Page last updated: 2024-11-08

chebulagic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID102004756
MeSH IDM0204962
PubMed CID442674
CHEBI ID3583

Synonyms (10)

Synonym
23094-71-5
chebulagic acid
.beta.-d-glucopyranose, cyclic 3,6-[(1r)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate] 1-(3,4,5-trihydroxybenzoate), cyclic
gn-29
2-[nonahydroxy-pentaoxo-(3,4,5-trihydroxybenzoyl)oxy-[?]yl]acetic acid
chebi:3583 ,
bdbm50366290
Q5089009
2-[(4r,5s,7r,25s,26r,29s,30s,31s)-13,14,15,18,19,20,31,35,36-nonahydroxy-2,10,23,28,32-pentaoxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,9,24,27,33-hexaoxaheptacyclo[28.7.1.04,25.07,26.011,16.017,22.034,38]octatriaconta-1(37),11,13,15,17,19,21,34(38),35-nonaen-
E80601

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"In both the prophylactic and therapeutic CHE dosing models, all clinical scores, serum levels of total and anticollagen IgG, and levels of interleukin-10 (IL-10) and IL-6 were reduced, while serum levels of transforming growth factor beta (TGFbeta) were markedly elevated."( Suppression of the onset and progression of collagen-induced arthritis by chebulagic acid screened from a natural product library.
Hyun, PM; Kim, BS; Kim, KS; Kim, SH; Lee, SI; Lee, SK; Lim, JS; Maeng, PJ, 2005
)
0.33
" Calculation of dose reduction index (DRI) for CA-Dox combinations also showed a significant decrease in the dosage of Dox in the presence of CA."( Chebulagic acid synergizes the cytotoxicity of doxorubicin in human hepatocellular carcinoma through COX-2 dependant modulation of MDR-1.
Achari, C; Reddanna, P; Reddy, GV; Reddy, TC, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tanninAny of a group of astringent polyphenolic vegetable principles or compounds, chiefly complex glucosides of catechol and pyrogallol.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA topoisomerase 1Homo sapiens (human)IC50 (µMol)0.07500.02101.862610.0000AID334464; AID334465
Squalene monooxygenase Rattus norvegicus (Norway rat)IC50 (µMol)3.20000.06102.344610.0000AID357307
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
DNA topological changeDNA topoisomerase 1Homo sapiens (human)
chromatin remodelingDNA topoisomerase 1Homo sapiens (human)
circadian rhythmDNA topoisomerase 1Homo sapiens (human)
response to xenobiotic stimulusDNA topoisomerase 1Homo sapiens (human)
programmed cell deathDNA topoisomerase 1Homo sapiens (human)
phosphorylationDNA topoisomerase 1Homo sapiens (human)
peptidyl-serine phosphorylationDNA topoisomerase 1Homo sapiens (human)
circadian regulation of gene expressionDNA topoisomerase 1Homo sapiens (human)
embryonic cleavageDNA topoisomerase 1Homo sapiens (human)
chromosome segregationDNA topoisomerase 1Homo sapiens (human)
DNA replicationDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA bindingDNA topoisomerase 1Homo sapiens (human)
chromatin bindingDNA topoisomerase 1Homo sapiens (human)
double-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
single-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
RNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA topoisomerase type I (single strand cut, ATP-independent) activityDNA topoisomerase 1Homo sapiens (human)
protein serine/threonine kinase activityDNA topoisomerase 1Homo sapiens (human)
protein bindingDNA topoisomerase 1Homo sapiens (human)
ATP bindingDNA topoisomerase 1Homo sapiens (human)
DNA binding, bendingDNA topoisomerase 1Homo sapiens (human)
protein domain specific bindingDNA topoisomerase 1Homo sapiens (human)
supercoiled DNA bindingDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nuclear chromosomeDNA topoisomerase 1Homo sapiens (human)
P-bodyDNA topoisomerase 1Homo sapiens (human)
fibrillar centerDNA topoisomerase 1Homo sapiens (human)
male germ cell nucleusDNA topoisomerase 1Homo sapiens (human)
nucleusDNA topoisomerase 1Homo sapiens (human)
nucleoplasmDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
perikaryonDNA topoisomerase 1Homo sapiens (human)
protein-DNA complexDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID400989Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 0.1 uM
AID400986Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 10 uM
AID358166Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID335603Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication after 3 days by p24 antigen capture assay
AID400987Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 100 uM
AID641104Antiviral activity against Hepatitis C virus infected in human Huh7.5 cells assessed as inhibition of viral replication after 96 hrs by quantitative RT-PCR analysis2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L.
AID1110810Antimicrobial activity against Pectobacterium carotovorum at 100 ug after 24 hr by disk diffusion method2005Phytochemistry, Jan, Volume: 66, Issue:2
Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID357307Inhibition of C-terminal hexahistidine-tagged rat recombinant squalene epoxidase without N-terminal putative membrane domain expressed in Escherichia coli2001Journal of natural products, Aug, Volume: 64, Issue:8
Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.
AID358915Antioxidant activity assessed as DPPH radical scavenging activity2001Journal of natural products, Dec, Volume: 64, Issue:12
Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica.
AID400991Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 10 uM
AID358168Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID400992Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 100 uM
AID357255Antifungal activity against Cryptococcus neoformans ATCC 901132002Journal of natural products, Dec, Volume: 65, Issue:12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
AID357254Antifungal activity against Candida albicans ATCC 900282002Journal of natural products, Dec, Volume: 65, Issue:12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
AID1110809Antimicrobial activity against Staphylococcus aureus at 100 ug after 24 hr by disk diffusion method2005Phytochemistry, Jan, Volume: 66, Issue:2
Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID1110806Inhibition of xanthine oxidase assessed as conversion of xanthine to uric acid incubated for 3 min2005Phytochemistry, Jan, Volume: 66, Issue:2
Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID358165Cytotoxicity against human PRMI7951 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID334464Inhibition of human COLO201 cellular topoisomerase-1 mediated plasmid DNA cleavage by electrophoresis in presence of 70 units of enzyme1992Journal of natural products, Apr, Volume: 55, Issue:4
A strategy for identifying novel, mechanistically unique inhibitors of topoisomerase I.
AID641102Inhibition of Hepatitic C virus NS3/4A protease by FRET assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L.
AID641103Selectivity index, ratio of CC50 for human Huh7.5 cells to EC50 for Hepatitis C virus infected in human HuH7.5 cells2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L.
AID400988Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 1000 uM
AID335621Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication at 10 uM treated during viral infection step by p24 antigen capture assay
AID400985Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 1 uM
AID400984Inhibition of AMV reverse transcriptase activity assessed as incorporation of dTMP in poly(rA)-oligo(dT) at 0.1 uM
AID1110807Antimicrobial activity against Candida albicans at 100 ug after 24 hr by disk diffusion method2005Phytochemistry, Jan, Volume: 66, Issue:2
Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID358167Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID1110808Antimicrobial activity against Corynebacterium accolens at 100 ug after 24 hr by disk diffusion method2005Phytochemistry, Jan, Volume: 66, Issue:2
Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.
AID641105Cytotoxicity against human Huh7.5 cells after 96 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L.
AID358169Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID335615Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication at 10 uM pretreated before viral infection by p24 antigen capture assay
AID335618Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication at 21 uM treated after viral infection by p24 antigen capture assay
AID400993Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 1000 uM
AID357253Inhibition of Saccharomyces cerevisiae fatty acid synthase2002Journal of natural products, Dec, Volume: 65, Issue:12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
AID334465Inhibition of human COLO201 cellular topoisomerase-1 mediated plasmid DNA cleavage by electrophoresis in presence of 14 units of enzyme1992Journal of natural products, Apr, Volume: 55, Issue:4
A strategy for identifying novel, mechanistically unique inhibitors of topoisomerase I.
AID335617Antiviral activity against HIV1 3B infected in human H9 cells assessed as inhibition of viral replication at 18 uM treated after viral infection by p24 antigen capture assay
AID400990Inhibition of AMV reverse transcriptase activity assessed as incorporation of dGMP in poly(rC)-oligo(dG) at 1 uM
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (46)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (6.52)18.2507
2000's13 (28.26)29.6817
2010's23 (50.00)24.3611
2020's7 (15.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.79

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index35.79 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.49 (4.65)
Search Engine Demand Index47.21 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews1 (2.44%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other40 (97.56%)84.16%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]