(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-bis(2H5)ethylprop-2-enamide

• ChemBase ID: 167930
• Molecular Formular: C14H15N3O5
• Molecular Mass: 305.286
• Monoisotopic Mass: 305.1011706
• SMILES: c1(c(c(cc(c1)/C=C(/C(=O)N(CC)CC)\C#N)[N+](=O)[O-])O)O
• Canonical SMILES: CCN(C(=O)/C(=C/c1cc(O)c(c(c1)[N+](=O)[O-])O)/C#N)CC
• InChI: InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
• InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-bis(^2H₅)ethylprop-2-enamide
• IUPAC Traditional name: (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-bis(^2H₅)ethylprop-2-enamide
• Synonyms: (2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-di-(ethyl-d5)-2-propenamide; OR-611-d10; Comtan-d10; Comtess-d10; Entacapone-d10

Database IDs

• PubChem SID: 162262063
• PubChem CID: 45039132

CALCULATED PROPERTIES

• Acid pKa: 5.683747
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.4189572
• LogD (pH = 7.4): 0.09753772
• Log P: 1.6348238
• Molar Refractivity: 80.5128 cm^3
• Polarizability: 29.13047 Å^3
• Polar Surface Area: 130.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow Crystalline Solid
• Melting Point: 162-163°C

DETAILS

Toronto Research Chemicals - E558502

(E)-Isomer of labelled Entacapone polymorphic form A. Peripherally acting inhibitor of catechol-O-methyl transferase (COMT), an enzyme involved in the metabolism of catecholamine neurotransmitters and related drugs. Antiparkinsonian.

REFERENCES

• Karlsson, M., et al.: J. Pharm. Biomed. Anal., 10, 593 (1992)
• Nissinen, E., et al.: Arch. Pharmacol., 346, 262 (1992)
• Wikberg, T., et al.: Eur. J. Drug Metab. Pharmacokinet., 18, 359 (1992)