Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:18 UTC
Primary IDFDB012166
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRacemethionine
DescriptionRacemethionine, also known as DL-methionine or hmet, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Racemethionine is a very strong basic compound (based on its pKa). Racemethionine exists in all living organisms, ranging from bacteria to humans. Racemethionine is a mild, acidic, and sulfurous tasting compound. Racemethionine is found, on average, in the highest concentration within a few different foods, such as wheats, oats, and ryes and in a lower concentration in yellow bell peppers, sunburst squash (pattypan squash), and turnips. This could make racemethionine a potential biomarker for the consumption of these foods.
CAS Number59-51-8
Structure
Thumb
Synonyms
SynonymSource
2-Amino-4-(methylsulfanyl)butanoic acidChEBI
2-Amino-4-(methylthio)butanoic acidChEBI
2-Amino-4-(methylthio)butyric acidChEBI
alpha-Amino-gamma-methylmercaptobutyric acidChEBI
DL-MethionineChEBI
HmetChEBI
MChEBI
MetChEBI
MethioninChEBI
MetioninaChEBI
PadamethKegg
2-Amino-4-(methylsulfanyl)butanoateGenerator
2-Amino-4-(methylsulphanyl)butanoateGenerator
2-Amino-4-(methylsulphanyl)butanoic acidGenerator
2-Amino-4-(methylthio)butanoateGenerator
2-Amino-4-(methylthio)butyrateGenerator
a-Amino-g-methylmercaptobutyrateGenerator
a-Amino-g-methylmercaptobutyric acidGenerator
alpha-Amino-gamma-methylmercaptobutyrateGenerator
Α-amino-γ-methylmercaptobutyrateGenerator
Α-amino-γ-methylmercaptobutyric acidGenerator
(+-)-MethionineHMDB
(+/-)-2-amino-4-(methylmercapto)butyric acidHMDB
2-Amino-4-(methylmercapto)butyric acidHMDB
2-Amino-4-(methylthio)-butyric acidHMDB
2-Amino-4-methylthiobutanoic acidHMDB
alpha-Amino-gamma-(methylthio)butyric acidHMDB
DL-2-Amino-4-(methylthio)-butyric acidHMDB
DL-2-Amino-4-(methylthio)butanoic acidHMDB
DL-2-Amino-4-(methylthio)butyric acidHMDB
DL-2-Amino-4-methylthiobutanoic acidHMDB
FEMA 3301HMDB
Racemethionine, usanHMDB
Methionine, L-isomerHMDB
PedamethHMDB
L-Isomer methionineHMDB
LiquimethHMDB
Methionine, L isomerHMDB
MethionineHMDB
L-MethionineHMDB
RacemethionineChEBI
(+/-)-2-Amino-4-(methylmercapto)butyric acidbiospider
2-amino-4-(methylthio)-Butyric acidHMDB
Butyric acid, 2-amino-4-(methylthio)-biospider
Methionine, DL-biospider
Racemethionine, USANdb_source
Predicted Properties
PropertyValueSource
Water Solubility23.9 g/LALOGPS
logP-1.9ALOGPS
logP-2.2ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.59 m³·mol⁻¹ChemAxon
Polarizability15.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H11NO2S
IUPAC name2-amino-4-(methylsulfanyl)butanoic acid
InChI IdentifierInChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
InChI KeyFFEARJCKVFRZRR-UHFFFAOYSA-N
Isomeric SMILESCSCCC(N)C(O)=O
Average Molecular Weight149.211
Monoisotopic Molecular Weight149.051049291
Classification
Description belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentMethionine and derivatives
Alternative Parents
Substituents
  • Methionine or derivatives
  • Alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.25%; H 7.43%; N 9.39%; O 21.44%; S 21.49%DFC
Melting PointMp 281° dec.DFC
Boiling PointNot Available
Experimental Water Solubility32.7 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKapKa2 9.28 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-c74bbe6da11b7c8f48f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0950000000-ce063fd901edea1f6f81JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-c74bbe6da11b7c8f48f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0950000000-ce063fd901edea1f6f81JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-11ba-9200000000-d3a1e52f439dfdcb1146JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0zpj-9500000000-1fe0ded8d1bcf170815aJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-1900000000-ce17a3e11ac74608abf5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-1900000000-c965767347d7c1622965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-c9263687f6e32445137aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-1900000000-83702a37901ca71b058cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zfr-9800000000-9f63601c65b44c2e05daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-08fr-9000000000-56a9aa89915835ec0897JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-a048656aba28bbb0d512JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-cfa6fd6d4117ae7059c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-490e68b186cda555b7d3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-2191bd36a8f292c32048JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-a8e6fe85bb6f29913a51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0910000000-071f595c8b078081b359JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-efe1cbd495dd26a50289JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-1aad026814aaabf843efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-cf96556b080c962000d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-1900000000-d03cf3d65f8ae64087f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-b2b15d90a670baea5490JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3900000000-d0af3c89f9d94853572fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-67e023372cdbac09cb36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-1e589df1b14865d84d74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-efb0cddabddaf5231dbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-9ef89c92bce71adb0b81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-8507980760c8afb7f454JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-544c2c943904dcca737eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-08ir-9200000000-99eac412c38ff09dedc2JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID853
ChEMBL IDNot Available
KEGG Compound IDC01733
Pubchem Compound ID876
Pubchem Substance IDNot Available
ChEBI ID16811
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33951
CRC / DFC (Dictionary of Food Compounds) IDHJR27-B:HDW31-H
EAFUS ID2197
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1031751
SuperScent IDNot Available
Wikipedia IDMethionine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sulfurous
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acidic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference