(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl](2,5,5-2H3)pyrrolidine-2-carboxylic acid

• ChemBase ID: 163608
• Molecular Formular: C9H15NO3S
• Molecular Mass: 217.2853
• Monoisotopic Mass: 217.07726435
• SMILES: N1(CCC[C@H]1C(=O)O)C(=O)[C@@H](CS)C
• Canonical SMILES: SC[C@H](C(=O)N1CCC[C@H]1C(=O)O)C
• InChI: InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
• InChIKey: FAKRSMQSSFJEIM-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl](2,5,5-^2H₃)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl](2,5,5-^2H₃)pyrrolidine-2-carboxylic acid
• Synonyms: (2S)-1-(3-Marcapto-2-methyl-1-oxopionyl]-L-proline-2,5,5-d3; SQ-14225-d3; Captopril-d3

Database IDs

• PubChem SID: 162257743
• PubChem CID: 71314500

CALCULATED PROPERTIES

• Acid pKa: 4.018635
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.7646909
• LogD (pH = 7.4): -2.422175
• Log P: 0.72692126
• Molar Refractivity: 54.6349 cm^3
• Polarizability: 21.422962 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 103-104°C

DETAILS

Toronto Research Chemicals - C175752

Orally active angiotensin-converting enzyme (ACE) inhibitor.

REFERENCES

• Rubin, B., et al.: Eur. J Pharmacol., 51, 377 (1978)