4-[(E)-[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino](1-13C,4,4-2H2)butan(15N)amide

• ChemBase ID: 176931
• Molecular Formular: C17H16ClFN2O2
• Molecular Mass: 336.75860694
• Monoisotopic Mass: 336.08882339
• SMILES: c1cc(cc(c1O)/C(=N/CCC[13C](=O)[15NH2])/c1ccc(cc1)Cl)F
• Canonical SMILES: [15NH2][13C](=O)CCC/N=C(/c1cc(F)ccc1O)\c1ccc(cc1)Cl
• InChI: InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,22H,1-2,9H2,(H2,20,23)/b21-17+/i16+1,20+1
• InChIKey: IBALRBWGSVJPAP-ANZYDMCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(E)-[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino](1-^1^3C,4,4-^2H₂)butan(^1^5N)amide
• IUPAC Traditional name: 4-[(E)-[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino](1-^1^3C,4,4-^2H₂)butan(^1^5N)amide
• Synonyms: 4-[[(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanamide-13C,15N,d2; Gabren-13C,15N,d2; Gabrene-13C,15N,d2; Halogabide-13C,15N,d2; SL 76-002-13C,15N,d2; SL 76002-13C,15N,d2; Progabide-13C,15N,d2

Database IDs

• PubChem SID: 164232841
• PubChem CID: 71751775

CALCULATED PROPERTIES

• Acid pKa: 8.500369
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.1911228
• LogD (pH = 7.4): 3.2739046
• Log P: 3.3088324
• Molar Refractivity: 87.9506 cm^3
• Polarizability: 33.21253 Å^3
• Polar Surface Area: 75.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P755352

Labelled Progabide (P755350). Progamide is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity.

REFERENCES

• Johno, I., et al.: J. Pharm. Sci., 71, 633 (1982)
• Shestakova., et al.: Bull. Exp. Biol. Med., 137, 255 (1982)