valnemulin   Click here for help

GtoPdb Ligand ID: 13813

Synonyms: Econor® (veterinary)
Compound class: Synthetic organic
Comment: Valnemulin is a pleuromutilin antibacterial compound. It is used in veterinary medicine.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 144.02
Molecular weight 564.82
XLogP 4.45
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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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/)

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Canonical SMILES C=C[C@]1(C)C[C@H]([C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@@H]23)[C@@H](C)[C@@H]1O)OC(=O)CSC(C)(C)CNC(=O)[C@@H](C(C)C)N
Isomeric SMILES C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CSC(C)(C)CNC(=O)[C@@H](C(C)C)N)C
InChI InChI=1S/C31H52N2O5S/c1-10-29(8)15-22(38-23(35)16-39-28(6,7)17-33-27(37)24(32)18(2)3)30(9)19(4)11-13-31(20(5)26(29)36)14-12-21(34)25(30)31/h10,18-20,22,24-26,36H,1,11-17,32H2,2-9H3,(H,33,37)/t19-,20+,22-,24-,25+,26+,29-,30+,31+/m1/s1
InChI Key LLYYNOVSVPBRGV-MVNKZKPCSA-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/)
No information available.
Summary of Clinical Use Click here for help
Valnemulin is not approved for use in humans, although it has been used in isolated cases to treat drug-resistant Mycoplasma infections in patients with common variable immunodeficiency (CVID) [2]. The drug is licensed for veterinary use by the European Medicines Agency (EMA) and is administered orally in the form of valnemulin hydrochloride. In swine, it is used to prevent or treat infectious diseases of the respiratory and gastrointestinal tract and in rabbits, it is used to reduce mortality during outbreaks of epizootic rabbit enteropathy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Valnemulin binds to the peptidyl transferase center (PTC) of the bacterial 50S ribosomal subunit, leading to inhibition of peptide bond formation [3-4].