(2R,3aS,7aS)-1-[(2S)-2-{[(2S)-1-oxo-1-(propan-2-yloxy)pentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

• ChemBase ID: 176389
• Molecular Formular: C20H34N2O5
• Molecular Mass: 382.49436
• Monoisotopic Mass: 382.2467722
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@@H](N2C(=O)[C@@H](N[C@@H](CCC)C(=O)OC(C)C)C)C(=O)O
• Canonical SMILES: CCC[C@@H](C(=O)OC(C)C)N[C@H](C(=O)N1[C@H]2CCCC[C@H]2C[C@@H]1C(=O)O)C
• InChI: InChI=1S/C20H34N2O5/c1-5-8-15(20(26)27-12(2)3)21-13(4)18(23)22-16-10-7-6-9-14(16)11-17(22)19(24)25/h12-17,21H,5-11H2,1-4H3,(H,24,25)/t13-,14-,15-,16-,17+/m0/s1
• InChIKey: CEIYXTQJLBUCRQ-QUSNUVHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3aS,7aS)-1-[(2S)-2-{[(2S)-1-oxo-1-(propan-2-yloxy)pentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
• IUPAC Traditional name: (2R,3aS,7aS)-1-[(2S)-2-{[(2S)-1-isopropoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydroindole-2-carboxylic acid
• Synonyms: (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-Methylethoxycarboxybutyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid; Perindoprilat Isopropyl Ester

Database IDs

• PubChem SID: 164232299
• PubChem CID: 71751534

CALCULATED PROPERTIES

• Acid pKa: 3.7860456
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.87940025
• LogD (pH = 7.4): -0.43044585
• Log P: 1.0475967
• Molar Refractivity: 100.1116 cm^3
• Polarizability: 40.165028 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P287540

An impurity of Perindopril (P287500).

REFERENCES

• Vincent, M., et al.: Drug Design Discovery, 9, 11 (1992)