Page last updated: 2024-12-04

digallic acid

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Description

digallic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID341
CHEMBL ID366356
CHEBI ID30814
SCHEMBL ID39415
MeSH IDM0185380

Synonyms (45)

Synonym
unii-404ko0584x
3-10-00-02086 (beilstein handbook reference)
404ko0584x ,
3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid
CHEBI:30814 ,
5,6-dihydroxy-3-carboxyphenyl ester of gallic acid
nsc-59263
benzoic acid,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-
m-galloylgallic acid
digallic acid, meta
gallic acid, 3-gallate
gallic acid 3-monogallate
einecs 208-624-7
nsc 59263
m-galloyl gallic acid
benzoic acid, 3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)-
3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoic acid
brn 2177723
3-galloyl gallic acid
m-digallic acid
nsc59263
3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-benzoic acid
benzoic acid, 3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-
C01572
digallic acid
536-08-3
NCIOPEN2_007819
FT-0666845
CHEMBL366356 ,
bdbm50056937
3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
digallic acid, m-
digallic acid [mi]
4,5-dihydroxybenzoic acid monogallate
gallic acid 5,6-dihydroxy-3-carboxyphenyl ester
3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoic acid
SCHEMBL39415
digallussaure
Q4140499
DTXSID50871747
BCP32287
m-digallic acid;gallic acid 3-monogallate;m-galloylgallic acid
discontinued. please see d445080
3-galloyloxy-4,5-dihydroxy-benzoic acid
AKOS040751568
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
benzoate esterEsters of benzoic acid or substituted benzoic acids.
gallate esterA benzoate ester that is any ester resulting from the formal condensation of the carboxy group of gallic acid (3,4,5-trihydroxybenzoic acid) with an alcoholic or phenolic hydroxy group.
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA polymerase betaHomo sapiens (human)Ki0.39000.39000.39000.3900AID397114
DNA polymerase alpha catalytic subunitHomo sapiens (human)Ki0.83000.83001.56502.3000AID397113
Prostaglandin G/H synthase 2Homo sapiens (human)Ki0.39000.00050.41861.5000AID397114
Anthrax toxin receptor 2Homo sapiens (human)IC50 (µMol)50.00000.30000.45350.6070AID725981
Integrase Human immunodeficiency virus 2IC50 (µMol)2.50000.50001.43752.5000AID91588
Integrase Human immunodeficiency virus 1IC50 (µMol)1.06670.00051.544310.0000AID91590; AID93680; AID93700; AID93702; AID93705; AID93707
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (92)

Processvia Protein(s)Taxonomy
nucleotide-excision repair, DNA gap fillingDNA polymerase betaHomo sapiens (human)
in utero embryonic developmentDNA polymerase betaHomo sapiens (human)
DNA-templated DNA replicationDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase betaHomo sapiens (human)
base-excision repairDNA polymerase betaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase betaHomo sapiens (human)
pyrimidine dimer repairDNA polymerase betaHomo sapiens (human)
inflammatory responseDNA polymerase betaHomo sapiens (human)
DNA damage responseDNA polymerase betaHomo sapiens (human)
salivary gland morphogenesisDNA polymerase betaHomo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageDNA polymerase betaHomo sapiens (human)
response to gamma radiationDNA polymerase betaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase betaHomo sapiens (human)
response to ethanolDNA polymerase betaHomo sapiens (human)
lymph node developmentDNA polymerase betaHomo sapiens (human)
spleen developmentDNA polymerase betaHomo sapiens (human)
homeostasis of number of cellsDNA polymerase betaHomo sapiens (human)
neuron apoptotic processDNA polymerase betaHomo sapiens (human)
response to hyperoxiaDNA polymerase betaHomo sapiens (human)
immunoglobulin heavy chain V-D-J recombinationDNA polymerase betaHomo sapiens (human)
DNA biosynthetic processDNA polymerase betaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
nucleotide-excision repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA synthesis involved in UV-damage excision repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA synthesis involved in DNA repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replicationDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replication, synthesis of primerDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replication initiationDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA strand elongation involved in DNA replicationDNA polymerase alpha catalytic subunitHomo sapiens (human)
leading strand elongationDNA polymerase alpha catalytic subunitHomo sapiens (human)
lagging strand elongationDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA repairDNA polymerase alpha catalytic subunitHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase alpha catalytic subunitHomo sapiens (human)
regulation of type I interferon productionDNA polymerase alpha catalytic subunitHomo sapiens (human)
mitotic DNA replication initiationDNA polymerase alpha catalytic subunitHomo sapiens (human)
prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 2Homo sapiens (human)
embryo implantationProstaglandin G/H synthase 2Homo sapiens (human)
learningProstaglandin G/H synthase 2Homo sapiens (human)
memoryProstaglandin G/H synthase 2Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell population proliferationProstaglandin G/H synthase 2Homo sapiens (human)
response to xenobiotic stimulusProstaglandin G/H synthase 2Homo sapiens (human)
response to nematodeProstaglandin G/H synthase 2Homo sapiens (human)
response to fructoseProstaglandin G/H synthase 2Homo sapiens (human)
response to manganese ionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 2Homo sapiens (human)
bone mineralizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fever generationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic plasticityProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergicProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin secretionProstaglandin G/H synthase 2Homo sapiens (human)
response to estradiolProstaglandin G/H synthase 2Homo sapiens (human)
response to lipopolysaccharideProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylationProstaglandin G/H synthase 2Homo sapiens (human)
response to vitamin DProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to heatProstaglandin G/H synthase 2Homo sapiens (human)
response to tumor necrosis factorProstaglandin G/H synthase 2Homo sapiens (human)
maintenance of blood-brain barrierProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of protein import into nucleusProstaglandin G/H synthase 2Homo sapiens (human)
hair cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of apoptotic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vasoconstrictionProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
decidualizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle cell proliferationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of inflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
response to glucocorticoidProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of calcium ion transportProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicProstaglandin G/H synthase 2Homo sapiens (human)
response to fatty acidProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to mechanical stimulusProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to lead ionProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to ATPProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to hypoxiaProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to non-ionic osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to fluid shear stressProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of transforming growth factor beta productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fibroblast growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of platelet-derived growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to homocysteineProstaglandin G/H synthase 2Homo sapiens (human)
response to angiotensinProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
damaged DNA bindingDNA polymerase betaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase betaHomo sapiens (human)
DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
protein bindingDNA polymerase betaHomo sapiens (human)
microtubule bindingDNA polymerase betaHomo sapiens (human)
lyase activityDNA polymerase betaHomo sapiens (human)
enzyme bindingDNA polymerase betaHomo sapiens (human)
metal ion bindingDNA polymerase betaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase betaHomo sapiens (human)
class I DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
nucleotide bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
chromatin bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase alpha catalytic subunitHomo sapiens (human)
protein bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
zinc ion bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
protein kinase bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
DNA replication origin bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
single-stranded DNA bindingDNA polymerase alpha catalytic subunitHomo sapiens (human)
peroxidase activityProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingProstaglandin G/H synthase 2Homo sapiens (human)
enzyme bindingProstaglandin G/H synthase 2Homo sapiens (human)
heme bindingProstaglandin G/H synthase 2Homo sapiens (human)
protein homodimerization activityProstaglandin G/H synthase 2Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 2Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingAnthrax toxin receptor 2Homo sapiens (human)
metal ion bindingAnthrax toxin receptor 2Homo sapiens (human)
transmembrane signaling receptor activityAnthrax toxin receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
nucleusDNA polymerase betaHomo sapiens (human)
nucleoplasmDNA polymerase betaHomo sapiens (human)
cytoplasmDNA polymerase betaHomo sapiens (human)
microtubuleDNA polymerase betaHomo sapiens (human)
spindle microtubuleDNA polymerase betaHomo sapiens (human)
protein-containing complexDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase alpha catalytic subunitHomo sapiens (human)
nuclear envelopeDNA polymerase alpha catalytic subunitHomo sapiens (human)
nucleoplasmDNA polymerase alpha catalytic subunitHomo sapiens (human)
alpha DNA polymerase:primase complexDNA polymerase alpha catalytic subunitHomo sapiens (human)
nucleolusDNA polymerase alpha catalytic subunitHomo sapiens (human)
cytosolDNA polymerase alpha catalytic subunitHomo sapiens (human)
nuclear matrixDNA polymerase alpha catalytic subunitHomo sapiens (human)
chromatinDNA polymerase alpha catalytic subunitHomo sapiens (human)
nuclear inner membraneProstaglandin G/H synthase 2Homo sapiens (human)
nuclear outer membraneProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulumProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum lumenProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 2Homo sapiens (human)
caveolaProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
protein-containing complexProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
extracellular regionAnthrax toxin receptor 2Homo sapiens (human)
endoplasmic reticulum membraneAnthrax toxin receptor 2Homo sapiens (human)
plasma membraneAnthrax toxin receptor 2Homo sapiens (human)
endosome membraneAnthrax toxin receptor 2Homo sapiens (human)
plasma membraneAnthrax toxin receptor 2Homo sapiens (human)
cell surfaceAnthrax toxin receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID397113Inhibition of DNA polymerase alpha from human KB3 cells
AID397120Inhibition of DNA polymerase beta from human KB3 cells assessed as competitive type inhibition using (rA)n.(dT)12-18 as substrate
AID397106Inhibition of DNA polymerase gamma from human KB3 cells up to 1 ug/ml
AID93707Inhibitory concentration of compound against strand transfer of HIV-1 integrase in experiment 21997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID397114Inhibition of DNA polymerase beta from human KB3 cells
AID397108Inhibition of HIV reverse transcriptase expressed in Escherichia coli by Dixon plot
AID397110Inhibition of HIV reverse transcriptase expressed in Escherichia coli assessed as non-competitive inhibition using dTTP as primer by double reciprocal plot
AID397103Inhibition of HIV reverse transcriptase expressed in Escherichia coli assessed as incorporation of [3H]dTMP at 1 ug/ml
AID91588Inhibitory concentration of compound against 3'-processing of HIV-2 integrase1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID91562Percentage inhibition against strand transfer of HIV-1 integrase at 100 ug/mL1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID397100Inhibition of Rauscher murine leukemia virus reverse transcriptase assessed as incorporation of [3H]dTMP at 0.2 ug/ml
AID397102Inhibition of Rauscher murine leukemia virus reverse transcriptase assessed as incorporation of [3H]dTMP at 1 ug/ml
AID397115Inhibition of DNA polymerase-1 from Escherichia coli up to 1 ug/ml
AID91590Inhibitory concentration of compound against strand transfer of HIV-1 integrase1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID93702Inhibitory concentration of compound against 3'-processing of HIV-1 integrase in experiment 21997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID93680Inhibitory activity against HIV-1 integrase2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
HIV-1 integrase pharmacophore model derived from diverse classes of inhibitors.
AID725981Inhibition of CMG2 (40 to 217) C175A and R40C double mutant (unknown origin) interaction to full length PA E733C mutant expressed in Escherichia coli by FRET assay2013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2.
AID93700Inhibitory concentration of compound against 3'-processing of HIV-1 integrase in experiment 11997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID397107Inhibition of terminal deoxynucleotidyltransferase from calf thymus up to 1 ug/ml
AID397121Inhibition of DNA polymerase beta from human KB3 cells assessed as non-competitive type inhibition using dTTP as substrate
AID397101Inhibition of HIV reverse transcriptase expressed in Escherichia coli assessed as incorporation of [3H]dTMP at 0.2 ug/ml
AID397109Inhibition of HIV reverse transcriptase expressed in Escherichia coli assessed as mixed-type inhibition using (rA)n.(dT)12-18 as primer by double reciprocal plot
AID91561Percentage inhibition of compound against 3'-processing of HIV-1 integrase at 100 ug/mL1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID93705Inhibitory concentration of compound against strand transfer of HIV-1 integrase in experiment 11997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID397119Inhibition of DNA polymerase alpha from human KB3 cells assessed as non-competitive type inhibition using dNTP as substrate
AID397112Inhibition of DNA polymerase alpha from human KB3 cells at 1 ug/ml
AID397118Inhibition of DNA polymerase alpha from human KB3 cells assessed as competitive type inhibition using activated DNA as substrate
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (14.29)18.2507
2000's2 (14.29)29.6817
2010's8 (57.14)24.3611
2020's2 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.80

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.80 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]