative-QTOFsplash10-0002-9000000000-9b1238b1c990e180a4762020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid LC-ESI-QTOF 35V, negative-QTOFsplash10-0002-9000000000-a0fb6b922f7482546f1f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 0V, negative-QTOFsplash10-0002-1900000000-f3facf4268a57538266c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 0V, negative-QTOFsplash10-0002-2900000000-71e4f52b95b529acc1a32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 0V, negative-QTOFsplash10-0002-5900000000-c6325fbf5479dbaa355c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 0V, negative-QTOFsplash10-0002-7900000000-bccb79b226dccd29e36f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 1V, negative-QTOFsplash10-0002-9700000000-8e6b66c2a5dd967a95392020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 1V, negative-QTOFsplash10-0002-9500000000-dee1d47be79038a62ac82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 1V, negative-QTOFsplash10-0002-9200000000-184f804af473361e56d42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 2V, negative-QTOFsplash10-0002-9200000000-9f652bc59797907a90e82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 2V, negative-QTOFsplash10-0002-9100000000-2924be77506cc359576f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 3V, negative-QTOFsplash10-0002-9000000000-ac83262a096530d8343f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 3V, negative-QTOFsplash10-0002-9000000000-12841f2d918636eb3ba82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid n/a 10V, negative-QTOFsplash10-0002-9000000000-beb5b9021683b7e71f412020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid n/a 10V, negative-QTOFsplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 0V, positive-QTOFsplash10-0006-0900000000-a7b6fa585a128c4bbf252020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 1V, positive-QTOFsplash10-0006-0900000000-5d4054fa9cdf6414108d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid Orbitrap 2V, positive-QTOFsplash10-0006-0900000000-70154862c61d3d6ece442020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid 10V, Positive-QTOFsplash10-0f8a-1900000000-ed36a40a48bf904312f42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid 20V, Positive-QTOFsplash10-0zir-9700000000-7bbe813aa31ceba0b5252015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid 40V, Positive-QTOFsplash10-0a6r-9100000000-89ba14ad10b374e8daab2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid 10V, Negative-QTOFsplash10-0002-9200000000-b9179ec180a89222c1472015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid 20V, Negative-QTOFsplash10-0002-9100000000-63d77e1e6b7bea5353fe2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxo-4-methylthiobutanoic acid 40V, Negative-QTOFsplash10-0002-9000000000-31b5d7804293c55c928e2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView 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
Good Scents 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 + Glutamic acid → 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 + 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
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 + 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