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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
References
1. Hoepfner D, McNamara CW, Lim CS, Studer C, Riedl R, Aust T, McCormack SL, Plouffe DM, Meister S, Schuierer S et al.. (2012)
Selective and specific inhibition of the plasmodium falciparum lysyl-tRNA synthetase by the fungal secondary metabolite cladosporin.
Cell Host Microbe, 11 (6): 654-63. [PMID:22704625]
2. Rusch M, Thevenon A, Hoepfner D, Aust T, Studer C, Patoor M, Rollin P, Livendahl M, Ranieri B, Schmitt E et al.. (2019)
Design and Synthesis of Metabolically Stable tRNA Synthetase Inhibitors Derived from Cladosporin.
Chembiochem, 20 (5): 644-649. [PMID:30462880]