cladosporin   Click here for help

GtoPdb Ligand ID: 10247

Synonyms: asperentin
PDB Ligand Antimalarial Ligand
Comment: Cladosporin is a tricyclic octaketide that is a secondary metabolite produced by several fungal genera including Cladosporium and Aspergillus. Cladosporin exhibits broad-spectrum bioactivity, including antimalarial, antifungal, antibiotic, plant growth inhibitory properties and mammalian anti-inflammatory effects.

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 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 75.99
Molecular weight 292.13
XLogP 2.56
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC1CCCC(O1)CC1OC(=O)c2c(C1)cc(cc2O)O
Isomeric SMILES C[C@H]1CCC[C@@H](O1)C[C@@H]1OC(=O)c2c(C1)cc(cc2O)O
InChI InChI=1S/C16H20O5/c1-9-3-2-4-12(20-9)8-13-6-10-5-11(17)7-14(18)15(10)16(19)21-13/h5,7,9,12-13,17-18H,2-4,6,8H2,1H3/t9-,12+,13+/m0/s1
InChI Key WOMKDMUZNBFXKG-ZWKOPEQDSA-N
Bioactivity Comments
The antiparasite activitity of cladosporin against both the liver stage and asexual blood stage of the Plasmodium lifecycle is provided in the interaction table below. Cladosporin is greater than 100-fold more potent against PfKRS1 relative to the human enzyme, which is conferred by the identity of two amino acids within the enzyme active site [1].
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum lysine--tRNA ligase Py Parasite liver stage assay - - 7.4 pIC50 - 1
pIC50 7.4 (IC50 3.91x10-8 M) Sporozoite hepatocyte invasion assay [1]
Lifecycle stages: Plasmodium liver stage (sporozoite, hepatic schizont, hepatic merozoite)
Plasmodium falciparum lysine--tRNA ligase Pf3D7 Parasite growth inhibition assay - - 7.3 pIC50 - 1
pIC50 7.3 (IC50 4.54x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum lysine--tRNA ligase PfD6 Parasite growth inhibition assay - - 7.1 pIC50 - 1
pIC50 7.1 (IC50 7.21x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum lysine--tRNA ligase PfK1 Parasite growth inhibition assay - - 7.1 pIC50 - 1
pIC50 7.1 (IC50 8.01x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum lysine--tRNA ligase PfNF54 Parasite growth inhibition assay - - 7.1 pIC50 - 1
pIC50 7.1 (IC50 8.79x10-8 M) SYBR Green assay [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)