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

• ChemBase ID: 177356
• Molecular Formular: C21H26N2O4
• Molecular Mass: 370.44214
• Monoisotopic Mass: 370.18925732
• SMILES: N12[C@@H](C[C@H]3[C@@H]2CCC3)C(=O)N([C@H](C1=O)C)[C@H](CCc1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](N1C(=O)[C@@H]2C[C@H]3[C@@H](N2C(=O)[C@@H]1C)CCC3)CCc1ccccc1
• InChI: InChI=1S/C21H26N2O4/c1-13-19(24)23-16-9-5-8-15(16)12-18(23)20(25)22(13)17(21(26)27)11-10-14-6-3-2-4-7-14/h2-4,6-7,13,15-18H,5,8-12H2,1H3,(H,26,27)/t13-,15-,16-,17+,18-/m0/s1
• InChIKey: DZRWPCCIYKIPJW-FUJDEKNSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.0^2,^6]dodecan-10-yl]-4-phenylbutanoic acid
• IUPAC Traditional name: (2R)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.0^2,^6]dodecan-10-yl]-4-phenylbutanoic acid
• 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; [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; Ramipril Diketopiperazine Acid; Ramiprilat Diketopiperazine

Database IDs

• CAS Number: 108736-10-3
• PubChem SID: 164233266
• PubChem CID: 29986823

CALCULATED PROPERTIES

• Acid pKa: 4.004958
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.9065686
• LogD (pH = 7.4): -0.74492854
• Log P: 2.4112906
• Molar Refractivity: 98.5913 cm^3
• Polarizability: 38.72183 Å^3
• Polar Surface Area: 77.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R111030

A metabolite of Ramipril (R111000).

REFERENCES

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