Structure via PubChem · Public domain (PubChem)
lugdunin
Sign in to saveLugdunin is an investigational antibiotic, classified as a thiazolidine-containing cyclic peptide. It was isolated in 2016 after Staphylococcus lugdunensis was identified as the species of bacteria from the human nose that suppressed growth of species of disease-causing bacteria in that part of the human microbiome.
Chemical data
- Formula
- C40H62N8O6S
- Molecular weight
- 783 g/mol
- IUPAC name
- (1R,4R,7S,10R,13S,16R,19S)-7-(1H-indol-3-ylmethyl)-10-(2-methylpropyl)-4,13,16,19-tetra(propan-2-yl)-21-thia-3,6,9,12,15,18,23-heptazabicyclo[18.2.1]tricosane-2,5,8,11,14,17-hexone
- SMILES
- CC(C)C[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C2N[C@@H](CS2)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CC3=CNC4=CC=CC=C43)C(C)C)C(C)C)C(C)C)C(C)C
- InChIKey
- QZNGYMKAHFFKCJ-ZBQZSICZSA-N
- XLogP
- 5.6
- Polar surface area
- 228 Ų
- H-bond donors
- 8
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 782.451302704
Show 4 more facts
- found in taxon
- Staphylococcus lugdunensis
- canonical SMILES
- CC(C)CC1C(=O)NC(C(=O)NC(C(=O)NC(C2NC(CS2)C(=O)NC(C(=O)NC(C(=O)N1)CC3=CNC4=CC=CC=C43)C(C)C)C(C)C)C(C)C)C(C)C
- isomeric SMILES
- CC(C)C[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C2N[C@@H](CS2)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CC3=CNC4=CC=CC=C43)C(C)C)C(C)C)C(C)C)C(C)C
- chemical formula
- C₄₀H₆₂N₈O₆S
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- Biosynthesis
- References
- External links
Lugdunin is an investigational antibiotic, classified as a thiazolidine-containing cyclic peptide. It was isolated in 2016 after Staphylococcus lugdunensis was identified as the species of bacteria from the human nose that suppressed growth of species of disease-causing bacteria in that part of the human microbiome.
Lugdunin is a non-ribosomally synthesized cyclic peptide that inhibits growth of Staphylococcus aureus strains. The lugdunin genes are located on a 30-kbp operon. The genes lugA, lugB, lugC, and lugD encode four non-ribosomal peptide synthases, which are preceded by a putative regulator gene lugR.
Excerpted from Wikipedia’s “lugdunin” article, available under the CC BY-SA 4.0 licence.