Page last updated: 2024-11-06

sakuranetin

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

Description

Sakuranetin is a flavonoid compound found in various plants, including citrus fruits and flowers. It exhibits a range of biological activities, including antioxidant, anti-inflammatory, and anti-cancer properties. Research on sakuranetin focuses on its potential therapeutic applications, particularly in preventing and treating diseases related to oxidative stress and inflammation. It is also studied for its potential role in promoting cardiovascular health and protecting against neurodegenerative diseases. The compound's synthesis has been investigated, with various methods being developed for its production. Sakuranetin's unique structure and biological activities make it a promising candidate for drug development and have led to ongoing research exploring its potential medicinal uses.'

sakuranetin: major rice phytoalexin; RN given for ((S)-(-))-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

sakuranetin : A flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group. [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]

Cross-References

ID SourceID
PubMed CID348130
CHEMBL ID74852
SCHEMBL ID555541
MeSH IDM0261711
PubMed CID73571
CHEMBL ID448297
CHEBI ID28927
SCHEMBL ID555542
MeSH IDM0261711

Synonyms (75)

Synonym
AC-20247
CHEMBL74852 ,
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one
5-hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-chroman-4-one
bdbm50049387
5,4''-dihydroxy-7-o-methoxyflavanone
4h-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
ACON1_000001
4h-1-benzopyran-4-one,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (s)-
flavanone,5-dihydroxy-7-methoxy-, (s)-(-)-
nsc-407228
NSC407228 ,
2957-21-3
MLS000876793
smr000440561
MEGXP0_000557
NCGC00168885-01
BRD-A32263173-001-01-2
L000892
FT-0650767
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
520-29-6
HMS2271F13
AKOS015965397
SCHEMBL555541
mfcd07782262
(rs)-sakuranetin
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4h-chromen-4-one #
DJOJDHGQRNZXQQ-UHFFFAOYSA-N
AC-34929
DTXSID10874774
A871097
XD161714
dihydrogenkwanin
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2h-1-benzopyran-4-one
flavanone, 4',5-dihydroxy-7-methoxy-, (s)-(-)-
einecs 220-980-5
unii-3o38p61299
nsc 407228
3o38p61299 ,
4h-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (s)-
(2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one
gtpl412
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one
4h-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (2s)-
(2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one
naringenin 7-methyl ether
(2s)-sakuranetin
sakuranetin
C09833
CHEBI:28927 ,
4',5-dihydroxy-7-methoxyflavanone
(s)-(-)-4',5-dihydroxy-7-methoxyflavanone
(s)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4h-1-benzopyran-4-one
(2s)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4h-chromen-4-one
(2s)--5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
(2s)-4',5-dihydroxy-7-methoxyflavanone
(2s)-5,4'-dihydroxy-7-methoxyflavan-4-one
LMPK12140571
3D04
5,4'-dihydroxy-7-methoxyflavanone
DB08517
7-o-methylnaringenin
CHEMBL448297 ,
5,4''-dihydroxy-7-methoxyflavanone
(s)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one
bdbm50312648
sakuranetin [mi]
SCHEMBL555542
sakuranetin, analytical standard
AKOS027321114
Q3459689
CS-0022916
HY-N3006
AS-79385

Research Excerpts

Overview

Sakuranetin (SAK) is a flavanone with antiparasitic, anti-inflammatory, antimutagenic, antiallergic, and antioxidant activity. It is an antifungal phytoalexin derived from the antibacterial precursor naringenin.

ExcerptReferenceRelevance
"Sakuranetin (SAK) is a flavanone with antiparasitic, anti-inflammatory, antimutagenic, antiallergic, and antioxidant activity."( Sakuranetin exerts anticonvulsant effect in bicuculline-induced seizures.
Beserra-Filho, JIA; Cardoso, GN; da Silva, RH; Dos Santos, JR; Lago, JHG; Prado, CM; Ribeiro, AM; Sarno, TA; Silva, SP; Silva-Freitas, FR; Silva-Martins, S; Soares-Silva, B; Ueno, AK; Vicente-Silva, W, 2022
)
2.89
"Sakuranetin is an antifungal phytoalexin derived from the antibacterial precursor, naringenin, via catalysis of naringenin-"( Sakuranetin protects rice from brown planthopper attack by depleting its beneficial endosymbionts.
Baldwin, IT; Bing, X; Chen, Y; Gershenzon, J; Hong, G; Jing, X; Li, H; Li, R; Liu, M; Lou, Y, 2023
)
3.07
"Sakuranetin (SAK) is a dihydroflavonoid compound extracted from plants."( Protective effect of sakuranetin in brain cells of dementia model rats.
Chen, S; He, Y; Hu, C; Li, C; Ma, Q; Wang, H; Wang, R, 2019
)
1.55
"Sakuranetin (1) is a flavanone phytoalexin that has been reported to play an important role in disease resistance in rice plants. "( Identification of Sternbin and Naringenin as Detoxified Metabolites from the Rice Flavanone Phytoalexin Sakuranetin by Pyricularia oryzae.
Hamana, K; Hasegawa, M; Horie, K; Katsumata, S; Toshima, H, 2017
)
2.11

Compound-Compound Interactions

ExcerptReferenceRelevance
" These combined results lead to the conclusion that this lipophilic compound may interact with the lipidic layers, preferentially at the lipid-air interface, to minimize the free energy, and reaches this conformation disturbing the thermodynamic, structural, mechanical, rheological, and morphological properties of the well-packed DPPC monolayer."( Sakuranetin interacting with cell membranes models: Surface chemistry combined with molecular simulation.
Amaral de Siqueira, LJ; Caseli, L; da Cruz Ramos Pires, GH; Freire, VT; Lago, JHG; Pereira, RG; Umehara, E, 2022
)
2.16
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
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.
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 (5)

ClassDescription
dihydroxyflavanoneAny hydroxyflavanone carrying two hydroxy substituents.
monomethoxyflavanoneAny methoxyflavanone that is flavanone substituted by a methoxy group.
flavonoid phytoalexinAny of a group of water-soluble phenolic derivatives containing a flavan skeleton, which possess antibiotic activity and are produced by plant tissues in response to infection.
4'-hydroxyflavanonesAny hydroxyflavanone having a hydroxy substituent located at position 4'.
(2S)-flavan-4-oneAny flavanone in which the chiral centre at position 2 has S-configuration.
[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
sakuranetin biosynthesis012
sakuranetin biosynthesis112

Protein Targets (27)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency56.23410.004023.8416100.0000AID485290
Chain A, Ferritin light chainEquus caballus (horse)Potency31.62285.623417.292931.6228AID485281
ATAD5 protein, partialHomo sapiens (human)Potency20.58780.004110.890331.5287AID504466
TDP1 proteinHomo sapiens (human)Potency21.14460.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency5.62340.180013.557439.8107AID1460
thioredoxin glutathione reductaseSchistosoma mansoniPotency50.11870.100022.9075100.0000AID485364
Smad3Homo sapiens (human)Potency22.38720.00527.809829.0929AID588855
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
glucocerebrosidaseHomo sapiens (human)Potency22.38720.01268.156944.6684AID2101
serine-protein kinase ATM isoform aHomo sapiens (human)Potency39.81070.707925.111941.2351AID485349
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency50.11870.354828.065989.1251AID504847
chromobox protein homolog 1Homo sapiens (human)Potency56.23410.006026.168889.1251AID540317
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency89.12510.425612.059128.1838AID504891
DNA polymerase eta isoform 1Homo sapiens (human)Potency15.84890.100028.9256213.3130AID588591
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency12.58930.00798.23321,122.0200AID2551
gemininHomo sapiens (human)Potency29.09290.004611.374133.4983AID624296
TAR DNA-binding protein 43Homo sapiens (human)Potency12.58931.778316.208135.4813AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A3Homo sapiens (human)Ki3.40000.00000.930610.0000AID34709; AID34885
Chain A, (3R)-hydroxymyristoyl-acyl carrier protein dehydrataseHelicobacter pyloriKi0.90000.90009.500014.9000AID977610
Chain B, (3R)-hydroxymyristoyl-acyl carrier protein dehydrataseHelicobacter pyloriKi0.90000.90009.500014.9000AID977610
Chain A, (3R)-hydroxymyristoyl-acyl carrier protein dehydrataseHelicobacter pyloriKi0.90000.90009.500014.9000AID977610
Chain B, (3R)-hydroxymyristoyl-acyl carrier protein dehydrataseHelicobacter pyloriKi0.90000.90009.500014.9000AID977610
Chain A, (3R)-hydroxymyristoyl-acyl carrier protein dehydrataseHelicobacter pyloriKi0.90000.90009.500014.9000AID977610
Chain B, (3R)-hydroxymyristoyl-acyl carrier protein dehydrataseHelicobacter pyloriKi0.90000.90009.500014.9000AID977610
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)19.55000.00103.39119.6000AID633943
Taste receptor type 2 member 31Homo sapiens (human)IC50 (µMol)3.60003.60003.60003.6000AID663967
Sialidase-2Homo sapiens (human)IC50 (µMol)890.00003.90006.73337.8000AID466938
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
inflammatory responseAdenosine receptor A3Homo sapiens (human)
signal transductionAdenosine receptor A3Homo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A3Homo sapiens (human)
regulation of heart contractionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A3Homo sapiens (human)
response to woundingAdenosine receptor A3Homo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell migrationAdenosine receptor A3Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activityAdenosine receptor A3Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A3Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A3Homo sapiens (human)
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of bitter tasteTaste receptor type 2 member 31Homo sapiens (human)
G protein-coupled receptor signaling pathwayTaste receptor type 2 member 31Homo sapiens (human)
glycoprotein catabolic processSialidase-2Homo sapiens (human)
ganglioside catabolic processSialidase-2Homo sapiens (human)
oligosaccharide catabolic processSialidase-2Homo sapiens (human)
glycosphingolipid catabolic processSialidase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A3Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
G protein-coupled receptor activityTaste receptor type 2 member 31Homo sapiens (human)
bitter taste receptor activityTaste receptor type 2 member 31Homo sapiens (human)
exo-alpha-sialidase activitySialidase-2Homo sapiens (human)
protein bindingSialidase-2Homo sapiens (human)
exo-alpha-(2->3)-sialidase activitySialidase-2Homo sapiens (human)
exo-alpha-(2->6)-sialidase activitySialidase-2Homo sapiens (human)
exo-alpha-(2->8)-sialidase activitySialidase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A3Homo sapiens (human)
presynaptic membraneAdenosine receptor A3Homo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A3Homo sapiens (human)
dendriteAdenosine receptor A3Homo sapiens (human)
plasma membraneAdenosine receptor A3Homo sapiens (human)
synapseAdenosine receptor A3Homo sapiens (human)
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
plasma membraneTaste receptor type 2 member 31Homo sapiens (human)
membraneTaste receptor type 2 member 31Homo sapiens (human)
membraneTaste receptor type 2 member 31Homo sapiens (human)
cytosolSialidase-2Homo sapiens (human)
catalytic complexSialidase-2Homo sapiens (human)
lysosomeSialidase-2Homo sapiens (human)
membraneSialidase-2Homo sapiens (human)
cytoplasmSialidase-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (62)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID33150Ability to displace [3H]-CGS- 21680 binding from adenosine A2A receptor.1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID30342Ability to displace [3H]N6-phenylisopropyladenosine binding from adenosine A1 receptor.1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID32357Displacement of specific [3H]PIA binding from adenosine A1 receptor in rat brain membranes.1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
Interactions of flavonoids and other phytochemicals with adenosine receptors.
AID33570Binding affinity at Adenosine A2 receptor in rat striatal membranes by [3H]-CGS- 21680 displacement.1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID231110Ratio of binding affinities between rA1 and rA3 of rat striatal membrane.1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID1434690Inhibition of sucrose loaded POPC/POPE/POPS/PtdIns(3,4,5)P3 (59:20:20:1) liposome binding to eGFP-fused PDK1 PH domain (unknown origin) expressed in Escherichia coli BL21 at 20 uM after 10 mins by fluorescence spectrophotometry based pull down assay relat2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Inhibitory potential of flavonoids on PtdIns(3,4,5)P3 binding with the phosphoinositide-dependent kinase 1 pleckstrin homology domain.
AID33936Affinity at Adenosine A2A receptor in rat striatal membranes by [3H]- CGS 21680 displacement.1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
Interactions of flavonoids and other phytochemicals with adenosine receptors.
AID34709Binding affinity against human adenosine A3 receptor in HEK293 cells using [125I]AB-MECA 21680 radioligand.1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID404008Cytotoxicity against human KB cells
AID353303Increase in EGR1 mRNA expression in human HEK293 cells at 20 ug/mL after 6 to 12 hrs by dual-glo luciferase assay relative to control2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.
AID32023Binding affinity at Adenosine A1 receptor in rat brain membranes by [3H]PIA displacement.1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID34885Displacement of [125I]AB-MECA binding to human Adenosine A3 receptor expressed in HEK293 cells1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
Interactions of flavonoids and other phytochemicals with adenosine receptors.
AID33195Ability to displace [125I]-AB-MECA binding from adenosine A3 receptor.1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID333447Antifungal activity against Cladosporium sphaerospermum assessed as minimum concentration required to inhibit growth after 72 hrs by TLC2004Journal of natural products, Nov, Volume: 67, Issue:11
Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum.
AID696744Inhibition of p-glycoprotein in human LoVo/DX cells assessed accumulation of rhodamine 123 at 20 to 100 uM after 60 mins by fluorescence assay2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID466939Selectivity for Trypanosoma cruzi trans-sialidase mutant over human Neu22010Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4
Potent inhibitor scaffold against Trypanosoma cruzi trans-sialidase.
AID696726Induction of apoptosis in human drug-sensitive LoVo/DX cells assessed as apoptotic cells at 100 uM after 48 hrs by annexin-V and propidium iodide staining based flow cytometry (Rvb = 6.16 +/- 1.67%)2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID332924Molluscicidal activity against Biomphalaria glabrata assessed as mortality after 24 hrs by microscopy1994Journal of natural products, Jan, Volume: 57, Issue:1
Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
AID466938Inhibition of human Neu2 assessed as MuNANA substrate hydrolysis in presence of 0.1% Triton X-100 by discontinuous fluorimetric assay2010Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4
Potent inhibitor scaffold against Trypanosoma cruzi trans-sialidase.
AID338974Inhibition of cow milk xanthine oxidase at 50 ug/mL
AID663967Inhibition of human TAS2R31 receptor expressed in HEK293T cells overexpressing chimeric G-protein alpha-subunit2011Journal of natural products, Jun-24, Volume: 74, Issue:6
The relevance of higher plants in lead compound discovery programs.
AID663892Adipogenic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 3 uM after 8 days relative to control2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.
AID633944Inhibition of iNOS-mediated NO production in LPS-stimulated mouse RAW264.7 cells after 24 hrs by Griess reagent method relative to control2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
AID332922Antibacterial activity against Micrococcus luteus ATCC 9341 by bioautographic assay1994Journal of natural products, Jan, Volume: 57, Issue:1
Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
AID696730Induction of apoptosis in human drug-sensitive LoVo cells assessed as necrotic cells at 100 uM after 48 hrs by annexin-V and propidium iodide staining based flow cytometry (Rvb = 10.44 +/- 3.23%)2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID696745Cytotoxicity against human drug-resistant LoVo/DX cells after 72 hrs by SRB assay2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID633946Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability after 3 hrs by alamar blue assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
AID332921Antibacterial activity against Bacillus subtilis ATCC 6633 by bioautographic assay1994Journal of natural products, Jan, Volume: 57, Issue:1
Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
AID663894Adipogenic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 30 uM after 8 days relative to control2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.
AID333446Antifungal activity against Cladosporium cladosporioides assessed as minimum concentration required to inhibit growth after 72 hrs by TLC2004Journal of natural products, Nov, Volume: 67, Issue:11
Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum.
AID1754175Antiinflammatory activity in mouse RAW264.7 assessed as inhibition of LPS-induced NO production preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by Griess reagent based assay2021Journal of natural products, 05-28, Volume: 84, Issue:5
Tulipiferamide A, an Alkamide from
AID405575Antitubercular activity against Mycobacterium tuberculosis H37Rv after 2 weeks by agar dilution method2008Journal of natural products, Jun, Volume: 71, Issue:6
Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica.
AID1754176Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability at 20 uM preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by MTT assay2021Journal of natural products, 05-28, Volume: 84, Issue:5
Tulipiferamide A, an Alkamide from
AID696722Induction of apoptosis in human drug-sensitive LoVo/DX cells assessed as necrotic cells at 100 uM after 48 hrs by annexin-V and propidium iodide staining based flow cytometry (Rvb = 9.57 +/- 2.83%)2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID466937Inhibition of Trypanosoma cruzi trans-sialidase containing catalytic domain (N58F, R200K) and lectin-like domain (S495 K, V496G, E520K, D593G, I597D, H599R) mutation expressed in Escherichia coli JM109 assessed as MuNANA substrate hydrolysis in presence o2010Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4
Potent inhibitor scaffold against Trypanosoma cruzi trans-sialidase.
AID1634796Inhibition of Saccharomyces cerevisiae alpha-glucosidase type-1 pre-incubated for 10 mins before pNPG substrate addition assessed as reduction in p-nitrophenol release2016Journal of natural products, Apr-22, Volume: 79, Issue:4
Identification of PTP1B and α-Glucosidase Inhibitory Serrulatanes from Eremophila spp. by Combined use of Dual High-Resolution PTP1B and α-Glucosidase Inhibition Profiling and HPLC-HRMS-SPE-NMR.
AID663893Adipogenic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 10 uM after 8 days relative to control2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.
AID696734Induction of apoptosis in human drug-sensitive LoVo cells assessed as apoptotic cells at 100 uM after 48 hrs by annexin-V and propidium iodide staining based flow cytometry (Rvb = 6.68 +/- 1.77%)2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID399170Trypanocidal activity against Trypanosoma cruzi Y strain trypomastigotes infected in Swiss albino mouse blood assessed as reduction of parasitemia at 500 ug/mL after 24 hrs relative to control1997Journal of natural products, Aug, Volume: 60, Issue:8
Trypanocidal flavonoids from Trixis vauthieri.
AID633943Inhibition of iNOS-mediated NO production in LPS-stimulated mouse RAW264.7 cells after 24 hrs by Griess reagent method2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
AID1754177Inhibition of LPS-indued NF-kappaB activation in mouse RAW264.7 cells preincubated for 30 mins followed by LPS stimulation and measured after 10 hrs by luciferase assay2021Journal of natural products, 05-28, Volume: 84, Issue:5
Tulipiferamide A, an Alkamide from
AID696746Cytotoxicity against human drug-sensitive LoVo cells after 72 hrs by SRB assay2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.
AID332923Antibacterial activity against Escherichia coli ATCC 25922 by bioautographic assay1994Journal of natural products, Jan, Volume: 57, Issue:1
Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
AID334444Chemopreventive activity in Syrian hamster embryo cells assessed as inhibition of metabolism of [3H]benzo(a)pyrene to water-soluble metabolites after 24 hrs at 20 ug/ml relative to control1992Journal of natural products, Mar, Volume: 55, Issue:3
Isolation of potential cancer chemopreventive agents from Eriodictyon californicum.
AID332920Cytotoxicity against human KB cells after 72 hrs1994Journal of natural products, Jan, Volume: 57, Issue:1
Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
AID1345822Human A3 receptor (Adenosine receptors)1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID1345618Human A2A receptor (Adenosine receptors)1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID1345630Rat A1 receptor (Adenosine receptors)1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2008Protein science : a publication of the Protein Society, Nov, Volume: 17, Issue:11
Three flavonoids targeting the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: crystal structure characterization with enzymatic inhibition assay.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (75)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's8 (10.67)18.2507
2000's17 (22.67)29.6817
2010's36 (48.00)24.3611
2020's14 (18.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.78

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 Index31.78 (24.57)
Research Supply Index4.23 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index42.09 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews3 (4.41%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
Other65 (95.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]