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

• ChemBase ID: 178799
• Molecular Formular: C30H42N2O11
• Molecular Mass: 606.66128
• Monoisotopic Mass: 606.27886017
• 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)OCC
• Canonical SMILES: CCOC(=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/C30H42N2O11/c1-3-41-28(39)19(14-13-17-9-5-4-6-10-17)31-16(2)26(36)32-20-12-8-7-11-18(20)15-21(32)29(40)43-30-24(35)22(33)23(34)25(42-30)27(37)38/h4-6,9-10,16,18-25,30-31,33-35H,3,7-8,11-15H2,1-2H3,(H,37,38)/t16-,18+,19-,20-,21-,22-,23-,24+,25-,30-/m0/s1
• InChIKey: XIVXFEAPQLOONX-UCXQGGPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2S,3aR,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-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,3aR,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydroindole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Trandolapril Acyl-β-D-glucuronide, 85%

Database IDs

• CAS Number: 1260617-50-2
• PubChem SID: 164234709
• PubChem CID: 71752644

CALCULATED PROPERTIES

• Acid pKa: 3.13058
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.8006834
• LogD (pH = 7.4): -1.8565601
• Log P: -0.41366318
• Molar Refractivity: 148.0864 cm^3
• Polarizability: 59.865437 Å^3
• Polar Surface Area: 192.16 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T713510

A metabolite of Trandolapril; 5,6-analog of Ramipril glucuronide.