(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid hydrate

• ChemBase ID: 178802
• Molecular Formular: C22H32N2O6
• Molecular Mass: 420.49928
• Monoisotopic Mass: 420.22603675
• SMILES: c1ccccc1CC[C@H](N[C@H](C(=O)N1[C@@H]2[C@@H](C[C@H]1C(=O)O)CCCC2)C)C(=O)O.O
• Canonical SMILES: C[C@@H](C(=O)N1[C@H]2CCCC[C@@H]2C[C@H]1C(=O)O)N[C@H](C(=O)O)CCc1ccccc1.O
• InChI: InChI=1S/C22H30N2O5.H2O/c1-14(23-17(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-18-10-6-5-9-16(18)13-19(24)22(28)29;/h2-4,7-8,14,16-19,23H,5-6,9-13H2,1H3,(H,26,27)(H,28,29);1H2/t14-,16+,17-,18-,19-;/m0./s1
• InChIKey: RCVUTQVXMHPLKS-CNTNIUBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid hydrate
• IUPAC Traditional name: (2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydroindole-2-carboxylic acid hydrate
• Synonyms: (2S,3aR,7aS)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid Monohydrate; Trandolaprilate Monohydrate; RU-44404; RU 44403; Trandolaprilat Monohydrate

Database IDs

• CAS Number: 951393-55-8
• PubChem SID: 164234712
• PubChem CID: 45040562

CALCULATED PROPERTIES

• Acid pKa: 3.126622
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.0577757
• LogD (pH = 7.4): -2.7354684
• Log P: 0.18969378
• Molar Refractivity: 106.2701 cm^3
• Polarizability: 42.127018 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 132-134°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T713520

A metabolite of Trandolapril, an antihypertensive.

REFERENCES

• Blankley, C.J., et al.: J. Med. Chem., 30, 992 (1987)