CHEBI:38319 - usnic acid

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ChEBI Name usnic acid
ChEBI ID CHEBI:38319
Definition A member of the class of dibenzofurans that is dibenzo[b,d]furan-1(9bH)-one substituted by acetyl groups at positions 2 and 6, hydroxy groups at positions 3 and 7 and methyl groups at positions 8 and 9b.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H16O7
Net Charge 0
Average Mass 344.31540
Monoisotopic Mass 344.090
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/h5,21-23H,1-4H3
InChIKey WEYVVCKOOFYHRW-UHFFFAOYSA-N
SMILES CC(=O)C1=C(O)C=C2Oc3c(c(O)c(C)c(O)c3C(C)=O)C2(C)C1=O
Roles Classification
Biological Role(s): lichen metabolite
Any metabolite that is produced during a metabolite reaction in lichens (composite organisms consisting of a fungus and a photosynthetic partner co-existing in a symbiotic relationship).
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application(s): acaricide
A substance used to destroy pests of the subclass Acari (mites and ticks).
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ChEBI Ontology
Outgoing usnic acid (CHEBI:38319) has role acaricide (CHEBI:22153)
usnic acid (CHEBI:38319) has role antifungal agent (CHEBI:35718)
usnic acid (CHEBI:38319) has role lichen metabolite (CHEBI:78361)
usnic acid (CHEBI:38319) is a dibenzofurans (CHEBI:38922)
usnic acid (CHEBI:38319) is a methyl ketone (CHEBI:51867)
usnic acid (CHEBI:38319) is a polyphenol (CHEBI:26195)
Incoming (−)-usnic acid (CHEBI:122) is a usnic acid (CHEBI:38319)
(+)-usnic acid (CHEBI:38320) is a usnic acid (CHEBI:38319)
IUPAC Name
2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one
Synonyms Sources
usnein ChemIDplus
usniacin ChemIDplus
usninic acid ChemIDplus
Usninsäure ChEBI
Manual Xref Database
Usnic_acid Wikipedia
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Registry Numbers Types Sources
125-46-2 CAS Registry Number ChemIDplus
346490 Beilstein Registry Number Beilstein
96699 Beilstein Registry Number Beilstein
96699 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11034349 PubMed citation Europe PMC
18887895 PubMed citation Europe PMC
19034791 PubMed citation Europe PMC
19349177 PubMed citation Europe PMC
20379653 PubMed citation Europe PMC
24770718 PubMed citation Europe PMC
Last Modified
15 July 2014