Showing metabocard for 2-Oxo-4-methylthiobutanoic acid (BMDB0001553)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:36 UTC
Update Date2020-05-21 16:29:03 UTC
MCDB ID BMDB0001553
Secondary Accession Numbers
  • BMDB01553
Metabolite Identification
Common Name2-Oxo-4-methylthiobutanoic acid
Description4-Methylthio-2-oxobutanoate, also known as 2-keto-4-methylthiobutyrate or 2-oxomethionine, 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. 4-Methylthio-2-oxobutanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Methylthio-2-oxobutanoate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
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
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0001553
DrugBank IDDB02238
Phenol Explorer Compound IDNot Available
FoodDB 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
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. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]