(2S,3S,4S,5R,6S)-6-[(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176380
• Molecular Formular: C25H40N2O11
• Molecular Mass: 544.5919
• Monoisotopic Mass: 544.26321011
• SMILES: [C@H]12[C@H](CCCC1)N([C@@H](C2)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(=O)[C@@H](N[C@@H](CCC)C(=O)OCC)C
• Canonical SMILES: CCC[C@@H](C(=O)OCC)N[C@H](C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C25H40N2O11/c1-4-8-14(23(34)36-5-2)26-12(3)21(31)27-15-10-7-6-9-13(15)11-16(27)24(35)38-25-19(30)17(28)18(29)20(37-25)22(32)33/h12-20,25-26,28-30H,4-11H2,1-3H3,(H,32,33)/t12-,13-,14-,15-,16-,17-,18-,19+,20-,25-/m0/s1
• InChIKey: VEYBPHDESXGJIN-STTHWTIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydroindole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Perindopril Acyl-β-D-glucuronide

Database IDs

• CAS Number: 120398-66-5
• PubChem SID: 164232290
• PubChem CID: 71751527

CALCULATED PROPERTIES

• Acid pKa: 3.1324174
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.9546844
• LogD (pH = 7.4): -2.9710321
• Log P: -1.718661
• Molar Refractivity: 127.9914 cm^3
• Polarizability: 52.20836 Å^3
• Polar Surface Area: 192.16 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 133-137°C

Safety Information

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

DETAILS

Toronto Research Chemicals - P287510

A metabolite of Perindopril, an angiotensin-converting enzyme (ACE) inhibitor. This compound is not stable in an aqueous solution.