ID: ALA450940

Max Phase: Phase

Molecular Formula: C15H10FNO3

Molecular Weight: 271.25

Molecule Type: Small molecule

Representations

Synonyms (3): Prinaberel | ERB-041 | PF-00913086
Synonyms from Alternative Forms(3):

Canonical SMILES:  C=Cc1cc(O)cc2nc(-c3ccc(O)c(F)c3)oc12

Standard InChI:  InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,18-19H,1H2

Standard InChI Key:  MQIMZDXIAHJKQP-UHFFFAOYSA-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: 271.25

Molecular Weight (Monoisotopic): 271.0645

AlogP: 3.69

#Rotatable Bonds: 2

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.53

CX Basic pKa: 1.00

CX LogP: 3.62

CX LogD: 3.36

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.75

Np Likeness Score: -0.19

References

1. Malamas MS, Manas ES, McDevitt RE, Gunawan I, Xu ZB, Collini MD, Miller CP, Dinh T, Henderson RA, Keith JC, Harris HA..  (2004)  Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-beta ligands.,  47  (21): [PMID:15456246] [10.1021/jm049719y]

2. Luan F, Liu HT, Ma WP, Fan BT..  (2008)  Classification of estrogen receptor-beta ligands on the basis of their binding affinities using support vector machine and linear discriminant analysis.,  43  (1): [PMID:17459530] [10.1016/j.ejmech.2007.03.002]

3. Asim M, El-Salfiti M, Qian Y, Choueiri C, Salari S, Cheng J, Shadnia H, Bal M, Christine Pratt MA, Carlson KE, Katzenellenbogen JA, Wright JS, Durst T..  (2009)  Deconstructing estradiol: removal of B-ring generates compounds which are potent and subtype-selective estrogen receptor agonists.,  19  (4): [PMID:19167882] [10.1016/j.bmcl.2008.12.080]

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

5. Unpublished dataset, 

6. Sampathi Perera KLI, Hanson AM, Lindeman S, Imhoff A, Lu X, Sem DS, Donaldson WA..  (2018)  Synthesis and evaluation of 4-cycloheptylphenols as selective Estrogen receptor-β agonists (SERBAs).,  157  [PMID:30144697] [10.1016/j.ejmech.2018.08.006]

7. 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]

8. 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]

9. 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]

10. 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]

11. 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]

12. 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]

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6