ID: ALA225963

Max Phase: Preclinical

Molecular Formula: C19H25ClN2OS

Molecular Weight: 364.94

Molecule Type: Small molecule

Representations

Synonyms (1): pyridaben
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)(C)c1ccc(CSc2cnn(C(C)(C)C)c(=O)c2Cl)cc1

Standard InChI:  InChI=1S/C19H25ClN2OS/c1-18(2,3)14-9-7-13(8-10-14)12-24-15-11-21-22(19(4,5)6)17(23)16(15)20/h7-11H,12H2,1-6H3

Standard InChI Key:  DWFZBUWUXWZWKD-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: 364.94

Molecular Weight (Monoisotopic): 364.1376

AlogP: 5.24

#Rotatable Bonds: 3

Polar Surface Area: 34.89

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -1.58

References

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2. Radeke H, Hanson K, Yalamanchili P, Hayes M, Zhang ZQ, Azure M, Yu M, Guaraldi M, Kagan M, Robinson S, Casebier D..  (2007)  Synthesis and biological evaluation of the mitochondrial complex 1 inhibitor 2-[4-(4-fluorobutyl)benzylsulfanyl]-3-methylchromene-4-one as a potential cardiac positron emission tomography tracer.,  50  (18): [PMID:17696417] [10.1021/jm0701831]

3. Purohit A, Radeke H, Azure M, Hanson K, Benetti R, Su F, Yalamanchili P, Yu M, Hayes M, Guaraldi M, Kagan M, Robinson S, Casebier D..  (2008)  Synthesis and biological evaluation of pyridazinone analogues as potential cardiac positron emission tomography tracers.,  51  (10): [PMID:18422306] [10.1021/jm701443n]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

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7. Chae SH, Kim SI, Yeon SH, Lee SW, Ahn YJ..  (2011)  Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci.,  59  (15): [PMID:21728333] [10.1021/jf201927t]

8. Ou J, Zhu X, Wang L, Xu C, Liu F, Ren L, Xu X, Wang Y, Rui C, Liu S..  (2012)  Synthesis and bioactivity study of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives.,  60  (44): [PMID:23088717] [10.1021/jf303376t]

9. KAI H, TOMIDA M, NAKAI T, KUMANO K, HIROSE S, MORITA K.  (2001)  Synthesis and Acaricidal Activities of New Benzophenone O-Methyloximes,  26  (2): [10.1584/jpestics.26.121]

10. Besard L, Mommaerts V, Vandeven J, Cuvelier X, Sterk G, Smagghe G..  (2010)  Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.,  66  (7): [PMID:20309850] [10.1002/ps.1943]

11. Kim MP, Sim C, Shin D, Suh E, Cho K..  (2006)  Residual and sublethal effects of fenpyroximate and pyridaben on the instantaneous rate of increase of Tetranychus urticae,  25  (6): [10.1016/j.cropro.2005.08.010]

12. Li M, Liu CL, Li L, Yang H, Li ZN, Zhang H, Li ZM..  (2010)  Design, synthesis and biological activities of new strobilurin derivatives containing substituted pyrazoles.,  66  (1): [PMID:19760633] [10.1002/ps.1837]

13. Van Pottelberge S, Van Leeuwen T, Khajehali J, Tirry L..  (2009)  Genetic and biochemical analysis of a laboratory-selected spirodiclofen-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae).,  65  (4): [PMID:19170251] [10.1002/ps.1698]

14. PubChem BioAssay data set, 

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. 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]

17. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

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19.  (2022)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomis Library 2 (Multiplex),  [10.6019/CHEMBL5058577]

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Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• EUbOPEN Chemogenomic Library
• IMI-CARE SARS-CoV-2 Data
• EU-OPENSCREEN dataset