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Showing metabocard for Methylcysteine (HMDB0002108)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2020-02-26 21:23:49 UTC
HMDB IDHMDB0002108
Secondary Accession Numbers
  • HMDB02108
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 ). Methylcystein is a biomarker for the consumption of dried and cooked beans
Structure
Data?1582752229
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2R)-2-Amino-3-(methylsulfanyl)propanoic acidHMDB
(R)-2-Amino-3-(methylthio)propanoic acidHMDB
3-(Methylthio)-L-alanineHMDB
L-MethylcysteineHMDB
S-Methyl-L-cysteineHMDB
(2R)-2-Amino-3-(methylsulfanyl)propanoateHMDB
(2R)-2-Amino-3-(methylsulphanyl)propanoateHMDB
(2R)-2-Amino-3-(methylsulphanyl)propanoic acidHMDB
(R)-2-Amino-3-(methylthio)propanoateHMDB
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
S-11C-Methyl-L-cysteineHMDB
S-Methylcysteine, (DL-cys)-isomerHMDB
S-Methylcysteine, hydrochloride, (L-cys)-isomerHMDB
S-Methylcysteine, (L-cys)-isomerHMDB
Chemical FormulaC4H9NO2S
Average Molecular Weight135.18
Monoisotopic Molecular Weight135.035399708
IUPAC Name(2S)-2-amino-3-(methylsulfanyl)propanoic acid
Traditional Name(2S)-2-amino-3-(methylsulfanyl)propanoic acid
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-/m1/s1
InChI KeyIDIDJDIHTAOVLG-GSVOUGTGSA-N
Chemical Taxonomy
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
  • S-alkyl-l-cysteine
  • Alpha-amino acid
  • D-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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

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 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
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.9 +/- 1.9 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003689
KNApSAcK IDNot Available
Chemspider ID22826
KEGG Compound IDNot Available
BioCyc IDS-METHYL-L-CYSTEINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6490
PubChem Compound24417
PDB IDNot Available
ChEBI ID45658
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. Rivlin RS: Is garlic alternative medicine? J Nutr. 2006 Mar;136(3 Suppl):713S-715S. [PubMed:16484549 ]
  2. 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. [PubMed:15161248 ]
  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. [PubMed:9591199 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Methylated-DNA--protein-cysteine methyltransferase
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. [PubMed: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. [PubMed:17016423 ]
Enzyme Details
2. Cathepsin D
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. [PubMed: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. [PubMed: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. [PubMed:10592235 ]