1-(4-(Trifluoromethoxy)benzyl)-2-(4-(trifluoromethoxy)phenyl)benzimidazole

ID: ALA1922088

PubChem CID: 11648120

Max Phase: Preclinical

Molecular Formula: C22H14F6N2O2

Molecular Weight: 452.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)Oc1ccc(Cn2c(-c3ccc(OC(F)(F)F)cc3)nc3ccccc32)cc1

Standard InChI:  InChI=1S/C22H14F6N2O2/c23-21(24,25)31-16-9-5-14(6-10-16)13-30-19-4-2-1-3-18(19)29-20(30)15-7-11-17(12-8-15)32-22(26,27)28/h1-12H,13H2

Standard InChI Key:  USFLLYIPZKRUAK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   15.1569   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1557   -3.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8706   -3.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8688   -2.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5841   -2.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5844   -3.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3745   -3.7477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8632   -3.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3744   -2.4018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6882   -3.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0971   -3.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9213   -3.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3344   -3.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9172   -2.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0943   -2.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3713   -4.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0913   -4.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1007   -5.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8198   -6.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5296   -5.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5157   -4.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7960   -4.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2502   -6.1764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1594   -3.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5731   -3.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3981   -3.7841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.1618   -4.5007    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.9792   -4.4958    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.2625   -7.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9830   -7.4031    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.5542   -7.4244    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.2542   -7.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15 10  1  0
  5  4  2  0
  7 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  8 10  1  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
 20 23  1  0
 10 11  2  0
 13 24  1  0
 24 25  1  0
 11 12  1  0
 25 26  1  0
  2  3  1  0
 25 27  1  0
 12 13  2  0
 25 28  1  0
  3  6  2  0
 23 29  1  0
 13 14  1  0
 29 30  1  0
  1  2  2  0
 29 31  1  0
 14 15  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1922088

   2-[4-(Trifluoromethoxy)phenyl]-1-[[4-(trifluoromethoxy)phenyl]methyl]benzimidazole

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: 452.35

Molecular Weight (Monoisotopic): 452.0959

AlogP: 6.55

#Rotatable Bonds: 5

Polar Surface Area: 36.28

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.74

CX LogP: 8.09

CX LogD: 8.09

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -1.12

References

1. Bandyopadhyay P, Sathe M, Ponmariappan S, Sharma A, Sharma P, Srivastava AK, Kaushik MP..  (2011)  Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.,  21  (24): [PMID:22047695] [10.1016/j.bmcl.2011.10.034]

Source

Source(1):

• Scientific Literature