Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2020-09-17 15:38:40 UTC
Primary IDFDB012683
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Methionine
DescriptionL-Methionine, also known as acimethin or H-met-H, 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. The L-enantiomer of methionine. L-Methionine is a drug which is used for protein synthesis including the formation of same, l-homocysteine, l-cysteine, taurine, and sulfate. L-Methionine is a very strong basic compound (based on its pKa). L-Methionine exists in all living species, ranging from bacteria to humans. Outside of the human body, L-Methionine is found, on average, in the highest concentration within a few different foods, such as milk (cow), beluga whales, and smelts and in a lower concentration in white cabbages, wax gourds, and coconuts. L-Methionine has also been detected, but not quantified in, several different foods, such as pepper (c. chinense), acerola, grass pea, oxheart cabbages, and sherries. This could make L-methionine a potential biomarker for the consumption of these foods. L-Methionine is a potentially toxic compound. L-Methionine, with regard to humans, has been found to be associated with several diseases such as autism, leukemia, obesity, and heart failure; L-methionine has also been linked to the inborn metabolic disorder celiac disease.
CAS Number63-68-3
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-4-(methylsulfanyl)butanoic acidChEBI
(S)-2-Amino-4-(methylthio)butanoic acidChEBI
(S)-2-Amino-4-(methylthio)butyric acidChEBI
(S)-MethionineChEBI
L-(-)-MethionineChEBI
L-alpha-Amino-gamma-methylmercaptobutyric acidChEBI
L-MethioninChEBI
MChEBI
MetChEBI
METHIONINEChEBI
L-2-Amino-4methylthiobutyric acidKegg
L-Methionine ZKegg
(2S)-2-Amino-4-(methylsulfanyl)butanoateGenerator
(2S)-2-Amino-4-(methylsulphanyl)butanoateGenerator
(2S)-2-Amino-4-(methylsulphanyl)butanoic acidGenerator
(S)-2-Amino-4-(methylthio)butanoateGenerator
(S)-2-Amino-4-(methylthio)butyrateGenerator
L-a-Amino-g-methylmercaptobutyrateGenerator
L-a-Amino-g-methylmercaptobutyric acidGenerator
L-alpha-Amino-gamma-methylmercaptobutyrateGenerator
L-Α-amino-γ-methylmercaptobutyrateGenerator
L-Α-amino-γ-methylmercaptobutyric acidGenerator
L-2-Amino-4methylthiobutyrateGenerator
(L)-MethionineHMDB
(S)-(+)-MethionineHMDB
(S)-2-Amino-4-(methylthio)-butanoateHMDB
(S)-2-Amino-4-(methylthio)-butanoic acidHMDB
2-Amino-4-(methylthio)butyrateHMDB
2-Amino-4-(methylthio)butyric acidHMDB
2-Amino-4-methylthiobutanoateHMDB
2-Amino-4-methylthiobutanoic acidHMDB
a-Amino-g-methylmercaptobutyrateHMDB
a-Amino-g-methylmercaptobutyric acidHMDB
AcimethinHMDB
alpha-Amino-alpha-aminobutyric acidHMDB
alpha-Amino-gamma-methylmercaptobutyrateHMDB
alpha-Amino-gamma-methylmercaptobutyric acidHMDB
CymethionHMDB
g-Methylthio-a-aminobutyrateHMDB
g-Methylthio-a-aminobutyric acidHMDB
gamma-Methylthio-alpha-aminobutyrateHMDB
gamma-Methylthio-alpha-aminobutyric acidHMDB
H-Met-HHMDB
H-Met-OHHMDB
L(-)-Amino-alpha-amino-alpha-aminobutyric acidHMDB
L(-)-Amino-gamma-methylthiobutyric acidHMDB
L-2-Amino-4-(methylthio)butyric acidHMDB
L-2-Amino-4-methylthiobutyric acidHMDB
L-a-Amino-g-methylthiobutyrateHMDB
L-a-Amino-g-methylthiobutyric acidHMDB
L-alpha-Amino-gamma-methylthiobutyrateHMDB
L-alpha-Amino-gamma-methylthiobutyric acidHMDB
L-gamma-Methylthio-alpha-aminobutyric acidHMDB
L-MethioninumHMDB
LiquimethHMDB
MepronHMDB
MethilaninHMDB
MethioninumHMDB
MetioninaHMDB
Neo-methidinHMDB
Poly-L-methionineHMDB
PolymethionineHMDB
S-MethionineHMDB
S-Methyl-L-homocysteineHMDB
Toxin warHMDB
L-Isomer methionineHMDB
Methionine, L-isomerHMDB
PedamethHMDB
Methionine, L isomerHMDB
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diolChEBI
Bo-xanChEBI
e 161bChEBI
XanthophyllChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diolGenerator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diolGenerator
(2S)-2-amino-4-(Methylsulphanyl)butanoateGenerator
(2S)-2-amino-4-(Methylsulphanyl)butanoic acidGenerator
(S)-(-)-Methioninebiospider
(S)-2-Amino-4-(methylmercapto)butyric acidbiospider
(S)-2-amino-4-(methylthio)-ButanoateHMDB
(S)-2-amino-4-(methylthio)-Butanoic acidHMDB
(S)-2-amino-4-(methylthio)ButyrateGenerator
2-amino-4-(methylthio)ButyrateHMDB
2-Amino-4-(methylthio)butyric acid, (S)-biospider
2-amino-4-MethylthiobutanoateHMDB
a-amino-g-MethylmercaptobutyrateHMDB
a-amino-g-Methylmercaptobutyric acidHMDB
alpha-amino-alpha-Aminobutyric acidHMDB
alpha-amino-gamma-MethylmercaptobutyrateHMDB
Butanoic acid, 2-amino-4-(methylthio)-, (S)-biospider
g-methylthio-a-AminobutyrateHMDB
g-methylthio-a-Aminobutyric acidHMDB
gamma-methylthio-alpha-AminobutyrateHMDB
gamma-methylthio-alpha-Aminobutyric acidHMDB
L-2-Amino-4-(methylthio)butanoic acidbiospider
L-2-amino-4-Methylthiobutyric acidHMDB
L-a-amino-g-MethylmercaptobutyrateGenerator
L-a-amino-g-Methylmercaptobutyric acidGenerator
L-alpha-amino-gamma-MethylmercaptobutyrateGenerator
L-Homocysteine, S-methyl-biospider
L-Methioninebiospider
L-α-amino-γ-methylmercaptobutyrateGenerator
L-α-amino-γ-methylmercaptobutyric acidGenerator
L(-)-amino-alpha-amino-alpha-Aminobutyric acidHMDB
L(-)-amino-gamma-Methylthiobutyric acidHMDB
Methionine, 9CI, INN; L-formdb_source
Methionine, L- (8CI)biospider
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
Polarizability15.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H11NO2S
IUPAC name(2S)-2-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)/t4-/m0/s1
InChI KeyFFEARJCKVFRZRR-BYPYZUCNSA-N
Isomeric SMILESCSCC[C@H](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
  • L-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.25%; H 7.43%; N 9.39%; O 21.44%; S 21.49%DFC
Melting PointMp 283° dec.DFC
Boiling PointNot Available
Experimental Water Solubility56.6 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.87HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.2 (20°, 0.15M NaClO4)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -14.9 (H2O); [a]D +34.6 (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Methionine, 2 TMS, GC-MS Spectrumsplash10-004i-0920000000-945c85aa7c9f5eb2dfbbSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-b837ee0f4413856560f1Spectrum
GC-MSL-Methionine, 2 TMS, GC-MS Spectrumsplash10-00b9-7910000000-5a1558fbb2f5e86edc9bSpectrum
GC-MSL-Methionine, 1 TMS, GC-MS Spectrumsplash10-0udi-1900000000-1a97567ce4f25c4e8263Spectrum
GC-MSL-Methionine, 2 TMS, GC-MS Spectrumsplash10-004i-0910000000-1b0477118cb20549bf4dSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0920000000-8ffae5d87508e0704903Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0920000000-945c85aa7c9f5eb2dfbbSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-b837ee0f4413856560f1Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-01bc-2692000000-c6a4af434abaeea2de87Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-00b9-7910000000-5a1558fbb2f5e86edc9bSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-1a97567ce4f25c4e8263Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-1b0477118cb20549bf4dSpectrum
Predicted GC-MSL-Methionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0mbd-9200000000-77e5cfb78936ad02d71cSpectrum
Predicted GC-MSL-Methionine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9510000000-c03dec8575710eed861eSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-1900000000-b991859b2c5bed6592a8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-08fr-9000000000-66855ace60e59837f131Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-08fr-9000000000-56a567791c824c6a9da6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0fe0-0900000000-d680295f21b2e2b40366Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-062d3540db4db22da836Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-84467513e2c9ec1a6851Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-88dc2bebb198eea550efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0920000000-b444ad79abeb16acde43Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6e24a8df417e5f3db58cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-c60ef880eb9a816a274bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a7b7d1a3481c0c691a5bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-9156f088f4cc9eafa892Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9200000000-f78ba2aab8d5a0e0b135Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-e7b819fd2d0ac3862860Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-c3557cb41fd6fe268819Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-6900000000-6bf5af2d1c561013948aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-08fr-9000000000-63c9b1c138f9a27490e5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-9000000000-e133c47b0efe4992589fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-dee78b4f34f8732fedb0Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0udi-0900000000-d3f03ff5e8eacc8b6c8eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-e0dd5ff44b7962f6a2d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-305916dde72c899993b6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-47e0a34a2ec02bd762bfSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID5907
ChEMBL IDCHEMBL42336
KEGG Compound IDC00073
Pubchem Compound ID6137
Pubchem Substance IDNot Available
ChEBI ID16643
Phenol-Explorer IDNot Available
DrugBank IDDB00134
HMDB IDHMDB00696
CRC / DFC (Dictionary of Food Compounds) IDHJR27-B:HJR24-Y
EAFUS ID2198
Dr. Duke IDMETHIONINE
BIGG ID33753
KNApSAcK IDC00001379
HET IDMET
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotic62868 Any compound that is able to prevent damage to the liver.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
emeticDUKE
essentialDUKE
glutathionigenicDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
lipotropicDUKE
urine acidifierDUKE
urine deodorantDUKE
Enzymes
NameGene NameUniProt ID
Tyrosine aminotransferaseTATP17735
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Methionine-R-sulfoxide reductase B1MSRB1Q9NZV6
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Glutamine synthetaseGLULP15104
Methionine--tRNA ligase, cytoplasmicMARSP56192
Methionine--tRNA ligase, mitochondrialMARS2Q96GW9
Mitochondrial peptide methionine sulfoxide reductaseMSRAQ9UJ68
Methionine-R-sulfoxide reductase B2, mitochondrialMSRB2Q9Y3D2
Methionine-R-sulfoxide reductase B3MSRB3Q8IXL7
Pathways
NameSMPDB LinkKEGG Link
Betaine MetabolismSMP00123 map00260
Glycine and Serine MetabolismSMP00004 map00260
Methionine MetabolismSMP00033 map00270
Spermidine and Spermine BiosynthesisSMP00445 Not Available
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).