2-[4-(4-chloro-4'-cyanobiphenyl-2-ylmethoxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carboxylic acid

ID: ALA209681

PubChem CID: 11847470

Max Phase: Preclinical

Molecular Formula: C34H28ClN3O3

Molecular Weight: 562.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2ccc(Cl)cc2COc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)cc2)cc1

Standard InChI:  InChI=1S/C34H28ClN3O3/c35-27-13-16-30(23-8-6-22(20-36)7-9-23)26(18-27)21-41-29-14-10-24(11-15-29)33-37-31-19-25(34(39)40)12-17-32(31)38(33)28-4-2-1-3-5-28/h6-19,28H,1-5,21H2,(H,39,40)

Standard InChI Key:  FQUMRIWAJBYZSF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 46  0  0  0  0  0  0  0  0999 V2000
    7.6612  -17.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6601  -18.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3744  -19.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3728  -17.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0876  -17.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0923  -18.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8838  -18.9614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3683  -18.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8762  -17.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1431  -19.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5929  -20.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8493  -21.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6567  -21.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2074  -20.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9507  -19.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1933  -18.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6054  -18.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4296  -18.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8389  -18.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4178  -17.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5950  -17.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638  -18.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0813  -18.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9063  -18.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3201  -19.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1443  -19.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5526  -18.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1307  -18.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3077  -18.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8873  -17.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2960  -16.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8762  -16.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0503  -16.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6461  -16.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0683  -17.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9442  -17.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9439  -16.6457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298  -17.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5614  -20.3926    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.6257  -15.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2042  -14.7151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
 21 16  1  0
  7 10  1  0
 19 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  1  0
 23 24  1  0
 24 25  2  0
  2  3  1  0
 25 26  1  0
  3  6  2  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 10 15  1  0
 28 29  2  0
 29 24  1  0
 11 12  1  0
 29 30  1  0
 12 13  1  0
 30 31  2  0
 13 14  1  0
 31 32  1  0
 14 15  1  0
 32 33  2  0
  5  4  2  0
 33 34  1  0
  8 16  1  0
 34 35  2  0
 35 30  1  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 36 37  2  0
 36 38  1  0
  1 36  1  0
 17 18  1  0
 26 39  1  0
  8  9  2  0
 18 19  2  0
 40 41  3  0
 33 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA209681

   2-[4-[[5-Chloro-2-(4-cyanophenyl)phenyl]methoxy]phenyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

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: 562.07

Molecular Weight (Monoisotopic): 561.1819

AlogP: 8.68

#Rotatable Bonds: 7

Polar Surface Area: 88.14

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.14

CX Basic pKa: 5.08

CX LogP: 7.34

CX LogD: 5.38

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: -1.10

References

1. Hirashima S, Suzuki T, Ishida T, Noji S, Yata S, Ando I, Komatsu M, Ikeda S, Hashimoto H..  (2006)  Benzimidazole derivatives bearing substituted biphenyls as hepatitis C virus NS5B RNA-dependent RNA polymerase inhibitors: structure-activity relationship studies and identification of a potent and highly selective inhibitor JTK-109.,  49  (15): [PMID:16854079] [10.1021/jm060269e]

2. Mahmoud AH, Elsayed MSA, ElHefnawi M.  (2013)  Structure-based predictive model for some benzimidazole inhibitors of hepatitis C virus NS5B polymerase,  22  (4): [10.1007/s00044-012-0186-8]

Source

Source(1):

• Scientific Literature