Page last updated: 2024-11-08

triptophenolide

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

Description

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

Cross-References

ID SourceID
PubMed CID173273
CHEMBL ID3039217
CHEBI ID114185
SCHEMBL ID19236270
MeSH IDM0107664

Synonyms (51)

Synonym
BRD-K73210450-001-02-3
DIVK1C_006662
SDCCGMLS-0066775.P001
SPECTRUM_001722
SPECTRUM4_001660
SPECTRUM5_000539
triptophenolide
BSPBIO_003528
KBIOSS_002202
KBIO2_002202
KBIO2_004770
KBIO1_001606
KBIOGR_002159
KBIO2_007338
KBIO3_002756
SPECPLUS_000566
SPBIO_001655
SPECTRUM2_001618
SPECTRUM3_001928
SPECTRUM1504005
CHEBI:114185
6-hydroxy-7-isopropyl-9b-methyl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e]isobenzofuran-1-one
A838080
74285-86-2
(3br,9bs)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e][2]benzofuran-1-one
CHEMBL3039217
phenanthro(1,2-c)furan-1(3h)-one, 3b,4,5,9b,10,11-hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)-, (3br-trans)-
tryptophenolide
S9045
CCG-38739
AKOS015897179
CS-3764
AC-34444
HY-N0475
(3br,9bs)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e]isobenzofuran-1-one
Q27195253
(-)-triptophenolide
SR-05000002569-1
sr-05000002569
bdbm50199857
SCHEMBL19236270
BCP26008
mfcd00210567
DTXSID80995809
6-hydroxy-9b-methyl-7-(propan-2-yl)-3b,4,5,9b,10,11-hexahydrophenanthro[1,2-c]furan-1(3h)-one
(+)-triptophenolide
hypolide
hypolide;(+)-triptophenolide
BRD-K73210450-001-03-1
phenanthro[1,2-c]furan-1(3h)-one,3b,4,5,9b,10,11-hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)-,(3br,9bs)-
MS-24563

Research Excerpts

Effects

ExcerptReferenceRelevance
"Triptophenolide, C20H24O3, has been assigned two isomeric structures. "( [The crystal structure of triptophenolide revisited].
Chen, YZ; Deng, FX; Huang, XY; Wu, QJ, 1992
)
2.03

Dosage Studied

ExcerptRelevanceReference
" It is very important to develop a new dosage form of high effect and low toxicity by making use of advanced technology according to its characteristics."( [Progress in research on triptolide].
Dong, J; Liu, MX; Xu, HB; Yang, XL; Yang, YJ, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
oxo steroid
[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)
Androgen receptorHomo sapiens (human)IC50 (µMol)0.37600.00000.875310.0000AID1324623; AID1324624; AID1324637
Androgen receptorRattus norvegicus (Norway rat)IC50 (µMol)0.46700.00101.979414.1600AID1324630
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
MAPK cascadeAndrogen receptorHomo sapiens (human)
in utero embryonic developmentAndrogen receptorHomo sapiens (human)
regulation of systemic arterial blood pressureAndrogen receptorHomo sapiens (human)
epithelial cell morphogenesisAndrogen receptorHomo sapiens (human)
transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
signal transductionAndrogen receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAndrogen receptorHomo sapiens (human)
cell-cell signalingAndrogen receptorHomo sapiens (human)
spermatogenesisAndrogen receptorHomo sapiens (human)
single fertilizationAndrogen receptorHomo sapiens (human)
positive regulation of cell population proliferationAndrogen receptorHomo sapiens (human)
negative regulation of cell population proliferationAndrogen receptorHomo sapiens (human)
positive regulation of gene expressionAndrogen receptorHomo sapiens (human)
male somatic sex determinationAndrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
androgen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
intracellular receptor signaling pathwayAndrogen receptorHomo sapiens (human)
positive regulation of intracellular estrogen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
Leydig cell differentiationAndrogen receptorHomo sapiens (human)
multicellular organism growthAndrogen receptorHomo sapiens (human)
positive regulation of phosphorylationAndrogen receptorHomo sapiens (human)
positive regulation of MAPK cascadeAndrogen receptorHomo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayAndrogen receptorHomo sapiens (human)
positive regulation of cell differentiationAndrogen receptorHomo sapiens (human)
negative regulation of integrin biosynthetic processAndrogen receptorHomo sapiens (human)
positive regulation of integrin biosynthetic processAndrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionAndrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIIAndrogen receptorHomo sapiens (human)
insulin-like growth factor receptor signaling pathwayAndrogen receptorHomo sapiens (human)
regulation of developmental growthAndrogen receptorHomo sapiens (human)
animal organ formationAndrogen receptorHomo sapiens (human)
male genitalia morphogenesisAndrogen receptorHomo sapiens (human)
epithelial cell proliferationAndrogen receptorHomo sapiens (human)
negative regulation of epithelial cell proliferationAndrogen receptorHomo sapiens (human)
positive regulation of NF-kappaB transcription factor activityAndrogen receptorHomo sapiens (human)
activation of prostate induction by androgen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
morphogenesis of an epithelial foldAndrogen receptorHomo sapiens (human)
lateral sprouting involved in mammary gland duct morphogenesisAndrogen receptorHomo sapiens (human)
prostate gland growthAndrogen receptorHomo sapiens (human)
prostate gland epithelium morphogenesisAndrogen receptorHomo sapiens (human)
epithelial cell differentiation involved in prostate gland developmentAndrogen receptorHomo sapiens (human)
tertiary branching involved in mammary gland duct morphogenesisAndrogen receptorHomo sapiens (human)
mammary gland alveolus developmentAndrogen receptorHomo sapiens (human)
positive regulation of epithelial cell proliferation involved in prostate gland developmentAndrogen receptorHomo sapiens (human)
cellular response to steroid hormone stimulusAndrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusAndrogen receptorHomo sapiens (human)
cellular response to testosterone stimulusAndrogen receptorHomo sapiens (human)
seminiferous tubule developmentAndrogen receptorHomo sapiens (human)
non-membrane-bounded organelle assemblyAndrogen receptorHomo sapiens (human)
positive regulation of miRNA transcriptionAndrogen receptorHomo sapiens (human)
regulation of protein localization to plasma membraneAndrogen receptorHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathwayAndrogen receptorHomo sapiens (human)
male gonad developmentAndrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingAndrogen receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificAndrogen receptorHomo sapiens (human)
RNA polymerase II general transcription initiation factor bindingAndrogen receptorHomo sapiens (human)
transcription coactivator bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificAndrogen receptorHomo sapiens (human)
chromatin bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityAndrogen receptorHomo sapiens (human)
nuclear receptor activityAndrogen receptorHomo sapiens (human)
G protein-coupled receptor activityAndrogen receptorHomo sapiens (human)
signaling receptor bindingAndrogen receptorHomo sapiens (human)
steroid bindingAndrogen receptorHomo sapiens (human)
androgen bindingAndrogen receptorHomo sapiens (human)
protein bindingAndrogen receptorHomo sapiens (human)
beta-catenin bindingAndrogen receptorHomo sapiens (human)
zinc ion bindingAndrogen receptorHomo sapiens (human)
enzyme bindingAndrogen receptorHomo sapiens (human)
ATPase bindingAndrogen receptorHomo sapiens (human)
molecular adaptor activityAndrogen receptorHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingAndrogen receptorHomo sapiens (human)
POU domain bindingAndrogen receptorHomo sapiens (human)
molecular condensate scaffold activityAndrogen receptorHomo sapiens (human)
estrogen response element bindingAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneAndrogen receptorHomo sapiens (human)
nucleusAndrogen receptorHomo sapiens (human)
nucleoplasmAndrogen receptorHomo sapiens (human)
cytoplasmAndrogen receptorHomo sapiens (human)
cytosolAndrogen receptorHomo sapiens (human)
nuclear speckAndrogen receptorHomo sapiens (human)
chromatinAndrogen receptorHomo sapiens (human)
protein-containing complexAndrogen receptorHomo sapiens (human)
nucleusAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (35)

Assay IDTitleYearJournalArticle
AID1324620Agonist activity at wild type AR in human PC3 cells assessed as receptor transcriptional activation at 50 to 5000 nM after 24 hrs in absence of DHT by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324625Antagonist activity at AR W741C/T877A double mutant (unknown origin) transfected in human PC3 cells assessed as inhibition of DHT-induced receptor transcriptional activation after 24 hrs by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1434297Cytotoxic activity against human SKOV3 cells assessed as reduction in cell viability after 72 hrs by SRB assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Identification of a diverse synthetic abietane diterpenoid library for anticancer activity.
AID1368174Antibacterial activity against Staphylococcus aureus measured after 24 hrs2017Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24
Identification of a diverse synthetic abietane diterpenoid library and insight into the structure-activity relationships for antibacterial activity.
AID1324626Antagonist activity at AR in human LNCAP cells assessed as downregulation of PSA mRNA levels at 500 nM after 24 hrs in presence of DHT by RT-PCR analysis2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324622Agonist activity at AR W741C/T877A double mutant (unknown origin) transfected in human PC3 cells assessed as receptor transcriptional activation at 50 to 5000 nM after 24 hrs in absence of DHT by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1368176Antibacterial activity against Escherichia coli measured after 24 hrs2017Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24
Identification of a diverse synthetic abietane diterpenoid library and insight into the structure-activity relationships for antibacterial activity.
AID1324623Antagonist activity at wild type AR in human PC3 cells assessed as suppression of DHT-induced receptor transcriptional activation after 24 hrs by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1368177Antibacterial activity against Pseudomonas fluorescens measured after 24 hrs2017Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24
Identification of a diverse synthetic abietane diterpenoid library and insight into the structure-activity relationships for antibacterial activity.
AID1324637Antagonist activity at AR F876L mutant (unknown origin) expressed in human PC3 cells assessed as inhibition of DHT-induced receptor transactivation after 24 hrs by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1298751Cytotoxicity against human Hep3B cells after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-15, Volume: 26, Issue:12
Kaurane and abietane diterpenoids from the roots of Tripterygium wilfordii and their cytotoxic evaluation.
AID1298755Cytotoxicity against human A549 cells after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-15, Volume: 26, Issue:12
Kaurane and abietane diterpenoids from the roots of Tripterygium wilfordii and their cytotoxic evaluation.
AID1298750Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-15, Volume: 26, Issue:12
Kaurane and abietane diterpenoids from the roots of Tripterygium wilfordii and their cytotoxic evaluation.
AID1434295Cytotoxic activity against human A549 cells assessed as reduction in cell viability after 72 hrs by SRB assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Identification of a diverse synthetic abietane diterpenoid library for anticancer activity.
AID1324621Agonist activity at AR T877A mutant (unknown origin) transfected in human PC3 cells assessed as receptor transcriptional activation at 50 to 5000 nM after 24 hrs in absence of DHT by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324630Displacement of fluormone-DHT green from His/GST-tagged rat AR ligand binding domain after 4 to 8 hrs by fluorescence polarization assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324624Antagonist activity at AR T877A mutant (unknown origin) transfected in human PC3 cells assessed as inhibition of DHT-induced receptor transcriptional activation after 24 hrs by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324629Cytotoxicity against human PC3 cells assessed as cell growth inhibition after 72 hrs by MTT assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1298753Cytotoxicity against human U251 cells after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-15, Volume: 26, Issue:12
Kaurane and abietane diterpenoids from the roots of Tripterygium wilfordii and their cytotoxic evaluation.
AID1324628Cytotoxicity against human LNCAP cells assessed as cell growth inhibition after 72 hrs by MTT assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1298754Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-15, Volume: 26, Issue:12
Kaurane and abietane diterpenoids from the roots of Tripterygium wilfordii and their cytotoxic evaluation.
AID1368175Antibacterial activity against Bacillus subtilis measured after 24 hrs2017Bioorganic & medicinal chemistry letters, 12-15, Volume: 27, Issue:24
Identification of a diverse synthetic abietane diterpenoid library and insight into the structure-activity relationships for antibacterial activity.
AID1324634Agonist activity at AR F876L mutant (unknown origin) expressed in human PC3 cells assessed as receptor transcriptional activation at 50 to 5000 nM after 24 hrs in absence of DHT by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1324616Antagonist activity at AR F876L mutant (unknown origin) transfected in human PC3 cells assessed as suppression of DHT-induced receptor transcriptional activity at 500 nM after 24 hrs by PSA-luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324617Antagonist activity at AR in human LNCAP cells assessed as suppression of DHT-induced receptor transcriptional activity at 5 uM after 24 hrs by dual luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1298752Cytotoxicity against human Bcap37 cells after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-15, Volume: 26, Issue:12
Kaurane and abietane diterpenoids from the roots of Tripterygium wilfordii and their cytotoxic evaluation.
AID1434299Cytotoxic activity against human PC3 cells assessed as reduction in cell viability after 72 hrs by SRB assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Identification of a diverse synthetic abietane diterpenoid library for anticancer activity.
AID1324618Antagonist activity at AR in human LNCAP cells assessed as suppression of DHT-induced receptor transcriptional activity at 500 nM after 24 hrs by dual luciferase reporter gene assay2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324631Antagonist activity at AR in human LNCAP cells assessed as downregulation of AR protein expression after 24 hrs by Western blot analysis2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324632Inhibition of DHT-induced AR nuclear translocation in human LNCAP cells assessed as reduction in ratio of nuclear to cytoplasmic AR levels at 5 uM after 24 hrs by DAPI-staining based confocal microscopic analysis relative DHT2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1324627Antagonist activity at AR in human LNCAP cells assessed as downregulation of PSA mRNA levels at 5 uM after 24 hrs in presence of DHT by RT-PCR analysis2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Identification of Triptophenolide from
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.88)18.7374
1990's3 (17.65)18.2507
2000's2 (11.76)29.6817
2010's10 (58.82)24.3611
2020's1 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.23

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 Index22.23 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.82 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.23)

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]