2-(4-((4-(acetylcarbamoyl)-4'-chlorobiphenyl-2-yl)methoxy)-2-fluorophenyl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylic acid

ID: ALA2296935

PubChem CID: 76309508

Max Phase: Preclinical

Molecular Formula: C36H31ClFN3O5

Molecular Weight: 640.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC(=O)c1ccc(-c2ccc(Cl)cc2)c(COc2ccc(-c3nc4cc(C(=O)O)ccc4n3C3CCCCC3)c(F)c2)c1

Standard InChI:  InChI=1S/C36H31ClFN3O5/c1-21(42)39-35(43)23-9-14-29(22-7-11-26(37)12-8-22)25(17-23)20-46-28-13-15-30(31(38)19-28)34-40-32-18-24(36(44)45)10-16-33(32)41(34)27-5-3-2-4-6-27/h7-19,27H,2-6,20H2,1H3,(H,44,45)(H,39,42,43)

Standard InChI Key:  QRWIOGIAJQSZGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 46 51  0  0  0  0  0  0  0  0999 V2000
   25.9795   -9.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9783  -10.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6864  -10.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6846   -9.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3932   -9.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3935  -10.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1764  -10.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6602   -9.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1760   -9.2138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2706   -9.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2704   -8.2506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5630   -9.4765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4302  -11.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8814  -11.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1312  -12.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9300  -12.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4788  -12.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2287  -11.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4741   -9.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8823  -10.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6988  -10.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1079   -9.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6947   -9.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8796   -9.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4689   -8.4658    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.9251   -9.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3349  -10.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1521  -10.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5577  -11.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3742  -11.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7824  -10.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3682   -9.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5531   -9.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7731   -9.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1500  -11.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3317  -11.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9221  -12.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3297  -13.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1511  -13.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5570  -12.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9209  -14.1167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.5903   -9.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3609   -8.4580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7658   -7.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3535   -7.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5829   -7.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 10 12  2  0
  1 10  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7 13  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  8 19  1  0
 24 25  1  0
 22 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 32 34  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
 29 35  1  0
 38 41  1  0
 34 42  2  0
 34 43  1  0
 43 44  1  0
 44 45  2  0
 44 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296935

   2-[4-[[5-(Acetylcarbamoyl)-2-(4-chlorophenyl)phenyl]methoxy]-2-fluorophenyl]-1-cyclohexylbenzimidazole-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: 640.11

Molecular Weight (Monoisotopic): 639.1936

AlogP: 8.22

#Rotatable Bonds: 8

Polar Surface Area: 110.52

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.76

CX Basic pKa: 3.05

CX LogP: 7.26

CX LogD: 4.34

Aromatic Rings: 5

Heavy Atoms: 46

QED Weighted: 0.18

Np Likeness Score: -1.10

References

1. 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