(2S)-2-amino-4-(ethylsulfanyl)butanoic acid

• ChemBase ID: 105936
• Molecular Formular: C6H13NO2S
• Molecular Mass: 163.23792
• Monoisotopic Mass: 163.06669966
• SMILES: CCSCC[C@H](N)C(=O)O
• Canonical SMILES: CCSCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
• InChIKey: GGLZPLKKBSSKCX-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(ethylsulfanyl)butanoic acid
• IUPAC Traditional name: (.+-.)-ethionine
• Synonyms: L-Ethionine; L-2-Amino-4-(ethylthio)butyric acid; S-Ethyl-L-homocysteine; (S)-2-Amino-4-(ethylthio)butanoic Acid; ETH; Ethionine; NSC 82393; S-Ethylhomocysteine; L-2-Amino-4-[ethylthio]butyric acid; L-ETHIONINE; DL-ETHIONINE; L-2-氨基-4-(乙硫基)丁酸; L-乙硫氨基酪酸

Database IDs

• CAS Number: 13073-35-3; 67-21-0
• EC Number: 235-966-4
• MDL Number: MFCD00002626
• PubChem SID: 162092627; 24894397
• PubChem CID: 25674

CALCULATED PROPERTIES

• Acid pKa: 2.6062443
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.936398
• LogD (pH = 7.4): -1.9391353
• Log P: -1.9361717
• Molar Refractivity: 42.3838 cm^3
• Polarizability: 16.90167 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >260°C (dec.); 280 °C (dec.)(lit.); 280°C (decomposes)
• Optical Rotation: [α]22/D +21.7°, c = 1 in 1 M HCl

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: ES6825300
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ~99%; ≥99% (TLC); 98%
• Linear Formula: C2H5SCH2CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 05205306

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02195170

Purity: ~99%

Sigma Aldrich - E1260

Biochem/physiol Actions
甲硫氨酸类似物，会干扰 DNA 的标准甲基化和其他甲基化途径，从而导致胰腺中毒和肝癌。但在动物研究中，也显示出与甲硫氨酸消耗的同步活动，以阻止甲硫氨酸依赖性肿瘤的生长和转移。

Sigma Aldrich - 219339

Biochem/physiol Actions
An analog of methionine that interferes with the normal methylation of DNA and other methylation pathways, and induces pancreatic toxicity and liver cancer. However, in animal studies, it has also been shown to act synergistically with methionine-depletion to block the growth and metastasis of methionine-dependent tumors.
Packaging
5 g in glass bottle

Toronto Research Chemicals - E890435

Ethionine-induced inhibition of protein synthesis and lowering of ATP level in the liver.

REFERENCES

• Rotig, A., et al.: Lancet, 356, 391 (2000)
• Forsgren, M., et al.: Biochem. J., 382, 519 (2000)
• Johnson, A., et al.: J. Biol. Chem., 280, 31397 (2000)
• Horvath, R., et al.: Neurology, 66, 253 (2000)
• Mollet, M., et al.: J. Clin. Invest., 117, 765 (2000)