N-(3-{[(2-hydroxynaphthalen-1-yl)methylidene]amino}phenyl)-2-phenylpropanamide

• ChemBase ID: 154460
• Molecular Formular: C26H22N2O2
• Molecular Mass: 394.46508
• Monoisotopic Mass: 394.16812795
• SMILES: CC(c1ccccc1)C(=O)Nc1cccc(c1)/N=C/c1c2ccccc2ccc1O
• Canonical SMILES: CC(c1ccccc1)C(=O)Nc1cccc(c1)/N=C/c1c(O)ccc2c1cccc2
• InChI: InChI=1S/C26H22N2O2/c1-18(19-8-3-2-4-9-19)26(30)28-22-12-7-11-21(16-22)27-17-24-23-13-6-5-10-20(23)14-15-25(24)29/h2-18,29H,1H3,(H,28,30)
• InChIKey: HQSSEGBEYORUBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-{[(2-hydroxynaphthalen-1-yl)methylidene]amino}phenyl)-2-phenylpropanamide
• IUPAC Traditional name: N-(3-{[(2-hydroxynaphthalen-1-yl)methylidene]amino}phenyl)-2-phenylpropanamide
• Synonyms: N-{3-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-phenyl}-2-phenyl-propionamide; Salermide

Database IDs

• CAS Number: 1105698-15-4
• MDL Number: MFCD12912446
• PubChem SID: 162248599
• PubChem CID: 42626405

CALCULATED PROPERTIES

• Acid pKa: 8.648076
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.148105
• LogD (pH = 7.4): 6.1247544
• Log P: 6.1484547
• Molar Refractivity: 123.9781 cm^3
• Polarizability: 46.966408 Å^3
• Polar Surface Area: 61.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: powder, yellow

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43-52/53
• Safety Statements: 36/37-61
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H412
• GHS Precautionary statements: P273-P280
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C26H22N2O2

DETAILS

Sigma Aldrich - S8825

Biochem/physiol Actions
Salermide is a novel Sirtuin 1 (Sirt1) and Sirtuin 2 (Sirt2) inhibitor (III histone deacetylases inhibitor). In vitro Salermide has a stronger inhibitory effect on Sirt2 than on Sirt1. Salermide induces massive apoptosis in tumor cells. The activity was ascribed to effect of Salermide to the reactivation of proapoptotic genes epigenetically repressed exclusively in cancer cells by Sirt1. Salermide is a stronger Sirtuin inhibitor than sirtinol (Cat. No.S7942).