(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(2H5)phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid

• ChemBase ID: 177346
• Molecular Formular: C23H32N2O5
• Molecular Mass: 416.51058
• Monoisotopic Mass: 416.23112213
• SMILES: c1ccccc1CC[C@H](N[C@H](C(=O)N1[C@@H]2[C@H](C[C@H]1C(=O)O)CCC2)C)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
• InChIKey: HDACQVRGBOVJII-JBDAPHQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
• IUPAC Traditional name: (2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
• Synonyms: (2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-(phenyl-d5)propyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid; Altace-d5; Cardace-d5; Delix-d5; HOE-498-d5; Pramace-d5; Ramace-d5; Unipril-d5; Ramipril-d5

Database IDs

• PubChem SID: 164233256
• PubChem CID: 46782850

CALCULATED PROPERTIES

• Acid pKa: 3.74893
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2103999
• LogD (pH = 7.4): -0.18272619
• Log P: 1.4738114
• Molar Refractivity: 111.1868 cm^3
• Polarizability: 44.232243 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 104-106°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R111002

A labelled antihypertensive. An angiotensin converting enzyme (ACE) inhibitor, converted to active, diacid metabolite.

REFERENCES

• Teetz, V., et al.: Arzneim.-Forsch., 34, 1399 (1984)
• Ruggenenti, P., et al.: Lancet, 352, (1984)
• Bosch, J., et al.: Br. Med. J., 324, 1 (1984)