Lomibuvir

ID: ALA3039503

Chembl Id: CHEMBL3039503

Max Phase: Phase

Molecular Formula: C25H35NO4S

Molecular Weight: 445.63

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lomibuvir | Vch-222 | VX-222

Canonical SMILES:  CC(C)(C)C#Cc1cc(N(C(=O)[C@H]2CC[C@H](C)CC2)[C@H]2CC[C@H](O)CC2)c(C(=O)O)s1

Standard InChI:  InChI=1S/C25H35NO4S/c1-16-5-7-17(8-6-16)23(28)26(18-9-11-19(27)12-10-18)21-15-20(13-14-25(2,3)4)31-22(21)24(29)30/h15-19,27H,5-12H2,1-4H3,(H,29,30)/t16-,17-,18-,19-

Standard InChI Key:  WPMJNLCLKAKMLA-VVPTUSLJSA-N

Alternative Forms

1. Parent:

   

   ALA3039503

   LOMIBUVIR

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

Calculated Properties

Molecular Weight: 445.63

Molecular Weight (Monoisotopic): 445.2287

AlogP: 5.31

#Rotatable Bonds: 4

Polar Surface Area: 77.84

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 5.61

CX LogD: 2.26

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: -0.42

References

1. Beaulieu PL, Coulombe R, Duan J, Fazal G, Godbout C, Hucke O, Jakalian A, Joly MA, Lepage O, Llinàs-Brunet M, Naud J, Poirier M, Rioux N, Thavonekham B, Kukolj G, Stammers TA..  (2013)  Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.,  23  (14): [PMID:23768906] [10.1016/j.bmcl.2013.05.037]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Lazerwith SE, Lew W, Zhang J, Morganelli P, Liu Q, Canales E, Clarke MO, Doerffler E, Byun D, Mertzman M, Ye H, Chong L, Xu L, Appleby T, Chen X, Fenaux M, Hashash A, Leavitt SA, Mabery E, Matles M, Mwangi JW, Tian Y, Lee YJ, Zhang J, Zhu C, Murray BP, Watkins WJ..  (2014)  Discovery of GS-9669, a thumb site II non-nucleoside inhibitor of NS5B for the treatment of genotype 1 chronic hepatitis C infection.,  57  (5): [PMID:24144213] [10.1021/jm401420j]

4. Unpublished dataset, 

5. Court JJ, Poisson C, Ardzinski A, Bilimoria D, Chan L, Chandupatla K, Chauret N, Collier PN, Das SK, Denis F, Dorsch W, Iyer G, Lauffer D, L'Heureux L, Li P, Luisi BS, Mani N, Nanthakumar S, Nicolas O, Rao BG, Ronkin S, Selliah S, Shawgo RS, Tang Q, Waal ND, Yannopoulos CG, Green J..  (2016)  Discovery of Novel Thiophene-Based, Thumb Pocket 2 Allosteric Inhibitors of the Hepatitis C NS5B Polymerase with Improved Potency and Physicochemical Profiles.,  59  (13): [PMID:27366941] [10.1021/acs.jmedchem.6b00541]

6. Li P, Dorsch W, Lauffer DJ, Bilimoria D, Chauret N, Court JJ, Das SK, Denis F, Mani N, Nanthakumar S, Nicolas O, Rao BG, Ronkin S, Selliah S, Shawgo RS, Stearns R, Tang Q, Waal ND, Green J..  (2017)  Discovery of Novel Allosteric HCV NS5B Inhibitors. 2. Lactam-Containing Thiophene Carboxylates.,  8  (2): [PMID:28197321] [10.1021/acsmedchemlett.6b00479]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names