(S)-2-[(1-Cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionic acid

ID: ALA353549

Chembl Id: CHEMBL353549

PubChem CID: 490750

Max Phase: Preclinical

Molecular Formula: C29H28N4O4

Molecular Weight: 496.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)c1ccc2c(c1)nc(-c1ccoc1)n2C1CCCCC1

Standard InChI:  InChI=1S/C29H28N4O4/c34-28(32-25(29(35)36)15-20-16-30-23-9-5-4-8-22(20)23)18-10-11-26-24(14-18)31-27(19-12-13-37-17-19)33(26)21-6-2-1-3-7-21/h4-5,8-14,16-17,21,25,30H,1-3,6-7,15H2,(H,32,34)(H,35,36)/t25-/m0/s1

Standard InChI Key:  OYJUPKPIVBUVPA-VWLOTQADSA-N

Alternative Forms

1. Parent:

   

   ALA353549

   (S)-2-(1-Cyclohexyl-2-(furan-3-yl)-1H-benzo[d]imidazole-5-carboxamido)-3-(1H-indol-3-yl)propanoic 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: 496.57

Molecular Weight (Monoisotopic): 496.2111

AlogP: 5.71

#Rotatable Bonds: 7

Polar Surface Area: 113.15

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.07

CX Basic pKa: 3.39

CX LogP: 4.82

CX LogD: 2.10

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: -0.56

References

1. Beaulieu PL, Bös M, Bousquet Y, DeRoy P, Fazal G, Gauthier J, Gillard J, Goulet S, McKercher G, Poupart MA, Valois S, Kukolj G..  (2004)  Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency.,  14  (4): [PMID:15013003] [10.1016/j.bmcl.2003.12.032]

2. Gordon CP, Keller PA..  (2005)  Control of hepatitis C: a medicinal chemistry perspective.,  48  (1): [PMID:15633995] [10.1021/jm0400101]

3. Yang W, Sun Y, Phadke A, Deshpande M, Huang M..  (2007)  Hepatitis C virus (HCV) NS5B nonnucleoside inhibitors specifically block single-stranded viral RNA synthesis catalyzed by HCV replication complexes in vitro.,  51  (1): [PMID:17088480] [10.1128/aac.00498-06]

4. Ganta NM, Gedda G, Rathnakar B, Satyanarayana M, Yamajala B, Ahsan MJ, Jadav SS, Balaraju T..  (2019)  A review on HCV inhibitors: Significance of non-structural polyproteins.,  164  [PMID:30639895] [10.1016/j.ejmech.2018.12.045]

Source

Source(1):

• Scientific Literature