(2R,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

• ChemBase ID: 176375
• Molecular Formular: C19H32N2O5
• Molecular Mass: 368.46778
• Monoisotopic Mass: 368.23112213
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@@H](N2C(=O)[C@@H](N[C@@H](CCC)C(=O)OCC)C)C(=O)O
• Canonical SMILES: CCC[C@@H](C(=O)OCC)N[C@H](C(=O)N1[C@H]2CCCC[C@H]2C[C@@H]1C(=O)O)C
• InChI: InChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16+/m0/s1
• InChIKey: IPVQLZZIHOAWMC-UVPYHEFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
• IUPAC Traditional name: (2R,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydroindole-2-carboxylic acid
• Synonyms: (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid; [2S-[1[R*(R*)],2α,3aβ,7aβ]]-1-[2-[[1-(Ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid; McN-A 2833; S 9490; Perindopril

Database IDs

• CAS Number: 82834-16-0
• PubChem SID: 164232285
• PubChem CID: 29986318

CALCULATED PROPERTIES

• Acid pKa: 3.7860548
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.4626669
• LogD (pH = 7.4): -0.8469951
• Log P: 0.63074386
• Molar Refractivity: 95.6928 cm^3
• Polarizability: 38.332016 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: Light Pink Solid
• Melting Point: 100-101°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P287500

An angiotensin-converting enzyme (ACE) inhibitor. Antihypertensive.

REFERENCES

• Lees, K.R., et al.: Brit. J. Clin. Pharmacol., 23, 159 (1987)
• Morgan, T., et al.: J. Cardiovasc. Pharmacol., 10, Supp. 7, S116, (1987)