5-hydroxy-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide

• ChemBase ID: 170321
• Molecular Formular: C15H12N2O2
• Molecular Mass: 252.26798
• Monoisotopic Mass: 252.08987763
• SMILES: c12c(cc(cc1)O)N(c1c(cccc1)C=C2)C(=O)N
• Canonical SMILES: Oc1ccc2c(c1)N(C(=O)N)c1ccccc1C=C2
• InChI: InChI=1S/C15H12N2O2/c16-15(19)17-13-4-2-1-3-10(13)5-6-11-7-8-12(18)9-14(11)17/h1-9,18H,(H2,16,19)
• InChIKey: QQCFBZCATDIWTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
• IUPAC Traditional name: 5-hydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
• Synonyms: 3-Hydroxy-5H-dibenz[b,f]azepine-5-carboxamide; 3-Hydroxy Carbamazepine

Database IDs

• CAS Number: 68011-67-6
• PubChem SID: 164226231
• PubChem CID: 135290

CALCULATED PROPERTIES

• Acid pKa: 9.194977
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.462378
• LogD (pH = 7.4): 2.4555995
• Log P: 2.462465
• Molar Refractivity: 73.8689 cm^3
• Polarizability: 27.536816 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: 240-242°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H884105

A metabolite of Carbamazepine (C175840).

REFERENCES

• Park, B., et al.: Biochem. Pharmacol., 36, 581 (1987)
• Yamazaki, H., et al.: Drug Metab. Dispos., 27, 1260 (1987)
• Dieckhaus, C., et al.: Chem. Res. Toxicol., 14, 958 (1987)