Record Information
Version1.0
Creation date2010-04-08 22:05:54 UTC
Update date2019-11-26 02:59:30 UTC
Primary IDFDB003689
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-N-Methylcysteine
DescriptionS-n-methylcysteine, also known as (2r)-2-amino-3-(methylsulfanyl)propanoic acid or 3-(methylthio)-L-alanine, is a member of the class of compounds known as L-cysteine-s-conjugates. L-cysteine-s-conjugates are compounds containing L-cysteine where the thio-group is conjugated. S-n-methylcysteine is soluble (in water) and a moderately acidic compound (based on its pKa). S-n-methylcysteine can be found in soft-necked garlic, which makes S-n-methylcysteine a potential biomarker for the consumption of this food product. S-n-methylcysteine can be found primarily in blood and urine.
CAS Number1187-84-4
Structure
Thumb
Synonyms
SynonymSource
(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
S-11C-Methyl-L-cysteineMeSH
S-Methylcysteine, (L-cys)-isomerMeSH
S-Methylcysteine, hydrochloride, (L-cys)-isomerMeSH
S-Methylcysteine, (DL-cys)-isomerMeSH
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9NO2S
IUPAC name(2R)-2-amino-3-(methylsulfanyl)propanoic acid
InChI IdentifierInChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyIDIDJDIHTAOVLG-VKHMYHEASA-N
Isomeric SMILESCSC[C@H](N)C(O)=O
Average Molecular Weight135.185
Monoisotopic Molecular Weight135.035399227
Classification
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
Ontology
Foods

Fruits and vegetables:

Herbs and spices:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9500000000-daa44ef1254b2abffd37JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-02t9-1950000000-7418765e9cc42b0155e4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fv-9000000000-d790345dc4143a2c43efJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9500000000-daa44ef1254b2abffd37JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-02t9-1950000000-7418765e9cc42b0155e4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-72d010b2583bd53b7e08JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006y-9400000000-3b5fc90a341033d6e213JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1900000000-4a373aa1d088e914beadJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-9000000000-04c165848579841841dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00fr-9000000000-1b77045ef8e2cb3b10e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03fv-9000000000-9377aea80fe674b0a8deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9700000000-8f3d25ac52279c092856JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-b405850a71df669cec12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-ace8060e79e2568e8fd6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-0100ccbfcee39a28f73dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-9000000000-77f7473e8f64b00cba29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-5f83877d00d54983d86cJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDS-N-METHYL-CYSTEINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).