cladosporin   Click here for help

GtoPdb Ligand ID: 10247

Synonyms: asperentin
PDB Ligand Antimalarial Ligand
Compound class: Natural product
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, antibacterial, 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
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]