(2R)-2-amino-3-(methylsulfanyl)propanoic acid

• ChemBase ID: 1968
• Molecular Formular: C4H9NO2S
• Molecular Mass: 135.18476
• Monoisotopic Mass: 135.03539953
• SMILES: CSC[C@H](N)C(=O)O
• Canonical SMILES: CSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
• InChIKey: IDIDJDIHTAOVLG-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(methylsulfanyl)propanoic acid
• IUPAC Traditional name: S-methylcysteine
• Synonyms: SMLC; S-Methyl-L-cysteine; (R)-2-Amino-3-(methylmercapto)propionic acid; S-METHYL-L-CYSTEINE; H-Cys(Me)-OH; S-Methylcysteine; (R)-2-Amino-3-(methylthio)propanoic acid

Database IDs

• CAS Number: 1187-84-4; 7728-98-5
• EC Number: 214-701-6
• MDL Number: MFCD00002612
• Beilstein Number: 1721675
• PubChem SID: 24884749; 46506571; 24897098; 160965423
• PubChem CID: 24417

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4449296
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.404761
• LogD (pH = 7.4): -2.4116535
• Log P: -2.4047441
• Molar Refractivity: 32.8746 cm^3
• Polarizability: 13.242182 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.21
• LOG S: -0.31
• Solubility (Water): 6.58e+01 g/l

PROPERTIES

Physical Property

• Melting Point: ~240 °C (dec.); 239-240°C
• Optical Rotation: [α]20/D -31±2°, c = 5% in H2O

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (NT); 95+%; 97%
• Grade: purum
• Linear Formula: CH3SCH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 05215366

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102316

Crystalline

DrugBank - DB02216

Drug information: experimental

Sigma Aldrich - M6626

包装
5, 25, 100 g in glass bottle
Biochem/physiol Actions
S-Methyl-L-cysteine (SMLC) is a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). SMLC is naturally present in garlic, cabbage, and turnips and has been studied as a theurapeutic for neurodegenerative diseases including Parkinson′s.1When used as a dietary supplement in the Drosphilia model of PD, SMLC increases the efficacy of the MRSA catalytic antioxidant system by providing additional substrate available leading to increased resistance to oxidative stress.1