3-(Methylthio)alanine (CHEM028376)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:24:53 UTC
Update Date2016-11-09 01:18:40 UTC
Accession NumberCHEM028376
Identification
Common Name3-(Methylthio)alanine
ClassSmall Molecule
DescriptionA cysteine derivative that is L-cysteine in which the hydrogen attached to the sulfur is replaced by a methyl group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Amino-3-(methylsulfanyl)propanoic acidChEBI
(R)-2-Amino-3-(methylthio)propanoic acidChEBI
3-(Methylthio)-L-alanineChEBI
L-MethylcysteineChEBI
S-Methyl-L-cysteineChEBI
(2R)-2-Amino-3-(methylsulfanyl)propanoateGenerator
(2R)-2-Amino-3-(methylsulphanyl)propanoateGenerator
(2R)-2-Amino-3-(methylsulphanyl)propanoic acidGenerator
(R)-2-Amino-3-(methylthio)propanoateGenerator
3-(methylthio)-L-(8CI)alanineHMDB
Acm-thiopropionateHMDB
Acm-thiopropionic acidHMDB
L-Aspartic acid dimethyl esterHMDB
S-Acetamidomethyl-deamino-cysteineHMDB
S-Methyl-(9ci)-L-cysteineHMDB
S-Methyl-cysteineHMDB
S-Methyl-DL-cysteineHMDB
S-MethylcysteineHMDB, MeSH
S-11C-Methyl-L-cysteineMeSH, HMDB
S-Methylcysteine, (DL-cys)-isomerMeSH, HMDB
S-Methylcysteine, hydrochloride, (L-cys)-isomerMeSH, HMDB
S-Methylcysteine, (L-cys)-isomerMeSH, HMDB
Chemical FormulaC4H9NO2S
Average Molecular Mass135.185 g/mol
Monoisotopic Mass135.035 g/mol
CAS Registry Number1187-84-4
IUPAC Name(2R)-2-amino-3-(methylsulfanyl)propanoic acid
Traditional NameS-methylcysteine
SMILESCSCC(N)C(O)=O
InChI IdentifierInChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
InChI KeyIDIDJDIHTAOVLG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Carbonyl group
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9500000000-daa44ef1254b2abffd37Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-02t9-1950000000-7418765e9cc42b0155e4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fv-9000000000-d790345dc4143a2c43efSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9500000000-daa44ef1254b2abffd37Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1950000000-7418765e9cc42b0155e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-72d010b2583bd53b7e08Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006y-9400000000-3b5fc90a341033d6e213Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1900000000-4a373aa1d088e914beadSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-9000000000-04c165848579841841dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00fr-9000000000-1b77045ef8e2cb3b10e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03fv-9000000000-9377aea80fe674b0a8deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9700000000-8f3d25ac52279c092856Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-b405850a71df669cec12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-ace8060e79e2568e8fd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-0100ccbfcee39a28f73dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-9000000000-77f7473e8f64b00cba29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-5f83877d00d54983d86cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bc-7900000000-15e4c05adb56715c93d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9000000000-5a8e96324e324aab8703Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-c69e8c7f456c0f6fa275Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d754Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d754Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d754Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02216
HMDB IDHMDB0302211
FooDB IDFDB003689
Phenol Explorer IDNot Available
KNApSAcK IDC00000747
BiGG IDNot Available
BioCyc IDS-METHYL-L-CYSTEINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID22826
ChEBI ID45658
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15161248
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19367645
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21110385
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23417484
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25650289
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26887651
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26928722
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=508804
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7451605
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=993852