Structure via PubChem · Public domain (PubChem)
Streptolydigin
Sign in to saveAlso known as Afragilimycin A, Portamycin
Streptolydigin (Stl) is an antibiotic that works by inhibiting nucleic acid chain elongation by binding to RNA polymerase, thus inhibiting RNA synthesis inside a cell. Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase. It has antibacterial activity against a number of Gram positive bacteria.
Chemical data
- Formula
- C32H44N2O9
- Molecular weight
- 600.7 g/mol
- IUPAC name
- (2S)-2-[(2S,4E)-4-[(2E,4E,6R)-6-[(1R,3R,4S,5R,8R)-1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxirane]-3-yl]-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide
- SMILES
- C[C@H]1[C@H]2C=C[C@@]3(CO3)[C@](O2)(O[C@@H]1[C@H](C)/C=C(\C)/C=C/C(=C\4/C(=O)[C@@H](N(C4=O)[C@@H]5CC[C@@H]([C@@H](O5)C)O)[C@H](C)C(=O)NC)/O)C
- InChIKey
- KVTPRMVXYZKLIG-NCAOFHFGSA-N
- XLogP
- 3.1
- Polar surface area
- 147 Ų
- H-bond donors
- 3
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
161 papers- Mycobacterium tuberculosis is resistant to streptolydigin.Tuberculosis (Edinburgh, Scotland) · 2013
- Three pathway-specific regulators control streptolydigin biosynthesis in Streptomyces lydicus.Microbiology (Reading, England) · 2012
- Antibiotic streptolydigin requires noncatalytic Mg2+ for binding to RNA polymerase.Antimicrobial agents and chemotherapy · 2014
- Streptolydigin-resistant mutants in an evolutionarily conserved region of the beta' subunit of Escherichia coli RNA polymerase.The Journal of biological chemistry · 1995
- Insights into the roles of exogenous glutamate and proline in improving streptolydigin production of Streptomyces lydicus with metabolomic analysis.Journal of industrial microbiology & biotechnology · 2013
via PubMed
Wikidata facts
- Mass
- 600.3046809879999
Show 4 more facts
- chemical formula
- C₃₂H₄₄N₂O₉
- canonical SMILES
- CC1C2C=CC3(CO3)C(O2)(OC1C(C)C=C(C)C=CC(=C4C(=O)C(N(C4=O)C5CCC(C(O5)C)O)C(C)C(=O)NC)O)C
- subject has role
- antibiotic
- isomeric SMILES
- C[C@H]1[C@H]2C=C[C@@]3(CO3)[C@](O2)(O[C@@H]1[C@H](C)/C=C(\C)/C=C/C(=C\4/C(=O)[C@@H](N(C4=O)[C@@H]5CC[C@@H]([C@@H](O5)C)O)[C@H](C)C(=O)NC)/O)C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Streptolydigin (Stl) is an antibiotic that works by inhibiting nucleic acid chain elongation by binding to RNA polymerase, thus inhibiting RNA synthesis inside a cell. Streptolydigin inhibits bacterial RNA polymerase, but not eukaryotic RNA polymerase. It has antibacterial activity against a number of Gram positive bacteria.
== References ==
Excerpted from Wikipedia’s “Streptolydigin” article, available under the CC BY-SA 4.0 licence.