(2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-[(2H5)phenylsulfanyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 179649
• Molecular Formular: C15H19NO3S2
• Molecular Mass: 325.44626
• Monoisotopic Mass: 325.08063547
• SMILES: C1[C@H](C[C@H](N1C(=O)[C@@H](CS)C)C(=O)O)Sc1ccccc1
• Canonical SMILES: SC[C@H](C(=O)N1C[C@H](C[C@H]1C(=O)O)Sc1ccccc1)C
• InChI: InChI=1S/C15H19NO3S2/c1-10(9-20)14(17)16-8-12(7-13(16)15(18)19)21-11-5-3-2-4-6-11/h2-6,10,12-13,20H,7-9H2,1H3,(H,18,19)/t10-,12+,13+/m1/s1
• InChIKey: UQWLOWFDKAFKAP-WXHSDQCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-[(^2H₅)phenylsulfanyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-[(^2H₅)phenylsulfanyl]pyrrolidine-2-carboxylic acid
• Synonyms: (4S)-1-[(2S)-3-Mercapto-2-methyl-1-oxopropyl]-4-(phenyl-d5-thio)-L-proline; [1(R*),2α,4α]-1-(3-Mercapto-2-methyl-1-oxopropyl)-4-(phenyl-d5-thio)-L-proline; SQ 26333-d5; Zofenoprilat-d5

Database IDs

• PubChem SID: 164235559
• PubChem CID: 46783274

CALCULATED PROPERTIES

• Acid pKa: 3.911476
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.81910414
• LogD (pH = 7.4): -0.79468316
• Log P: 2.413754
• Molar Refractivity: 86.6838 cm^3
• Polarizability: 34.028233 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 60-62°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - Z587052

The active metabolite of Zofenopril, an ACE inhibitor.

REFERENCES

• Cushman, D., et al.: Br. J. Clin. Pharmacol., 28, 115S (1989)
• Kelly, J., et al.: Clin. Pharmacokinet., 19, 177 (1989)
• Liu, X., et al.: Cardiv. Drugs Ther., 6, 437 (1989)
• Marzo, A., et al.: Arzneim.- Forsch., 49, 992 (1989)
• Subissi, A., et al.: Cardiv