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

• ChemBase ID: 177358
• 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-ZMHJYQQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aR,6aR)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
• IUPAC Traditional name: (2S,3aR,6aR)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
• Synonyms: (2R,3aR,6aR)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid; [2R-[1[S*(S*)],2α,3aβ,6aβ]]-1-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid; (2R,3aR,6aR)-Ramipril

Database IDs

• CAS Number: 129939-63-5
• PubChem SID: 164233268
• PubChem CID: 53870828

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: 44.21084 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R111035

An isomer of the angiotensin-converting enzyme (ACE) inhibitor Ramipril (R111000). Ramipril impurity N.

REFERENCES

• Hogan, B.L. et al.: J. Pharmac. Biomed. Anal., 23, 637 (2000)
• Ito, M. et al.: J. Liq. Chrom., 13, 991 (2000)