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Showing Compound 2-oxo-4-methylthiobutanoate (FDB030353)

Record Information
Version1.0
Creation date2015-05-07 19:05:28 UTC
Update date2019-11-26 03:21:42 UTC
Primary IDFDB030353
Secondary Accession Numbers
  • FDB011626
Chemical Information
FooDB Name2-oxo-4-methylthiobutanoate
Description2-oxo-4-methylthiobutanoic acid, also known as 2-keto-4-methylthiobutyrate or 4-methylthio-2-oxobutanoate, 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-methylthiobutanoic acid is considered to be a fatty acid lipid molecule. 2-oxo-4-methylthiobutanoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-oxo-4-methylthiobutanoic acid can be synthesized from L-methionine and butyric acid. 2-oxo-4-methylthiobutanoic acid can also be synthesized into S-adenosyl-4-methylthio-2-oxobutanoic acid. 2-oxo-4-methylthiobutanoic acid can be found in a number of food items such as leek, hickory nut, brussel sprouts, and giant butterbur, which makes 2-oxo-4-methylthiobutanoic acid a potential biomarker for the consumption of these food products. 2-oxo-4-methylthiobutanoic acid can be found primarily in urine. 2-oxo-4-methylthiobutanoic acid exists in all living species, ranging from bacteria to humans. In humans, 2-oxo-4-methylthiobutanoic acid is involved in the methionine metabolism. 2-oxo-4-methylthiobutanoic acid is also involved in several metabolic disorders, some of which include s-adenosylhomocysteine (SAH) hydrolase deficiency, homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, glycine n-methyltransferase deficiency, and cystathionine beta-synthase deficiency.
CAS Number583-92-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Chemical FormulaC5H8O3S
IUPAC name4-(methylsulfanyl)-2-oxobutanoic acid
InChI IdentifierInChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeySXFSQZDSUWACKX-UHFFFAOYSA-N
Isomeric SMILESCSCCC(=O)C(O)=O
Average Molecular Weight148.18
Monoisotopic Molecular Weight148.019414812
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS4-(Methylthio)-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0f79-9620000000-a37f1649aaa00fe355f6Spectrum
GC-MS4-(Methylthio)-2-oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0uyr-7940000000-be5c411217da093f2c8aSpectrum
GC-MS4-(Methylthio)-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0f79-9620000000-a37f1649aaa00fe355f6Spectrum
GC-MS4-(Methylthio)-2-oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0uyr-7940000000-be5c411217da093f2c8aSpectrum
Predicted GC-MS4-(Methylthio)-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-9200000000-1471d6fe57ac965a873dSpectrum
Predicted GC-MS4-(Methylthio)-2-oxobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4j-9400000000-16ddd3b5c053991fac9aSpectrum
Predicted GC-MS4-(Methylthio)-2-oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0a6t-0900000000-ed86a80611ad68e921e22020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-9000000000-9b1238b1c990e180a4762020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0002-9000000000-a0fb6b922f7482546f1f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-1900000000-f3facf4268a57538266c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-2900000000-71e4f52b95b529acc1a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-5900000000-c6325fbf5479dbaa355c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-7900000000-bccb79b226dccd29e36f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9700000000-8e6b66c2a5dd967a95392020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9500000000-dee1d47be79038a62ac82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9200000000-184f804af473361e56d42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-9f652bc59797907a90e82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9100000000-2924be77506cc359576f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-ac83262a096530d8343f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-12841f2d918636eb3ba82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0002-9000000000-beb5b9021683b7e71f412020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-a7b6fa585a128c4bbf252020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-0900000000-5d4054fa9cdf6414108d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-0900000000-70154862c61d3d6ece442020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-1900000000-ed36a40a48bf904312f42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zir-9700000000-7bbe813aa31ceba0b5252015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-89ba14ad10b374e8daab2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-b9179ec180a89222c1472015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-63d77e1e6b7bea5353fe2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-31b5d7804293c55c928e2015-05-27View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference