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

• ChemBase ID: 176387
• Molecular Formular: C17H28N2O5
• Molecular Mass: 340.41462
• Monoisotopic Mass: 340.19982201
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@@H](N2C(=O)[C@@H](N[C@@H](CCC)C(=O)O)C)C(=O)O
• Canonical SMILES: CCC[C@@H](C(=O)O)N[C@H](C(=O)N1[C@H]2CCCC[C@H]2C[C@@H]1C(=O)O)C
• InChI: InChI=1S/C17H28N2O5/c1-3-6-12(16(21)22)18-10(2)15(20)19-13-8-5-4-7-11(13)9-14(19)17(23)24/h10-14,18H,3-9H2,1-2H3,(H,21,22)(H,23,24)/t10-,11-,12-,13-,14+/m0/s1
• InChIKey: ODAIHABQVKJNIY-HTVCTNPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3aS,7aS)-1-[(2S)-2-{[(1S)-1-carboxybutyl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
• IUPAC Traditional name: (2R,3aS,7aS)-1-[(2S)-2-{[(1S)-1-carboxybutyl]amino}propanoyl]-octahydroindole-2-carboxylic acid
• Synonyms: (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-Carboxybutyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid; [2S-[1[R*(R*)],2α,3aβ,7aβ]]-1-[2-[(1-Carboxybutyl)amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid; S 9780; Perindoprilat

Database IDs

• CAS Number: 95153-31-4
• PubChem SID: 164232297
• PubChem CID: 29986327

CALCULATED PROPERTIES

• H Donor: 3
• LogD (pH = 5.5): -2.2150965
• LogD (pH = 7.4): -3.8784485
• Log P: -0.8543393
• Molar Refractivity: 86.1751 cm^3
• Polarizability: 34.427002 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 3.076256
• H Acceptors: 6

PROPERTIES

Physical Property

• Solubility: Ethanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 153-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P287530

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

REFERENCES

• Pascard, C., et al.: J. Med. Chem., 34, 663 (1991)