(8R)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

• ChemBase ID: 177853
• Molecular Formular: C22H30N2O5S2
• Molecular Mass: 466.614
• Monoisotopic Mass: 466.15961407
• SMILES: c1cccc(c1)CC[C@H](N[C@H](C(=O)N1[C@H](CC2(C1)SCCS2)C(=O)O)C)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)N1CC2(C[C@@H]1C(=O)O)SCCS2)C)CCc1ccccc1
• InChI: InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18+/m0/s1
• InChIKey: HRWCVUIFMSZDJS-RYQLBKOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
• IUPAC Traditional name: (8R)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
• Synonyms: (8S)-7-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic Acid Monohydrochloride; Renormax; Renpress; Sandopril; TI 211-950; Spirapril Hydrochloride

Database IDs

• CAS Number: 94841-17-5
• PubChem SID: 164233763
• PubChem CID: 71752232

CALCULATED PROPERTIES

• Acid pKa: 3.6249576
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.301563
• LogD (pH = 7.4): -0.0290567
• Log P: 1.6036346
• Molar Refractivity: 121.9396 cm^3
• Polarizability: 48.518734 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 161-163°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S682500

Angiotensin-converting enzyme (ACE) inhibior. Antihypertensive.

REFERENCES

• Smith, E.M., et al.: J. Med. Chem., 32, 1600(1989)
• Hossein-Nia, M., et al.: Ther. Drug Monit., 14, 234 (1989)
• Reams, G.P., et al.: J. Clin. Pharmacol., 33, 348 (1989)