Page last updated: 2024-11-11

ermanin

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

Description

ermanin: from Tanacetum microphyllum; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3,4'-dimethylkaempferol : A dimethoxyflavone that is kaempferol in which the hydroxy groups at position 3 and 4' have been replaced by methoxy groups. It is a component of bee glue and isolated from several plant species including Tanacetum microphyllum. [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]

FloraRankFlora DefinitionFamilyFamily Definition
TanacetumgenusA plant genus of the family ASTERACEAE. Some species of the CHRYSANTHEMUM and the old Pyrethrum genera have been reclassified to this genus. The common name of tansy usually refers to this but also forms part of the common name of other plants such as Tansy Ragwort (SENECIO) and Tansyaster (HAPLOPAPPUS).[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID5352001
CHEMBL ID309061
CHEBI ID146142
SCHEMBL ID2875089
MeSH IDM0273624

Synonyms (43)

Synonym
CHEMBL309061 ,
kaempferol 3,4'-dimethyl ether
NSC31882 ,
nsc-31882
chrysin,4'-dimethoxy-
20869-95-8
3,4'-dimethoxychrysin
NCI60_002742
MEGXP0_000250
4h-1-benzopyran-4-one, 5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-
5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)chromen-4-one
ermanin
kaempferol-3,4'-dimethylether
5,7-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one
bdbm50240619
5,7-dihydroxy-3,4''-dimethoxyflavone
kaempferol-3,4''-di-o-methyl ether
LMPK12112697
kaempferol 3,4'-di-o-methyl ether
5,7-dihydroxy-3,4'-dimethoxyflavone
3,4'-dimethoxy-5,7-dihydroxyflavone
5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-4h-chromen-4-one
5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-4-benzopyrone
5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
3,4'-dimethoxykaempferol
3,4'-dimethylkaempferol
CHEBI:146142
einecs 244-093-8
850d90yjn3 ,
nsc 31882
unii-850d90yjn3
AKOS015963884
FT-0638054
SCHEMBL2875089
5,7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-4h-chromen-4-one #
chrysin, 3,4'-dimethoxy-
DTXSID90174986
Q3056707
FS-9547
5,7-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)chromen-4-one
CS-0024327
HY-N3848
kaempferol-3,4'-dimethyl ether
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
anti-inflammatory agentAny compound that has anti-inflammatory effects.
antimycobacterial drugA drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role 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]

Drug Classes (2)

ClassDescription
dihydroxyflavoneAny hydroxyflavone in which two ring hydrogens are replaced by hydroxy substituents.
dimethoxyflavoneAny methoxyflavone with two methoxy substituents.
[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]

Pathways (1)

PathwayProteinsCompounds
polymethylated kaempferol biosynthesis110

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 3A4Homo sapiens (human)IC50 (µMol)21.80000.00011.753610.0000AID402936
Cytochrome P450 2D6Homo sapiens (human)IC50 (µMol)45.50000.00002.015110.0000AID402937
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID401494Inhibition of PMA-induced ear edema in Swiss mouse at 3 mg/ear after 5 hrs1997Journal of natural products, Feb, Volume: 60, Issue:2
Isolation of two flavonoids from Tanacetum microphyllum as PMA-induced ear edema inhibitors.
AID510838Cytotoxicity against human A549 cells after 72 hrs by XTT assay2010European journal of medicinal chemistry, Sep, Volume: 45, Issue:9
Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation.
AID357365Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins2001Journal of natural products, Aug, Volume: 64, Issue:8
Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia.
AID401493Inhibition of PMA-induced ear edema in Swiss mouse at 3 mg/ear after 3 hrs1997Journal of natural products, Feb, Volume: 60, Issue:2
Isolation of two flavonoids from Tanacetum microphyllum as PMA-induced ear edema inhibitors.
AID162238Minimum drug concentration at which 99% of the polio virus is inhibited1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID162242Maximal non-toxic dose (MNTD) that shows antiviral activity.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID235260Therapeutic Index measured as the ratio of CyD50(polio) / ED99(polio) values1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID252875Caspase 3/7 activity is expressed as ratio of caspase activation in treated human colonic cell line (HT-29) to that of untreated control cells after 5 hr2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study.
AID404067In vivo antitumor activity against mouse S180 cells
AID404064Cytotoxicity against mouse 26-L5 cells after 24 hrs by MTT assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents of Brazilian propolis and their cytotoxic activities.
AID404070In vivo antitumor activity against mouse CA-755 cells
AID377540Cytotoxicity against human HT1080 cells by MTT assay2000Journal of natural products, Sep, Volume: 63, Issue:9
Two novel cytotoxic benzofuran derivatives from Brazilian propolis.
AID336952Inhibition of bovine thymocytes protein tyrosine kinase assessed as angiotensin 1 phosphorylation
AID510837Cytotoxicity against human HeLa cells after 72 hrs by XTT assay2010European journal of medicinal chemistry, Sep, Volume: 45, Issue:9
Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation.
AID162249Minimal dose which produces titer reduction at 10 ug/mL (mD RF10e3)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID162237Cytotoxic dose at which 50% growth of normal cells is inhibited1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID402937Inhibition of human CYP2D6 by radiometric assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.
AID250527Antiproliferative effect against human colonic cell line (HT-29) after 6 hr at a concentration of 50 uM2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study.
AID404063Cytotoxicity against human HT1080 cells after 24 hrs by MTT assay1998Journal of natural products, Jul, Volume: 61, Issue:7
Chemical constituents of Brazilian propolis and their cytotoxic activities.
AID377539Cytotoxicity against mouse 26-L5 cells by MTT assay2000Journal of natural products, Sep, Volume: 63, Issue:9
Two novel cytotoxic benzofuran derivatives from Brazilian propolis.
AID401492Inhibition of PMA-induced ear edema in Swiss mouse at 3 mg/ear after 1 hr1997Journal of natural products, Feb, Volume: 60, Issue:2
Isolation of two flavonoids from Tanacetum microphyllum as PMA-induced ear edema inhibitors.
AID402936Inhibition of human CYP3A4 by radiometric assay2004Journal of natural products, Jul, Volume: 67, Issue:7
Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.
AID510839Cytotoxicity against human HT-29 cells after 72 hrs by XTT assay2010European journal of medicinal chemistry, Sep, Volume: 45, Issue:9
Prenylflavonoids and prenyl/alkyl-phloroacetophenones: synthesis and antitumour biological evaluation.
AID250567Antiproliferative effect against human colonic cell line (HT-29) after 24 hr at a concentration of 50 uM2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study.
AID144650In vitro cytotoxic potency against NCI-60 human tumor cell line1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Structure-activity requirements for flavone cytotoxicity and binding to tubulin.
AID404069In vivo antitumor activity against mouse L1210 cells
[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's4 (28.57)18.2507
2000's5 (35.71)29.6817
2010's4 (28.57)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.93

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 Index20.93 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.93)

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%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]