(E)-1-(3-chlorobenzyl)-N-((5-nitrofuran-2-yl)methylene)-1H-benzo[d]imidazol-2-amine

ID: ALA2270718

PubChem CID: 15034556

Max Phase: Preclinical

Molecular Formula: C19H13ClN4O3

Molecular Weight: 380.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(/C=N/c2nc3ccccc3n2Cc2cccc(Cl)c2)o1

Standard InChI:  InChI=1S/C19H13ClN4O3/c20-14-5-3-4-13(10-14)12-23-17-7-2-1-6-16(17)22-19(23)21-11-15-8-9-18(27-15)24(25)26/h1-11H,12H2/b21-11+

Standard InChI Key:  HIQVFDHHUVTZHW-SRZZPIQSSA-N

Molfile:  

     RDKit          2D

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    0.8001  -24.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989  -24.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5137  -25.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119  -23.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273  -24.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276  -24.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187  -25.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063  -24.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176  -23.8768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313  -24.5489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7439  -25.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5689  -25.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0540  -25.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8387  -25.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8386  -24.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0539  -24.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5071  -26.1601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2607  -25.8245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209  -26.9806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212  -25.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988  -26.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1747  -26.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524  -27.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550  -28.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842  -28.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028  -27.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892  -28.7917    0.0000 Cl  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
 25 27  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270718

   (E)-N-[1-[(3-chlorophenyl)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: 380.79

Molecular Weight (Monoisotopic): 380.0676

AlogP: 4.99

#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: 5.46

CX LogD: 5.46

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -1.95

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