N-hydroxynaphthalene-1-carboxamide

• ChemBase ID: 153293
• Molecular Formular: C11H9NO2
• Molecular Mass: 187.19466
• Monoisotopic Mass: 187.06332853
• SMILES: c1ccc2c(c1)cccc2C(=O)NO
• Canonical SMILES: ONC(=O)c1cccc2c1cccc2
• InChI: InChI=1S/C11H9NO2/c13-11(12-14)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,14H,(H,12,13)
• InChIKey: JRZGPWOEHDOVMC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxynaphthalene-1-carboxamide
• IUPAC Traditional name: N-hydroxynaphthalene-1-carboxamide
• Synonyms: N-Hydroxynaphthalene-1-carboxamide; NSC 57457; a-Naphthohydroxamic acid; 1-Naphthohydroxamic Acid

Database IDs

• CAS Number: 6953-61-3
• MDL Number: MFCD00059546
• PubChem SID: 162247432
• PubChem CID: 23382

CALCULATED PROPERTIES

• Acid pKa: 9.535726
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.8101413
• LogD (pH = 7.4): 1.8070289
• Log P: 1.8101811
• Molar Refractivity: 53.3512 cm^3
• Polarizability: 21.291967 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H9NO2

DETAILS

Sigma Aldrich - SML0078

Biochem/physiol Actions
1-Naphthohydroxamic Acid is a cell-permeable, potent, and selective histone deacetylase 8 (HDAC8) inhibitor. 1-Naphthohydroxamic acid selectively inhibits HDAC8 (IC50 = 14 μM) over class I HDAC1 and class II HDAC6 (IC50 >100 μM). Treatment of cells with 1-Naphthohydroxamic acid does not increase neither global histone H4 nor tubulin acetylation . Also in contrast to the pan-HDAC inhibitors the compound is not reducing total intracellular HDAC activity.