N-{1-[2-(morpholin-4-yl)ethyl]-1H-1,3-benzodiazol-2-yl}-3-nitrobenzamide

• ChemBase ID: 153916
• Molecular Formular: C20H21N5O4
• Molecular Mass: 395.41184
• Monoisotopic Mass: 395.15935418
• SMILES: c1ccc2c(c1)nc(n2CCN1CCOCC1)NC(=O)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: O=C(c1cccc(c1)[N+](=O)[O-])Nc1nc2c(n1CCN1CCOCC1)cccc2
• InChI: InChI=1S/C20H21N5O4/c26-19(15-4-3-5-16(14-15)25(27)28)22-20-21-17-6-1-2-7-18(17)24(20)9-8-23-10-12-29-13-11-23/h1-7,14H,8-13H2,(H,21,22,26)
• InChIKey: QTCFYQHZJIIHBS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{1-[2-(morpholin-4-yl)ethyl]-1H-1,3-benzodiazol-2-yl}-3-nitrobenzamide
• IUPAC Traditional name: N-{1-[2-(morpholin-4-yl)ethyl]-1,3-benzodiazol-2-yl}-3-nitrobenzamide
• Synonyms: 1-(2-(4-Morpholinyl)ethyl)-2-(3-nitrobenzoylamino)benzimidazole; N-(2-Morpholinylethyl)-2-(3-nitrobenzoylamido)-benzimidazole; IRAK-1/4 Inhibitor I

Database IDs

• MDL Number: MFCD09752602
• PubChem SID: 162248055
• PubChem CID: 11983295

CALCULATED PROPERTIES

• Acid pKa: 10.590189
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.8160918
• LogD (pH = 7.4): 2.927229
• Log P: 2.999443
• Molar Refractivity: 109.2903 cm^3
• Polarizability: 41.581303 Å^3
• Polar Surface Area: 105.21 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: off-white to light yellow solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H21N5O4

DETAILS

Sigma Aldrich - I5409

Biochem/physiol Actions
IRAK-1/4 Inhibitor I is a novel benzimidazole that is a potent inhibitor of interleukin-1 receptor-associated kinases 1/4 (IRAK 1/4). IC50 values were 300 nM and 200 nM for IRAK-1 and -4, respectively, and >10,000 nM for a panel of 27 other kinases tested.