Page last updated: 2024-09-27

4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en

Description

4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en: RN given for (3R-(3alpha,3abeta,4beta,8aalpha))-isomer; a natural benzyl ester of a carotyl type azulene sesquiterpenoid; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID354654
CHEMBL ID465040
SCHEMBL ID12512403
MeSH IDM0287728

Synonyms (24)

Synonym
benzoic acid, 4-hydroxy-, 1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester, (3r-(3alpha,3abeta,4beta,8aalpha))-
4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en
41743-44-6
benzoic acid, 4-hydroxy-, (3r,3as,4s,8ar)-1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester
tefestrol
nsc-606959
jaeschkeanadiol p-hydroxy benzoate
nsc606959
from ferula tingiatana
ferutinine
ferutinin
[(3r,3as,4s,8ar)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate
jaeschkeanadiol p-hydroxybenzoate
CHEMBL465040
SCHEMBL12512403
4MG7
ferutinin, >=98% (hplc)
(3r,3as,4s,8ar)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate
Q27452770
3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate
DTXSID20961947
bdbm50539730
HY-125703
CS-0093377

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Estrogen receptorHomo sapiens (human)IC50 (µMol)0.03310.00000.723732.7000AID1651702
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (42)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
antral ovarian follicle growthEstrogen receptorHomo sapiens (human)
epithelial cell developmentEstrogen receptorHomo sapiens (human)
chromatin remodelingEstrogen receptorHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
signal transductionEstrogen receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEstrogen receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEstrogen receptorHomo sapiens (human)
androgen metabolic processEstrogen receptorHomo sapiens (human)
male gonad developmentEstrogen receptorHomo sapiens (human)
negative regulation of gene expressionEstrogen receptorHomo sapiens (human)
positive regulation of phospholipase C activityEstrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayEstrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptorHomo sapiens (human)
response to estradiolEstrogen receptorHomo sapiens (human)
regulation of toll-like receptor signaling pathwayEstrogen receptorHomo sapiens (human)
negative regulation of smooth muscle cell apoptotic processEstrogen receptorHomo sapiens (human)
negative regulation of canonical NF-kappaB signal transductionEstrogen receptorHomo sapiens (human)
negative regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
response to estrogenEstrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
fibroblast proliferationEstrogen receptorHomo sapiens (human)
positive regulation of fibroblast proliferationEstrogen receptorHomo sapiens (human)
stem cell differentiationEstrogen receptorHomo sapiens (human)
regulation of inflammatory responseEstrogen receptorHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
RNA polymerase II preinitiation complex assemblyEstrogen receptorHomo sapiens (human)
uterus developmentEstrogen receptorHomo sapiens (human)
vagina developmentEstrogen receptorHomo sapiens (human)
prostate epithelial cord elongationEstrogen receptorHomo sapiens (human)
prostate epithelial cord arborization involved in prostate glandular acinus morphogenesisEstrogen receptorHomo sapiens (human)
regulation of branching involved in prostate gland morphogenesisEstrogen receptorHomo sapiens (human)
mammary gland branching involved in pregnancyEstrogen receptorHomo sapiens (human)
mammary gland alveolus developmentEstrogen receptorHomo sapiens (human)
epithelial cell proliferation involved in mammary gland duct elongationEstrogen receptorHomo sapiens (human)
protein localization to chromatinEstrogen receptorHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptorHomo sapiens (human)
negative regulation of miRNA transcriptionEstrogen receptorHomo sapiens (human)
regulation of epithelial cell apoptotic processEstrogen receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (26)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
TFIIB-class transcription factor bindingEstrogen receptorHomo sapiens (human)
transcription coregulator bindingEstrogen receptorHomo sapiens (human)
transcription corepressor bindingEstrogen receptorHomo sapiens (human)
transcription coactivator bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
chromatin bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
nuclear receptor activityEstrogen receptorHomo sapiens (human)
steroid bindingEstrogen receptorHomo sapiens (human)
protein bindingEstrogen receptorHomo sapiens (human)
calmodulin bindingEstrogen receptorHomo sapiens (human)
beta-catenin bindingEstrogen receptorHomo sapiens (human)
zinc ion bindingEstrogen receptorHomo sapiens (human)
TBP-class protein bindingEstrogen receptorHomo sapiens (human)
enzyme bindingEstrogen receptorHomo sapiens (human)
protein kinase bindingEstrogen receptorHomo sapiens (human)
nitric-oxide synthase regulator activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor bindingEstrogen receptorHomo sapiens (human)
estrogen response element bindingEstrogen receptorHomo sapiens (human)
identical protein bindingEstrogen receptorHomo sapiens (human)
ATPase bindingEstrogen receptorHomo sapiens (human)
14-3-3 protein bindingEstrogen receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingEstrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusEstrogen receptorHomo sapiens (human)
nucleoplasmEstrogen receptorHomo sapiens (human)
transcription regulator complexEstrogen receptorHomo sapiens (human)
cytoplasmEstrogen receptorHomo sapiens (human)
Golgi apparatusEstrogen receptorHomo sapiens (human)
cytosolEstrogen receptorHomo sapiens (human)
plasma membraneEstrogen receptorHomo sapiens (human)
membraneEstrogen receptorHomo sapiens (human)
chromatinEstrogen receptorHomo sapiens (human)
euchromatinEstrogen receptorHomo sapiens (human)
protein-containing complexEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID623032Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID361391Displacement of [2,4,6,7-3H]estradiol from human recombinant ERalpha receptor2002Journal of natural products, Nov, Volume: 65, Issue:11
Daucane phytoestrogens: a structure-activity study.
AID377760Estrogenic effect in human MCF7 cells assessed as stimulation of cell proliferation at 10 ug/ml relative to control by [3H]hypoxanthine incorporation assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID623038Cytotoxicity against human SEM cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID1651695Anti-austeritic activity against human PANC1 cells in nutrient-deprived medium measured after 24 hrs by WST8 assay
AID1651700Inhibition of colony formation in human PANC1 cells incubated for 10 days by crystal violet staining based assay
AID623033Cytotoxicity against human A549 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID377759Estrogenic effect in human MCF7 cells assessed as stimulation of cell proliferation at 1 ug/ml relative to control by [3H]hypoxanthine incorporation assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID623036Cytotoxicity against human K562 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID359208Antimicrobial activity against Candida albicans ATCC 900282001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID697853Inhibition of horse BChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID623037Cytotoxicity against human RS4:11 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID1651701Inhibition of colony formation in human PANC1 cells at 12.5 uM incubated for 10 days by crystal violet staining based assay relative to control
AID359207Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC 433002001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID1651696Anti-austeritic activity against human PANC1 cells in nutrient-rich medium measured after 24 hrs by WST8 assay
AID359210Antimicrobial activity against Aspergillus fumigatus ATCC 909062001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID361390Binding affinity to human ERalpha expressed in yeast relative to estradiol2002Journal of natural products, Nov, Volume: 65, Issue:11
Daucane phytoestrogens: a structure-activity study.
AID1651698Induction of morphological changes in human PANC1 cells assessed as plasma blebbing at 5 uM in nutrient-deprived medium measured after 10 hrs by time-lapse microscopy
AID1651699Induction of apoptosis in human PANC1 cells at 5 uM in nutrient-deprived medium measured within 24 hrs by time-lapse microscopy
AID697852Inhibition of electric eel AChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID362785Inhibition of human recombinant PDE5A1 expressed in COS7 cells2008Journal of natural products, Sep, Volume: 71, Issue:9
Potent inhibition of human phosphodiesterase-5 by icariin derivatives.
AID623034Cytotoxicity against human HL60 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID359212Antimicrobial activity against Mycobacterium intracellular ATCC 230682001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID359206Antimicrobial activity against Staphylococcus aureus ATCC 292132001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID1651702Inhibition of ligand binding to ERalpha (unknown origin) by fluorescence polarization assay
AID623035Cytotoxicity against human Jurkat cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.
AID359209Antimicrobial activity against Cryptococcus neoformans ATCC 901132001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID377758Estrogenic effect in human MCF7 cells assessed as stimulation of cell proliferation at 0.1 ug/ml relative to control by [3H]hypoxanthine incorporation assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID361392Displacement of [2,4,6,7-3H]estradiol from human recombinant ERbeta receptor2002Journal of natural products, Nov, Volume: 65, Issue:11
Daucane phytoestrogens: a structure-activity study.
AID359211Antimicrobial activity against Pseudomonas aeruginosa ATCC 278532001Journal of natural products, Mar, Volume: 64, Issue:3
Daucane sesquiterpenes from Ferula hermonis.
AID1651697Induction of morphological changes in human PANC1 cells assessed as cell shrinkage at 5 uM in nutrient-deprived medium measured within 4 hrs by time-lapse microscopy
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2014Environmental health perspectives, Dec, Volume: 122, Issue:12
Structural and functional profiling of environmental ligands for estrogen receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (52)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (1.92)18.2507
2000's14 (26.92)29.6817
2010's24 (46.15)24.3611
2020's13 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (5.36%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other53 (94.64%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Ferutinin: A phytoestrogen from ferula and its anticancer, antioxidant, and toxicity properties.
Journal of biochemical and molecular toxicology, Volume: 35, Issue: 4
2021
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (2)

ArticleYear
Structural and histomorphometric evaluations of ferutinin effects on the uterus of ovariectomized rats during osteoporosis treatment.
Life sciences, Jan-16, Volume: 90, Issue: 3-4
2012
The phytoestrogen ferutinin improves sexual behavior in ovariectomized rats.
Phytomedicine : international journal of phytotherapy and phytopharmacology, Volume: 16, Issue: 6-7
2009
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (3)

ArticleYear
Structural and histomorphometric evaluations of ferutinin effects on the uterus of ovariectomized rats during osteoporosis treatment.
Life sciences, Jan-16, Volume: 90, Issue: 3-4
2012
Influence of ferutinin on bone metabolism in ovariectomized rats. I: role in preventing osteoporosis.
Journal of bone and mineral metabolism, Volume: 27, Issue: 5
2009
The phytoestrogen ferutinin improves sexual behavior in ovariectomized rats.
Phytomedicine : international journal of phytotherapy and phytopharmacology, Volume: 16, Issue: 6-7
2009
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]