2-(4-Methoxy-2-nitrophenyl)-5-trifluoromethyl-1H-benzimidazole

ID: ALA1092095

PubChem CID: 46886470

Max Phase: Preclinical

Molecular Formula: C15H10F3N3O3

Molecular Weight: 337.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nc3cc(C(F)(F)F)ccc3[nH]2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H10F3N3O3/c1-24-9-3-4-10(13(7-9)21(22)23)14-19-11-5-2-8(15(16,17)18)6-12(11)20-14/h2-7H,1H3,(H,19,20)

Standard InChI Key:  GHYYUUFQHMDLOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -4.6931   -8.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6943   -9.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794   -9.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9812   -8.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2659   -8.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656   -9.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751   -9.6673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -8.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4756   -8.3227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651   -8.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529   -9.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0713   -9.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -8.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672   -8.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557   -8.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4077   -8.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079   -7.3460    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280   -8.5836    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250   -7.7583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094   -8.9926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231   -9.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -7.5666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959   -7.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7606   -6.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 13 20  1  0
  4  1  1  0
 20 21  1  0
  5  6  1  0
 10 11  2  0
 22 23  2  0
 22 24  1  0
 15 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1092095

   2-(4-Methoxy-2-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: 337.26

Molecular Weight (Monoisotopic): 337.0674

AlogP: 4.17

#Rotatable Bonds: 3

Polar Surface Area: 81.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.70

CX Basic pKa: 4.38

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -1.50

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