2-(4-hydroxycyclohexanecarbonyl)-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

• ChemBase ID: 171167
• Molecular Formular: C19H24N2O3
• Molecular Mass: 328.40546
• Monoisotopic Mass: 328.17869264
• SMILES: c1ccc2c(c1)C1N(CC2)C(=O)CN(C1)C(=O)C1CC[C@H](CC1)O
• Canonical SMILES: O[C@@H]1CCC(CC1)C(=O)N1CC(=O)N2C(C1)c1ccccc1CC2
• InChI: InChI=1S/C19H24N2O3/c22-15-7-5-14(6-8-15)19(24)20-11-17-16-4-2-1-3-13(16)9-10-21(17)18(23)12-20/h1-4,14-15,17,22H,5-12H2/t14?,15-,17?
• InChIKey: OKTGUGBZQBTMHZ-WXXKKXNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-hydroxycyclohexanecarbonyl)-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
• IUPAC Traditional name: 2-(4-hydroxycyclohexanecarbonyl)-1H,3H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
• Synonyms: 1,2,3,6,7,11b-Hexahydro-2-[(cis-4-hydroxycyclohexyl)carbonyl]-4H-pyrazino[2,1-a]isoquinolin-4-one; cis-(+/-)-1,2,3,6,7,11b-Hexahydro-2-[(4-hydroxycyclohexyl)carbonyl]- 4H-pyrazino[2,1-a]isoquinolin-4-one; cis-Hydroxy Praziquantel; trans-1,2,3,6,7,11b-Hexahydro-2-[(4-hydroxycyclohexyl)carbonyl]- 4H-pyrazino[2,1-a]isoquinolin-4-one; trans-Hydroxy Praziquantel

Database IDs

• CAS Number: 134924-68-8; 134924-71-3
• PubChem SID: 164227077
• PubChem CID: 173759

CALCULATED PROPERTIES

• Acid pKa: 18.15645
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.9148432
• LogD (pH = 7.4): 0.91484404
• Log P: 0.9148441
• Molar Refractivity: 90.4546 cm^3
• Polarizability: 35.12219 Å^3
• Polar Surface Area: 60.85 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 150-155°C; 169-171°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H952405

The main trans-monohydroxylated metabolite of Praziquantel (P702095).

Toronto Research Chemicals - H952400

The main cis-monohydroxylated metabolite of Praziquantel (P702095).

REFERENCES

• Buehring, K., et al.: Eur. J. Drug Metab. Pharm., 3, 179 (1978)
• Moldeus, P., et al.: Methods Enzymol., 52, 60 (1978)
• Cioli, D., et al.: Pharmacol. Ther., 68, 35 (1978)
• Buehring, K., et al.: Eur. J. Drug Metab. Pharm., 3, 179 (1978)
• Moldeus, P., et al.: Methods Enzymol., 52, 60 (1978)
• Cioli, D., et al.: Pharmacol. Ther., 68, 35 (1978)