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

• ChemBase ID: 178804
• Molecular Formular: C28H38N2O11
• Molecular Mass: 578.60812
• Monoisotopic Mass: 578.24756005
• SMILES: c1ccccc1CC[C@H](N[C@H](C(=O)N1[C@@H]2[C@@H](C[C@H]1C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)CCCC2)C)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](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)CCc1ccccc1
• InChI: InChI=1S/C28H38N2O11/c1-14(29-17(25(35)36)12-11-15-7-3-2-4-8-15)24(34)30-18-10-6-5-9-16(18)13-19(30)27(39)41-28-22(33)20(31)21(32)23(40-28)26(37)38/h2-4,7-8,14,16-23,28-29,31-33H,5-6,9-13H2,1H3,(H,35,36)(H,37,38)/t14-,16+,17-,18-,19-,20-,21-,22+,23-,28-/m0/s1
• InChIKey: ZEDQQJMZPSYJNF-DCEOHSSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydro-1H-indole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydroindole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Trandolaprilat Acyl-β-D-glucuronide, 65%

Database IDs

• CAS Number: 1260610-97-6
• PubChem SID: 164234714
• PubChem CID: 71752647

CALCULATED PROPERTIES

• Acid pKa: 2.8664758
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.4059613
• LogD (pH = 7.4): -4.8957024
• Log P: -1.6519425
• Molar Refractivity: 138.5687 cm^3
• Polarizability: 55.975544 Å^3
• Polar Surface Area: 203.16 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T713525

A metabolite of Trandolaprilat; 5,6-analog of Ramiprilat glucuronide.