2-(2-Amino-4-methoxyphenyl)-5-trifluoromethyl-1Hbenzimidazole

ID: ALA1091257

PubChem CID: 46886471

Max Phase: Preclinical

Molecular Formula: C15H12F3N3O

Molecular Weight: 307.28

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H12F3N3O/c1-22-9-3-4-10(11(19)7-9)14-20-12-5-2-8(15(16,17)18)6-13(12)21-14/h2-7H,19H2,1H3,(H,20,21)

Standard InChI Key:  HDJHXWOQMVKLAP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    5.0152   -8.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0141   -9.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7289   -9.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7271   -7.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4425   -8.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4427   -9.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2332   -9.4631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7215   -8.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2328   -8.1185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5433   -8.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9554   -9.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7796   -9.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1927   -8.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7755   -8.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9527   -8.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3007   -7.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3005   -7.1418    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863   -8.3795    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -7.5542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0177   -8.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4314   -9.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5379   -7.3634    0.0000 N   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
 13 20  1  0
  4  1  1  0
 20 21  1  0
  5  6  1  0
 15 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091257

   5-Methoxy-2-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]aniline

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: 307.28

Molecular Weight (Monoisotopic): 307.0932

AlogP: 3.84

#Rotatable Bonds: 2

Polar Surface Area: 63.93

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.42

CX Basic pKa: 4.93

CX LogP: 3.18

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: -1.14

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