tiamulin   Click here for help

GtoPdb Ligand ID: 13651

Synonyms: 81.723 hfu | Denagard® (veterinary) | thiamutilin
PDB Ligand
Compound class: Synthetic organic
Comment: Tiamulin is a pleuromutilin antibacterial compound [1-2]. It is used in veterinary medicine.

tiamulin is commercially available from our sponsors

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 5
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 92.14
Molecular weight 493.74
XLogP 4.88
No. Lipinski's rules broken 0

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)CSCCN(CC)CC
Isomeric SMILES CCN(CC)CCSCC(=O)O[C@@H]1C[C@@]([C@H]([C@@H]([C@@]23CC[C@H]([C@@]1([C@@H]2C(=O)CC3)C)C)C)O)(C)C=C
InChI InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1
InChI Key UURAUHCOJAIIRQ-QGLSALSOSA-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/)
References
1. Drews J, Georgopoulos A, Laber G, Schütze E, Unger J. (1975)
Antimicrobial activities of 81.723 hfu, a new pleuromutilin derivative.
Antimicrob Agents Chemother, 7 (5): 507-16. [PMID:1170807]
2. Egger H, Reinshagen H. (1976)
New pleuromutilin derivatives with enhanced antimicrobial activity.II.Structure-activity correlations.
J Antibiot (Tokyo), 29 (9): 923-7. [PMID:993132]
3. Islam KM, Klein U, Burch DG. (2009)
The activity and compatibility of the antibiotic tiamulin with other drugs in poultry medicine--A review.
Poult Sci, 88 (11): 2353-9. [PMID:19834086]
4. Long KS, Hansen LH, Jakobsen L, Vester B. (2006)
Interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center.
Antimicrob Agents Chemother, 50 (4): 1458-62. [PMID:16569865]
5. Poulsen SM, Karlsson M, Johansson LB, Vester B. (2001)
The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome.
Mol Microbiol, 41 (5): 1091-9. [PMID:11555289]
6. van Duijkeren E, Greko C, Pringle M, Baptiste KE, Catry B, Jukes H, Moreno MA, Pomba MC, Pyörälä S, Rantala M et al.. (2014)
Pleuromutilins: use in food-producing animals in the European Union, development of resistance and impact on human and animal health.
J Antimicrob Chemother, 69 (8): 2022-31. [PMID:24793902]