chlorotonil A   Click here for help

GtoPdb Ligand ID: 13589

Antimalarial Ligand
Compound class: Natural product
Comment: Chlorotonil A is a macrolide produced by the myxobacterium Sorangium cellulosum [2]. It has antibacterial activity against Gram-positive bacteria, antifungal activity and antimalarial activity.

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
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 60.44
Molecular weight 479.44
XLogP 6.03
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES CC1=C[C@@H](C)[C@@H]2[C@H](C=C[C@H]3[C@H](C)/C=C\C=C\[C@H](C)OC(=O)[C@@H](C)C(=O)C(C(=O)[C@H]32)(Cl)Cl)C1
Isomeric SMILES C[C@@H]1/C=C\C=C\[C@@H](OC(=O)[C@H](C(=O)C(C(=O)[C@@H]2[C@H]1C=C[C@H]3[C@H]2[C@@H](C=C(C3)C)C)(Cl)Cl)C)C
InChI InChI=1S/C26H32Cl2O4/c1-14-12-16(3)21-19(13-14)10-11-20-15(2)8-6-7-9-17(4)32-25(31)18(5)23(29)26(27,28)24(30)22(20)21/h6-12,15-22H,13H2,1-5H3/b8-6-,9-7+/t15-,16-,17+,18+,19-,20+,21-,22-/m1/s1
InChI Key RQYZFUUTQJMTMJ-JCSZEPHKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(1S,2R,3Z,5E,7S,10S,14R,15R,16S,20S)-12,12-dichloro-2,7,10,16,18-pentamethyl-8-oxatricyclo[12.8.0.015,20]docosa-3,5,17,21-tetraene-9,11,13-trione
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Chlorotonil A
Other databases
CAS Registry No. 1009813-26-6 (source: Scifinder)
ChEBI CHEBI:202669
ChEMBL Ligand CHEMBL4290170
GtoPdb PubChem SID 504705408
PubChem CID 24742044
Search Google for chemical match using the InChIKey RQYZFUUTQJMTMJ-JCSZEPHKSA-N
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UniChem Compound Search for chemical match using the InChIKey RQYZFUUTQJMTMJ-JCSZEPHKSA-N
UniChem Connectivity Search for chemical match using the InChIKey RQYZFUUTQJMTMJ-JCSZEPHKSA-N