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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:43:31 UTC
Update Date2018-03-12 22:06:47 UTC
HMDB IDHMDB0033951
Secondary Accession Numbers
  • HMDB33951
Metabolite Identification
Common NameRacemethionine
DescriptionRacemethionine is a flavouring ingredient; dietary supplement.Methionine is an alpha-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
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
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-isomerMeSH
PedamethMeSH
L-Isomer methionineMeSH
LiquimethMeSH
Methionine, L isomerMeSH
MethionineMeSH
L-MethionineMeSH
Chemical FormulaC5H11NO2S
Average Molecular Weight149.211
Monoisotopic Molecular Weight149.051049291
IUPAC Name2-amino-4-(methylsulfanyl)butanoic acid
Traditional Namemethionine
CAS Registry Number59-51-8
SMILES
CSCCC(N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
InChI KeyFFEARJCKVFRZRR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methionine and derivatives. These 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point281 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility32.7 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.9 g/LALOGPS
logP-1.8ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-c74bbe6da11b7c8f48f8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0950000000-ce063fd901edea1f6f81View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-c74bbe6da11b7c8f48f8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0950000000-ce063fd901edea1f6f81View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-11ba-9200000000-d3a1e52f439dfdcb1146View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0zpj-9500000000-1fe0ded8d1bcf170815aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-1900000000-ce17a3e11ac74608abf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-1900000000-c965767347d7c1622965View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-c9263687f6e32445137aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-1900000000-83702a37901ca71b058cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zfr-9800000000-9f63601c65b44c2e05daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-08fr-9000000000-56a9aa89915835ec0897View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-a048656aba28bbb0d512View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-cfa6fd6d4117ae7059c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-490e68b186cda555b7d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-2191bd36a8f292c32048View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-a8e6fe85bb6f29913a51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0910000000-071f595c8b078081b359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-efe1cbd495dd26a50289View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-1aad026814aaabf843efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-0900000000-cf96556b080c962000d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0f89-1900000000-d03cf3d65f8ae64087f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-b2b15d90a670baea5490View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3900000000-d0af3c89f9d94853572fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-67e023372cdbac09cb36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-1e589df1b14865d84d74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-efb0cddabddaf5231dbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-9ef89c92bce71adb0b81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-8507980760c8afb7f454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-544c2c943904dcca737eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-08ir-9200000000-99eac412c38ff09dedc2View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB012166
KNApSAcK IDNot Available
Chemspider ID853
KEGG Compound IDC01733
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethionine
METLIN IDNot Available
PubChem Compound876
PDB IDNot Available
ChEBI ID16811
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hayes DE, Ward RA: Sporozoite transmission of falciparum malaria (Burma-Thau. strain) from man to Aotus monkey. Am J Trop Med Hyg. 1977 Jan;26(1):184-5. [PubMed:402864 ]
  2. Abe M, Okada H, Matsumura D, Sato H, Funaba M, Iriki T: Methionine imbalance and toxicity in calves. J Anim Sci. 2000 Oct;78(10):2722-30. [PubMed:11048939 ]
  3. CASTELLANI L, ADEZATI L: [Utilization of amino acids in the synthesis of purine compounds. IV. Effect of dlmethionine and dl-histidine in the protein-deficient rat]. Arch Maragliano Patol Clin. 1951 Nov-Dec;6(6):1057-60. [PubMed:14924829 ]
  4. HARPER HA, UYEYAMA K: Plasma methionine after oral administration of DLmethionine in human subjects. Proc Soc Exp Biol Med. 1948 Jun;68(2):296-300. [PubMed:18869325 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .