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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:43:31 UTC
Update Date2022-03-07 02:53:55 UTC
HMDB IDHMDB0033951
Secondary Accession Numbers
  • HMDB33951
Metabolite Identification
Common 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. Methionine is an alpha-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar. 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 spinachs, white cabbages, and green zucchinis. Racemethionine is used as a flavouring ingredient and dietary supplement.
Structure
Data?1563862486
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
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-isomerMeSH, HMDB
PedamethMeSH, HMDB
L-Isomer methionineMeSH, HMDB
LiquimethMeSH, HMDB
Methionine, L isomerMeSH, HMDB
MethionineMeSH, HMDB
L-MethionineMeSH, HMDB
RacemethionineChEBI
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
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point281 °CNot Available
Boiling Point300.00 to 301.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility32.7 mg/mL at 25 °CNot Available
LogP0.217 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+130.44631661259
DarkChem[M-H]-126.90931661259
DeepCCS[M+H]+132.68930932474
DeepCCS[M-H]-129.92630932474
DeepCCS[M-2H]-166.32330932474
DeepCCS[M+Na]+141.07530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RacemethionineCSCCC(N)C(O)=O2393.1Standard polar33892256
RacemethionineCSCCC(N)C(O)=O1302.1Standard non polar33892256
RacemethionineCSCCC(N)C(O)=O1618.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Racemethionine,1TMS,isomer #1CSCCC(N)C(=O)O[Si](C)(C)C1408.2Semi standard non polar33892256
Racemethionine,1TMS,isomer #2CSCCC(N[Si](C)(C)C)C(=O)O1499.1Semi standard non polar33892256
Racemethionine,2TMS,isomer #1CSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1524.5Semi standard non polar33892256
Racemethionine,2TMS,isomer #1CSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1498.0Standard non polar33892256
Racemethionine,2TMS,isomer #2CSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1686.0Semi standard non polar33892256
Racemethionine,2TMS,isomer #2CSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1566.7Standard non polar33892256
Racemethionine,3TMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1709.5Semi standard non polar33892256
Racemethionine,3TMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1627.3Standard non polar33892256
Racemethionine,1TBDMS,isomer #1CSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C1637.0Semi standard non polar33892256
Racemethionine,1TBDMS,isomer #2CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O1739.6Semi standard non polar33892256
Racemethionine,2TBDMS,isomer #1CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1980.2Semi standard non polar33892256
Racemethionine,2TBDMS,isomer #1CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1929.9Standard non polar33892256
Racemethionine,2TBDMS,isomer #2CSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2097.0Semi standard non polar33892256
Racemethionine,2TBDMS,isomer #2CSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2000.5Standard non polar33892256
Racemethionine,3TBDMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2369.6Semi standard non polar33892256
Racemethionine,3TBDMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2255.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Racemethionine GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-c74bbe6da11b7c8f48f82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Racemethionine GC-EI-TOF (Non-derivatized)splash10-0a4i-0950000000-ce063fd901edea1f6f812017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Racemethionine GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-c74bbe6da11b7c8f48f82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Racemethionine GC-EI-TOF (Non-derivatized)splash10-0a4i-0950000000-ce063fd901edea1f6f812018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (Non-derivatized) - 70eV, Positivesplash10-11ba-9200000000-d3a1e52f439dfdcb11462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (1 TMS) - 70eV, Positivesplash10-0zpj-9500000000-1fe0ded8d1bcf170815a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Racemethionine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-08ir-9200000000-99eac412c38ff09dedc22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-IT , negative-QTOFsplash10-0udi-1900000000-ce17a3e11ac74608abf52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine , negative-QTOFsplash10-0002-1900000000-c965767347d7c16229652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0900000000-c9263687f6e32445137a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-QTOF , positive-QTOFsplash10-0udi-1900000000-83702a37901ca71b058c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-QTOF , positive-QTOFsplash10-0zfr-9800000000-9f63601c65b44c2e05da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-QTOF , positive-QTOFsplash10-08fr-9000000000-56a9aa89915835ec08972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-a048656aba28bbb0d5122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-cfa6fd6d4117ae7059c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-490e68b186cda555b7d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0f89-0900000000-2191bd36a8f292c320482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-a8e6fe85bb6f29913a512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0f89-0910000000-071f595c8b078081b3592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0f89-0900000000-efe1cbd495dd26a502892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0f89-0900000000-1aad026814aaabf843ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0f89-0900000000-cf96556b080c962000d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0f89-1900000000-d03cf3d65f8ae64087f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-b2b15d90a670baea54902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine , positive-QTOFsplash10-0udi-3900000000-d0af3c89f9d94853572f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Racemethionine 35V, Positive-QTOFsplash10-0f89-0900000000-3fb024c4de3a6e9c90fc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Racemethionine 10V, Positive-QTOFsplash10-0udi-2900000000-67e023372cdbac09cb362015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Racemethionine 20V, Positive-QTOFsplash10-0udi-9800000000-1e589df1b14865d84d742015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Racemethionine 40V, Positive-QTOFsplash10-056r-9000000000-efb0cddabddaf5231dbd2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Racemethionine 10V, Negative-QTOFsplash10-0002-6900000000-9ef89c92bce71adb0b812015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Racemethionine 20V, Negative-QTOFsplash10-0002-9300000000-8507980760c8afb7f4542015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Racemethionine 40V, Negative-QTOFsplash10-0002-9000000000-544c2c943904dcca737e2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB012166
KNApSAcK IDNot Available
Chemspider ID853
KEGG Compound IDC01733
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethionine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16811
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031751
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.. .