Page last updated: 2024-11-12

endiandrin a

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Description

endiandrin A: a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Endiandragenus[no description available]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]

Cross-References

ID SourceID
PubMed CID16756780
CHEMBL ID228274
MeSH IDM0512653

Synonyms (6)

Synonym
endiandrin a
CHEMBL228274 ,
8-beta,8''-alpha-dimethyl-7-alpha,7''-beta-bis(3-methoxy-4-hydroxy-phenyl)cyclobutane
4,4''-((1r,2r,3s,4s)-3,4-dimethylcyclobutane-1,2-diyl)bis(2-methoxyphenol)
bdbm50216277
4-[(1r,2r,3s,4s)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenol

Research Excerpts

Effects

ExcerptReferenceRelevance
"Endiandrin A (End A) has been identified as GR receptor binder."( The plant-derived glucocorticoid receptor agonist Endiandrin A acts as co-stimulator of colonic epithelial sodium channels (ENaC) via SGK-1 and MAPKs.
Bergann, T; Dames, P; Davis, RA; Fromm, A; Fromm, M; Kuntzsch, D; Melzig, MF; Schulzke, JD, 2012
)
1.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Ki368.00000.00001.372610.0000AID588186
Carbonic anhydrase 2Homo sapiens (human)Ki11.70000.00000.72369.9200AID588187
Glucocorticoid receptorHomo sapiens (human)IC50 (µMol)0.90000.00000.495310.0000AID291923
Carbonic anhydrase Mycobacterium tuberculosis H37RvKi8.92000.01202.72389.1200AID588182
Beta-carbonic anhydrase 1Mycobacterium tuberculosis H37RvKi0.82000.00483.38419.8400AID588183
Carbonic anhydrase Cryptococcus neoformans var. grubiiKi0.77000.01000.73648.3470AID588185
Carbonic anhydraseCandida albicans SC5314Ki0.73000.01051.44448.3470AID588184
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Kinact368.00000.01000.93878.6000AID456398
Carbonic anhydrase 2Homo sapiens (human)Kinact11.70000.00300.794610.0000AID456397
Carbonic anhydrase 5A, mitochondrialHomo sapiens (human)Kinact0.09100.02000.85809.4000AID456399
Carbonic anhydrase 5B, mitochondrialHomo sapiens (human)Kinact0.06900.00900.92319.0400AID456400
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (44)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
negative regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
regulation of gluconeogenesisGlucocorticoid receptorHomo sapiens (human)
chromatin organizationGlucocorticoid receptorHomo sapiens (human)
regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
apoptotic processGlucocorticoid receptorHomo sapiens (human)
chromosome segregationGlucocorticoid receptorHomo sapiens (human)
signal transductionGlucocorticoid receptorHomo sapiens (human)
glucocorticoid metabolic processGlucocorticoid receptorHomo sapiens (human)
gene expressionGlucocorticoid receptorHomo sapiens (human)
microglia differentiationGlucocorticoid receptorHomo sapiens (human)
adrenal gland developmentGlucocorticoid receptorHomo sapiens (human)
regulation of glucocorticoid biosynthetic processGlucocorticoid receptorHomo sapiens (human)
synaptic transmission, glutamatergicGlucocorticoid receptorHomo sapiens (human)
maternal behaviorGlucocorticoid receptorHomo sapiens (human)
intracellular glucocorticoid receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
glucocorticoid mediated signaling pathwayGlucocorticoid receptorHomo sapiens (human)
positive regulation of neuron apoptotic processGlucocorticoid receptorHomo sapiens (human)
negative regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
astrocyte differentiationGlucocorticoid receptorHomo sapiens (human)
cell divisionGlucocorticoid receptorHomo sapiens (human)
mammary gland duct morphogenesisGlucocorticoid receptorHomo sapiens (human)
motor behaviorGlucocorticoid receptorHomo sapiens (human)
cellular response to steroid hormone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to glucocorticoid stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to dexamethasone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to transforming growth factor beta stimulusGlucocorticoid receptorHomo sapiens (human)
neuroinflammatory responseGlucocorticoid receptorHomo sapiens (human)
positive regulation of miRNA transcriptionGlucocorticoid receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
response to bacteriumCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
core promoter sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activityGlucocorticoid receptorHomo sapiens (human)
RNA bindingGlucocorticoid receptorHomo sapiens (human)
nuclear receptor activityGlucocorticoid receptorHomo sapiens (human)
nuclear glucocorticoid receptor activityGlucocorticoid receptorHomo sapiens (human)
steroid bindingGlucocorticoid receptorHomo sapiens (human)
protein bindingGlucocorticoid receptorHomo sapiens (human)
zinc ion bindingGlucocorticoid receptorHomo sapiens (human)
TBP-class protein bindingGlucocorticoid receptorHomo sapiens (human)
protein kinase bindingGlucocorticoid receptorHomo sapiens (human)
identical protein bindingGlucocorticoid receptorHomo sapiens (human)
Hsp90 protein bindingGlucocorticoid receptorHomo sapiens (human)
steroid hormone bindingGlucocorticoid receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingGlucocorticoid receptorHomo sapiens (human)
estrogen response element bindingGlucocorticoid receptorHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleoplasmGlucocorticoid receptorHomo sapiens (human)
cytoplasmGlucocorticoid receptorHomo sapiens (human)
mitochondrial matrixGlucocorticoid receptorHomo sapiens (human)
centrosomeGlucocorticoid receptorHomo sapiens (human)
spindleGlucocorticoid receptorHomo sapiens (human)
cytosolGlucocorticoid receptorHomo sapiens (human)
membraneGlucocorticoid receptorHomo sapiens (human)
nuclear speckGlucocorticoid receptorHomo sapiens (human)
synapseGlucocorticoid receptorHomo sapiens (human)
chromatinGlucocorticoid receptorHomo sapiens (human)
protein-containing complexGlucocorticoid receptorHomo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID456397Inhibition of human recombinant carbonic anhydrase 2 by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID368328Cytotoxicity against human A549 cells at 100 uM2009Bioorganic & medicinal chemistry, Feb-01, Volume: 17, Issue:3
Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum.
AID588187Inhibition of human recombinant alpha-carbonic anhydrase 2 after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588182Inhibition of Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588196Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Candida albicans recombinant Nce103 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456398Inhibition of human recombinant carbonic anhydrase 1 by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID291923Binding affinity to glucocorticoid receptor by GR binding assay2007Journal of natural products, Jul, Volume: 70, Issue:7
Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum.
AID456400Inhibition of human recombinant carbonic anhydrase 5B by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID456404Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5B2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID456402Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5A2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588184Inhibition of Candida albicans recombinant Nce103 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456401Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5A2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588195Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588194Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456403Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5B2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588183Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456399Inhibition of human recombinant carbonic anhydrase 5A by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588192Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Candida albicans recombinant Nce103 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588193Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588190Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588191Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588186Inhibition of human recombinant alpha-carbonic anhydrase 1 after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588197Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588185Inhibition of Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (40.00)29.6817
2010's3 (60.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.63

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

MetricThis Compound (vs All)
Research Demand Index12.63 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]