SC83288   Click here for help

GtoPdb Ligand ID: 10175

Antimalarial Ligand
Compound class: Synthetic organic
Comment: SC83288 is an amicarbalide derivative and the clinical development candidate for this novel antimalarial chemotype [2].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 13
Topological polar surface area 220.85
Molecular weight 629.17
XLogP 1.86
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC(=O)N1CCN(CC1)C(=N)c1cccc(c1)NC(=O)Nc1ccc(cc1)S(=O)(=O)NCc1ccc(cc1)S(=O)(=O)N
Isomeric SMILES COC(=O)N1CCN(CC1)C(=N)c1cccc(c1)NC(=O)Nc1ccc(cc1)S(=O)(=O)NCc1ccc(cc1)S(=O)(=O)N
InChI InChI=1S/C27H31N7O7S2/c1-41-27(36)34-15-13-33(14-16-34)25(28)20-3-2-4-22(17-20)32-26(35)31-21-7-11-24(12-8-21)43(39,40)30-18-19-5-9-23(10-6-19)42(29,37)38/h2-12,17,28,30H,13-16,18H2,1H3,(H2,29,37,38)(H2,31,32,35)
InChI Key UJKWTQWUYKHLGQ-UHFFFAOYSA-N
References
1. Duffey M, Sanchez CP, Lanzer M. (2018)
Profiling of the anti-malarial drug candidate SC83288 against artemisinins in Plasmodium falciparum.
Malar. J., 17 (1): 121. [PMID:29558913]
2. Pegoraro S, Duffey M, Otto TD, Wang Y, Rösemann R, Baumgartner R, Fehler SK, Lucantoni L, Avery VM, Moreno-Sabater A et al.. (2017)
SC83288 is a clinical development candidate for the treatment of severe malaria.
Nat Commun, 8: 14193. [PMID:28139658]