Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2018-05-29 01:00:07 UTC
Primary IDFDB012683
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Methionine
DescriptionDietary supplement and nutrient Methionine is an alpha-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar. L-Methionine is found in many foods, some of which are broad bean, atlantic cod, celeriac, and rowal.
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-Methionine ZKegg
L-2-Amino-4methylthiobutyric acidKegg
(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
(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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-004i-0920000000-945c85aa7c9f5eb2dfbbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0910000000-b837ee0f4413856560f1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00b9-7910000000-5a1558fbb2f5e86edc9bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-1900000000-1a97567ce4f25c4e8263View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-0910000000-1b0477118cb20549bf4dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0920000000-8ffae5d87508e0704903View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0920000000-945c85aa7c9f5eb2dfbbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0910000000-b837ee0f4413856560f1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-01bc-2692000000-c6a4af434abaeea2de87View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-7910000000-5a1558fbb2f5e86edc9bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1900000000-1a97567ce4f25c4e8263View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-0910000000-1b0477118cb20549bf4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0mbd-9200000000-77e5cfb78936ad02d71cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9510000000-c03dec8575710eed861eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-1900000000-b991859b2c5bed6592a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-08fr-9000000000-66855ace60e59837f131View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-08fr-9000000000-56a567791c824c6a9da6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0fe0-0900000000-d680295f21b2e2b40366View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-062d3540db4db22da836View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-84467513e2c9ec1a6851View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-88dc2bebb198eea550efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0920000000-b444ad79abeb16acde43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6e24a8df417e5f3db58cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-c60ef880eb9a816a274bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a7b7d1a3481c0c691a5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-9156f088f4cc9eafa892View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9200000000-f78ba2aab8d5a0e0b135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-e7b819fd2d0ac3862860View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-c3557cb41fd6fe268819View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-6900000000-6bf5af2d1c561013948aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-08fr-9000000000-63c9b1c138f9a27490e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-9000000000-e133c47b0efe4992589fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-dee78b4f34f8732fedb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0udi-0900000000-d3f03ff5e8eacc8b6c8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-e0dd5ff44b7962f6a2d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-305916dde72c899993b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-47e0a34a2ec02bd762bfView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).