ID: ALA388676

Max Phase: Preclinical

Molecular Formula: C9H8Cl3NO2S

Molecular Weight: 300.59

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  O=C1C2CC=CCC2C(=O)N1SC(Cl)(Cl)Cl

Standard InChI:  InChI=1S/C9H8Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-2,5-6H,3-4H2

Standard InChI Key:  LDVVMCZRFWMZSG-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: 300.59

Molecular Weight (Monoisotopic): 298.9341

AlogP: 2.91

#Rotatable Bonds: 1

Polar Surface Area: 37.38

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 0

Heavy Atoms: 16

QED Weighted: 0.32

Np Likeness Score: 0.44

References

1. Shilabin AG, Kasanah N, Wedge DE, Hamann MT..  (2007)  Lysosome and HER3 (ErbB3) selective anticancer agent kahalalide F: semisynthetic modifications and antifungal lead-exploration studies.,  50  (18): [PMID:17696332] [10.1021/jm061288r]

2. Wedge DE, Nagle DG..  (2000)  A new 2D-TLC bioautography method for the discovery of novel antifungal agents To control plant pathogens.,  63  (8): [PMID:10978195] [10.1021/np990628r]

3. Malterud KE, Bremnes TE, Faegri A, Moe T, Dugstad EKS, Anthonsen T, Henriksen LM.  (1985)  Flavonoids from the Wood of Salix caprea as Inhibitors of Wood-Destroying Fungi,  48  (4): [10.1021/np50040a007]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Wedge DE, Klun JA, Tabanca N, Demirci B, Ozek T, Baser KH, Liu Z, Zhang S, Cantrell CL, Zhang J..  (2009)  Bioactivity-guided fractionation and GC/MS fingerprinting of Angelica sinensis and Angelica archangelica root components for antifungal and mosquito deterrent activity.,  57  (2): [PMID:19113871] [10.1021/jf802820d]

8. Meepagala KM, Schrader KK, Burandt CL, Wedge DE, Duke SO..  (2010)  New class of algicidal compounds and fungicidal activities derived from a chromene amide of Amyris texana.,  58  (17): [PMID:20695429] [10.1021/jf101626g]

9. Sobolev VS, Khan SI, Tabanca N, Wedge DE, Manly SP, Cutler SJ, Coy MR, Becnel JJ, Neff SA, Gloer JB..  (2011)  Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids.,  59  (5): [PMID:21314127] [10.1021/jf104742n]

10. Nel B, Steinberg C, Labuschagne N, Viljoen A..  (2007)  Evaluation of fungicides and sterilants for potential application in the management of Fusarium wilt of banana,  26  (4): [10.1016/j.cropro.2006.06.008]

11. Thobunluepop P..  (2009)  Implementation of bio-fungicides and seed treatment in organic rice cv. KDML 105 farming.,  12  (16): [PMID:19899322] [10.3923/pjbs.2009.1119.1126]

12. Tabanca N, Demirci B, Crockett SL, Başer KH, Wedge DE..  (2007)  Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils.,  55  (21): [PMID:17894463] [10.1021/jf071379c]

13. Labbé C, Faini F, Villagrán C, Coll J, Rycroft DS..  (2005)  Antifungal and insect antifeedant 2-phenylethanol esters from the liverwort Balantiopsis cancellata from Chile.,  53  (2): [PMID:15656657] [10.1021/jf048935c]

14. Fokialakis N, Cantrell CL, Duke SO, Skaltsounis AL, Wedge DE..  (2006)  Antifungal activity of thiophenes from Echinops ritro.,  54  (5): [PMID:16506815] [10.1021/jf052702j]

15. Tabanca N, Demirci B, Baser KH, Aytac Z, Ekici M, Khan SI, Jacob MR, Wedge DE..  (2006)  Chemical composition and antifungal activity of Salvia macrochlamys and Salvia recognita essential oils.,  54  (18): [PMID:16939314] [10.1021/jf0608773]

16. Cantrell CL, Case BP, Mena EE, Kniffin TM, Duke SO, Wedge DE..  (2008)  Isolation and identification of antifungal fatty acids from the basidiomycete Gomphus floccosus.,  56  (13): [PMID:18557621] [10.1021/jf8008662]

17. da Silva MF, Soares MS, Fernandes JB, Vieria PC..  (2007)  Alkyl, aryl, alkylarylquinoline, and related alkaloids.,  64  [PMID:18085331] [10.1016/s1099-4831(07)64004-8]

18. Macedo PEF, Maffia LA, Cota LV, Louren^|^ccedil;o V, Mizubuti ESG.  (2012)  Sensitivity of four isolates of Clonostachys rosea to pesticides used in the strawberry crop in Brazil,  37  (4): [10.1584/jpestics.D11-055]

19. Oliva A, Meepagala KM, Wedge DE, Harries D, Hale AL, Aliotta G, Duke SO..  (2003)  Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.,  51  (4): [PMID:12568545] [10.1021/jf0259361]

20. Berbegal M, Armengol J, García-Jiménez J..  (2011)  Evaluation of fungicides to control circular leaf spot of persimmon caused by Mycosphaerella nawae,  30  (11): [10.1016/j.cropro.2011.05.017]

21. Tabanca N, Wedge DE, Ali A, Khan IA, Kaplancikli ZA, Altintop MD.  (2013)  Antifungal, mosquito deterrent, and larvicidal activity of N-(benzylidene)-3-cyclohexylpropionic acid hydrazide derivatives,  22  (6): [10.1007/s00044-012-0250-4]

22. PubChem BioAssay data set, 

23. PubChem BioAssay data set, 

24. PubChem BioAssay data set, 

25. PubChem BioAssay data set, 

26. 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]

27. 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]

28. 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]

29. 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(4):

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