2-(2-sulfanylpropanamido)acetic acid

• ChemBase ID: 134150
• Molecular Formular: C5H9NO3S
• Molecular Mass: 163.19486
• Monoisotopic Mass: 163.03031415
• SMILES: CC(C(=O)NCC(=O)O)S
• Canonical SMILES: CC(C(=O)NCC(=O)O)S
• InChI: InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
• InChIKey: YTGJWQPHMWSCST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-sulfanylpropanamido)acetic acid
• IUPAC Traditional name: tiopronin
• Synonyms: N-(2-Mercaptopropionyl)glycine; Tiopronin; N-(2-Mercaptopropionyl)glycine; Tiopronin; N-(2-Mercapto-1-oxopropyl)glycine; Acadione; Capen; Captimer; Epatiol; Hepadigest; Meprin; Mucolysin; Sutilan; Thiolpropionamidoacetic Acid; Thiopronin; Thiopronine; Tiopronin; Tiopronin (Thiola); N-(2-巯基丙酰)-甘氨酸; 硫普罗宁; 硫普罗宁; N-(2-巯基丙酰)-甘氨酸

Database IDs

• CAS Number: 1953-02-2
• EC Number: 217-778-4
• MDL Number: MFCD00004861
• Beilstein Number: 1859822
• PubChem SID: 162228427; 24860692; 24882897; 24897101
• PubChem CID: 5483

CALCULATED PROPERTIES

• Acid pKa: 3.8646846
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.1731064
• LogD (pH = 7.4): -3.7692945
• Log P: -0.53329927
• Molar Refractivity: 37.7703 cm^3
• Polarizability: 14.848331 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 78-80°C; 93-98 °C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: MC0596500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98.0% (RT); 99%
• Grade: purum; VETRANAL™, analytical standard
• Salt Data: Free Base
• Linear Formula: CH3CH(SH)CONHCH2COOH

DETAILS

Sigma Aldrich - M6635

Biochem/physiol Actions
N-(2-Mercaptopropionyl)glycine is a free radical scavenger.

Sigma Aldrich - 63794

Other Notes
Minimizes the effect of the chemical carcinogen DMBA (dimethylbenzanthracene) in regenerating mouse liver1; Significantly stimulates NADPH-dependent lipid peroxidation by rat liver microsomes2

Sigma Aldrich - 33986

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T444780

It is used as antidote against heavy metal poisoning; hepatoprotectant; mucolytic.

REFERENCES

• Capasso, F., et al.: Agents Actions, 11, 741 (1981)
• Amor, B., et al.: Arthritis Rheum., 25, 698 (1981)
• Ichida, F., et al.: J. Int. Med. Res., 10, 325 (1981)