ethyl (2R)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.02,6]dodecan-10-yl]-4-phenylbutanoate

• ChemBase ID: 177349
• Molecular Formular: C23H30N2O4
• Molecular Mass: 398.4953
• Monoisotopic Mass: 398.22055745
• SMILES: N12[C@@H](C[C@H]3[C@@H]2CCC3)C(=O)N([C@H](C1=O)C)[C@H](CCc1ccccc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@H](N1C(=O)[C@@H]2C[C@H]3[C@@H](N2C(=O)[C@@H]1C)CCC3)CCc1ccccc1
• InChI: InChI=1S/C23H30N2O4/c1-3-29-23(28)19(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-18-11-7-10-17(18)14-20(25)22(24)27/h4-6,8-9,15,17-20H,3,7,10-14H2,1-2H3/t15-,17-,18-,19+,20-/m0/s1
• InChIKey: KOVMAAYRBJCASY-XCZFOBESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.0^2,^6]dodecan-10-yl]-4-phenylbutanoate
• IUPAC Traditional name: ethyl (2R)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.0^2,^6]dodecan-10-yl]-4-phenylbutanoate
• Synonyms: (αS,3S,5aS,8aS,9aS)-Decahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazine-2-acetic Acid Ethyl Ester; [3S-[2(R*),3α,5aβ,8aβ,9aβ]]-Decahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazine-2-acetic Acid Ethyl Ester; Ramipril Diketopiperazine

Database IDs

• CAS Number: 108731-95-9
• PubChem SID: 164233259
• PubChem CID: 29986817

CALCULATED PROPERTIES

• Acid pKa: 19.624525
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.9139926
• LogD (pH = 7.4): 2.9139926
• Log P: 2.9139926
• Molar Refractivity: 108.109 cm^3
• Polarizability: 42.643845 Å^3
• Polar Surface Area: 66.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R111008

A metabolite of Ramipril (R111000).

REFERENCES

• Tabata, S., et al.: J. Biopharm. Sci., 1, 235 (1990)