Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H8O5 |
Molecular Weight | 220.1782 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C(O)=C1O)C(=O)C(O)=CC=C2
InChI
InChIKey=WDGFFVCWBZVLCE-UHFFFAOYSA-N
InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)
Molecular Formula | C11H8O5 |
Molecular Weight | 220.1782 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24002379Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26055176 | https://www.ncbi.nlm.nih.gov/pubmed/22449709 |
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24002379
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26055176 | https://www.ncbi.nlm.nih.gov/pubmed/22449709 |
Purpurogallin (2,3,4,5 tetrahydroxybenzo[7]annulen 6 one) is a benzotropolone containing the natural product, which occurs in the nut gall of Quercus spp. Purpurogallin is synthesized by the chemical oxidation of pyrogallol and has been shown to have biological properties, such as hydroxyl radical scavenging properties and to protect erythrocytes against lysis induced by peroxyl radicals. Purpurogallin can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by catechol-O-methyltransferase, human immunodeficiency virus 1, integrase and prolyl endopeptidases. In addition, purpurogallin has also been known to have anticancer activities through the inhibition of the DNA synthesis of tumor cells (20), tyrosine-specific protein kinases and the interaction between Bcl xL and BH3 peptides. A number of studies have reported the antioxidant and anti-inflammatory effects of purpurogallin (15,23 27); however, the actual molecular mechanisms involving signal transduction cascades underlying the purpurogallin induced anti-inflammatory effects have not yet been elucidated.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094128 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26055176 |
17.0 µM [IC50] | ||
Target ID: CHEMBL3024 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26055176 |
0.3 µM [IC50] | ||
Target ID: CHEMBL4625 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13678404 |
2.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8983887 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995 Apr |
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Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds. | 2001 Jul 23 |
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Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins. | 2003 Sep 25 |
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Metabolism of pyrogallol to purpurogallin by human erythrocytic hemoglobin. | 2004 Aug |
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[Separation and identification of two benzotropolones from teapigment]. | 2004 Jun |
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Potent inhibitory effects of black tea theaflavins on off-odor formation from citral. | 2006 Apr 19 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Phytic Acid Exposure Alters AflatoxinB1-induced Reproductive and Oxidative Toxicity in Albino Rats (Rattus norvegicus). | 2009 Sep |
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Computational analysis of phosphopeptide binding to the polo-box domain of the mitotic kinase PLK1 using molecular dynamics simulation. | 2010 Aug 12 |
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Natural products in regression and slowing of progression of atherosclerosis. | 2010 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25485154
Rats: 200 ug/kg/day
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24002379
BV2 murine microglial cells were used for activity evaluation. Cell viability was measured based on the formation of blue formazan metabolized from colorless MTT (Sigma Aldrich) by mitochondrial dehydrogenases, which are active only in live cells. In brief, BV2 cells were plated into 24 well plates at a density of 2x105 cells/well for 24 h and then washed. The cells incubated with various concentrations of purpurogallin for 1 h were treated with or without 0.5 μg/ml LPS for 24 h and then incubated in 0.5 mg/ml MTT solution. Three hours later, the supernatant was removed and the forma¬tion of formazan was measured at 540 nm using a microplate reader.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:53:02 GMT 2023
by
admin
on
Fri Dec 15 17:53:02 GMT 2023
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Record UNII |
L3Z7U4N28P
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Record Status |
Validated (UNII)
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Record Version |
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