ID: ALA2181776

Max Phase: Phase

Molecular Formula: C34H34N4O4

Molecular Weight: 562.67

Molecule Type: Small molecule

Representations

Synonyms (3): BILB 1941 | Bilb-1941 | BILB-1941ZW
Synonyms from Alternative Forms(3):

Canonical SMILES:  Cn1c(-c2ccccn2)c(C2CCCC2)c2ccc(C(=O)NC3(C(=O)Nc4ccc(/C=C/C(=O)O)cc4)CCC3)cc21

Standard InChI:  InChI=1S/C34H34N4O4/c1-38-28-21-24(13-16-26(28)30(23-7-2-3-8-23)31(38)27-9-4-5-20-35-27)32(41)37-34(18-6-19-34)33(42)36-25-14-10-22(11-15-25)12-17-29(39)40/h4-5,9-17,20-21,23H,2-3,6-8,18-19H2,1H3,(H,36,42)(H,37,41)(H,39,40)/b17-12+

Standard InChI Key:  JBSNALXXNTWUEC-SFQUDFHCSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 562.67

Molecular Weight (Monoisotopic): 562.2580

AlogP: 6.29

#Rotatable Bonds: 8

Polar Surface Area: 113.32

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.48

CX Basic pKa: 4.09

CX LogP: 5.31

CX LogD: 2.69

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.22

Np Likeness Score: -0.64

References

1. Beaulieu PL, Bös M, Cordingley MG, Chabot C, Fazal G, Garneau M, Gillard JR, Jolicoeur E, LaPlante S, McKercher G, Poirier M, Poupart MA, Tsantrizos YS, Duan J, Kukolj G..  (2012)  Discovery of the first thumb pocket 1 NS5B polymerase inhibitor (BILB 1941) with demonstrated antiviral activity in patients chronically infected with genotype 1 hepatitis C virus (HCV).,  55  (17): [PMID:22849725] [10.1021/jm3006788]

2. Beaulieu PL, Anderson PC, Bethell R, Bös M, Bousquet Y, Brochu C, Cordingley MG, Fazal G, Garneau M, Gillard JR, Kawai S, Marquis M, McKercher G, Poupart MA, Stammers T, Thavonekham B, Wernic D, Duan J, Kukolj G..  (2014)  Discovery of BI 207524, an indole diamide NS5B thumb pocket 1 inhibitor with improved potency for the potential treatment of chronic hepatitis C virus infection.,  57  (23): [PMID:25393851] [10.1021/jm501532z]

3. Beaulieu PL, Bolger G, Deon D, Duplessis M, Fazal G, Gagnon A, Garneau M, LaPlante S, Stammers T, Kukolj G, Duan J..  (2015)  Multi-parameter optimization of aza-follow-ups to BI 207524, a thumb pocket 1 HCV NS5B polymerase inhibitor. Part 2: Impact of lipophilicity on promiscuity and in vivo toxicity.,  25  (5): [PMID:25599836] [10.1016/j.bmcl.2014.12.078]

4. Unpublished dataset, 

5. 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]

6. Zhou Z, Zhang J, Zhou E, Ren C, Wang J, Wang Y..  (2022)  Small molecule NS5B RdRp non-nucleoside inhibitors for the treatment of HCV infection: A medicinal chemistry perspective.,  240  [PMID:35868125] [10.1016/j.ejmech.2022.114595]

Source

Source(2):

• Scientific Literature
• Clinical Candidates