2-(4-Nitrophenyl)-5-trifluoromethyl-1H-benzimidazole

ID: ALA1091258

PubChem CID: 22387245

Max Phase: Preclinical

Molecular Formula: C14H8F3N3O2

Molecular Weight: 307.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(-c2nc3cc(C(F)(F)F)ccc3[nH]2)cc1

Standard InChI:  InChI=1S/C14H8F3N3O2/c15-14(16,17)9-3-6-11-12(7-9)19-13(18-11)8-1-4-10(5-2-8)20(21)22/h1-7H,(H,18,19)

Standard InChI Key:  PWSFZFIGZXVJBH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   14.4902   -7.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4891   -8.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2039   -9.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2021   -7.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9175   -7.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9177   -8.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7082   -9.0048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1965   -8.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7078   -7.6602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0183   -8.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4304   -9.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2546   -9.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6677   -8.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2505   -7.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4277   -7.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7757   -7.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7755   -6.6835    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.0613   -7.9211    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.0583   -7.0958    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.4941   -8.3296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9054   -7.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9078   -9.0434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  5  4  2  0
  1 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 16 18  1  0
  8  9  2  0
 16 19  1  0
  9  5  1  0
  4  1  1  0
  5  6  1  0
 20 21  2  0
 20 22  1  0
 13 20  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1091258

   2-(4-Nitrophenyl)-5-(trifluoromethyl)-1H-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: 307.23

Molecular Weight (Monoisotopic): 307.0569

AlogP: 4.16

#Rotatable Bonds: 2

Polar Surface Area: 71.82

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.22

CX Basic pKa: 4.80

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -1.72

References

1. Tonelli M, Simone M, Tasso B, Novelli F, Boido V, Sparatore F, Paglietti G, Pricl S, Giliberti G, Blois S, Ibba C, Sanna G, Loddo R, La Colla P..  (2010)  Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives.,  18  (8): [PMID:20359898] [10.1016/j.bmc.2010.02.037]

Source

Source(1):

• Scientific Literature