ID: ALA528437

Max Phase: Preclinical

Molecular Formula: C22H14F6N4

Molecular Weight: 448.37

Molecule Type: Small molecule

Representations

Synonyms (3): TCMDC-124162 | MMV665794 | TCMDC-124162
Synonyms from Alternative Forms(3):

Canonical SMILES:  FC(F)(F)c1cccc(Nc2nc3ccccc3nc2Nc2cccc(C(F)(F)F)c2)c1

Standard InChI:  InChI=1S/C22H14F6N4/c23-21(24,25)13-5-3-7-15(11-13)29-19-20(32-18-10-2-1-9-17(18)31-19)30-16-8-4-6-14(12-16)22(26,27)28/h1-12H,(H,29,31)(H,30,32)

Standard InChI Key:  FOQJAGNDQYWIRF-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 448.37

Molecular Weight (Monoisotopic): 448.1123

AlogP: 7.15

#Rotatable Bonds: 4

Polar Surface Area: 49.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 2.23

CX LogP: 7.12

CX LogD: 7.12

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -0.99

References

1. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

2. Simon Macdonald, Paul Willis, Paul Kowalczyk, Thomas Spangenberg, Jeremy Burrows and Tim Wells. Medicines for Malaria Venture (MMV), PO Box 1826, 20, rte de Pré-Bois, 1215 Geneva 15, Switzerland and SCYNEXIS Inc. P.O. Box 12878 Research Triangle Park, North Carolina 27709-2878 USA. Malaria Box,  [10.6019/CHEMBL2028040]

3. Ben Gold, Thulasi Warrier, Selin Somersan, Landys Lopez-Quezada, Julia Roberts, David Little and Carl Nathan.. Malaria Box Tuberculosis Screening Data,  [10.6019/CHEMBL2094260]

4. Conor Caffrey and Brian Suzuki; Center for Discovery and Innovation in Parasitic Diseases, Dept. of Pathology, University of California San Francisco (www.cdipd.org).. Malaria Box Schistosomiasis Screening Data,  [10.6019/CHEMBL2363022]

5. UCSF DeRisi Lab. UCSF DeRisi Lab MMV Box Apicoplast Screening,  [10.6019/CHEMBL2448809]

6. University of Vermont. MMV Box Cryptosporidium parvum screening set,  [10.6019/CHEMBL3137356]

7. Nao-aki Watanabe, Takaaki Horii and Koji Sagane. Next Generation Systems Core Function Unit, Eisai Production Creation Systems, Eisai Co., Ltd. 1-3 Tokodai 5 - Chome, Tsukuba-shi, Ibaraki 300-2635, JAPAN. MMV Box P. falciparum screening,  [10.6019/CHEMBL3137361]

8. Northwick Park. MMV Box Onchocerca lienalis screening set,  [10.6019/CHEMBL3137381]

9. Boyom, F.F., Fokou, P.V.T., Tchokouaha, L.R.Y., Spangenberg, T., Mfopa, A.N., Kouipou, R.M.T., Mbouna, C.J., Donkeng Donfack, V.F., Zollo, P.H.A. University of Yaoundé, IMPM Yaoundé and MMV.. MMV Malaria Box screening against Toxoplasma gondii and Entamoeba histolytica.,  [10.6019/CHEMBL3301448]

10. Imperial-Medicines for Malaria Venture Centre of Excellence, Imperial College, London.. MMV Malaria Box gametocyte functional viability assay screening.,  [10.6019/CHEMBL3301451]

11. Medicines for Malaria Venture.. MMV Malaria Box hERG screening.,  [10.6019/CHEMBL3301458]

12. Hui Lab, SGC, University of Toronto, Canada.. MMV Malaria Box thermal shift screening.,  [10.6019/CHEMBL3301461]

13. Igarashi Lab, National Research Center for Protozoan Diseases, Obihiro University of Agriculture and Veterinary Medicine, Obihiro, Japan. MMV Malaria Box anti-babesial screening.,  [10.6019/CHEMBL3301464]

14. Kaiser Lab, University Hospital Essen, Germany.. MMV Malaria Box screening against Plasmodium falciparum Deoxyhypusine hydroxylase,  [10.6019/CHEMBL3301470]

15. Ketas, T., Moore, J.P., Weill Cornell Medical College, USA.. MMV Malaria Box HIV and cytotoxicity screening.,  [10.6019/CHEMBL3301472]

16. National Cancer Institute, NIH.. MMV Malaria Box screening against the the NCI60 panel of human tumor cell lines.,  [10.6019/CHEMBL3301486]

17. St Onge, R.P. Yeast Chemical Genomics Laboratory, Stanford Genome Technology Center, Stanford University.. MMV Malaria Box yeast growth screening.,  [10.6019/CHEMBL3301546]

18. Poulsen, S-A., Andrews, K.T., Tonissen, K.F., Nawaratna, S., Eskitis Institute for Drug Discovery, Griffith University, Australia.. MMV Mararia Box screening against P. falciparum asexual stage parasites under hypoxia and bicarbonate modified culture conditions.,  [10.6019/CHEMBL3301550]

19. Taramelli Lab, University of Milan, Italy.. MMV Malaria Box screening in pLDH viability assay against Plasmodium falciparum gametocytes.,  [10.6019/CHEMBL3301555]

20. Van Voorhis Lab, University of Washington, USA.. MMV Box screening against Plasmodium falciparum protein kinases and aminoacyl tRNA synthetases.,  [10.6019/CHEMBL3301562]

21. Horrocks lab, Keele University, UK.. MMV box screening in the Dd2 P. falciparum strain,  [10.6019/CHEMBL3392922]

22. LT Jensen lab, Mahidol University, Thailand (submitted by: Laran T. Jensen, Worathad Chindaudomsate, Amornrat Naranuntarat Jensen). MMV box selection for compounds with potential use in combination with artemisinin using S. cerevisiae,  [10.6019/CHEMBL3392924]

23. TropIQ Health Sciences. MMV Malaria Box gametocyte standard membrane feeding assay screening.,  [10.6019/CHEMBL3430850]

24. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

25. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

26.  (2017)  Aryl amine substituted quinoxaline used as anticancer drugs, 

27. Padalino G, El-Sakkary N, Liu LJ, Liu C, Harte DSG, Barnes RE, Sayers E, Forde-Thomas J, Whiteland H, Bassetto M, Ferla S, Johnson G, Jones AT, Caffrey CR, Chalmers I, Brancale A, Hoffmann KF..  (2021)  Anti-schistosomal activities of quinoxaline-containing compounds: From hit identification to lead optimisation.,  226  [PMID:34536671] [10.1016/j.ejmech.2021.113823]

Source

Source(5):

• Scientific Literature
• GSK Malaria Screening
• MMV Malaria Box
• St Jude Leishmania Screening
• Patent Bioactivity Data