| Common Name |
Methylcysteine
| Description |
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 organoslifur agents derived from garlic colid protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascliar diseases. (PMID 15161248 ). It may also exert some chemopreventive effects on chemical carcinogenesis. However, it sholid be borne in mind that may also demonstrate promotion potential, depending on the organ examined. (PMID 9591199 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(2R)-2-amino-3-(Methylslifanyl)propanoic acidChEBI
(R)-2-amino-3-(methylthio)Propanoic acidChEBI
3-(methylthio)-L-AlanineChEBI
L-MethylcysteineChEBI
S-Methyl-L-cysteineChEBI
(2R)-2-amino-3-(Methylslifanyl)propanoateGenerator
(2R)-2-amino-3-(Methylsliphanyl)propanoateGenerator
(2R)-2-amino-3-(Methylsliphanyl)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
S-11C-Methyl-L-cysteineMeSH
S-Methylcysteine, (DL-cys)-isomerMeSH
S-Methylcysteine, hydrochloride, (L-cys)-isomerMeSH
S-Methylcysteine, (L-cys)-isomerMeSH
| Chemical Formlia |
C4H9NO2S
| Average Molecliar Weight |
135.185
| Monoisotopic Molecliar Weight |
135.035399227
| IUPAC Name |
(2R)-2-amino-3-(methylslifanyl)propanoic acid
| Traditional Name |
S-methylcysteine
| CAS Registry Number |
1187-84-4
| 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 Key |
IDIDJDIHTAOVLG-VKHMYHEASA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
L-cysteine-S-conjugates
| Alternative Parents |
L-alpha-amino acids
Amino acids
Slifenyl compounds
Monocarboxylic acids and derivatives
Dialkylthioethers
Carboxylic acids
Organopnictogen compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
L-cysteine-s-conjugate
Alpha-amino acid
L-alpha-amino acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Slifenyl compound
Dialkylthioether
Carbonyl group
Amine
Primary amine
Organoslifur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
S-alkyl-L-cysteine (CHEBI:45658 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Food
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (1 TMS)splash10-0006-9500000000-daa44ef1254b2abffd37View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-02t9-1950000000-7418765e9cc42b0155e4View in MoNA
| GC-MS |
GC-MS Spectrum – EI-Bsplash10-03fv-9000000000-d790345dc4143a2c43efView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1900000000-4a373aa1d088e914beadView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-00b9-9000000000-04c165848579841841dbView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-00fr-9000000000-1b77045ef8e2cb3b10e8View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – EI-B (HITACHI M-80) , Positivesplash10-03fv-9000000000-9377aea80fe674b0a8deView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified3.9 +/- 1.9 uMAdlit (>18 years old)BothNormal
508804
details
UrineDetected and Quantified0.34-0.82 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified0.35-0.63 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
UrineDetected and Quantified0.0796-0.717 umol/mmol creatinineAdlit (>18 years old)MaleNormal
21110385
details
UrineDetected and Quantified0.0177-0.619 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
21110385
details
UrineDetected and Quantified0.34-0.82 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified0.35-0.63 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB02216
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB012676
| KNApSAcK ID |
Not Available
| Chemspider ID |
22826
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02108
| Metagene Link |
HMDB02108
| METLIN ID |
6490
| PubChem Compound |
24417
| PDB ID |
SMC
| ChEBI ID |
497729
Product: Trichlormethine
References |
| Synthesis Reference |
Ma, 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 |
- 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 ]
- Rivlin RS: Is garlic alternative medicine? J Nutr. 2006 Mar;136(3 Suppl):713S-715S. [PubMed:16484549 ]
- 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 ]
|
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
- 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 ]
- 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 ]
- 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
- 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 ]
- 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 ]
- 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 ]
PMID: 19158669