Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H6O3 |
Molecular Weight | 174.1528 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=CC2=C1C(=O)C=CC2=O
InChI
InChIKey=KQPYUDDGWXQXHS-UHFFFAOYSA-N
InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16393859Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19726363 | https://www.ncbi.nlm.nih.gov/pubmed/25466185 | https://www.ncbi.nlm.nih.gov/pubmed/29276721 | https://www.ncbi.nlm.nih.gov/pubmed/29039537 | https://www.ncbi.nlm.nih.gov/pubmed/19815401
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16393859
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19726363 | https://www.ncbi.nlm.nih.gov/pubmed/25466185 | https://www.ncbi.nlm.nih.gov/pubmed/29276721 | https://www.ncbi.nlm.nih.gov/pubmed/29039537 | https://www.ncbi.nlm.nih.gov/pubmed/19815401
Juglone (5-hydroxy-1,4-naphthalenedione, C.I. Natural Brown 7, C.I. 75500) is an isomer of lawsone occurs naturally in the leaves, roots, husks, fruit (the epicarp), and bark of plants in the Juglandaceae family, particularly the black walnut (Juglans nigra). Juglone is an allelopathic compound, a substance that is produced by a plant to stunt the growth of another. Juglone is occasionally used as a herbicide. Traditionally, juglone has been used as a natural dye for clothing and fabrics, particularly wool, and as ink. Because of its tendency to create dark orange-brown stains, juglone has also found use as a coloring agent for foods and cosmetics, such as hair dyes. Juglone is currently being studied for its anticancer properties and It has been shown to decrease the probability of intestinal tumors in rats that have been exposed to carcinogens. One of the potential pathways through which juglone achieves its anticancer properties is through the formation of the semiquinone radical; the semiquinone radical causes superoxide anion radicals to form which can lead to apoptosis when present in large concentrations. This conversion from juglone to semiquinone radical that causes the superoxide anion radical to form takes place in the mitochondria as well as the cytosol.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19028102 |
1.98 µM [IC50] | ||
Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18318466 |
1.0 µM [IC50] | ||
Target ID: CHEMBL2288 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25466185 |
10.12 µM [IC50] | ||
Target ID: CHEMBL5623 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19028102 |
13.0 µM [IC50] | ||
Target ID: CHEMBL5511 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19028102 |
12.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibitors of human immunodeficiency virus integrase. | 1993 Mar 15 |
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Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. | 1995 Nov 15 |
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Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases. | 2001 Mar |
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Heterologous expression of the naphthocyclinone hydroxylase gene from Streptomyces arenae for production of novel hybrid polyketides. | 2001 Sep |
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Addition of hydrogen sulfide to juglone. | 2002 Jun 15 |
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Ultrasound-mediated release of iron from ferritin. | 2003 Dec |
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Characterization of a new member of the flavoprotein disulfide reductase family of enzymes from Mycobacterium tuberculosis. | 2004 Dec 10 |
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Photoreactions of 1,4-Naphthoquinones: effects of substituents and water on the intermediates and reactivity. | 2005 Mar-Apr |
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Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4-naphthoquinones. | 2005 May |
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5-Hydr-oxy-8-nitro-1,4-naphthoquinone. | 2008 Jul 19 |
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The prolyl isomerase Pin1 induces LC-3 expression and mediates tamoxifen resistance in breast cancer. | 2010 Jul 30 |
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Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative. | 2010 Mar 30 |
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Digalactosyl-diacylglycerol-deficiency lowers the thermal stability of thylakoid membranes. | 2010 Sep |
|
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
|
Discovery and characterization of a nonphosphorylated cyclic peptide inhibitor of the peptidylprolyl isomerase, Pin1. | 2011 Jun 9 |
|
The peptidyl-prolyl isomerase Pin1 up-regulation and proapoptotic function in dopaminergic neurons: relevance to the pathogenesis of Parkinson disease. | 2013 Jul 26 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16393859
Rats were treated with Juglone (i.v 0.1mg/kg; dermally 4mg/kg; oral 0.1, 1 or 10mg/kg)
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19726363
BEL-7402 cells were incubated in the presence of 12.5 micromol/L juglone for 24 h, and fixed in 2.5% glutaraldehyde for HE staining and Coomassie brilliant blue staining and scanning electron microscopy. Incubation with juglone resulted in obvious changes in the cell morphology and cytoskeletal alterations of the cells. Scanning electron microscopy revealed reduced volume of the cell bodies, dissociation of the cells, curling and malformation of the microvilli on the cell surface with rupture of the intercellular junction and enlargement of the intercellular space. The formation of apoptotic bodies was observed. Transmission electron microscopy showed expansion of the endoplasmic reticula, mitochondrial cristea disintegration, nucleolar fragmentation and formation of the apoptotic bodies after the exposure to juglone for 24 h.
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JUGLONE
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SUBSTANCE RECORD