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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:21:31 UTC
Update Date2023-02-21 17:25:35 UTC
HMDB IDHMDB0037115
Secondary Accession Numbers
  • HMDB37115
Metabolite Identification
Common Name(±)-2-Hydroxy-4-(methylthio)butanoic acid
Description(±)-2-Hydroxy-4-(methylthio)butanoic acid 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. Based on a literature review a small amount of articles have been published on (±)-2-Hydroxy-4-(methylthio)butanoic acid.
Structure
Data?1677000335
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, MeSH
alpha-Hydroxy-gamma-(methylmercapto)butyric acidHMDB
alpha-Hydroxy-gamma-(methylthio)butyric acidHMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acidHMDB, MeSH
DesmeninolHMDB
gamma-(methylthio)-alpha-Hydroxybutyric acidHMDB
Methionine hydroxy analogHMDB, MeSH
MHAHMDB
Mha acidHMDB
Mha-faHMDB
(+-)-Isomer OF alpha-hydroxy-gamma-methylmercaptobutyric acidMeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt(+-)-isomerMeSH, HMDB
2-Hydroxy-4-methylthiobutanoic acidMeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium saltMeSH, HMDB
2-Hydroxy-4-methylthiobutyrateMeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, monosodium salt (S)-isomerMeSH, HMDB
alpha-HydroxymethionineMeSH, HMDB
4-methylthio-2-HydroxybutyrateMeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, calcium salt (2:1)MeSH, HMDB
alpha-Hydroxy-gamma-methylmercaptobutyric acid, monosodium saltMeSH, HMDB
alpha-Hydroxy-gamma-methylthiobutyrateMeSH, HMDB
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.77631661259
DarkChem[M-H]-126.9231661259
DeepCCS[M+H]+132.13630932474
DeepCCS[M-H]-129.37230932474
DeepCCS[M-2H]-165.7330932474
DeepCCS[M+Na]+140.49530932474
AllCCS[M+H]+133.732859911
AllCCS[M+H-H2O]+129.832859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.432859911
AllCCS[M-H]-134.832859911
AllCCS[M+Na-2H]-137.532859911
AllCCS[M+HCOO]-140.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-2-Hydroxy-4-(methylthio)butanoic acidCSCCC(O)C(O)=O2597.4Standard polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acidCSCCC(O)C(O)=O1278.0Standard non polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acidCSCCC(O)C(O)=O1415.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TMS,isomer #1CSCCC(O[Si](C)(C)C)C(=O)O1415.7Semi standard non polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TMS,isomer #2CSCCC(O)C(=O)O[Si](C)(C)C1363.7Semi standard non polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,2TMS,isomer #1CSCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1451.2Semi standard non polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TBDMS,isomer #1CSCCC(O[Si](C)(C)C(C)(C)C)C(=O)O1651.1Semi standard non polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,1TBDMS,isomer #2CSCCC(O)C(=O)O[Si](C)(C)C(C)(C)C1605.9Semi standard non polar33892256
(??)-2-Hydroxy-4-(methylthio)butanoic acid,2TBDMS,isomer #1CSCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1907.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i3-9200000000-b3f347c37bb602b8bb452017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9350000000-44bc7640c746eddc98892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic 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-Hydroxy-4-(methylthio)butanoic acid 10V, Negative-QTOFsplash10-0002-9100000000-88410fbd7b98e54f151e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Negative-QTOFsplash10-0002-9000000000-34be18dc4b552cce009e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Negative-QTOFsplash10-0002-9000000000-ca06cb2a413f50f341e02021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Positive-QTOFsplash10-0ue9-1900000000-dd2e58391a4c5f61dcd52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Positive-QTOFsplash10-056r-9700000000-8b98bae25421e4ce82fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Positive-QTOFsplash10-06vr-9000000000-7372f5d3aafd65f14b512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Negative-QTOFsplash10-0002-7900000000-3be7113c98ed233885282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Negative-QTOFsplash10-0002-9300000000-b2110ea4fabace846c652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Negative-QTOFsplash10-0002-9000000000-860ffaaedb18b65817fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Negative-QTOFsplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Negative-QTOFsplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Negative-QTOFsplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 10V, Positive-QTOFsplash10-0a59-6900000000-7ef5ccb88b6ef1b9a20d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 20V, Positive-QTOFsplash10-03dr-9300000000-c248fe9ce5cc0b99282c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-4-(methylthio)butanoic acid 40V, Positive-QTOFsplash10-03di-9000000000-9563ed6a85515f3e490e2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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
MarkerDB IDNot Available
Good Scents 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.