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

ID: ALA2270472

PubChem CID: 15034555

Max Phase: Preclinical

Molecular Formula: C18H20N4O3

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCn1c(/N=C/c2ccc([N+](=O)[O-])o2)nc2ccccc21

Standard InChI:  InChI=1S/C18H20N4O3/c1-2-3-4-7-12-21-16-9-6-5-8-15(16)20-18(21)19-13-14-10-11-17(25-14)22(23)24/h5-6,8-11,13H,2-4,7,12H2,1H3/b19-13+

Standard InChI Key:  NBPXXSMPGWLJJM-CPNJWEJPSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.9959  -18.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947  -18.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7095  -19.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7077  -17.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4231  -18.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4234  -18.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2139  -19.2040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7022  -18.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2134  -17.8602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5272  -18.5322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9397  -19.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7647  -19.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2499  -19.9128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0345  -19.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0344  -18.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2498  -18.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7029  -20.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4565  -19.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6167  -20.9639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691  -19.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9174  -20.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1727  -21.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6209  -21.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8762  -22.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3245  -23.3976    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  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270472

   (E)-N-(1-hexylbenzimidazol-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: 340.38

Molecular Weight (Monoisotopic): 340.1535

AlogP: 4.87

#Rotatable Bonds: 8

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: 2.37

CX LogP: 5.34

CX LogD: 5.34

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.25

Np Likeness Score: -1.50

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