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

• ChemBase ID: 170320
• Molecular Formular: C15H12N2O2
• Molecular Mass: 252.26798
• Monoisotopic Mass: 252.08987763
• SMILES: c12c(ccc(c1)O)N(c1c(cccc1)C=C2)C(=O)N
• Canonical SMILES: Oc1ccc2c(c1)C=Cc1c(N2C(=O)N)cccc1
• InChI: InChI=1S/C15H12N2O2/c16-15(19)17-13-4-2-1-3-10(13)5-6-11-9-12(18)7-8-14(11)17/h1-9,18H,(H2,16,19)
• InChIKey: VPZIYMMSJFWLSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 68011-66-5
• PubChem SID: 164226230
• PubChem CID: 129274

CALCULATED PROPERTIES

• Acid pKa: 9.14861
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.4623682
• LogD (pH = 7.4): 2.4548333
• Log P: 2.462465
• Molar Refractivity: 73.8689 cm^3
• Polarizability: 27.536879 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Tan Solid
• Melting Point: >205°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H884100

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)