ID: ALA5314343

Max Phase: Preclinical

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight:

Molecular Weight (Monoisotopic):

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Nicholas GM, Li R, MacMillan JB, Molinski TF..  (2002)  Antifungal activity of bifunctional sphingolipids. Intramolecular synergism within long-chain alpha,omega-bis-aminoalcohols.,  12  (16): [PMID:12127527] [10.1016/s0960-894x(02)00367-0]

2. Hill TA, Odell LR, Quan A, Abagyan R, Ferguson G, Robinson PJ, McCluskey A..  (2004)  Long chain amines and long chain ammonium salts as novel inhibitors of dynamin GTPase activity.,  14  (12): [PMID:15149689] [10.1016/j.bmcl.2004.03.096]

3. Calas M, Cordina G, Bompart J, Ben Bari M, Jei T, Ancelin ML, Vial H..  (1997)  Antimalarial activity of molecules interfering with Plasmodium falciparum phospholipid metabolism. Structure-activity relationship analysis.,  40  (22): [PMID:9357523] [10.1021/jm9701886]

4. Bodor N, Kaminski JJ, Selk S..  (1980)  Soft drugs. 1. Labile quaternary ammonium salts as soft antimicrobials.,  23  (5): [PMID:7381846] [10.1021/jm00179a001]

5. Calas M, Ancelin ML, Cordina G, Portefaix P, Piquet G, Vidal-Sailhan V, Vial H..  (2000)  Antimalarial activity of compounds interfering with Plasmodium falciparum phospholipid metabolism: comparison between mono- and bisquaternary ammonium salts.,  43  (3): [PMID:10669577] [10.1021/jm9911027]

6. Haldar J, Kondaiah P, Bhattacharya S..  (2005)  Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles. Incorporation of multiple head groups leads to impressive antibacterial activity.,  48  (11): [PMID:15916434] [10.1021/jm049106l]

7. Choubey V, Maity P, Guha M, Kumar S, Srivastava K, Puri SK, Bandyopadhyay U..  (2007)  Inhibition of Plasmodium falciparum choline kinase by hexadecyltrimethylammonium bromide: a possible antimalarial mechanism.,  51  (2): [PMID:17145794] [10.1128/aac.00919-06]

8. Necula M, Kayed R, Milton S, Glabe CG..  (2007)  Small molecule inhibitors of aggregation indicate that amyloid beta oligomerization and fibrillization pathways are independent and distinct.,  282  (14): [PMID:17284452] [10.1074/jbc.m608207200]

9. Pérez L, Pinazo A, Teresa García M, Lozano M, Manresa A, Angelet M, Pilar Vinardell M, Mitjans M, Pons R, Rosa Infante M..  (2009)  Cationic surfactants from lysine: synthesis, micellization and biological evaluation.,  44  (5): [PMID:19070403] [10.1016/j.ejmech.2008.11.003]

10. Lukác M, Mojzis J, Mojzisová G, Mrva M, Ondriska F, Valentová J, Lacko I, Bukovský M, Devínsky F, Karlovská J..  (2009)  Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity.,  44  (12): [PMID:19762125] [10.1016/j.ejmech.2009.08.011]

11. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. Zhang J, Redman N, Litke AP, Zeng J, Zhan J, Chan KY, Chang CW..  (2011)  Synthesis and antibacterial activity study of a novel class of cationic anthraquinone analogs.,  19  (1): [PMID:21111625] [10.1016/j.bmc.2010.11.001]

15. Floyd JL, Smith KP, Kumar SH, Floyd JT, Varela MF..  (2010)  LmrS is a multidrug efflux pump of the major facilitator superfamily from Staphylococcus aureus.,  54  (12): [PMID:20855745] [10.1128/aac.00580-10]

16. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

17. LaDow JE, Warnock DC, Hamill KM, Simmons KL, Davis RW, Schwantes CR, Flaherty DC, Willcox JA, Wilson-Henjum K, Caran KL, Minbiole KP, Seifert K..  (2011)  Bicephalic amphiphile architecture affects antibacterial activity.,  46  (9): [PMID:21794958] [10.1016/j.ejmech.2011.06.026]

18. Chan KY, Zhang J, Chang CW..  (2011)  Mode of action investigation for the antibacterial cationic anthraquinone analogs.,  21  (21): [PMID:21937226] [10.1016/j.bmcl.2011.08.107]

19. Rejman D, Rabatinová A, Pombinho AR, Kovačková S, Pohl R, Zborníková E, Kolář M, Bogdanová K, Nyč O, Sanderová H, Látal T, Bartůněk P, Krásný L..  (2011)  Lipophosphonoxins: new modular molecular structures with significant antibacterial properties.,  54  (22): [PMID:22007704] [10.1021/jm2009343]

20. PubChem BioAssay data set, 

21. Lukáč M, Mrva M, Garajová M, Mojžišová G, Varinská L, Mojžiš J, Sabol M, Kubincová J, Haragová H, Ondriska F, Devínsky F..  (2013)  Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride.,  66  [PMID:23792315] [10.1016/j.ejmech.2013.05.033]

22. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

23. Foley TL, Rai G, Yasgar A, Daniel T, Baker HL, Attene-Ramos M, Kosa NM, Leister W, Burkart MD, Jadhav A, Simeonov A, Maloney DJ..  (2014)  4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a potent inhibitor of bacterial phosphopantetheinyl transferase that attenuates secondary metabolism and thwarts bacterial growth.,  57  (3): [PMID:24450337] [10.1021/jm401752p]

24. PubChem BioAssay data set, 

25. PubChem BioAssay data set, 

26. González-Delgado JA, Kennedy PJ, Ferreira M, Tomé JP, Sarmento B..  (2016)  Use of Photosensitizers in Semisolid Formulations for Microbial Photodynamic Inactivation.,  59  (10): [PMID:26569024] [10.1021/acs.jmedchem.5b01129]

27. Zimmermann L, Das I, Désiré J, Sautrey G, Barros R S V, El Khoury M, Mingeot-Leclercq MP, Décout JL..  (2016)  New Broad-Spectrum Antibacterial Amphiphilic Aminoglycosides Active against Resistant Bacteria: From Neamine Derivatives to Smaller Neosamine Analogues.,  59  (20): [PMID:27690420] [10.1021/acs.jmedchem.6b00818]

28. Hoque J, Konai MM, Sequeira SS, Samaddar S, Haldar J..  (2016)  Antibacterial and Antibiofilm Activity of Cationic Small Molecules with Spatial Positioning of Hydrophobicity: An in Vitro and in Vivo Evaluation.,  59  (23): [PMID:27809517] [10.1021/acs.jmedchem.6b01435]

29. Yang X, Goswami S, Gorityala BK, Domalaon R, Lyu Y, Kumar A, Zhanel GG, Schweizer F..  (2017)  A Tobramycin Vector Enhances Synergy and Efficacy of Efflux Pump Inhibitors against Multidrug-Resistant Gram-Negative Bacteria.,  60  (9): [PMID:28399372] [10.1021/acs.jmedchem.7b00156]

30. 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]

31. Li SA, Cadelis MM, Sue K, Blanchet M, Vidal N, Brunel JM, Bourguet-Kondracki ML, Copp BR..  (2019)  6-Bromoindolglyoxylamido derivatives as antimicrobial agents and antibiotic enhancers.,  27  (10): [PMID:30975502] [10.1016/j.bmc.2019.04.004]

32. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

33. 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]

34. 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]

35. Terekhova NV, Tatarinov DA, Shaihutdinova ZM, Pashirova TN, Lyubina AP, Voloshina AD, Sapunova AS, Zakharova LY, Mironov VF..  (2020)  Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action.,  30  (13): [PMID:32386856] [10.1016/j.bmcl.2020.127234]

36. Fouotsa H, Le Pogam P, Mkounga P, Lannang AM, Bernadat G, Vanheuverzwijn J, Zhou Z, Leblanc K, Rharrabti S, Nkengfack AE, Gallard JF, Fontaine V, Meyer F, Poupon E, Beniddir MA..  (2021)  Voatriafricanines A and B, Trimeric Vobasine-Aspidosperma-Aspidosperma Alkaloids from Voacanga africana.,  84  (10.0): [PMID:34569237] [10.1021/acs.jnatprod.1c00812]

Source

Source(3):

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