(-)-S-Methyl-L-cysteine
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Basic information
- CAS
1187-84-4- Standard SMILES
CSC[C@H](N)C(=O)O- InChIKey
IDIDJDIHTAOVLG-VKHMYHEASA-N- Molecular formula
- C4H9NO2S
- Average molar mass
- 135.19 g/mol
- Monoisotopic mass
- 135.03539953
Overview
S-methylcysteine is a cysteine derivative that is L-cysteine in which the hydrogen attached to the sulfur is replaced by a methyl group. It has a role as a plant metabolite and a human urinary metabolite. It is a tautomer of a S-methylcysteine zwitterion.
Names & identifiers
- Preferred name
- (-)-S-Methyl-L-cysteine
- IUPAC
- (2R)-2-amino-3-methylsulfanylpropanoic acid
- English name
- S-Methyl-L-cysteine
- Molecular formula
- C4H9NO2S
- Molecular weight
- 135.18
Names & synonyms
S-Methyl-L-cysteine1187-84-4S-MethylcysteineL-Cysteine, S-methyl-ALANINE, 3-(METHYLTHIO)-, L-(2R)-2-amino-3-(methylsulfanyl)propanoic acid(-)-S-Methyl-L-cysteine(2R)-2-amino-3-methylsulfanylpropanoic acidA34I1H07YMCHEBI:45658NSC-15387RefChem:884264
Show more names
MethylcysteineSMCSMLCL-Cys（me）-OHH-L-CYS(ME)-OHS-Methyl-L-Cys-OHS-MethyI-L-cysteine
(2R)-2-azaniumyl-3-methylsulfanylpropanoate214-701-6231-787-07728-98-5H-Cys(Me)-OHS-methyl-cysteineMFCD00002612(R)-2-amino-3-(methylthio)propanoic acid
Database identifiers
- CAS
1187-84-4、19651-44-6、7728-98-5- PubChem CID
- 24417
- DTXSID
DTXSID50862579- ChEMBL
CHEMBL394875- ChEBI
CHEBI:45658
Properties
Computed structural propertiesFilling in
- XLogP
- -2.7
- Topological polar surface area
- 88.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 86.1
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionBeige powder; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 240 °C · ~240 °C (dec.)
- alpha
- -29.5 · -29.5 º (c=1,water)
- Boiling point
- 300.3 · 300.3±37.0 °C(Predicted)
- Density
- 1.149 · 1.149 (estimate)
- refractive index
- -30 ° · -30 ° (C=2, H2O)
- storage temp.
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- solubility
- Aqueous Acid (Slightly, Sonicated), Aqueous Base (Sparingly, Sonicated)
- form
- Solid
- pka
- 1 · pK1:8.97 (25°C)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazards SummaryNot considered hazardous by GHS classification; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29309090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-24/25-36/37/39-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H335-H319-H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Applications
UsesS-Methyl-L-cysteine is a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). It has been studied as a theurapeutic for neurodegenerative diseases including Parkinson′s.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A cysteine derivative that is L-cysteine in which the hydrogen attached to the sulfur is replaced by a methyl group.
Related reactions
3 records
Compound notes
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