ID: ALA372199

Max Phase: Preclinical

Molecular Formula: C19H17ClF5NO4S2

Molecular Weight: 517.93

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=S(=O)(N[C@H]1CC[C@@](c2cc(F)ccc2F)(S(=O)(=O)c2ccc(Cl)cc2)CC1)C(F)(F)F

Standard InChI:  InChI=1S/C19H17ClF5NO4S2/c20-12-1-4-15(5-2-12)31(27,28)18(16-11-13(21)3-6-17(16)22)9-7-14(8-10-18)26-32(29,30)19(23,24)25/h1-6,11,14,26H,7-10H2/t14-,18+

Standard InChI Key:  WDZVWDXOIGQJIO-UJKQEGAGSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 517.93

Molecular Weight (Monoisotopic): 517.0208

AlogP: 4.67

#Rotatable Bonds: 5

Polar Surface Area: 80.31

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.20

CX Basic pKa:

CX LogP: 5.54

CX LogD: 4.76

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -1.02

References

1. Churcher I, Beher D, Best JD, Castro JL, Clarke EE, Gentry A, Harrison T, Hitzel L, Kay E, Kerrad S, Lewis HD, Morentin-Gutierrez P, Mortishire-Smith R, Oakley PJ, Reilly M, Shaw DE, Shearman MS, Teall MR, Williams S, Wrigley JD..  (2006)  4-substituted cyclohexyl sulfones as potent, orally active gamma-secretase inhibitors.,  16  (2): [PMID:16275079] [10.1016/j.bmcl.2005.10.009]

2. Zhao Z, Pissarnitski DA, Josien HB, Wu WL, Xu R, Li H, Clader JW, Burnett DA, Terracina G, Hyde L, Lee J, Song L, Zhang L, Parker EM..  (2015)  Discovery of a Novel, Potent Spirocyclic Series of γ-Secretase Inhibitors.,  58  (22): [PMID:26496070] [10.1021/acs.jmedchem.5b00774]

3. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

4. Kumar R, Juillerat-Jeanneret L, Golshayan D..  (2016)  Notch Antagonists: Potential Modulators of Cancer and Inflammatory Diseases.,  59  (17): [PMID:27045975] [10.1021/acs.jmedchem.5b01516]

5. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

6. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

7. Rodríguez Sarmiento RM, Bissantz C, Bylund J, Limberg A, Neidhart W, Jakob-Roetne R, Wang L, Baumann K..  (2020)  Stepwise Design of γ-Secretase Modulators with an Advanced Profile by Judicious Coordinated Structural Replacements and an Unconventional Phenyl Ring Bioisostere.,  63  (15): [PMID:32706964] [10.1021/acs.jmedchem.0c00909]

8.  (2021)  EUbOPEN Chemogenomics Library wave 1,  [10.6019/CHEMBL4689842]

9. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

10. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

11. EUbOPEN.  (2023)  Affinity Phenotypic Cellular Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5209897]

12. EUbOPEN.  (2023)  Affinity Biochemical Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5210307]

13. EUbOPEN.  (2023)  Selectivity Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5212743]

Source

Source(5):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• EUbOPEN Chemogenomic Library
• Fraunhofer HDAC6
• Literature data from EUbOPEN Chemogenomic Library