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

ID: ALA376462

PubChem CID: 11844939

Max Phase: Preclinical

Molecular Formula: C34H29ClN2O5

Molecular Weight: 581.07

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C34H29ClN2O5/c35-26-12-6-21(7-13-26)29-16-10-23(33(38)39)18-25(29)20-42-28-14-8-22(9-15-28)32-36-30-19-24(34(40)41)11-17-31(30)37(32)27-4-2-1-3-5-27/h6-19,27H,1-5,20H2,(H,38,39)(H,40,41)

Standard InChI Key:  PSSGURHHKDYGHJ-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA376462

   2-[4-(4-carboxy-4''-chlorobiphenyl-2-ylmethoxy)phenyl]-1-cyclohexyl-1H-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: 581.07

Molecular Weight (Monoisotopic): 580.1765

AlogP: 8.50

#Rotatable Bonds: 8

Polar Surface Area: 101.65

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.14

CX Basic pKa: 5.12

CX LogP: 7.12

CX LogD: 2.05

Aromatic Rings: 5

Heavy Atoms: 42

QED Weighted: 0.19

Np Likeness Score: -0.76

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