usnic acid (CED0006482)

Record Information

Version

1.0

Creation Date

2016-06-03 10:58:09 UTC

Update Date

2026-08-19 23:32:47 UTC

Accession Number

CHEM043486

Identification

Common Name

usnic acid

Class

Small Molecule

Description

Usnic acid is a compound with the formula C18H16O7 and an average molecular weight of 344.32 g/mol. It is used as an industrial biocide and a biological antioxidant (PMC10646315, PMC9495557). In terms of its chemical categorization, usnic acid belongs to the acetophenones, a subclass of benzene and substituted derivatives within the organic compounds. The compound is found in or released from 13 recorded sources. Within the category of electrical and electronic equipment, it is associated with antennas, amplifiers, electric switches, electrically stimulated smoking devices, conductors or conductive bodies characterised by the conductive materials, and three additional sources. In the realm of household cleaning and consumer products, usnic acid is found in soap detergents, bleaching agents, perfumes within detergents and soaps, and cigar cigarettes. Additionally, it is utilized in food, food processing and cookware for food preservation.

Contaminant Type

Insecticide

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9BH)-dibenzofurandione	MeSH
Usnate	Generator

Chemical Formula

C₁₈H₁₆O₇

Average Molecular Mass

344.315 g/mol

Monoisotopic Mass

344.090 g/mol

CAS Registry Number

125-46-2

IUPAC Name

4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraene-3,5-dione

Traditional Name

7-hydroxy-(S)-usnate

SMILES

CC(=O)C1C(=O)C=C2OC3=C(C(O)=C(C)C(O)=C3C(C)=O)C2(C)C1=O

InChI Identifier

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

InChI Key

CUCUKLJLRRAKFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Acetophenones

Direct Parent

Acetophenones

Alternative Parents

Substituents

Acetophenone
Coumaran
Aryl ketone
Aryl alkyl ketone
Cyclohexenone
1,3-diketone
1,3-dicarbonyl compound
Vinylogous ester
Vinylogous acid
Ketone
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzofurans (CHEBI:2264 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

antioxidant

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	2.77	ALOGPS
logP	2.39	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.55 m³·mol⁻¹	ChemAxon
Polarizability	33.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-6289000000-24f885e6ce84efc8666e	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0009000000-8529f7e2fc24cc2d2eea	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03gi-0394000000-23a711c12ce3792a5098	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056r-0079000000-910689424749b20916c9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-0009000000-86385e1c88063c7f9e6c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004j-0109000000-e88990b8900522f06abf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0btl-6695000000-c2833b897d51d2cbd56d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-4cbcc44f66d8ec7fa68b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0059000000-35648b46b5fadeabfa24	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02di-3951000000-fe24f4d5b98ed6ab4370	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
571.0	Log mg/kg	[320:1000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
490		Personal care & cosmetics	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
555	Bleaching Agents	Household cleaning & consumer products	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
563	Soap Detergents	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Protein kinase C-like 1	P43057	Candida albicans	Predicted (SEA)	1.16774
Click to view 3D structure	Elongation factor 2	P58252	Mus musculus	Predicted (SEA)	1.86838
Click to view 3D structure	Glycogen synthase kinase 3 alpha	I6LNT8	Sus scrofa	Predicted (SEA)	1.16774
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	5497.63
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	5607.48
Click to view 3D structure	Protein kinase C alpha type	P17252	Humans	Predicted (SEA)	4751.45
Click to view 3D structure	Mediator of RNA polymerase II transcription subunit 25	Q71SY5	Humans	Predicted (SEA)	9.57545
Click to view 3D structure	Protein kinase C gamma type	P05129	Humans	Predicted (SEA)	6602.63
Click to view 3D structure	Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform	Q76MZ3	Mus musculus	Predicted (SEA)	1.71268
Click to view 3D structure	Protein kinase C beta type	P05771	Humans	Predicted (SEA)	4909.25
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	4641.37
Click to view 3D structure	MAP kinase-interacting serine/threonine-protein kinase 1	Q9BUB5	Humans	Predicted (SEA)	5024.93
Click to view 3D structure	MAP kinase-interacting serine/threonine-protein kinase 2	Q9HBH9	Humans	Predicted (SEA)	6892.07
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	3566.12
Click to view 3D structure	Phospholipase A2, membrane associated	P14555	Humans	Predicted (SEA)	2277.32
Click to view 3D structure	Serine palmitoyltransferase small subunit B	Q8NFR3	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	Thioredoxin, mitochondrial	Q99757	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Q63470	Rattus norvegicus	Predicted (SEA)	1891.35
Click to view 3D structure	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1	P10686	Rattus norvegicus	Predicted (SEA)	20.7857
Click to view 3D structure	ALK tyrosine kinase receptor	Q9UM73	Humans	Predicted (SEA)	7314.4
Click to view 3D structure	Hepatocyte growth factor receptor	P08581	Humans	Predicted (SEA)	7369.05
Click to view 3D structure	Insulin-like growth factor 1 receptor	P08069	Humans	Predicted (SEA)	7310.98
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	5644.85
Click to view 3D structure	Serine/threonine-protein kinase PLK1	P53350	Humans	Predicted (SEA)	7314.95
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	7544.6