2-[(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino]-N-(1-phenylethyl)benzamide

• ChemBase ID: 66343
• Molecular Formular: C26H22N2O2
• Molecular Mass: 394.46508
• Monoisotopic Mass: 394.16812795
• SMILES: C(=O)(c1c(cccc1)/N=C/c1c(ccc2ccccc12)O)NC(C)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1/N=C/c1c(O)ccc2c1cccc2)NC(c1ccccc1)C
• InChI: InChI=1S/C26H22N2O2/c1-18(19-9-3-2-4-10-19)28-26(30)22-13-7-8-14-24(22)27-17-23-21-12-6-5-11-20(21)15-16-25(23)29/h2-18,29H,1H3,(H,28,30)/b27-17+
• InChIKey: UXJFDYIHRJGPFS-WPWMEQJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino]-N-(1-phenylethyl)benzamide; 2-{[(2-hydroxynaphthalen-1-yl)methylidene]amino}-N-(1-phenylethyl)benzamide
• IUPAC Traditional name: 2-[(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino]-N-(1-phenylethyl)benzamide; 2-{[(2-hydroxynaphthalen-1-yl)methylidene]amino}-N-(1-phenylethyl)benzamide
• Synonyms: Sirtinol; 2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]-N-(1-phenethyl)benzamide; Sirtinol

Database IDs

• CAS Number: 410536-97-9
• MDL Number: MFCD00810186
• PubChem SID: 24899771; 162032081
• PubChem CID: 5717148

CALCULATED PROPERTIES

• Acid pKa: 8.646475
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.748473
• LogD (pH = 7.4): 5.724998
• Log P: 5.7487826
• Molar Refractivity: 122.8252 cm^3
• Polarizability: 46.75234 Å^3
• Polar Surface Area: 61.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Sirtuin
• Gene Information: human ... SIRT1(23411), SIRT2(22933)

Product Information

• Purity: ≥95% (NMR); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C26H22N2O2

DETAILS

Sigma Aldrich - S7942

Biochem/physiol Actions
Sirtinol inhibits yeast Sir2p transcriptional silencing activity in vivo, yeast Sir2p and human SIRT2 deacetylase activity in vitro.
Sirtinol inhibits yeast Sir2p transcriptional silencing activity in vivo, yeast Sir2p, and human SIRT2 deacetylase activity in vitro.