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
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-GOSISDBHSA-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-/m1/s1
| 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 |
(-)-Usnic acid is the 'S-' 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. In contrast (+)-usnic acid showed higher cytotoxic activity in cancerous cells, and (+)-usnic acid appears to be selective against Streptococcus mutants without perturbing side effects on the oral saprophyte flora.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A review on usnic acid, an interesting natural compound. | 2002 Apr |
|
| The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents. | 2004 Mar-Apr |
|
| Cytotoxic activity of compounds from the lichen: Cladonia convoluta. | 2004 Sep |
|
| 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 |
|
| Insecticidal activity of major lichen compounds, (-)- and (+)-usnic acid, against the larvae of house mosquito, Culex pipiens L. | 2008 May |
|
| Cellular mechanisms of the anticancer effects of the lichen compound usnic acid. | 2010 Jul |
|
| Membrane-damaging potential of natural L-(-)-usnic acid in Staphylococcus aureus. | 2012 Dec |
|
| Potential of lichen secondary metabolites against Plasmodium liver stage parasites with FAS-II as the potential target. | 2013 Jun 28 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:05:42 GMT 2023
by
admin
on
Sat Dec 16 08:05:42 GMT 2023
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| Record UNII |
5HYW08F205
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| Record Status |
Validated (UNII)
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| Record Version |
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