1-(3-benzyl-2-imino-2,3-dihydro-1H-1,3-benzodiazol-1-yl)-3-phenoxypropan-2-ol hydrochloride

• ChemBase ID: 154479
• Molecular Formular: C23H24ClN3O2
• Molecular Mass: 409.90856
• Monoisotopic Mass: 409.1557047
• SMILES: c1ccc(cc1)Cn1c2ccccc2n(c1=N)CC(COc1ccccc1)O.Cl
• Canonical SMILES: OC(Cn1c2ccccc2n(c1=N)Cc1ccccc1)COc1ccccc1.Cl
• InChI: InChI=1S/C23H23N3O2.ClH/c24-23-25(15-18-9-3-1-4-10-18)21-13-7-8-14-22(21)26(23)16-19(27)17-28-20-11-5-2-6-12-20;/h1-14,19,24,27H,15-17H2;1H
• InChIKey: KDMXJFUGIDGZQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-benzyl-2-imino-2,3-dihydro-1H-1,3-benzodiazol-1-yl)-3-phenoxypropan-2-ol hydrochloride
• IUPAC Traditional name: 1-(3-benzyl-2-imino-1,3-benzodiazol-1-yl)-3-phenoxypropan-2-ol hydrochloride
• Synonyms: 1H-Benzimidazole-1-ethanol, 2,3-dihydro-2-imino-alpha-(phenoxymethyl)-3-(phenylmethyl)- monohydrochloride; BEPP monohydrochloride

Database IDs

• CAS Number: 455311-98-5
• MDL Number: MFCD00964481
• PubChem SID: 162248618
• PubChem CID: 2858173

CALCULATED PROPERTIES

• Acid pKa: 14.046119
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.5611564
• LogD (pH = 7.4): 2.422192
• Log P: 3.9394574
• Molar Refractivity: 122.0637 cm^3
• Polarizability: 42.29547 Å^3
• Polar Surface Area: 59.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H23N3O2 HCl

DETAILS

Sigma Aldrich - B2938

Biochem/physiol Actions
BEPP is a double-strand RNA-dependent protein kinase (PKR) activator. The double-strand RNA (dsRNA)-dependent protein kinase is a ubiquitously expressed serine threonine kinase, inducible by interferon γ. PRK is involved in several curtail cellular regulations including phosphorylation of eIF2α (which leads to inhibition of protein synthesis and eliciting antivirus and antitumor activities), modulating activities of eIF2α, NF-κB, ATF-3, and p53. BEPP also inhibits the growth of a human lung cancer cell line overexpressing PKR.