(2S,3S,4S,5R,6S)-6-[(2S,3aS,7aS)-1-(2-{[(1S)-1-carboxybutyl]amino}(2H4)propanoyl)-octahydro-1H-indole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176391
• Molecular Formular: C23H36N2O11
• Molecular Mass: 516.53874
• Monoisotopic Mass: 516.23190998
• 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(N[C@@H](CCC)C(=O)O)C
• Canonical SMILES: CCC[C@@H](C(=O)O)NC(C(=O)N1[C@@H](C[C@H]2[C@@H]1CCCC2)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C23H36N2O11/c1-3-6-12(20(30)31)24-10(2)19(29)25-13-8-5-4-7-11(13)9-14(25)22(34)36-23-17(28)15(26)16(27)18(35-23)21(32)33/h10-18,23-24,26-28H,3-9H2,1-2H3,(H,30,31)(H,32,33)/t10?,11-,12-,13-,14-,15-,16-,17+,18-,23-/m0/s1
• InChIKey: YROROJVGTQGFDB-SODUADHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2S,3aS,7aS)-1-(2-{[(1S)-1-carboxybutyl]amino}(^2H₄)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-(2-{[(1S)-1-carboxybutyl]amino}(^2H₄)propanoyl)-octahydroindole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Perindoprilat-d4 Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 164232301
• PubChem CID: 71751536

CALCULATED PROPERTIES

• Acid pKa: 2.831777
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -4.576089
• LogD (pH = 7.4): -6.036831
• Log P: -2.7842913
• Molar Refractivity: 118.4737 cm^3
• Polarizability: 48.335915 Å^3
• Polar Surface Area: 203.16 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >300°C

DETAILS

Toronto Research Chemicals - P287562

A labelled metabolite of Perindoprilat, an angiotensin-converting enzyme (ACE) inhibitor.