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Details

Stereochemistry RACEMIC
Molecular Formula C18H16O7
Molecular Weight 344.3154
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of USNIC ACID

SMILES

CC(=O)C1=C2OC3=CC(O)=C(C(C)=O)C(=O)C3(C)C2=C(O)C(C)=C1O

InChI

InChIKey=WEYVVCKOOFYHRW-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C18H16O7
Molecular Weight 344.3154
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25996207

Since its first isolation in 1844, usnic acid has become the most extensively studied lichen metabolite and one of the few that are commercially available. Lichens belonging to usnic acid-containing genera have been used as crude drugs throughout the world. There are indications of usnic acid being a potentially interesting candidate for such activities as anti-inflammatory, analgesic, healing, antioxidant, antimicrobial, antiprotozoal, antiviral, larvicidal and UV protection. However, some studies reported the liver toxicity and contact allergy. Usnic acid reduced the production of Junin virus in infected Vero cells in a dependent dose manner, and 50% inhibition was obtained at an effective concentration (EC50) of 9.9 µM. Regarding the TCRV arenavirus, the effective concentration was 20.6 uM. The selectivity indexes (CC50/EC50) of usnic acid for JUNV and TCRV arenavirus were 6.8 and 3.2, respectively, indicating a specific antiviral activity against these viruses and not just a general consequence of its action on cellular toxicity.

Originator

Knop, W.
4
Curator's Comment: Usnic acid was first isolated by German scientist W. Knop in 1844

Approval Year

2014
503
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 9.9 µM [EC50]
Inhibitor
8504
 20.6 µM [EC50]
Inhibitor
8504
Inhibitor
8504
 17.7 µM [IC50]
Inhibitor
8504
 75.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antimycobacterial activity of lichen substances.
2010-04
Microbial degradation of usnic acid in the reindeer rumen.
2010-03
Anti-mutagenic lichen extract has double-edged effect on azoxymethane-induced colorectal oncogenesis in C57BL/6J mice.
2010-01
Protoplast isolation from cultured lichen Usnea ghattensis, their fusion with protoplasts of Aspergillus nidulans, fusant regeneration and production of usnic acid.
2009-09
[Oral acute toxicity of (+)-usnic acid in mice and its cytotoxicity in rat cardiac fibroblasts].
2009-08
Raman spectroscopic identification of usnic acid in hydrothermal minerals as a potential Martian analogue.
2009-08
Resveratrol exhibits a strong cytotoxic activity in cultured cells and has an antiviral action against polyomavirus: potential clinical use.
2009-07-01
Phytochemical investigation of the Australian lichens Ramalina glaucescens and Xanthoria parietina.
2009-07
In vitro anti-Helicobacter pylori activity of usnic acid.
2009-07
The chemoenzymatic synthesis of usnic acid.
2009-05-01
Antiproliferative effects on tumour cells and promotion of keratinocyte wound healing by different lichen compounds.
2009-05
Lichens--photophysical studies of potential new sunscreens.
2009-04-02
Effect of (+)-usnic acid on mitochondrial functions as measured by mitochondria-specific oligonucleotide microarray in liver of B6C3F1 mice.
2009-04
Lichen extracts.
2009-03-27
Usnic acid is a promising synergist for biopreparations based on entomopathogenic microorganisms.
2009-02-14
Novel chiral molecular tweezer from (+)-usnic acid.
2009-02-05
Elucidation of the complexation mechanism between (+)-usnic acid and cyclodextrins studied by isothermal titration calorimetry and phase-solubility diagram experiments.
2009-01-21
Lichen substances prevent lichens from nutrient deficiency.
2009-01
Dissociation and metal-binding characteristics of yellow lichen substances suggest a relationship with site preferences of lichens.
2009-01
In vitrouptake and antimycobacterial activity of liposomal usnic acid formulation.
2009
Ancient horizontal gene transfer from bacteria enhances biosynthetic capabilities of fungi.
2009
[In vitro effect of (+)-usnic acid on Toxoplasma gondii tachyzoites].
2008-12-30
Preparation and characterization of copper(II) and nickel(II) complexes of a new chiral salen ligand derived from (+)-usnic acid.
2008-12-14
Lichen photobionts show tolerance against lichen acids produced by lichen mycobionts.
2008-12
Down-regulatory effect of usnic acid on nuclear factor-kappaB-dependent tumor necrosis factor-alpha and inducible nitric oxide synthase expression in lipopolysaccharide-stimulated macrophages RAW 264.7.
2008-12
Review of usnic acid and Usnea barbata toxicity.
2008-11-27
Evaluation of the antimicrobial activity of the acetone extract of the lichen Ramalina farinacea and its (+)-usnic acid, norstictic acid, and protocetraric acid constituents.
2008-11-13
Usnic acid controls the acidity tolerance of lichens.
2008-11
Testing for treatment effects on gene ontology.
2008-08-12
Eubacterium rangiferina, a novel usnic acid-resistant bacterium from the reindeer rumen.
2008-08
Synthesis and cytotoxic activities of usnic acid derivatives.
2008-07-15
Mycosporine-like amino acids and marine toxins--the common and the different.
2008-05-22
Insecticidal activity of major lichen compounds, (-)- and (+)-usnic acid, against the larvae of house mosquito, Culex pipiens L.
2008-05
Usimines A-C, bioactive usnic acid derivatives from the Antarctic lichen Stereocaulon alpinum.
2008-04
Hepatotoxic slimming aids and other herbal hepatotoxins.
2008-03
Metabolism and related human risk factors for hepatic damage by usnic acid containing nutritional supplements.
2008-03
A new antifungal and antiprotozoal depside from the Andean lichen Protousnea poeppigii.
2008-03
Quantitative determination of secondary metabolites in Cladina stellaris and other lichens by micellar electrokinetic chromatography.
2008-02-22
Cloning and sequence characterization of a non-reducing polyketide synthase gene from the lichen Xanthoparmelia semiviridis.
2008-02
Production and bioactivity of common lichen metabolites as exemplified by Heterodea muelleri (Hampe) Nyl.
2008-02
Purification, identification and activity of phomodione, a furandione from an endophytic Phoma species.
2008-02
Toxicity of the lichen secondary metabolite (+)-usnic acid in domestic sheep.
2008-01
Usnea barbata extract prevents ultraviolet-B induced prostaglandin E2 synthesis and COX-2 expression in HaCaT keratinocytes.
2007-11-12
Lichen secondary metabolites from the cultured lichen mycobionts of Teloschistes chrysophthalmus and Ramalina celastri and their antiviral activities.
2007-10-05
Forest successional stage affects the cortical secondary chemistry of three old forest lichens.
2007-08
The phenolic compounds in Cladonia lichens are not antimicrobial in soils.
2007-05
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007-02-26
Identification and quantitation of usnic acid from the lichen Usnea species of Anatolia and antimicrobial activity.
2007-02-14
[Investigation of the germicidal effect of usnic acid, betadine, savlosol, and desderman on the protoscolexes of lung hydatid cysts].
2007
In vitro cytotoxic activities of (+)-usnic acid and (-)-usnic acid on V79, A549, and human lymphocyte cells and their non-genotoxicity on human lymphocytes.
2006-12
Patents

Patents

20020165283
2
JPH04112826A
2
JPH0987106A
2

Sample Use Guides

In Vivo Use Guide
Rats were oral-gavaged once daily with a 1 mL/100 g dose of usnic acid.
Route of Administration: Oral
In Vitro Use Guide
Treatment of A549 human lung carcinoma cells with usnic acid at the concentration of 25–100 uM for 24 and 48 h decreased the number of cells from 39%–67% and 68%–89%, respectively, and increased cell death two- to eight-fold, respectively. Usnic acid at the concentration of 1–10 uM significantly suppressed the formation of A549 cell colonies.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:00:32 GMT 2025
Edited
by admin
on Mon Mar 31 18:00:32 GMT 2025
Record UNII
0W584PFJ77
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-8517
Preferred Name English
USNIC ACID
HSDB   INCI   MI   WHO-DD  
INCI  
Official Name English
1,3-(2H,9BH)-DIBENZOFURANDIONE, 2,6-DIACETYL-7,9-DIHYDROXY-8,9B-DIMETHYL-
Common Name English
USNINIC ACID
Common Name English
USNIC ACID [HSDB]
Common Name English
USNEIN
Common Name English
Usnic Acid [WHO-DD]
Common Name English
(±)-USNIC ACID
Common Name English
1,3(2H,9BH)-DIBENZOFURANDIONE, 2,6-DIACETYL-7,9-DIHYDROXY-8,9B-DIMETHYL-
Systematic Name English
USNIACIN
Common Name English
USNIC ACID [MI]
Common Name English
2,6-DIACETYL-7,9-DIHYDROXY-8,9B-DIMETHYL-1,3(2H,9BH)-DIBENZOFURANDIONE
Common Name English
USNO
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548493
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
Code System Code Type Description
MERCK INDEX
m11348
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY Merck Index
HSDB
7170
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
SMS_ID
100000139086
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
MESH
C073339
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
CAS
125-46-2
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
FDA UNII
0W584PFJ77
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
CHEBI
38319
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
CAS
21987-06-4
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
ALTERNATIVE
ECHA (EC/EINECS)
204-740-7
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
WIKIPEDIA
USNIC ACID
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID0040123
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
RXCUI
1546707
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY RxNorm
EVMPD
SUB81758
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
CAS
17669-01-1
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
ALTERNATIVE
NSC
8517
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
PUBCHEM
24211
Created by admin on Mon Mar 31 18:00:32 GMT 2025 , Edited by admin on Mon Mar 31 18:00:32 GMT 2025
PRIMARY
Related Record Type Details
Structure of SODIUM USNATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of USNIC ACID
ACTIVE MOIETY
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