Compound ID | 708

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Neopyrrolomycin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule;
Spectrum of activity: Gram-positive
Mechanism of action: Unknown
Target Pathogen: Active against Staphylococcus aureus (including strains resistant to methicillin, vancomycin, and linezolid), Streptococcus pneumoniae (including strains resistant to vancomycin and penicillin)
Description: Natural product from Streptomyces sp.; natural analogues reported; the base compound had been synthesised from 3, 5-dichloroanisole which was then chemically manipulated to generate a number of analogs. Many demonstrated toxicity. The less chlorinated analogue had broad spectrum activity and reduced toxicity.
Institute where first reported: Wasada University, Japan
Year first mentioned: 1994
Development status: Experimental
Chemical structure(s):
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Molecular weight: 331.41
Iso. SMILES: C1=CN(C(=C1Cl)Cl)C2=C(C(=C(C=C2O)Cl)Cl)Cl
InChI Key: VQUHAXJBUPCVDX-UHFFFAOYSA-N
Can. SMILES: C1=CN(C2=C(C(=C(C=C2O)Cl)Cl)Cl)C(=C1Cl)Cl
InChI: InChI=1S/C10H4Cl5NO/c11-4-1-2-16(10(4)15)9-6(17)3-5(12)7(13)8(9)14/h1-3,17H
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/125512
Guide to Pharmacology: neopyrrolomycin
Citations:
  • http://pubs.acs.org/doi/abs/10.1021/np800632f
  • https://doi.org/10.7164/antibiotics.43.1192

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