3,4-dihydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide

• ChemBase ID: 167782
• Molecular Formular: C14H12N2O4
• Molecular Mass: 272.25608
• Monoisotopic Mass: 272.07970687
• SMILES: c1ccc(c(c1)/C=N/NC(=O)c1cc(c(cc1)O)O)O
• Canonical SMILES: O=C(c1ccc(c(c1)O)O)N/N=C/c1ccccc1O
• InChI: InChI=1S/C14H12N2O4/c17-11-4-2-1-3-10(11)8-15-16-14(20)9-5-6-12(18)13(19)7-9/h1-8,17-19H,(H,16,20)/b15-8+
• InChIKey: GWVYHPUGEQGQSF-OVCLIPMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dihydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide
• IUPAC Traditional name: 3,4-dihydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide
• Synonyms: 3,4-Dihydroxybenzoic Acid (2E)-2-[(2-Hydroxyphenyl)methylene]hydrazide Methanol Hydrate; 3,4-Dihydroxy-N'-(2-hydroxybenzylidene)benzohydrazide Hemimethanolate Sesquihydrate

Database IDs

• CAS Number: 1108233-34-6
• PubChem SID: 162261915
• PubChem CID: 5411040

CALCULATED PROPERTIES

• Acid pKa: 8.194273
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.0515609
• LogD (pH = 7.4): 1.9863871
• Log P: 2.0524387
• Molar Refractivity: 74.1782 cm^3
• Polarizability: 27.16459 Å^3
• Polar Surface Area: 102.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452180

Hydrazones were analyzed as potential inhibitors of anthrax lethal factor.

REFERENCES

• Molloy, S., et al.: J. Biol. Chem., 267, 16396 (1992)
• Bradley, K., et al.: Biochem. Pharmacol., 65, 309 (1992)