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

• ChemBase ID: 176386
• Molecular Formular: C19H30N2O4
• Molecular Mass: 350.4525
• Monoisotopic Mass: 350.22055745
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@@H]1N2C(=O)[C@@H](N(C1=O)[C@@H](CCC)C(=O)OCC)C
• Canonical SMILES: CCOC(=O)[C@@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)C[C@H]1[C@@H]2CCCC1)CCC
• InChI: InChI=1S/C19H30N2O4/c1-4-8-15(19(24)25-5-2)20-12(3)17(22)21-14-10-7-6-9-13(14)11-16(21)18(20)23/h12-16H,4-11H2,1-3H3/t12-,13-,14-,15-,16-/m0/s1
• InChIKey: BSZZSBSELAVBAG-QXKUPLGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-[(3S,5aS,9aS,10aS)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]pentanoate
• IUPAC Traditional name: ethyl (2S)-2-[(3S,5aS,9aS,10aS)-3-methyl-1,4-dioxo-octahydro-3H-piperazino[1,2-a]indol-2-yl]pentanoate
• Synonyms: (αS,3S,5aS,9aS,10aS)-Decahydro-3-methyl-1,4-dioxo-α-propylpyrazino[1,2-a]indole-2(1H)-acetic Acid Ethyl Ester; [3S-[2(R*),3α,5aβ,9aβ,10aβ]]-Decahydro-3-methyl-1,4-dioxo-α-propylpyrazino[1,2-a]indole-2(1H)-acetic Acid Ethyl Ester; Perindopril Diketopiperazine

Database IDs

• CAS Number: 129970-98-5
• PubChem SID: 164232296
• PubChem CID: 57703964

CALCULATED PROPERTIES

• Acid pKa: 19.624647
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.2247572
• LogD (pH = 7.4): 2.2247572
• Log P: 2.2247572
• Molar Refractivity: 92.615 cm^3
• Polarizability: 36.759365 Å^3
• Polar Surface Area: 66.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 98-101°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P287525

Perindopril Diketopiperazine is an impurity of Perindopril (P287500).

REFERENCES

• Koenigbauer, M., et al.: Pharm. Res., 11, 777 (1994)
• Andres, C., et al.: Int. J. Pharm., 218, 153 (1994)
• Chadha, R., et al.: Pharmazie, 58, 631 (1994)