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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
Structure of PURPUROGALLIN

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)

HIDE SMILES / InChI

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

Description
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.

Originator

Sources: Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences (1882), (18), From: J. Am. Chem. Soc. 4(10), 237 1882.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
17.0 µM [IC50]
0.3 µM [IC50]
2.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations.
1995 Apr
Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds.
2001 Jul 23
Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins.
2003 Sep 25
Metabolism of pyrogallol to purpurogallin by human erythrocytic hemoglobin.
2004 Aug
[Separation and identification of two benzotropolones from teapigment].
2004 Jun
Potent inhibitory effects of black tea theaflavins on off-odor formation from citral.
2006 Apr 19
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Phytic Acid Exposure Alters AflatoxinB1-induced Reproductive and Oxidative Toxicity in Albino Rats (Rattus norvegicus).
2009 Sep
Computational analysis of phosphopeptide binding to the polo-box domain of the mitotic kinase PLK1 using molecular dynamics simulation.
2010 Aug 12
Natural products in regression and slowing of progression of atherosclerosis.
2010 Dec
Patents

Sample Use Guides

Rats: 200 ug/kg/day
Route of Administration: Intraperitoneal
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 Fri Dec 15 17:53:02 GMT 2023
Edited
by admin
on Fri Dec 15 17:53:02 GMT 2023
Record UNII
L3Z7U4N28P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PURPUROGALLIN
MI  
INCI  
Official Name English
NSC-646653
Code English
NSC-35676
Code English
PURPUROGALLIN [MI]
Common Name English
PURPUROGALLIN [INCI]
Common Name English
PURPUROGALLINE
Common Name English
2,3,4,6-TETRAHYDROXY-5H-BENZO(A)CYCLOHEPTEN-5-ONE
Systematic Name English
2,3,4,6-TETRAHYDROXY-5H-BENZOCYCLOHEPTEN-5-ONE
Systematic Name English
Code System Code Type Description
CHEBI
8647
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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WIKIPEDIA
Purpurogallin
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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NSC
35676
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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CAS
569-77-7
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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PUBCHEM
5281571
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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NSC
646653
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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MERCK INDEX
m9327
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
PRIMARY Merck Index
FDA UNII
L3Z7U4N28P
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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EPA CompTox
DTXSID40205436
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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ECHA (EC/EINECS)
209-324-9
Created by admin on Fri Dec 15 17:53:02 GMT 2023 , Edited by admin on Fri Dec 15 17:53:02 GMT 2023
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