analog 18 [PMID: 28696697]   Click here for help

GtoPdb Ligand ID: 11567

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Analog 18 is the lead from a class of antimalarial compounds based on the naturally derived tripeptide molecule carmaphycin B [1]. Functionally these compounds inhibit the Plasmodium proteasome.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 20
Topological polar surface area 116.9
Molecular weight 481.35
XLogP 4.31
No. Lipinski's rules broken 1
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Canonical SMILES CCCC[C@@H](C(=O)N[C@H](C(=O)[C@]1(C)OC1)CC(C)C)NC(=O)[C@@H](C(C)C)NC(=O)CCCCC
Isomeric SMILES CCCC[C@@H](C(=O)N[C@H](C(=O)[C@]1(C)OC1)CC(C)C)NC(=O)[C@@H](C(C)C)NC(=O)CCCCC
InChI InChI=1S/C26H47N3O5/c1-8-10-12-14-21(30)29-22(18(5)6)25(33)27-19(13-11-9-2)24(32)28-20(15-17(3)4)23(31)26(7)16-34-26/h17-20,22H,8-16H2,1-7H3,(H,27,33)(H,28,32)(H,29,30)/t19-,20-,22+,26+/m0/s1
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum proteasome subunit beta type-5 PfDd2 Parasite growth inhibition assay - - 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.27x10-9 M) SYBR Green I assay (72h) [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum proteasome subunit beta type-5 PfNF54 Parasite late stage (V) gametocyte assay - - 6.9 pIC50 - 1
pIC50 6.9 (IC50 1.3x10-7 M) [1]