(2S)-2-[(3S,8aS)-3-methyl-1,4-dioxo-octahydropyrrolo[1,2-a]piperazin-2-yl]-4-phenylbutanoic acid

• ChemBase ID: 168001
• Molecular Formular: C18H22N2O4
• Molecular Mass: 330.37828
• Monoisotopic Mass: 330.15795719
• SMILES: N1([C@@H](CCc2ccccc2)C(=O)O)C(=O)[C@H]2N(C(=O)[C@@H]1C)CCC2
• Canonical SMILES: OC(=O)[C@@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)CCC2)CCc1ccccc1
• InChI: InChI=1S/C18H22N2O4/c1-12-16(21)19-11-5-8-14(19)17(22)20(12)15(18(23)24)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15H,5,8-11H2,1H3,(H,23,24)/t12-,14-,15-/m0/s1
• InChIKey: PDBULCBUWNSQTL-QEJZJMRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3S,8aS)-3-methyl-1,4-dioxo-octahydropyrrolo[1,2-a]piperazin-2-yl]-4-phenylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(3S,8aS)-3-methyl-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]piperazin-2-yl]-4-phenylbutanoic acid
• Synonyms: (αS,3S,8aS)-Hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)pyrrolo[1,2-a]pyrazine-2(1H)-acetic Acid; [3S-[2(R*),3α,8aβ]]-Hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)pyrrolo[1,2-a]pyrazine-2(1H)-acetic Acid; Enalapril Diketopiperazine Acid

Database IDs

• CAS Number: 115623-21-7
• PubChem SID: 162262133
• PubChem CID: 71316330

CALCULATED PROPERTIES

• Acid pKa: 3.9638495
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.026727565
• LogD (pH = 7.4): -1.6084902
• Log P: 1.5709462
• Molar Refractivity: 86.9791 cm^3
• Polarizability: 33.9373 Å^3
• Polar Surface Area: 77.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E555275

Enalapril Diketopiperazine Acid is a degradation product of Enalapril (E555250).

REFERENCES

• Bhardwaj, S. et al.: J. Pharmac. Biomed. Anal., 46, 113 (2008)