3-{5-[(2S,4S,5S,7S)-4-amino-7-[(2-carbamoyl-2,2-dimethylethyl)carbamoyl]-5-hydroxy-2,7-bis(propan-2-yl)heptyl]-2-methoxyphenoxy}propanoic acid

• ChemBase ID: 166371
• Molecular Formular: C29H49N3O7
• Molecular Mass: 551.71526
• Monoisotopic Mass: 551.35705092
• 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)OCCC(=O)O
• Canonical SMILES: COc1ccc(cc1OCCC(=O)O)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
• InChI: InChI=1S/C29H49N3O7/c1-17(2)20(12-19-8-9-24(38-7)25(13-19)39-11-10-26(34)35)14-22(30)23(33)15-21(18(3)4)27(36)32-16-29(5,6)28(31)37/h8-9,13,17-18,20-23,33H,10-12,14-16,30H2,1-7H3,(H2,31,37)(H,32,36)(H,34,35)/t20-,21-,22-,23-/m0/s1
• InChIKey: WGLWFINTGGHHBQ-MLCQCVOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{5-[(2S,4S,5S,7S)-4-amino-7-[(2-carbamoyl-2,2-dimethylethyl)carbamoyl]-5-hydroxy-2,7-bis(propan-2-yl)heptyl]-2-methoxyphenoxy}propanoic acid
• IUPAC Traditional name: 3-{5-[(2S,4S,5S,7S)-4-amino-7-[(2-carbamoyl-2,2-dimethylethyl)carbamoyl]-5-hydroxy-2,7-diisopropylheptyl]-2-methoxyphenoxy}propanoic acid
• Synonyms: 3-[5-[(2S,4S,5S,7S)-4-amino-7-[[(3-Amino-2,2-dimethyl-3-oxopropyl)amino]carbonyl]-5-hydroxy-8-methyl-2-(1-methylethyl)nonyl]-2-methoxyphenoxy]propanoic Acid; 3'-Desmethoxy Aliskiren 3'-Carboxylic Acid

Database IDs

• CAS Number: 949925-75-1
• PubChem SID: 162260504
• PubChem CID: 71315706

CALCULATED PROPERTIES

• Acid pKa: 3.6337216
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.55912596
• LogD (pH = 7.4): 0.56122047
• Log P: 0.5627789
• Molar Refractivity: 149.1934 cm^3
• Polarizability: 59.06954 Å^3
• Polar Surface Area: 174.2 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290685

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

REFERENCES

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