2-(2-benzyl-3-sulfanylpropanamido)acetic acid

• ChemBase ID: 103788
• Molecular Formular: C12H15NO3S
• Molecular Mass: 253.3174
• Monoisotopic Mass: 253.07726435
• SMILES: OC(=O)CNC(=O)C(CS)Cc1ccccc1
• Canonical SMILES: SCC(C(=O)NCC(=O)O)Cc1ccccc1
• InChI: InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)
• InChIKey: LJJKNPQAGWVLDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-benzyl-3-sulfanylpropanamido)acetic acid
• IUPAC Traditional name: thiorphan
• Synonyms: (±)-N-(3-Mercapto-2-benzylpropionyl)glycine; DL-3-Mercapto-2-benzylpropanoylglycine; DL-Thiorphan; N-[2-(Mercaptomethyl)-1-oxo-3-phenylpropyl]glycine; 2-Mercaptomethyl-3-phenylpropionylaminoacetic Acid; D,L-3-Mercapto-2-benzylpropanoylglycine; (+/-)-Thiorphan; DL-3-Mercapto-2-benzyl-propanoyl]-glycine; DL-THIORPHAN; Thiorphan

Database IDs

• CAS Number: 76721-89-6
• MDL Number: MFCD00058435
• Beilstein Number: 4872101
• PubChem SID: 162091379; 24278747
• PubChem CID: 3132
• CHEMBL: 10247
• Chemspider ID: 3020
• DrugBank ID: DB08626
• Wikipedia Title: Thiorphan

CALCULATED PROPERTIES

• Acid pKa: 4.017452
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.028880706
• LogD (pH = 7.4): -1.6859314
• Log P: 1.4638641
• Molar Refractivity: 67.1479 cm^3
• Polarizability: 26.171062 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; ethanol: soluble50 mg/mL, clear, colorless; Methanol
• Apperance: Off-White Solid
• Melting Point: 138-140 °C; 138-140°C

Safety Information

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

Pharmacology Properties

• Gene Information: human ... ACE(1636), ECE1(1889)rat ... Ace(24310), Mme(24590)

Product Information

• Purity: ≥98% (TLC); ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C12H15NO3S

DETAILS

MP Biomedicals - 02152841

A potent and specific enkephalinase inhibitor with antinociceptive activity.

Sigma Aldrich - T6031

Biochem/physiol Actions
Enkephalinase inhibitor.

Sigma Aldrich - 89035

Biochem/physiol Actions
Enkephalinase inhibitor.
Other Notes
Enkephalinase inhibitor1

Toronto Research Chemicals - T369500

The active metabolite of Racecadotril (R070600).

REFERENCES

• Roques, B.P., et al., Nature, 288: 286, (1980).
• Roques, B.P., et al, Life Sci., 31: 1749, (1982).
• Evans, D.A., et al., J. Org. Chem., 50: 1830, (1985).
• Roques, B.P., et al.: Nature, 288, 286 (1980)
• Tiraboschi, G., et al.: Protein Engineering, 12, 2, 141 (1999)