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
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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 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
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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 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/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes
Approved drug? Yes.
IUPAC Name Click here for help
[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-4-dimethylamino-5-hydroxy-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-propanoyloxy-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] propanoate
International Nonproprietary Names Click here for help
INN number INN
3461 midecamycin
Synonyms Click here for help
espinomycin A | platenomycin B1 | rubimycin | SF-837 | turimycin P3
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Midecamycin
Other databases
CAS Registry No. 35457-80-8 (source: Scifinder)
ChEBI CHEBI:31845
ChEMBL Ligand CHEMBL444963
DrugBank Ligand DB13456
DrugCentral Ligand 1861
GtoPdb PubChem SID 491299940
PubChem CID 5282169
Search Google for chemical match using the InChIKey DMUAPQTXSSNEDD-QALJCMCCSA-N
Search Google for chemicals with the same backbone DMUAPQTXSSNEDD
Search PubMed clinical trials midecamycin
Search PubMed titles midecamycin
Search PubMed titles/abstracts midecamycin
UniChem Compound Search for chemical match using the InChIKey DMUAPQTXSSNEDD-QALJCMCCSA-N
UniChem Connectivity Search for chemical match using the InChIKey DMUAPQTXSSNEDD-QALJCMCCSA-N

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MedChemExpress
Midecamycin (links to external site)
Cat. No. HY-B1908