Streptolydigin

Also 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.

In the Vinony graph

Within Vinony's link graph, Streptolydigin is referenced by 2 other articles, and connects out to cell, bacteria and antibiotic.

It sits within the topics Antibiotics, Drugboxes which contain changes to verified fields and Drugs not assigned an ATC code.

Its subject is documented across 5 Wikipedia language editions.

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 Å²
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

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