(3S,5S,6S)-6-[(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177354
• Molecular Formular: C27H36N2O11
• Molecular Mass: 564.58154
• Monoisotopic Mass: 564.23190998
• SMILES: c1ccccc1CC[C@H](N[C@H](C(=O)N1[C@@H]2[C@H](C[C@H]1C(=O)O[C@@H]1OC([C@@H](O)C(O)[C@H]1O)C(=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@@H]1OC(C(=O)O)[C@H](C([C@H]1O)O)O)C)CCc1ccccc1
• InChI: InChI=1S/C27H36N2O11/c1-13(28-16(24(34)35)11-10-14-6-3-2-4-7-14)23(33)29-17-9-5-8-15(17)12-18(29)26(38)40-27-21(32)19(30)20(31)22(39-27)25(36)37/h2-4,6-7,13,15-22,27-28,30-32H,5,8-12H2,1H3,(H,34,35)(H,36,37)/t13-,15-,16-,17-,18-,19?,20-,21-,22?,27-/m0/s1
• InChIKey: AEFYTLSQBCRSSC-ZCNCQCNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S,6S)-6-[(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (3S,5S,6S)-6-[(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylate] β-D-Glucopyranuronic Acid; Ramiprilat Acyl-β-D-glucuronide >65%

Database IDs

• CAS Number: 1357570-22-9
• PubChem SID: 164233264
• PubChem CID: 71751969

CALCULATED PROPERTIES

• Acid pKa: 2.8800535
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.8342826
• LogD (pH = 7.4): -5.3326144
• Log P: -2.0969505
• Molar Refractivity: 133.9677 cm^3
• Polarizability: 54.152622 Å^3
• Polar Surface Area: 203.16 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >240°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - R111020

A metabolite of Ramipril (R111000).This product contains an unquantified amount of ramiprilat.