cladosporin   

GtoPdb Ligand ID: 10247

Synonyms: asperentin
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.
2D Structure
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Physico-chemical Properties
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
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
Guide to Malaria Pharmacology Comments
Although cladosporin exhibits potent antimalarial activity, poor oral bioavailability has precluded the compound from further advancement in the antimalarial drug development pipeline. A recent SAR study has identified a simplified cladosporin analogue (compound 28) that has higher antimalarial potency and improved metabolic stability [2].

Potential Target/Mechanism Of Action: Postgenomic methods indicate that cladosporin inhibits protein synthesis by directly targeting P. falciparum lysine--tRNA ligase (PfKRS1) [1].