5-[4-methyl(2H4)benzoyl]-3-nitrobenzene-1,2-diol

• ChemBase ID: 178699
• Molecular Formular: C14H11NO5
• Molecular Mass: 273.24084
• Monoisotopic Mass: 273.06372246
• SMILES: c1(c(c(cc(c1)C(=O)c1ccc(cc1)C)[N+](=O)[O-])O)O
• Canonical SMILES: Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[O-])O
• InChI: InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
• InChIKey: MIQPIUSUKVNLNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[4-methyl(^2H₄)benzoyl]-3-nitrobenzene-1,2-diol
• IUPAC Traditional name: 5-[4-methyl(^2H₄)benzoyl]-3-nitrobenzene-1,2-diol
• Synonyms: (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl-d4)methanone; Ro-40-7592-d4; Tasmar-d4; Tolcapone-d4

Database IDs

• PubChem SID: 164234609
• PubChem CID: 71752606

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.7906816
• LogD (pH = 7.4): 1.5077089
• Log P: 3.2788737
• Molar Refractivity: 72.9612 cm^3
• Polarizability: 26.881105 Å^3
• Polar Surface Area: 103.35 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 5.167245

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Dark Yellow Solid
• Melting Point: 142-144°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T535252

Orally active inhibitor of central and peripheral catechol-O-methyltransferase (COMT). Antiparkinsonian.

REFERENCES

• Dingemanse, J., et al.: Clin. Pharmacol. Ther., 57, 508 (1995)
• Keating, K.A., Drugs, 19, 165 (1995)