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

• ChemBase ID: 171119
• Molecular Formular: C18H19N3O2
• Molecular Mass: 309.36236
• Monoisotopic Mass: 309.14772686
• SMILES: c12c3c(n(c1c(ccc2)O)C)CCC(C3=O)Cn1c(ncc1)C
• Canonical SMILES: O=C1C(CCc2c1c1cccc(c1n2C)O)Cn1ccnc1C
• InChI: InChI=1S/C18H19N3O2/c1-11-19-8-9-21(11)10-12-6-7-14-16(18(12)23)13-4-3-5-15(22)17(13)20(14)2/h3-5,8-9,12,22H,6-7,10H2,1-2H3
• InChIKey: XVDKMEPUFIAQFH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-hydroxy-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one
• IUPAC Traditional name: 8-hydroxy-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one
• Synonyms: 1,2,3,9-Tetrahydro-8-hydroxy-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one; 8-Hydroxy Ondansetron

Database IDs

• CAS Number: 126671-71-4
• PubChem SID: 164227029
• PubChem CID: 19734439

CALCULATED PROPERTIES

• Acid pKa: 9.092647
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.0340478
• LogD (pH = 7.4): 1.7945627
• Log P: 1.9336073
• Molar Refractivity: 88.7604 cm^3
• Polarizability: 34.61041 Å^3
• Polar Surface Area: 60.05 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H951155

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)