calcium bis((2R,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate)

• ChemBase ID: 179645
• Molecular Formular: C44H44CaN2O8S4
• Molecular Mass: 897.16676
• Monoisotopic Mass: 896.16064136
• SMILES: c1cccc(c1)C(=O)SC[C@H](C(=O)N1C[C@H](C[C@@H]1C(=O)[O-])Sc1ccccc1)C.[Ca+2].c1cccc(c1)C(=O)SC[C@H](C(=O)N1C[C@H](C[C@@H]1C(=O)[O-])Sc1ccccc1)C
• Canonical SMILES: O=C(N1C[C@H](C[C@@H]1C(=O)[O-])Sc1ccccc1)[C@@H](CSC(=O)c1ccccc1)C.O=C(N1C[C@H](C[C@@H]1C(=O)[O-])Sc1ccccc1)[C@@H](CSC(=O)c1ccccc1)C.[Ca+2]
• InChI: InChI=1S/2C22H23NO4S2.Ca/c2*1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17;/h2*2-11,15,18-19H,12-14H2,1H3,(H,25,26);/q;;+2/p-2/t2*15-,18+,19-;/m11./s1
• InChIKey: NSYUKKYYVFVMST-GXZDBRSVSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium bis((2R,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate)
• IUPAC Traditional name: calcium bis((2R,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate)
• Synonyms: [1(S),4(S)]-1-(3-Mercapto-2-methyl-1-oxopropyl)-4-phenyl-thio-L-proline-S-benzoyl Ester Calcium Salt; Bifril-d5; Zofenil; Zofenopril Calcium Salt

Database IDs

• CAS Number: 81938-43-4
• PubChem SID: 164235555
• PubChem CID: 71753025

CALCULATED PROPERTIES

• Acid pKa: 3.5040753
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.32077
• LogD (pH = 7.4): 0.9343686
• Log P: 4.308536
• Molar Refractivity: 127.6592 cm^3
• Polarizability: 45.4219 Å^3
• Polar Surface Area: 77.51 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White to Off-White Solid
• Melting Point: 249-251°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Z587000

Angiotensin-converting enzyme ACE inhibitor. A prodrug that is de-esterified to the active inhibitor, the sulfhydryl group containing metabolite, Zofenoprilat.

REFERENCES

• Gorren, A., et al.: Biochem. J., 331, 801 (1998)
• Subissi, A., et al.: Cardivascular Drug Reviews, 17, 2 (1998)
• Marchand, C., et al.: Mol. Pharmacol., 64, 600 (1998)
• Maurin, C., et al.: J. Med. Chem., 47, 5583 (1998)