6-hydroxy-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one

• ChemBase ID: 171117
• Molecular Formular: C18H19N3O2
• Molecular Mass: 309.36236
• Monoisotopic Mass: 309.14772686
• SMILES: c12c3c(n(c1ccc(c2)O)C)CCC(C3=O)Cn1c(ncc1)C
• Canonical SMILES: Oc1ccc2c(c1)c1C(=O)C(CCc1n2C)Cn1ccnc1C
• InChI: InChI=1S/C18H19N3O2/c1-11-19-7-8-21(11)10-12-3-5-16-17(18(12)23)14-9-13(22)4-6-15(14)20(16)2/h4,6-9,12,22H,3,5,10H2,1-2H3
• InChIKey: LMMFEGYKXLPLFC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one
• IUPAC Traditional name: 6-hydroxy-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one
• Synonyms: 1,2,3,9-Tetrahydro-6-hydroxy-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one; 6-Hydroxy Ondansetron

Database IDs

• CAS Number: 110708-17-3
• PubChem SID: 164227027
• PubChem CID: 20152440

CALCULATED PROPERTIES

• Acid pKa: 9.11421
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.0340533
• LogD (pH = 7.4): 1.7949932
• Log P: 1.9352251
• Molar Refractivity: 88.7604 cm^3
• Polarizability: 34.604233 Å^3
• Polar Surface Area: 60.05 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H951145

A metabolite of Ondansetron.

REFERENCES

• Colthup, P., et al.: J. Pharm. Sci., 80, 868 (1991)
• Miyauchi, S., et al.: Pharm. Res.,10, 434 (1991)
• Ekins, S., et al.: Drug Metab. Dispos., 23, 1274 (1991)
• Worboys, P., et al.: Xenobiotica, 26, 897 (1991)