N-hydroxy-3-[(1E)-2-(hydroxycarbamoyl)eth-1-en-1-yl]benzamide

• ChemBase ID: 163695
• Molecular Formular: C10H10N2O4
• Molecular Mass: 222.1974
• Monoisotopic Mass: 222.06405681
• SMILES: c1(cccc(c1)/C=C/C(=O)NO)C(=O)NO
• Canonical SMILES: ONC(=O)/C=C/c1cccc(c1)C(=O)NO
• InChI: InChI=1S/C10H10N2O4/c13-9(11-15)5-4-7-2-1-3-8(6-7)10(14)12-16/h1-6,15-16H,(H,11,13)(H,12,14)/b5-4+
• InChIKey: OYKBQNOPCSXWBL-SNAWJCMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxy-3-[(1E)-2-(hydroxycarbamoyl)eth-1-en-1-yl]benzamide
• IUPAC Traditional name: N-hydroxy-3-[(1E)-2-(hydroxycarbamoyl)eth-1-en-1-yl]benzamide
• Synonyms: N-Hydroxy-3-[3-(hydroxyamino)-3-oxo-1-propen-1-yl]benzamide; CBHA; m-Carboxycinnamic Acid Bishydroxamide

Database IDs

• CAS Number: 174664-65-4
• PubChem SID: 162257830
• PubChem CID: 5353484

CALCULATED PROPERTIES

• Acid pKa: 9.29169
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.17335069
• LogD (pH = 7.4): 0.16789396
• Log P: 0.17342049
• Molar Refractivity: 57.4897 cm^3
• Polarizability: 21.051428 Å^3
• Polar Surface Area: 98.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C177840

Histone deacetylase inhibitor II. A cell-permeable second generation hybrid polar agent that inhibits HDAC activity. Inhibition is believed to arise as a result of the binding of the hydroxamic moiety to the active site zinc. Induces apoptosis and Fas/Fas

REFERENCES

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• Ryan, Q., et al.: J. Clin. Oncol., 23, 3912 (1990)
• Rahnama, F., et al.: Endocrinology, 147, 5275