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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:21:31 UTC
Update Date2019-07-23 06:22:59 UTC
HMDB IDHMDB0037115
Secondary Accession Numbers
  • HMDB37115
Metabolite Identification
Common Name(±)-2-Hydroxy-4-(methylthio)butanoic acid
Description(±)-2-Hydroxy-4-(methylthio)butanoic acid, also known as alpha-hydroxy-gamma-methylmercaptobutyric acid or MHA, 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 (±)-2-Hydroxy-4-(methylthio)butanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862979
Synonyms
ValueSource
(±)-2-hydroxy-4-(methylthio)butanoateGenerator
(+-)-2-Hydroxy-4-(methylthio)butyric acidHMDB
2-Hydroxy-4-(methylthio) butanoic acidHMDB
2-Hydroxy-4-(methylthio)-butanoic acidHMDB
2-Hydroxy-4-(methylthio)-butyric acidHMDB
2-Hydroxy-4-(methylthio)butanoic acidHMDB
2-Hydroxy-4-(methylthio)butyric acidHMDB
4857-44-7 (Calcium[2:1] salt)HMDB
AlimetHMDB
alpha-Hydroxy-gamma-(methylmercapto)butyric acidHMDB
alpha-Hydroxy-gamma-(methylthio)butyric acidHMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acidHMDB
DesmeninolHMDB
gamma-(Methylthio)-alpha-hydroxybutyric acidHMDB
Methionine hydroxy analogHMDB
MHAHMDB
Mha acidHMDB
Mha-faHMDB
(+-)-Isomer OF alpha-hydroxy-gamma-methylmercaptobutyric acidHMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt(+-)-isomerHMDB
2-Hydroxy-4-methylthiobutanoic acidHMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium saltHMDB
2-Hydroxy-4-methylthiobutyrateHMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, monosodium salt (S)-isomerHMDB
alpha-HydroxymethionineHMDB
4-Methylthio-2-hydroxybutyrateHMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt (2:1)HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, monosodium saltHMDB
alpha-Hydroxy-gamma-methylthiobutyrateHMDB
2-Hydroxy-4-(methylthio)butanoateGenerator
Chemical FormulaC5H10O3S
Average Molecular Weight150.196
Monoisotopic Molecular Weight150.035064876
IUPAC Name2-hydroxy-4-(methylsulfanyl)butanoic acid
Traditional Namemethionine hydroxy analog
CAS Registry Number120-91-2
SMILES
CSCCC(O)C(O)=O
InChI Identifier
InChI=1S/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
InChI KeyONFOSYPQQXJWGS-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
  • Hydroxy fatty acid
  • Thia fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.9 g/LALOGPS
logP-0.4ALOGPS
logP0.18ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.93 m³·mol⁻¹ChemAxon
Polarizability15.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i3-9200000000-b3f347c37bb602b8bb45Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9350000000-44bc7640c746eddc9889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1900000000-dd2e58391a4c5f61dcd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9700000000-8b98bae25421e4ce82fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vr-9000000000-7372f5d3aafd65f14b51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-7900000000-3be7113c98ed23388528Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-b2110ea4fabace846c65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-860ffaaedb18b65817fdSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016108
KNApSAcK IDNot Available
Chemspider ID10946
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11427
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.