1-Methyl-2-[4-(4-methyl-1-piperazinyl)acetylaminophenyl]-5-trifluoromethyl-1H-benzimidazole

ID: ALA1093874

PubChem CID: 46886230

Max Phase: Preclinical

Molecular Formula: C22H24F3N5O

Molecular Weight: 431.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(CC(=O)Nc2ccc(-c3nc4cc(C(F)(F)F)ccc4n3C)cc2)CC1

Standard InChI:  InChI=1S/C22H24F3N5O/c1-28-9-11-30(12-10-28)14-20(31)26-17-6-3-15(4-7-17)21-27-18-13-16(22(23,24)25)5-8-19(18)29(21)2/h3-8,13H,9-12,14H2,1-2H3,(H,26,31)

Standard InChI Key:  CIVZFJQGEPBXRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.7598    0.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7609   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461   -0.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0479    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325    0.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -0.5881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422    0.7565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317    0.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0046   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177    0.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005    0.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    0.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427    0.0866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743    0.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4745    1.7332    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887    0.4955    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1917    1.3208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6540    0.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790    0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403    1.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903    1.5183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    1.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247    2.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    2.9419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886    2.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4728    2.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1285    3.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 10  1  0
  8 10  1  0
  5  4  2  0
 13 16  1  0
  6  7  1  0
  1 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 17 19  1  0
  9  5  1  0
 17 20  1  0
  4  1  1  0
  7 21  1  0
  5  6  1  0
 16 22  1  0
 10 11  2  0
 22 23  1  0
 22 24  2  0
 11 12  1  0
 23 25  1  0
 25 26  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 14 15  2  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093874

   2-(4-methylpiperazin-1-yl)-N-[4-[1-methyl-5-(trifluoromethyl)benzimidazol-2-yl]phenyl]acetamide

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: 431.46

Molecular Weight (Monoisotopic): 431.1933

AlogP: 3.45

#Rotatable Bonds: 4

Polar Surface Area: 53.40

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 7.21

CX LogP: 3.36

CX LogD: 3.15

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -2.00

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