(E)-1-(4-methylbenzyl)-N-((5-nitrofuran-2-yl)methylene)-1H-benzo[d]imidazol-2-amine

ID: ALA2270720

PubChem CID: 15034558

Max Phase: Preclinical

Molecular Formula: C20H16N4O3

Molecular Weight: 360.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(Cn2c(/N=C/c3ccc([N+](=O)[O-])o3)nc3ccccc32)cc1

Standard InChI:  InChI=1S/C20H16N4O3/c1-14-6-8-15(9-7-14)13-23-18-5-3-2-4-17(18)22-20(23)21-12-16-10-11-19(27-16)24(25)26/h2-12H,13H2,1H3/b21-12+

Standard InChI Key:  NONDSDFGGRCKQN-CIAFOILYSA-N

Molfile:  

     RDKit          2D

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   17.1917  -23.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1906  -24.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9054  -25.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9036  -23.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6190  -23.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6192  -24.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4104  -24.8865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8980  -24.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4093  -23.5435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230  -24.2155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1356  -24.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9606  -24.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4457  -25.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2303  -25.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2302  -24.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4456  -24.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8987  -25.8268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6524  -25.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8125  -26.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8129  -25.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3905  -26.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5664  -26.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1441  -27.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5466  -27.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3759  -27.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7945  -27.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1252  -28.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
 17 18  2  0
 17 19  1  0
 14 17  1  0
  7 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270720

   (E)-N-[1-[(4-methylphenyl)methyl]benzimidazol-2-yl]-1-(5-nitrofuran-2-yl)methanimine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.37

Molecular Weight (Monoisotopic): 360.1222

AlogP: 4.64

#Rotatable Bonds: 5

Polar Surface Area: 86.46

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.30

CX LogP: 5.37

CX LogD: 5.37

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -1.65

References

1. Vlaovic D, Canadanovic-Brunet J, Balaz J, Juranic I, Djokovic D, Mackenzie K.  (1992)  Synthesis, AntiBacteriol, and Antifungal Activities of Some New Benzimidazoles,  56  (2): [10.1271/bbb.56.199]

Source

Source(1):

• Scientific Literature