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

• ChemBase ID: 176173
• Molecular Formular: C17H26N2O4
• Molecular Mass: 322.39934
• Monoisotopic Mass: 322.18925732
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@H]1N2C(=O)[C@@H](N(C1=O)[C@@H](CCC)C(=O)O)C
• Canonical SMILES: CCC[C@H](N1[C@@H](C)C(=O)N2[C@@H](C1=O)C[C@H]1[C@@H]2CCCC1)C(=O)O
• InChI: InChI=1S/C17H26N2O4/c1-3-6-13(17(22)23)18-10(2)15(20)19-12-8-5-4-7-11(12)9-14(19)16(18)21/h10-14H,3-9H2,1-2H3,(H,22,23)/t10-,11-,12-,13-,14+/m0/s1
• InChIKey: GBVXUKWRYVJUFG-HTVCTNPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3S,5aS,9aS,10aR)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]pentanoic acid
• IUPAC Traditional name: (2S)-2-[(3S,5aS,9aS,10aR)-3-methyl-1,4-dioxo-octahydro-3H-piperazino[1,2-a]indol-2-yl]pentanoic acid
• Synonyms: (αS,3S,5aS,9aS,10aR)-Decahydro-3-methyl-1,4-dioxo-α-propylpyrazino[1,2-a]indole-2(1H)-acetic Acid; [3S-[2(R*),3α,5aβ,9aβ,10aα]]-Decahydro-3-methyl-1,4-dioxo-α-propylpyrazino[1,2-a]indole-2(1H)-acetic Acid; 10aR-Perindoprilat Diketopiperazine; Perindoprilat Lactam B

Database IDs

• CAS Number: 130061-28-8
• PubChem SID: 164232083
• PubChem CID: 59253360

CALCULATED PROPERTIES

• Acid pKa: 4.038679
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.24967171
• LogD (pH = 7.4): -1.4144105
• Log P: 1.7220553
• Molar Refractivity: 83.0973 cm^3
• Polarizability: 32.850372 Å^3
• Polar Surface Area: 77.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: >182°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P287575

The active metabolite of Perindopril (P287500) in plasma and urine.

REFERENCES

• Hillaert, S., et al.: J. Pharm. Biomed. Anal., 25, 775 (2001)
• Ozoemena, K., et al.: Talanta, 62, 681 (2001)