Page last updated: 2024-12-06

taxodione

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

Description

Taxodione is a diterpenoid compound isolated from the bark and foliage of the bald cypress tree (Taxodium distichum). It exhibits a broad spectrum of biological activities, including anti-cancer, anti-inflammatory, and antimicrobial properties. Taxodione has been shown to inhibit the growth of various cancer cell lines, including those of breast, lung, and prostate cancer. Its anti-inflammatory effects are attributed to its ability to suppress the production of pro-inflammatory cytokines. Taxodione has also been found to possess antibacterial and antifungal properties. The compound's unique structure and its promising biological activities have made it a subject of ongoing research, with efforts focused on understanding its mechanism of action, developing synthetic analogues with enhanced efficacy, and exploring its potential as a therapeutic agent. Its potential as a lead compound for drug development is being investigated, particularly in the areas of cancer treatment and anti-inflammatory therapies.'

taxodione: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73588
CHEMBL ID235195
CHEBI ID9419
SCHEMBL ID3847860
MeSH IDM0054032

Synonyms (26)

Synonym
taxodion
nsc-122419
taxodione, (+)-
taxodione
19026-31-4
C09194
(4bs,8as)-4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a-tetrahydrophenanthrene-3,9-dione
3,9-phenanthrenedione, 4b,5,6,7,8,8a-hexahydro-4-hydroxy-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bs,8as)-
chebi:9419 ,
CHEMBL235195
AC1L2K4Y ,
(4bs,8as)-4-hydroxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a-tetrahydrophenanthrene-3,9-dione
AC1Q6CEN ,
w96g420hjx ,
podocarpa-7,9(11),13-triene-6,12-dione, 11-hydroxy-13-isopropyl-
3,9-phenanthrenedione, 4b,5,6,7,8,8a-hexahydro-4-hydroxy-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bs-trans)-
nsc 122419
unii-w96g420hjx
SCHEMBL3847860
taxodione [mi]
(+)-taxodione
4P0X
(4bs)-4-hydroxy-2-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a-hexahydrophenanthrene-3,9-dione
[taxodione]
Q27108386
bdbm50528245

Research Excerpts

Effects

ExcerptReferenceRelevance
"Taxodione has antioxidant activity and protects PC12 cells against oxidative stress-induced apoptotic cell death."( Anti-apoptotic effect of taxodione on serum/glucose deprivation-induced PC12 cells death.
Asili, J; Emami, SA; Shafaei-Bajestani, N; Tayarani-Najaran, Z, 2014
)
1.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diterpenoidAny terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histone acetyltransferase p300Homo sapiens (human)IC50 (µMol)4.85000.26004.00008.5000AID1607715; AID1727405
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (59)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIHistone acetyltransferase p300Homo sapiens (human)
response to hypoxiaHistone acetyltransferase p300Homo sapiens (human)
somitogenesisHistone acetyltransferase p300Homo sapiens (human)
thigmotaxisHistone acetyltransferase p300Homo sapiens (human)
behavioral defense responseHistone acetyltransferase p300Homo sapiens (human)
stimulatory C-type lectin receptor signaling pathwayHistone acetyltransferase p300Homo sapiens (human)
regulation of glycolytic processHistone acetyltransferase p300Homo sapiens (human)
protein acetylationHistone acetyltransferase p300Homo sapiens (human)
internal protein amino acid acetylationHistone acetyltransferase p300Homo sapiens (human)
apoptotic processHistone acetyltransferase p300Homo sapiens (human)
canonical NF-kappaB signal transductionHistone acetyltransferase p300Homo sapiens (human)
nervous system developmentHistone acetyltransferase p300Homo sapiens (human)
heart developmentHistone acetyltransferase p300Homo sapiens (human)
skeletal muscle tissue developmentHistone acetyltransferase p300Homo sapiens (human)
learning or memoryHistone acetyltransferase p300Homo sapiens (human)
circadian rhythmHistone acetyltransferase p300Homo sapiens (human)
animal organ morphogenesisHistone acetyltransferase p300Homo sapiens (human)
regulation of autophagyHistone acetyltransferase p300Homo sapiens (human)
negative regulation of autophagyHistone acetyltransferase p300Homo sapiens (human)
macrophage derived foam cell differentiationHistone acetyltransferase p300Homo sapiens (human)
regulation of mitochondrion organizationHistone acetyltransferase p300Homo sapiens (human)
positive regulation of neuron projection developmentHistone acetyltransferase p300Homo sapiens (human)
N-terminal peptidyl-lysine acetylationHistone acetyltransferase p300Homo sapiens (human)
internal peptidyl-lysine acetylationHistone acetyltransferase p300Homo sapiens (human)
peptidyl-lysine acetylationHistone acetyltransferase p300Homo sapiens (human)
B cell differentiationHistone acetyltransferase p300Homo sapiens (human)
platelet formationHistone acetyltransferase p300Homo sapiens (human)
lung developmentHistone acetyltransferase p300Homo sapiens (human)
positive regulation of transforming growth factor beta receptor signaling pathwayHistone acetyltransferase p300Homo sapiens (human)
negative regulation of protein-containing complex assemblyHistone acetyltransferase p300Homo sapiens (human)
protein destabilizationHistone acetyltransferase p300Homo sapiens (human)
cellular response to nutrient levelsHistone acetyltransferase p300Homo sapiens (human)
cellular response to UVHistone acetyltransferase p300Homo sapiens (human)
multicellular organism growthHistone acetyltransferase p300Homo sapiens (human)
megakaryocyte developmentHistone acetyltransferase p300Homo sapiens (human)
swimmingHistone acetyltransferase p300Homo sapiens (human)
positive regulation of protein import into nucleusHistone acetyltransferase p300Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorHistone acetyltransferase p300Homo sapiens (human)
response to estrogenHistone acetyltransferase p300Homo sapiens (human)
positive regulation by host of viral transcriptionHistone acetyltransferase p300Homo sapiens (human)
fat cell differentiationHistone acetyltransferase p300Homo sapiens (human)
negative regulation of gluconeogenesisHistone acetyltransferase p300Homo sapiens (human)
transcription initiation-coupled chromatin remodelingHistone acetyltransferase p300Homo sapiens (human)
positive regulation of DNA-templated transcriptionHistone acetyltransferase p300Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIHistone acetyltransferase p300Homo sapiens (human)
positive regulation of receptor signaling pathway via JAK-STATHistone acetyltransferase p300Homo sapiens (human)
protein stabilizationHistone acetyltransferase p300Homo sapiens (human)
positive regulation of DNA-binding transcription factor activityHistone acetyltransferase p300Homo sapiens (human)
face morphogenesisHistone acetyltransferase p300Homo sapiens (human)
regulation of androgen receptor signaling pathwayHistone acetyltransferase p300Homo sapiens (human)
peptidyl-lysine propionylationHistone acetyltransferase p300Homo sapiens (human)
cellular response to L-leucineHistone acetyltransferase p300Homo sapiens (human)
regulation of tubulin deacetylationHistone acetyltransferase p300Homo sapiens (human)
peptidyl-lysine crotonylationHistone acetyltransferase p300Homo sapiens (human)
peptidyl-lysine butyrylationHistone acetyltransferase p300Homo sapiens (human)
regulation of cellular response to heatHistone acetyltransferase p300Homo sapiens (human)
regulation of signal transduction by p53 class mediatorHistone acetyltransferase p300Homo sapiens (human)
positive regulation of TORC1 signalingHistone acetyltransferase p300Homo sapiens (human)
positive regulation of T-helper 17 cell lineage commitmentHistone acetyltransferase p300Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (38)

Processvia Protein(s)Taxonomy
transcription coregulator bindingHistone acetyltransferase p300Homo sapiens (human)
transcription coactivator bindingHistone acetyltransferase p300Homo sapiens (human)
p53 bindingHistone acetyltransferase p300Homo sapiens (human)
DNA bindingHistone acetyltransferase p300Homo sapiens (human)
chromatin bindingHistone acetyltransferase p300Homo sapiens (human)
damaged DNA bindingHistone acetyltransferase p300Homo sapiens (human)
transcription coactivator activityHistone acetyltransferase p300Homo sapiens (human)
histone acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
lysine N-acetyltransferase activity, acting on acetyl phosphate as donorHistone acetyltransferase p300Homo sapiens (human)
protein bindingHistone acetyltransferase p300Homo sapiens (human)
beta-catenin bindingHistone acetyltransferase p300Homo sapiens (human)
zinc ion bindingHistone acetyltransferase p300Homo sapiens (human)
histone H3 acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone H4 acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
acyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
nuclear receptor bindingHistone acetyltransferase p300Homo sapiens (human)
peptide N-acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone H3K18 acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone H2B acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone H3K27 acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
tau protein bindingHistone acetyltransferase p300Homo sapiens (human)
nuclear androgen receptor bindingHistone acetyltransferase p300Homo sapiens (human)
NF-kappaB bindingHistone acetyltransferase p300Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingHistone acetyltransferase p300Homo sapiens (human)
peptide-lysine-N-acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
protein propionyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
pre-mRNA intronic bindingHistone acetyltransferase p300Homo sapiens (human)
STAT family protein bindingHistone acetyltransferase p300Homo sapiens (human)
peptide 2-hydroxyisobutyryltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone lactyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
acetylation-dependent protein bindingHistone acetyltransferase p300Homo sapiens (human)
peptide butyryltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone crotonyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
histone butyryltransferase activityHistone acetyltransferase p300Homo sapiens (human)
DNA-binding transcription factor bindingHistone acetyltransferase p300Homo sapiens (human)
histone H3K122 acetyltransferase activityHistone acetyltransferase p300Homo sapiens (human)
chromatin DNA bindingHistone acetyltransferase p300Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
cytoplasmHistone acetyltransferase p300Homo sapiens (human)
cytosolHistone acetyltransferase p300Homo sapiens (human)
nucleusHistone acetyltransferase p300Homo sapiens (human)
nucleoplasmHistone acetyltransferase p300Homo sapiens (human)
cytosolHistone acetyltransferase p300Homo sapiens (human)
chromatinHistone acetyltransferase p300Homo sapiens (human)
protein-DNA complexHistone acetyltransferase p300Homo sapiens (human)
transcription regulator complexHistone acetyltransferase p300Homo sapiens (human)
histone acetyltransferase complexHistone acetyltransferase p300Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2014Proceedings of the National Academy of Sciences of the United States of America, Jun-24, Volume: 111, Issue:25
Taxodione and arenarone inhibit farnesyl diphosphate synthase by binding to the isopentenyl diphosphate site.
AID769610Cytotoxicity against human MOLT3 cells after 72 hrs by MTT assay2013Journal of natural products, Aug-23, Volume: 76, Issue:8
Antiproliferative activity of abietane diterpenoids against human tumor cells.
AID1304622Selectivity index, ratio of IC50 for human HT-29 cells to IC50 for Leishmania donovani LV82 promastigotes expressing red fluorescent protein2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Antileishmanial and Cytotoxic Activity of Some Highly Oxidized Abietane Diterpenoids from the Bald Cypress, Taxodium distichum.
AID1607715Inhibition of P300 (unknown origin)2019European journal of medicinal chemistry, Sep-15, Volume: 178Histone acetyltransferase inhibitors: An overview in synthesis, structure-activity relationship and molecular mechanism.
AID1727405Inhibition of N-terminal His/GST-tagged human p300 HAT (965 to 1810 residues) expressed in Sf9 insect cells using H3 peptide as substrate in presence of Ac-CoA measured after 60 mins2021European journal of medicinal chemistry, Jan-01, Volume: 209Current development of CBP/p300 inhibitors in the last decade.
AID301828Inhibition of tubulin polymerization at 100 uM after 30 mins2007Bioorganic & medicinal chemistry letters, Nov-01, Volume: 17, Issue:21
Taxodistines A and B, abietane-type diterpenes from Taxodium distichum.
AID769608Cytotoxicity against human SK-MEL-1 cells after 72 hrs by MTT assay2013Journal of natural products, Aug-23, Volume: 76, Issue:8
Antiproliferative activity of abietane diterpenoids against human tumor cells.
AID769609Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay2013Journal of natural products, Aug-23, Volume: 76, Issue:8
Antiproliferative activity of abietane diterpenoids against human tumor cells.
AID1304621Antileishmanial activity against Leishmania donovani LV82 promastigotes expressing red fluorescent protein after 72 hrs by flow cytometric analysis2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Antileishmanial and Cytotoxic Activity of Some Highly Oxidized Abietane Diterpenoids from the Bald Cypress, Taxodium distichum.
AID769611Cytotoxicity against human U937 cells after 72 hrs by MTT assay2013Journal of natural products, Aug-23, Volume: 76, Issue:8
Antiproliferative activity of abietane diterpenoids against human tumor cells.
AID1304624Selectivity index, ratio of IC50 for human HT-29 cells to IC50 for Leishmania amazonensis amastigotes2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Antileishmanial and Cytotoxic Activity of Some Highly Oxidized Abietane Diterpenoids from the Bald Cypress, Taxodium distichum.
AID1304623Antileishmanial activity against transgenic Leishmania amazonensis amastigotes infected in CD-1 mouse peritoneal macrophages assessed as beta-lactamase activity after 72 hrs by nitrocefin dye-based spectrophotometric analysis2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Antileishmanial and Cytotoxic Activity of Some Highly Oxidized Abietane Diterpenoids from the Bald Cypress, Taxodium distichum.
AID1304620Cytotoxicity against human HT-29 cells after 72 hrs by SRB assay2016Journal of natural products, Mar-25, Volume: 79, Issue:3
Antileishmanial and Cytotoxic Activity of Some Highly Oxidized Abietane Diterpenoids from the Bald Cypress, Taxodium distichum.
AID769612Cytotoxicity against human HL60 cells after 72 hrs by MTT assay2013Journal of natural products, Aug-23, Volume: 76, Issue:8
Antiproliferative activity of abietane diterpenoids against human tumor cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (6.25)18.2507
2000's2 (12.50)29.6817
2010's12 (75.00)24.3611
2020's1 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.11

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 Index23.11 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.41 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (11.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (88.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]