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

• ChemBase ID: 177347
• Molecular Formular: C29H40N2O11
• Molecular Mass: 592.6347
• Monoisotopic Mass: 592.26321011
• 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)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@@H]1OC(C(=O)O)[C@H](C([C@H]1O)O)O)C)CCc1ccccc1
• InChI: InChI=1S/C29H40N2O11/c1-3-40-27(38)18(13-12-16-8-5-4-6-9-16)30-15(2)25(35)31-19-11-7-10-17(19)14-20(31)28(39)42-29-23(34)21(32)22(33)24(41-29)26(36)37/h4-6,8-9,15,17-24,29-30,32-34H,3,7,10-14H2,1-2H3,(H,36,37)/t15-,17-,18-,19-,20-,21?,22-,23-,24?,29-/m0/s1
• InChIKey: ZJZVWDOXIZGYPD-XHPMATLTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S,6S)-6-[(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]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-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]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-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylate] β-D-Glucopyranuronic Acid; Ramipril Acyl-β-D-glucuronide, ~ 80% By HPLC

Database IDs

• CAS Number: 1357570-21-8
• PubChem SID: 164233257
• PubChem CID: 71751963

CALCULATED PROPERTIES

• Acid pKa: 3.13058
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.245252
• LogD (pH = 7.4): -2.3011289
• Log P: -0.85823184
• Molar Refractivity: 143.4854 cm^3
• Polarizability: 58.039436 Å^3
• Polar Surface Area: 192.16 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol Water
• Apperance: Pale Yellow Solid
• Melting Point: 128-130°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - R111005

A metabolite of Ramipril (R111000). This compound is not stable in an aqueous solution.