ID: ALA337173

Max Phase: Preclinical

Molecular Formula: C15H16ClN3O3

Molecular Weight: 321.76

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-663284
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1C(Cl)=C(NCCN2CCOCC2)C(=O)c2ncccc21

Standard InChI:  InChI=1S/C15H16ClN3O3/c16-11-13(18-4-5-19-6-8-22-9-7-19)15(21)12-10(14(11)20)2-1-3-17-12/h1-3,18H,4-9H2

Standard InChI Key:  BMKPVDQDJQWBPD-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 321.76

Molecular Weight (Monoisotopic): 321.0880

AlogP: 0.83

#Rotatable Bonds: 4

Polar Surface Area: 71.53

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 4.19

CX LogP: 0.13

CX LogD: 0.13

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.89

Np Likeness Score: -0.99

References

1. Lazo JS, Aslan DC, Southwick EC, Cooley KA, Ducruet AP, Joo B, Vogt A, Wipf P..  (2001)  Discovery and biological evaluation of a new family of potent inhibitors of the dual specificity protein phosphatase Cdc25.,  44  (24): [PMID:11708908] [10.1021/jm0102046]

2. Lavergne O, Fernandes AC, Bréhu L, Sidhu A, Brézak MC, Prévost G, Ducommun B, Contour-Galcera MO..  (2006)  Synthesis and biological evaluation of novel heterocyclic quinones as inhibitors of the dual specificity protein phosphatase CDC25C.,  16  (1): [PMID:16216500] [10.1016/j.bmcl.2005.09.030]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Vintonyak VV, Waldmann H, Rauh D..  (2011)  Using small molecules to target protein phosphatases.,  19  (7): [PMID:21420867] [10.1016/j.bmc.2011.02.047]

6. PubChem BioAssay data set, 

7. Tsuchiya A, Hirai G, Koyama Y, Oonuma K, Otani Y, Osada H, Sodeoka M..  (2012)  Dual-Specificity Phosphatase CDC25A/B Inhibitor Identified from a Focused Library with Nonelectrophilic Core Structure.,  3  (4): [PMID:22506091] [10.1021/ml2002778]

8. Lin SY, Liu CL, Chang YM, Zhao J, Perlman S, Hou MH..  (2014)  Structural basis for the identification of the N-terminal domain of coronavirus nucleocapsid protein as an antiviral target.,  57  (6): [PMID:24564608] [10.1021/jm500089r]

9. Kaniskan HÜ, Konze KD, Jin J..  (2015)  Selective inhibitors of protein methyltransferases.,  58  (4): [PMID:25406853] [10.1021/jm501234a]

10. George Rosenker KM, Paquette WD, Johnston PA, Sharlow ER, Vogt A, Bakan A, Lazo JS, Wipf P..  (2015)  Synthesis and biological evaluation of 3-aminoisoquinolin-1(2H)-one based inhibitors of the dual-specificity phosphatase Cdc25B.,  23  (12): [PMID:25703307] [10.1016/j.bmc.2015.01.043]

11. 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]

12. Jing L, Wu G, Hao X, Olotu FA, Kang D, Chen CH, Lee KH, Soliman MES, Liu X, Song Y, Zhan P..  (2019)  Identification of highly potent and selective Cdc25 protein phosphatases inhibitors from miniaturization click-chemistry-based combinatorial libraries.,  183  [PMID:31541869] [10.1016/j.ejmech.2019.111696]

13. Alfadhli A, Mack A, Harper L, Berk S, Ritchie C, Barklis E..  (2016)  Analysis of quinolinequinone reactivity, cytotoxicity, and anti-HIV-1 properties.,  24  (21): [PMID:27663546] [10.1016/j.bmc.2016.09.028]

14. Zhou H, Che X, Bao G, Wang N, Peng L, Barnash KD, Frye SV, James LI, Bai X..  (2016)  Design, synthesis, and protein methyltransferase activity of a unique set of constrained amine containing compounds.,  26  (18): [PMID:27528434] [10.1016/j.bmcl.2016.08.004]

15. 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]

16. 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]

17. 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]

18. 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]

19. 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]

20. Institute for Molecular Medicine Finland - High Throughput Biomedicine Unit.  (2023)  ECBD screening data for assay EOS300108,  [10.6019/EOS300108]

21. Institute for Molecular Medicine Finland - High Throughput Biomedicine Unit.  (2023)  ECBD screening data for assay EOS300108,  [10.6019/EOS300108]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset