5-methoxy-3-[(E)-2-nitroethenyl]-1H-indole

• ChemBase ID: 130655
• Molecular Formular: C11H10N2O3
• Molecular Mass: 218.2087
• Monoisotopic Mass: 218.06914219
• SMILES: COc1ccc2c(c1)c(c[nH]2)/C=C/[N+](=O)[O-]
• Canonical SMILES: COc1ccc2c(c1)c(c[nH]2)/C=C/[N+](=O)[O-]
• InChI: InChI=1S/C11H10N2O3/c1-16-9-2-3-11-10(6-9)8(7-12-11)4-5-13(14)15/h2-7,12H,1H3/b5-4+
• InChIKey: NAIAZIKEFZGLDL-SNAWJCMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methoxy-3-[(E)-2-nitroethenyl]-1H-indole
• IUPAC Traditional name: 5-methoxy-3-[(E)-2-nitroethenyl]-1H-indole
• Synonyms: 5-Methoxy-3-(2′-nitroethenyl)indole; NSC 88875; 5-Methoxy-3-(2-nitrovinyl)indole; 5-甲氧基-3-(2-硝基乙烯基)吲哚

Database IDs

• CAS Number: 61675-19-2
• MDL Number: MFCD00047180
• PubChem SID: 24896594; 162224933
• PubChem CID: 5869315

CALCULATED PROPERTIES

• Acid pKa: 16.02003
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.0684388
• LogD (pH = 7.4): 2.0684388
• Log P: 2.0684388
• Molar Refractivity: 59.598 cm^3
• Polarizability: 23.457043 Å^3
• Polar Surface Area: 70.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3

DETAILS

Sigma Aldrich - M2014

Application
Reactant for preparation of:
• Inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)1
• Indole lipoic acid derivatives as antioxidants effective against lipid peroxidation2
• Indole ethylamine derivatives as melatonin analogs3