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

• ChemBase ID: 166372
• Molecular Formular: C29H52ClN3O6
• Molecular Mass: 574.19268
• Monoisotopic Mass: 573.35446408
• SMILES: c1(c(ccc(c1)C[C@@H](C[C@@H]([C@H](C[C@H](C(=O)NCC(C(=O)N)(C)C)C(C)C)O)N)C(C)C)OC)OCCCO.Cl
• Canonical SMILES: OCCCOc1cc(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/C29H51N3O6.ClH/c1-18(2)21(13-20-9-10-25(37-7)26(14-20)38-12-8-11-33)15-23(30)24(34)16-22(19(3)4)27(35)32-17-29(5,6)28(31)36;/h9-10,14,18-19,21-24,33-34H,8,11-13,15-17,30H2,1-7H3,(H2,31,36)(H,32,35);1H/t21-,22-,23-,24-;/m0./s1
• InChIKey: KYYXOXFOABSMRC-JPIABUGISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[3-(3-hydroxypropoxy)-4-methoxyphenyl]methyl}-8-methyl-2-(propan-2-yl)nonanamide hydrochloride
• IUPAC Traditional name: (2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[3-(3-hydroxypropoxy)-4-methoxyphenyl]methyl}-2-isopropyl-8-methylnonanamide hydrochloride
• Synonyms: (αS,γS,δS,ζS)-δ-Amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-γ-hydroxy-3-(3-hydroxypropoxy)-4-methoxy-α,ζ-bis(1-methylethyl)benzeneoctanamide Hydrochloride; 3'-O-Desmethyl Aliskiren Hydrochloride

Database IDs

• PubChem SID: 162260505
• PubChem CID: 71315707

CALCULATED PROPERTIES

• Acid pKa: 14.537872
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.5138747
• LogD (pH = 7.4): 0.36149493
• Log P: 2.4813857
• Molar Refractivity: 149.5671 cm^3
• Polarizability: 59.153786 Å^3
• Polar Surface Area: 157.13 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290690

A metabolite of of the direct renin inhibitor Aliskiren (A536000).

REFERENCES

• Waldmeier, F. et al.: Drug Metab. Disp., 35, 1418 (2007)