tilmicosin   Click here for help

GtoPdb Ligand ID: 13690

Synonyms: EL-870 | Micotil® (veterinary)
Compound class: Synthetic organic
Comment: Tilmicosin is a 16-membered macrolide antibacterial compound derived from tylosin [2-3]. It was developed for use 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 15
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 186.15
Molecular weight 869.13
XLogP 1.89
No. Lipinski's rules broken 3

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 CC[C@@H]1[C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@H](CCN2C[C@H](C)C[C@H](C)C2)[C@@H]([C@@H](C)[C@@H](CC(=O)O1)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)N(C)C)O)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](C)O4)O)OC)OC
Isomeric SMILES CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)N(C)C)O)CCN3C[C@@H](C[C@@H](C3)C)C)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
InChI InChI=1S/C46H80N2O13/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3/b15-14+,25-19+/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,38+,39-,40-,41-,42-,43-,44-,45+,46-/m1/s1
InChI Key JTSDBFGMPLKDCD-XVFHVFLVSA-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. Andersen NM, Poehlsgaard J, Warrass R, Douthwaite S. (2012)
Inhibition of protein synthesis on the ribosome by tildipirosin compared with other veterinary macrolides.
Antimicrob Agents Chemother, 56 (11): 6033-6. [PMID:22926570]
2. Debono M, Willard KE, Kirst HA, Wind JA, Crouse GD, Tao EV, Vicenzi JT, Counter FT, Ott JL, Ose EE et al.. (1989)
Synthesis and antimicrobial evaluation of 20-deoxo-20-(3,5-dimethylpiperidin-1-yl)desmycosin (tilmicosin, EL-870) and related cyclic amino derivatives.
J Antibiot (Tokyo), 42 (8): 1253-67. [PMID:2668243]
3. Ose EE. (1987)
In vitro antibacterial properties of EL-870, a new semi-synthetic macrolide antibiotic.
J Antibiot (Tokyo), 40 (2): 190-4. [PMID:3570967]
4. Poehlsgaard J, Andersen NM, Warrass R, Douthwaite S. (2012)
Visualizing the 16-membered ring macrolides tildipirosin and tilmicosin bound to their ribosomal site.
ACS Chem Biol, 7 (8): 1351-5. [PMID:22563863]
5. Veenhuizen MF, Wright TJ, McManus RF, Owens JG. (2006)
Analysis of reports of human exposure to Micotil 300 (tilmicosin injection).
J Am Vet Med Assoc, 229 (11): 1737-42. [PMID:17144818]