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

• ChemBase ID: 168000
• Molecular Formular: C20H26N2O4
• Molecular Mass: 358.43144
• Monoisotopic Mass: 358.18925732
• SMILES: N1([C@@H](CCc2ccccc2)C(=O)OCC)C(=O)[C@H]2N(C(=O)[C@@H]1C)CCC2
• Canonical SMILES: CCOC(=O)[C@@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)CCC2)CCc1ccccc1
• InChI: InChI=1S/C20H26N2O4/c1-3-26-20(25)17(12-11-15-8-5-4-6-9-15)22-14(2)18(23)21-13-7-10-16(21)19(22)24/h4-6,8-9,14,16-17H,3,7,10-13H2,1-2H3/t14-,16-,17-/m0/s1
• InChIKey: BMZHNHHJUGMMLV-XIRDDKMYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 115729-52-7
• PubChem SID: 162262132
• PubChem CID: 14962498

CALCULATED PROPERTIES

• Acid pKa: 19.764711
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.0736482
• LogD (pH = 7.4): 2.0736482
• Log P: 2.0736482
• Molar Refractivity: 96.4968 cm^3
• Polarizability: 37.85452 Å^3
• Polar Surface Area: 66.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E555270

An impurity of Enalapril (E555250).

REFERENCES

• Pilatti, C. et al.: Drug Dev. Ind. Pharm., 25, 807 (1999)
• Toporisic, R. et al.: J. Pharmac. Biomed. Anal., 52, 294 (1999)