Compound ID | 2086

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Thiolutin

Synonym(s): Farcinicin  |  Propiopyvothine  |  Acetopyrrothine

Class: RNA polymerase inhibitor (dithiolopyrrolone)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Inhibits bacterial DNA-dependent RNA polymerase, thus inhibiting RNA synthesis. Pro-drug that needs to be activated in cells. May have different mode of action against prokaryotes versus eukaryotes.
Description: Natural product produced by several species of Streptomyces, Saccharothrix and Gram-negative bacteria; total synthesis and several analogues; functionally related to holomycin; related to Pseudomonic acid A (mupirocin). Activity as angiogenesis inhibitor and antineoplastic agent
Year first mentioned: 1950
Development status: Experimental
Reason Dropped: Toxic
Chemical structure(s):
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Molecular weight: 228.29
Iso. SMILES: CC(=O)NC1=C2C(=CSS2)N(C1=O)C
InChI Key: MHMRAFONCSQAIA-UHFFFAOYSA-N
Can. SMILES: CC(=O)NC1=C2C(=CSS2)N(C)C1=O
InChI: InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6870
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3826145/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4132845/
  • https://academic.oup.com/nar/article/52/5/2546/7517493
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC444489/

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