(1S,9S)-9-{[(1S)-1-carboxy-3-phenylpropyl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

• ChemBase ID: 164757
• Molecular Formular: C20H27N3O5
• Molecular Mass: 389.44548
• Monoisotopic Mass: 389.19507098
• SMILES: [C@@H]1(CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)N[C@@H](CCc1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](N[C@H]1CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C20H27N3O5/c24-18-15(8-4-12-22-13-5-9-17(20(27)28)23(18)22)21-16(19(25)26)11-10-14-6-2-1-3-7-14/h1-3,6-7,15-17,21H,4-5,8-13H2,(H,25,26)(H,27,28)/t15-,16-,17-/m0/s1
• InChIKey: UVAUYSRYXACKSC-ULQDDVLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S)-9-{[(1S)-1-carboxy-3-phenylpropyl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
• IUPAC Traditional name: (1S,9S)-9-{[(1S)-1-carboxy-3-phenylpropyl]amino}-10-oxo-octahydropyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
• Synonyms: (1S,9S)-9-[[(1S)-1-Carboxy-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid; Ro 31-3113; Cilazaprilat

Database IDs

• CAS Number: 90139-06-3
• PubChem SID: 162258892
• PubChem CID: 64766

CALCULATED PROPERTIES

• Acid pKa: 3.1717684
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.5639658
• LogD (pH = 7.4): -4.29429
• Log P: -1.3631841
• Molar Refractivity: 101.046 cm^3
• Polarizability: 39.89213 Å^3
• Polar Surface Area: 110.18 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 223-225°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C441210

The active metabolite of Cilazapril. An ACE inhibitor. Antihypertensive.

REFERENCES

• Natoff, I.L., et al.: J. Cardiovasc. Pharmacol., 7, 569 (1985)
• Szucs, T., et al.: Drugs, 41, Suppl.1, 18 (1985)
• Pordy, R.C., et al.: Cardiology, 86, 41 (1985)