sodium (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate

• ChemBase ID: 179648
• Molecular Formular: C15H18NNaO3S2
• Molecular Mass: 347.42809
• Monoisotopic Mass: 347.06257972
• SMILES: C1[C@H](C[C@H](N1C(=O)[C@@H](CS)C)C(=O)[O-])Sc1ccccc1.[Na+]
• Canonical SMILES: SC[C@H](C(=O)N1C[C@H](C[C@H]1C(=O)[O-])Sc1ccccc1)C.[Na+]
• InChI: InChI=1S/C15H19NO3S2.Na/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);/q;+1/p-1/t10-,12+,13+;/m1./s1
• InChIKey: GQXRQXSQRGQHKC-QNULRCCRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate
• IUPAC Traditional name: sodium (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate
• Synonyms: (4S)-1-[(2S)-3-Mercapto-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline Sodium; [1(R*),2α,4α]-1-(3-Mercapto-2-methyl-1-oxopropyl)-4-(phenylthio)-L-proline Sodium; Zofenoprilat Sodium Salt (90%)

Database IDs

• PubChem SID: 164235558
• PubChem CID: 57347771

CALCULATED PROPERTIES

• Acid pKa: 3.911476
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.81910414
• LogD (pH = 7.4): -0.79468316
• Log P: 2.413754
• Molar Refractivity: 97.5209 cm^3
• Polarizability: 33.896847 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: >148°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - Z587050

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