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Record Information
Version3.6
Creation Date2006-05-22 14:17:36 UTC
Update Date2016-06-10 21:23:09 UTC
HMDB IDHMDB02108
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethylcysteine
DescriptionMethylcysteine 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 ).
Structure
Thumb
Synonyms
ValueSource
3-(methylthio)-L-(8CI)alanineHMDB
3-(methylthio)-L-AlanineHMDB
Acm-thiopropionateHMDB
Acm-thiopropionic acidHMDB
L-Aspartic acid dimethyl esterHMDB
L-MethylcysteineHMDB
S-Acetamidomethyl-deamino-cysteineHMDB
S-Methyl-(9ci)-L-cysteineHMDB
S-Methyl-cysteineHMDB
S-Methyl-DL-cysteineHMDB
S-Methyl-L-cysteineHMDB
S-MethylcysteineHMDB
Chemical FormulaC4H9NO2S
Average Molecular Weight135.185
Monoisotopic Molecular Weight135.035399227
IUPAC Name(2R)-2-amino-3-(methylsulfanyl)propanoic acid
Traditional NameS-methylcysteine
CAS Registry Number1187-84-4
SMILES
CSC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyInChIKey=IDIDJDIHTAOVLG-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as s-alkyl-l-cysteines. These are cysteine derivatives that carry an alkyl chain attached to the sulfanyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentS-alkyl-L-cysteines
Alternative Parents
Substituents
  • S-alkyl-l-cysteine
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility65.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.87 m3·mol-1ChemAxon
Polarizability13.56 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9500000000-daa44ef1254b2abffd37View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-02t9-1950000000-7418765e9cc42b0155e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1900000000-4a373aa1d088e914beadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-9000000000-04c165848579841841dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00fr-9000000000-1b77045ef8e2cb3b10e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03fv-9000000000-9377aea80fe674b0a8deView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.9 +/- 1.9 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.34-0.82 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.35-0.63 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0796-0.717 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0177-0.619 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.34-0.82 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.35-0.63 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02216
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012676
KNApSAcK IDNot Available
Chemspider ID22826
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02108
Metagene LinkHMDB02108
METLIN ID6490
PubChem Compound24417
PDB IDSMC
ChEBI ID497729
References
Synthesis ReferenceMa, Chengjun; Yao, Fei; Zhang, Guanyong. Synthesis of S-methyl-L-cysteine. Huaxue Shijie (2003), 44(7), 370-372.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Huang CN, Horng JS, Yin MC: Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. J Agric Food Chem. 2004 Jun 2;52(11):3674-8. [15161248 ]
  2. Rivlin RS: Is garlic alternative medicine? J Nutr. 2006 Mar;136(3 Suppl):713S-715S. [16484549 ]
  3. Fukushima S, Takada N, Hori T, Wanibuchi H: Cancer prevention by organosulfur compounds from garlic and onion. J Cell Biochem Suppl. 1997;27:100-5. [9591199 ]

Enzymes

General function:
Involved in methylated-DNA-[protein]-cysteine S-methyltransferase activity
Specific function:
Involved in the cellular defense against the biological effects of O6-methylguanine (O6-MeG) in DNA. Repairs alkylated guanine in DNA by stoichiometrically transferring the alkyl group at the O-6 position to a cysteine residue in the enzyme. This is a suicide reaction:the enzyme is irreversibly inactivated
Gene Name:
MGMT
Uniprot ID:
P16455
Molecular weight:
21645.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General function:
Involved in aspartic-type endopeptidase activity
Specific function:
Acid protease active in intracellular protein breakdown. Involved in the pathogenesis of several diseases such as breast cancer and possibly Alzheimer disease
Gene Name:
CTSD
Uniprot ID:
P07339
Molecular weight:
44551.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]