1-cyclohexyl-2-[4-(4,3'-dichlorobiphenyl-2-ylmethoxy)phenyl]-1H-benzimidazole-5-carboxylic acid

ID: ALA378284

PubChem CID: 10144618

Max Phase: Preclinical

Molecular Formula: C33H28Cl2N2O3

Molecular Weight: 571.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2c(c1)nc(-c1ccc(OCc3cc(Cl)ccc3-c3cccc(Cl)c3)cc1)n2C1CCCCC1

Standard InChI:  InChI=1S/C33H28Cl2N2O3/c34-25-6-4-5-22(17-25)29-15-12-26(35)18-24(29)20-40-28-13-9-21(10-14-28)32-36-30-19-23(33(38)39)11-16-31(30)37(32)27-7-2-1-3-8-27/h4-6,9-19,27H,1-3,7-8,20H2,(H,38,39)

Standard InChI Key:  NBCUIHSPCQSERV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.7964  -22.8408    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  9  5  1  0
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  5  6  1  0
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 31 32  1  0
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  5  4  2  0
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  8 16  1  0
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  6  7  1  0
 16 17  2  0
  7  8  1  0
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  1 36  1  0
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  8  9  2  0
 34 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA378284

   2-[4-[[5-Chloro-2-(3-chlorophenyl)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: 571.50

Molecular Weight (Monoisotopic): 570.1477

AlogP: 9.46

#Rotatable Bonds: 7

Polar Surface Area: 64.35

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.14

CX Basic pKa: 5.08

CX LogP: 8.09

CX LogD: 6.13

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: -0.97

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