Compound ID | 2998

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Usnic acid

Synonym(s): 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule;
Spectrum of activity: Gram-positive
Mechanism of action: Unknown
Target Pathogen: Active against Clostridium perfringens, Propionibacterium acnes, Enterococcus faecalis, Enterococcus faecium, and methicillin-resistant and -susceptible Staphylococcus aureus
Description: Natural product from lichen; low solubility therefore only useful in either topical ointment, polymer, or oral care formulations; also inhibits Staphylococcus aureus biofilm growth
Year first mentioned: 1948
Development status: Experimental
Chemical structure(s):
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Molecular weight: 344.32
Iso. SMILES: CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
InChI Key: CUCUKLJLRRAKFN-UHFFFAOYSA-N
Can. SMILES: CC1=C(C2=C(C(=C1O)C(=O)C)OC3=CC(=O)C(C(=O)C)C(=O)C32C)O
InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5646
Citations:
  • https://www.jstage.jst.go.jp/article/yoken1948/1/2/1_2_152/_article
  • https://journals.asm.org/doi/10.1128/aac.48.11.4360-4365.2004?site=AntimicrobAgentsChemother&utm_source=TrendMDAntimicrobAgentsChemother&utm_medium=trendmdantimicrobagentschemother&utm_campaign=TrendMD_AACCLIN_0
  • https://journals.asm.org/doi/10.1128/aac.39.11.2541

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