(2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-2-(propan-2-yl)nonanamide hydrochloride

• ChemBase ID: 159651
• Molecular Formular: C30H54ClN3O6
• Molecular Mass: 588.21926
• Monoisotopic Mass: 587.37011414
• SMILES: c1(c(ccc(c1)C[C@@H](C[C@@H]([C@H](C[C@H](C(=O)NCC(C)(C)C(=O)N)C(C)C)O)N)C(C)C)OC)OCCCOC.Cl
• Canonical SMILES: COCCCOc1cc(ccc1OC)C[C@H](C(C)C)C[C@@H]([C@H](C[C@H](C(=O)NCC(C(=O)N)(C)C)C(C)C)O)N.Cl
• InChI: InChI=1S/C30H53N3O6.ClH/c1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36;/h10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35);1H/t22-,23-,24-,25-;/m0./s1
• InChIKey: BSJUIBZAXCXFMZ-NATPOTRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-2-(propan-2-yl)nonanamide hydrochloride
• IUPAC Traditional name: aliskiren hydrochloride
• Synonyms: (αS,γS,δS,zS)-δ-Amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,z-bis(1-methylethyl)benzeneoctanamide Hydrochloride; CGP 60536; CGP60536B; Rasilez Hydrochloride; SPP 100; Tekturna Hydrochloride; Aliskiren Hydrochloride

Database IDs

• CAS Number: 173399-03-6
• PubChem SID: 162253786
• PubChem CID: 23625795

CALCULATED PROPERTIES

• Acid pKa: 14.557217
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.12925176
• LogD (pH = 7.4): 1.0046214
• Log P: 3.1245122
• Molar Refractivity: 154.3183 cm^3
• Polarizability: 61.064808 Å^3
• Polar Surface Area: 146.13 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 76-78°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A536000

An orally active, synthetic nonpeptide renin inhibitor. Antihypertensive.

REFERENCES

• Lefevre, G., et al.: J. Immunoassay, 21, 65 (2000)
• Allikments, K., et al.: Curr. Opin. Invest. Drugs, 3, 1479 (2000)
• Wood, J.M., et al.: Biochem. Biophys. Res. Commun., 308, 698 (2000)
• Grandman, A.H., et al.: Circulation, 111, 1012 (2000)