(2R,3aR,6aR)-1-[(2S)-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid

• ChemBase ID: 177350
• Molecular Formular: C21H28N2O5
• Molecular Mass: 388.45742
• Monoisotopic Mass: 388.19982201
• SMILES: c1cccc(c1)CC[C@@H](N[C@H](C(=O)N1[C@H]2[C@@H](C[C@@H]1C(=O)O)CCC2)C)C(=O)O
• Canonical SMILES: OC(=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/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15+,16+,17+,18+/m0/s1
• InChIKey: KEDYTOTWMPBSLG-CZIOMAOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3aR,6aR)-1-[(2S)-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
• IUPAC Traditional name: (2R,3aR,6aR)-1-[(2S)-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
• Synonyms: (2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid; HOE 498 Diacid; Ramipril Diacid; Ramipril Impurity E (EP),; Ramiprilat

Database IDs

• CAS Number: 87269-97-4
• PubChem SID: 164233260
• PubChem CID: 71751965

CALCULATED PROPERTIES

• Acid pKa: 3.1311913
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5305548
• LogD (pH = 7.4): -3.1913881
• Log P: -0.18361667
• Molar Refractivity: 101.6691 cm^3
• Polarizability: 40.29253 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R111010

A metabolite of Ramipril (R111000).

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)