ID: ALA1237255

Max Phase: Preclinical

Molecular Formula: C23H20N8O4

Molecular Weight: 472.47

Molecule Type: Small molecule

Representations

Synonyms (3): TCMDC-124127 | MMV666689 | TCMDC-124127
Synonyms from Alternative Forms(3):

Canonical SMILES:  COc1ccc(Nc2nc(N/N=C/c3ccc(O)cc3)nc(Nc3ccc([N+](=O)[O-])cc3)n2)cc1

Standard InChI:  InChI=1S/C23H20N8O4/c1-35-20-12-6-17(7-13-20)26-22-27-21(25-16-4-8-18(9-5-16)31(33)34)28-23(29-22)30-24-14-15-2-10-19(32)11-3-15/h2-14,32H,1H3,(H3,25,26,27,28,29,30)/b24-14+

Standard InChI Key:  PPSIRBXGBCWYRP-ZVHZXABRSA-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: 472.47

Molecular Weight (Monoisotopic): 472.1608

AlogP: 4.43

#Rotatable Bonds: 9

Polar Surface Area: 159.72

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.11

CX Basic pKa: 3.77

CX LogP: 6.08

CX LogD: 6.07

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.16

Np Likeness Score: -1.10

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

8. 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]

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

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

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

12. 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]

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

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

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

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

17. 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]

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

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

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

21. 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]

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

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

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

Source

Source(3):

• GSK Malaria Screening
• MMV Malaria Box
• St Jude Leishmania Screening