USNIC ACID, (R)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H16O7
Molecular Weight	344.3154
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)C1=C(O)C(C)=C(O)C2=C1OC3=CC(O)=C(C(C)=O)C(=O)[C@]23C

InChI

InChIKey=WEYVVCKOOFYHRW-SFHVURJKSA-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/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H16O7
Molecular Weight	344.3154
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23099095 | https://www.ncbi.nlm.nih.gov/pubmed/17393655 | https://www.ncbi.nlm.nih.gov/pubmed/27004468

(+)-Usnic acid is the 'R-' isomer of usnic acid a bioactive compound mainly found as a secondary metabolite in lichens. Meaningful differences have been noted in the bioactivity of (+)- and (-)- usnic acid. For Example (-)-usnic acid is more active as an antiviral against H1N1 influenza; but, derivitization reverses this specificity (-)-usnic acid is also a selective natural herbicide because of its blocking action against a specific key plant enzyme. The (+)-usnic has been reported to have anti-inflammatory, antibacterial, anti-parasitology, and even anti-cancer activities. Recently it was revealed, that (+)-usnic acid could be a potential agent for treating toxoplasmosis.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
toxoplasmosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27437438	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A review on usnic acid, an interesting natural compound.	2002 Apr	12061397
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 Dec	17393655
Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009.	2012 Dec 1	23099095

Sample Use Guides

In Vivo Use Guide

Swiss Webster mice: were infected with RH strain tachyzoites of Toxoplasma gondii through peritoneal injection. Two hours after inoculation, all the infected mice were administrated orally with (+)-Usnic acid

Route of Administration: Oral

In Vitro Use Guide

The cultured rat cardiofibroblasts were infected by tachyzoites simultaneously to investigate the invasion of tachyzoites. Briefly, monolayers of rat cardiofibroblasts were prepared in 24 well culture plates containing cover glasses for 24 h. All cells were divided into seven groups with three wells in each group. The tachyzoites were treated by different final concentrations of (+)-usnic acid (the range of concentrations were: 2.5*10(-7)M till 4*10(-6))M and acetylespiramycin for 4 h at 37 °C. Then treated tachyzoites were added to the cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:05:40 GMT 2023` Edited by `admin` on `Sat Dec 16 08:05:40 GMT 2023`
Record UNII	663456969I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

USNIC ACID, (R)-

Common Name

English

(R)-USNIC ACID

Common Name

English

(+)-USNINIC ACID

Common Name

English

(+)-USNIC ACID

Common Name

English

1(9BH)-DIBENZOFURANONE, 2,6-DIACETYL-3,7,9-TRIHYDROXY-8,9B-DIMETHYL-, (R)-

Systematic Name

English

USNIC ACID, D-

Common Name

English

1(9BH)-DIBENZOFURANONE, 2,6-DIACETYL-3,7,9-TRIHYDROXY-8,9B-DIMETHYL-, (9BR)-

Systematic Name

English

(R)-(+)-USNIC ACID

Common Name

English

NSC-5890

Code

English

USNIC ACID, (+)-

Common Name

English

USNIC ACID D-FORM [MI]

Common Name

English

1,3(2H,9BH)-DIBENZOFURANDIONE, 2,6-DIACETYL-7,9-DIHYDROXY-8,9B-DIMETHYL-, (9BR)-

Systematic Name

English

Code System Code Type Description

NSC

5890