Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2019-11-26 03:07:22 UTC
Primary IDFDB012676
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-(Methylthio)alanine
DescriptionOccurs in all members of the genus Allium, at least two genera of Brassicaceae family (Brassica and Raphanus) and sporadically in the families Compositae, Leguminosae and Umbelliferae. Found in kidney bean seeds (Phaseolus vulgaris) Methylcysteine is one of the identified number of bioactive substances in garlic that are water soluble. (PMID 16484549); It has been suggested that the use of these organosulfur agents derived from garlic could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases. (PMID 15161248); It may also exert some chemopreventive effects on chemical carcinogenesis. However, it should be borne in mind that may also demonstrate promotion potential, depending on the organ examined. (PMID 9591199). S-Methylcystein is a biomarker for the consumption of dried and cooked beans.
CAS Number1187-84-4
Structure
Thumb
Synonyms
SynonymSource
S-Methylcysteine, (DL-cys)-isomerMeSH
S-11C-Methyl-L-cysteineMeSH
S-Methylcysteine, (L-cys)-isomerMeSH
S-Methylcysteine, hydrochloride, (L-cys)-isomerMeSH
(R)-2-Amino-3-(methylmercapto)propionic acidbiospider
3-(methylthio)-L-(8CI)alaninebiospider
3-(methylthio)-L-alaninebiospider
3-(Methylthio)alaninedb_source
Acm-thiopropionatebiospider
Acm-thiopropionic acidbiospider
Alanine, 3-(methylthio)-, L-biospider
Alanine, 3-(methylthio)-, L- (8CI)biospider
CYMbiospider
Cysteine, s-methyl-biospider
L-aspartic acid dimethyl esterbiospider
L-cysteine, s-methyl-biospider
L-Cysteine, S-methyl- (9CI)biospider
L-methylcysteinebiospider
Methylcysteine, l-biospider
S-acetamidomethyl-deamino-cysteinebiospider
S-methyl-(9CI)-L-cysteinebiospider
S-methyl-cysteinebiospider
S-methyl-DL-cysteinebiospider
S-methyl-l-cysteinebiospider
S-Methylcysteinedb_source
SMCbiospider
Predicted Properties
PropertyValueSource
Water Solubility65.8 g/LALOGPS
logP-2.2ALOGPS
logP-2.4ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)2.44ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.87 m³·mol⁻¹ChemAxon
Polarizability13.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H9NO2S
IUPAC name2-amino-3-(methylsulfanyl)propanoic acid
InChI IdentifierInChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
InChI KeyIDIDJDIHTAOVLG-UHFFFAOYSA-N
Isomeric SMILESCSCC(N)C(O)=O
Average Molecular Weight135.185
Monoisotopic Molecular Weight135.035399227
Classification
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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 ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 35.54%; H 6.71%; N 10.36%; O 23.67%; S 23.72%DFC
Melting PointMp 234-236 dec. (207-211°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -32 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9700000000-8f3d25ac52279c0928562016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-b405850a71df669cec122016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-ace8060e79e2568e8fd62016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-0100ccbfcee39a28f73d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-9000000000-77f7473e8f64b00cba292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-5f83877d00d54983d86c2016-08-03View Spectrum
NMRNot Available
ChemSpider ID22826
ChEMBL IDCHEMBL394875
KEGG Compound IDNot Available
Pubchem Compound ID24417
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02216
HMDB IDHMDB02108
CRC / DFC (Dictionary of Food Compounds) IDHJQ86-N:HJQ76-K
EAFUS IDNot Available
Dr. Duke IDS-METHYL-CYSTEINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSMC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
Enzymes
NameGene NameUniProt ID
Cathepsin DCTSDP07339
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).