cresomycin

Cresomycin is an experimental antibiotic. It binds to the bacterial ribosome in both Gram-negative and Gram-positive bacteria, and it has been found to be effective against multi-drug-resistant stains of Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. It belongs to the bridged macrobicyclic oxepanoprolinamide antibiotics, which have similarities with lincosamides antibiotics.

In the Vinony graph

Within Vinony's link graph, cresomycin is referenced by 109 other articles, and connects out to neomycin, Harvard University and antibiotic.

It sits within the topics Antibiotics, Carboxamides and Chemical pages without ChemSpiderID.

Its subject is documented across 5 Wikipedia language editions.

Chemical data

Formula: C25H42N2O6S
Molecular weight: 498.7 g/mol
IUPAC name: (4S,5aS,8S,8aR)-4-(2-methylpropyl)-N-[(1R,5Z,7R,8R,9R,10R,11S,12R)-10,11,12-trihydroxy-7-methyl-13-oxa-2-thiabicyclo[7.3.1]tridec-5-en-8-yl]-3,4,5,5a,6,7,8,8a-octahydro-2H-oxepino[2,3-c]pyrrole-8-carboxamide
SMILES: C[C@@H]1/C=C\CCS[C@@H]2[C@@H]([C@H]([C@H]([C@@H]([C@@H]1NC(=O)[C@@H]3[C@H]4[C@@H](C[C@@H](CCO4)CC(C)C)CN3)O2)O)O)O
InChIKey: GMONVEGLHZWYNO-JBYNEVPESA-N
XLogP: 1.9
Polar surface area: 146 Å²
H-bond donors: 5
H-bond acceptors: 8
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 498.2763580639999
Has use: antibiotic

Show 3 more facts

canonical SMILES: CC1C=CCCSC2C(C(C(C(C1NC(=O)C3C4C(CC(CCO4)CC(C)C)CN3)O2)O)O)O
isomeric SMILES: C[C@@H]1/C=C\CCS[C@@H]2[C@@H]([C@H]([C@H]([C@@H]([C@@H]1NC(=O)[C@@H]3[C@H]4[C@@H](C[C@@H](CCO4)CC(C)C)CN3)O2)O)O)O
chemical formula: C₂₅H₄₂N₂O₆S

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Encyclopedic overview

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Contents

References

Cresomycin has been specially designed to bind in a preorganised way with the bacterial ribosome, resulting to improved binding. This allows cresomycin to overcome the ribosomal methylase genes that are responsible for the bacterial resistance against other antibiotics that bind to the peptidyl transferase center of the ribosome, such as lincosamides. Cresomycin was synthesized based on iboxamycin, another oxepanoprolinamide antibiotic, with the addition of a 10-membered ring to it.

Excerpted from Wikipedia’s “cresomycin” article, available under the CC BY-SA 4.0 licence.