From August 18th 2026, GtoPdb will require users to register to use the website. Please see our blog post for more information.

midecamycin   Click here for help

GtoPdb Ligand ID: 13158

Synonyms: espinomycin A | platenomycin B1 | rubimycin | SF-837 | turimycin P3
Approved drug
midecamycin is an approved drug
Compound class: Natural product
Comment: Midecamycin is a 16-membered macrolide antibacterial, originally isolated from culture broth of Streptomyces mycarofaciens [1-2].

midecamycin is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 16
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 206.05
Molecular weight 813.97
XLogP 2.13
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
Click here for help

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/)

✖
Canonical SMILES CCC(=O)O[C@@H]1CC(=O)O[C@H](C)C/C=C/C=C/[C@@H]([C@H](C)C[C@H](CC=O)[C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](C)O2)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)OC(=O)CC)O)N(C)C)O)O
Isomeric SMILES CCC(=O)O[C@@H]1CC(=O)O[C@@H](C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C
InChI InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1
InChI Key DMUAPQTXSSNEDD-QALJCMCCSA-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
Midecamycin was first marketed in Japan in 1974 by Meiji Seika Pharma and used as an oral treatment for a wide range of infections caused by susceptible bacteria. There is no information regarding current approval for clinical use of this drug on the US FDA or European Medicines Agency (EMA) websites. However, midecamycin does have marketing authorisation in a number of jurisdictions, including Bulgaria and Slovenia.