ethyl (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]-4-phenylbutanoate

• ChemBase ID: 178800
• Molecular Formular: C24H32N2O4
• Molecular Mass: 412.52188
• Monoisotopic Mass: 412.23620751
• SMILES: N12[C@@H]3[C@@H](C[C@H]1C(=O)N([C@H](C2=O)C)[C@H](CCc1ccccc1)C(=O)OCC)CCCC3
• Canonical SMILES: CCOC(=O)[C@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)C[C@@H]1[C@@H]2CCCC1)CCc1ccccc1
• InChI: InChI=1S/C24H32N2O4/c1-3-30-24(29)20(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-19-12-8-7-11-18(19)15-21(26)23(25)28/h4-6,9-10,16,18-21H,3,7-8,11-15H2,1-2H3/t16-,18+,19-,20+,21-/m0/s1
• InChIKey: AKUCMKAPHCGRFV-OSTWSGHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]-4-phenylbutanoate
• IUPAC Traditional name: ethyl (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-octahydro-3H-piperazino[1,2-a]indol-2-yl]-4-phenylbutanoate
• Synonyms: (αS,3S,5aS,9aR,10aS)-Decahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)pyrazino[1,2-a]indole-2(1H)-acetic Acid Ethyl Ester; RU 46178; Trandolapril Diketopiperazine

Database IDs

• CAS Number: 149881-40-3
• PubChem SID: 164234710
• PubChem CID: 71752645

CALCULATED PROPERTIES

• Acid pKa: 19.624527
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.3585613
• LogD (pH = 7.4): 3.3585613
• Log P: 3.3585613
• Molar Refractivity: 112.71 cm^3
• Polarizability: 44.48192 Å^3
• Polar Surface Area: 66.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T713515

Trandolapril Diketopiperazine is a metabolite of the antihypertensive Trandolapril (Ru44570) (T713500), an angiotensin-converting enzyme inhibitor.

REFERENCES

• Bakshi, M., et al.: J. Pharm. Biomed. Anal., 28, 1011 (2002)
• Cedrowska, I., et al.: Acta Pol. Pharm., 60, 141 (2002)
• Singh, S., et al.: J. Pharm. Biomed. Anal., 41, 1037 (2002)