Page last updated: 2024-11-11

drupanin

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Description

Drupanin: anti-oxidant and anti-cancer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6440361
CHEMBL ID464997
SCHEMBL ID3680290
MeSH IDM000604667

Synonyms (16)

Synonym
(e)-3-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-2-propenoic acid
CHEMBL464997
drupanin
(e)-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
53755-58-1
2-propenoic acid, 3-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-, (2e)-
bdbm50362837
SCHEMBL3680290
(e)-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)acrylic acid
4-hydroxy-3-prenylcinnamic acid
MS-23328
2-propenoic acid, 3-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-, (2e)-
(2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
HY-N10361
DTXSID301318722
CS-0434414
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B10Homo sapiens (human)IC50 (µMol)49.00000.00101.94459.6000AID641086
Aldo-keto reductase family 1 member B1Homo sapiens (human)IC50 (µMol)38.00000.00101.191310.0000AID641085
Aldo-keto reductase family 1 member C3Homo sapiens (human)IC50 (µMol)15.28300.05002.207010.0000AID1630031; AID1645794; AID664542
Aldo-keto reductase family 1 member C2 Homo sapiens (human)IC50 (µMol)113.63100.37004.09519.2800AID1630032; AID1645793; AID664541
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
retinoid metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
farnesol catabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B10Homo sapiens (human)
cellular detoxification of aldehydeAldo-keto reductase family 1 member B10Homo sapiens (human)
retinoid metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
epithelial cell maturationAldo-keto reductase family 1 member B1Homo sapiens (human)
renal water homeostasisAldo-keto reductase family 1 member B1Homo sapiens (human)
carbohydrate metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
C21-steroid hormone biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
L-ascorbic acid biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
regulation of urine volumeAldo-keto reductase family 1 member B1Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
negative regulation of apoptotic processAldo-keto reductase family 1 member B1Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
fructose biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
cellular hyperosmotic salinity responseAldo-keto reductase family 1 member B1Homo sapiens (human)
metanephric collecting duct developmentAldo-keto reductase family 1 member B1Homo sapiens (human)
retinoid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
G protein-coupled receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
response to nutrientAldo-keto reductase family 1 member C3Homo sapiens (human)
steroid metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of cell population proliferationAldo-keto reductase family 1 member C3Homo sapiens (human)
male gonad developmentAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to starvationAldo-keto reductase family 1 member C3Homo sapiens (human)
farnesol catabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
cyclooxygenase pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
keratinocyte differentiationAldo-keto reductase family 1 member C3Homo sapiens (human)
progesterone metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
retinal metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
macromolecule metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of retinoic acid receptor signaling pathwayAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
renal absorptionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to calcium ionAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to corticosteroid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to jasmonic acid stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
cellular response to prostaglandin D stimulusAldo-keto reductase family 1 member C3Homo sapiens (human)
negative regulation of retinoic acid biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
regulation of testosterone biosynthetic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of endothelial cell apoptotic processAldo-keto reductase family 1 member C3Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
G protein-coupled receptor signaling pathwayAldo-keto reductase family 1 member C2 Homo sapiens (human)
digestionAldo-keto reductase family 1 member C2 Homo sapiens (human)
steroid metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
positive regulation of cell population proliferationAldo-keto reductase family 1 member C2 Homo sapiens (human)
epithelial cell differentiationAldo-keto reductase family 1 member C2 Homo sapiens (human)
progesterone metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member C2 Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionAldo-keto reductase family 1 member C2 Homo sapiens (human)
cellular response to jasmonic acid stimulusAldo-keto reductase family 1 member C2 Homo sapiens (human)
cellular response to prostaglandin D stimulusAldo-keto reductase family 1 member C2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (33)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
aldo-keto reductase (NADPH) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B10Homo sapiens (human)
alcohol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
geranylgeranyl reductase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
indanol dehydrogenase activityAldo-keto reductase family 1 member B10Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B10Homo sapiens (human)
retinal dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B1Homo sapiens (human)
electron transfer activityAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glyceraldehyde oxidoreductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
L-glucuronate reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glycerol dehydrogenase [NADP+] activityAldo-keto reductase family 1 member B1Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
retinal dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
aldo-keto reductase (NADPH) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
oxidoreductase activity, acting on NAD(P)H, quinone or similar compound as acceptorAldo-keto reductase family 1 member C3Homo sapiens (human)
phenanthrene 9,10-monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
dihydrotestosterone 17-beta-dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin D2 11-ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
geranylgeranyl reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketoreductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
prostaglandin-F synthase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
15-hydroxyprostaglandin-D dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androsterone dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
5alpha-androstane-3beta,17beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone dehydrogenase (NAD+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
androstan-3-alpha,17-beta-diol dehydrogenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
ketosteroid monooxygenase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
Delta4-3-oxosteroid 5beta-reductase activityAldo-keto reductase family 1 member C3Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member C3Homo sapiens (human)
bile acid bindingAldo-keto reductase family 1 member C3Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
oxidoreductase activity, acting on NAD(P)H, quinone or similar compound as acceptorAldo-keto reductase family 1 member C2 Homo sapiens (human)
phenanthrene 9,10-monooxygenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
carboxylic acid bindingAldo-keto reductase family 1 member C2 Homo sapiens (human)
bile acid bindingAldo-keto reductase family 1 member C2 Homo sapiens (human)
androstan-3-alpha,17-beta-diol dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
ketosteroid monooxygenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
indanol dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
androsterone dehydrogenase activityAldo-keto reductase family 1 member C2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
extracellular regionAldo-keto reductase family 1 member B10Homo sapiens (human)
lysosomeAldo-keto reductase family 1 member B10Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B10Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B10Homo sapiens (human)
mitochondrionAldo-keto reductase family 1 member B10Homo sapiens (human)
extracellular spaceAldo-keto reductase family 1 member B1Homo sapiens (human)
nucleoplasmAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
nucleusAldo-keto reductase family 1 member C3Homo sapiens (human)
cytoplasmAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C3Homo sapiens (human)
cytosolAldo-keto reductase family 1 member C2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID1752495Antiproliferative activity against human MDA-MB-231 cells assessed as cell viability for 72 hrs by MTT assay2021Bioorganic & medicinal chemistry, 10-01, Volume: 47Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.
AID1630032Inhibition of recombinant AKR1C2 (unknown origin) assessed as reduction in S-tetralol catalyzed oxidation in presence of NADPH by fluorescence assay2016ACS medicinal chemistry letters, Aug-11, Volume: 7, Issue:8
Selective AKR1C3 Inhibitors Potentiate Chemotherapeutic Activity in Multiple Acute Myeloid Leukemia (AML) Cell Lines.
AID614376Cytotoxicity against human HCT116 cells assessed as cell viability under hypoxic condition at 200 uM after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID1752499Antiproliferative activity against human PC-3 cells assessed as cell viability for 72 hrs by MTT assay2021Bioorganic & medicinal chemistry, 10-01, Volume: 47Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.
AID641086Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis2012European journal of medicinal chemistry, Feb, Volume: 48Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID614392Inhibition of HIF1-dependent HK2 mRNA expression in human HCT116 cells under hypoxic condition at 50 uM after 24 hrs by RT-PCR analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID664541Inhibition of human recombinant AKR1C2 expressed in Escherichia coli using S-tetralol as substrate by fluorometry2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
AID377981Antimutagenic activity in Salmonella Typhimurium TA100 assessed as inhibition of ethyl methanesulfonate-induced mutation at 15.6 ug/mL treated for 30 mins and measured after 2 days by modified Ames test1999Journal of natural products, Jan, Volume: 62, Issue:1
Structure-antimutagenic activity relationship study of plicatin B.
AID664561Cytotoxicity against human MCF7 cells at <100 uM after 6 hrs by MTT assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
AID1645793Inhibition of recombinant human AKR1C2 expressed in Escherichia coli BL21 (D3) using S-tetralol as substrate in presence of NADP+ by UV-spectrophotometric method2019Journal of medicinal chemistry, 04-11, Volume: 62, Issue:7
Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.
AID614378Modulation of HIF1 expressed in HEK293 cells assessed as luciferase activity under hypoxic condition at 50 uM after 24 hrs by luminometer analysis relative to hypoxic control2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID377975Antimutagenic activity in Salmonella Typhimurium TA100 assessed as inhibition of ethyl methanesulfonate-induced mutation at 3.9 uM treated for 30 mins and measured after 2 days by modified Ames test1999Journal of natural products, Jan, Volume: 62, Issue:1
Structure-antimutagenic activity relationship study of plicatin B.
AID402401Growth inhibition of last instar larvae of Tenebrio molitor assessed as duration of pupal stage at 120 ug/larvae, applied topically measured every 24 hrs for 30 days1998Journal of natural products, Oct, Volume: 61, Issue:10
Growth-inhibitory activities of benzofuran and chromene derivatives toward Tenebrio molitor.
AID614393Inhibition of HIF1-dependent VEGFA mRNA expression in human HCT116 cells under hypoxic condition at 50 uM after 24 hrs by RT-PCR analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID614381Cytotoxicity against human HCT116 cells assessed as cell viability under normoxic condition at 200 uM after 7 days by clonogenic assay2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID614390Inhibition of HIF1alpha expression in human HCT116 cells under hypoxic condition after 4 hrs by immunoblotting2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID1630033Selectivity ratio of IC50 for recombinant AKR1C2 (unknown origin) to IC50 for recombinant AKR1C3 (unknown origin)2016ACS medicinal chemistry letters, Aug-11, Volume: 7, Issue:8
Selective AKR1C3 Inhibitors Potentiate Chemotherapeutic Activity in Multiple Acute Myeloid Leukemia (AML) Cell Lines.
AID1645792Selectivity ratio of IC50 for recombinant human AKR1C2 expressed in Escherichia coli BL21 (D3) to IC50 for recombinant human AKR1C3 expressed in Escherichia coli BL21 (D3)2019Journal of medicinal chemistry, 04-11, Volume: 62, Issue:7
Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.
AID1630098Inhibition of AKR1C3 in human HL60 cells assessed as potentiation of etoposide-induced cytotoxicity by measuring reduction in cell viability at 0.1 to 10 uM coincubated with 1 uM etoposide after 72 hrs by MTS assay2016ACS medicinal chemistry letters, Aug-11, Volume: 7, Issue:8
Selective AKR1C3 Inhibitors Potentiate Chemotherapeutic Activity in Multiple Acute Myeloid Leukemia (AML) Cell Lines.
AID664542Inhibition of human recombinant AKR1C3 expressed in Escherichia coli JM109 cells using S-tetralol as substrate by fluorometry2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
AID1752503Cytotoxicity against human PNT2 cells assessed as cell viability for 72 hrs by MTT assay2021Bioorganic & medicinal chemistry, 10-01, Volume: 47Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.
AID1752500Antiproliferative activity against human DU-145 cells assessed as cell viability for 72 hrs by MTT assay2021Bioorganic & medicinal chemistry, 10-01, Volume: 47Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.
AID614388Modulation of HIF1 expressed in HEK293 cells assessed as luciferase activity under hypoxic condition after 24 hrs by luminometer analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID664547Inhibition of human recombinant GST-tagged AKR1C4 expressed in Escherichia coli using S-tetralol as substrate at 100 uM by fluorometry2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
AID402400Growth inhibition of last instar larvae of Tenebrio molitor assessed as successful pupation at 120 ug/larvae, applied topically measured every 24 hrs for 30 days1998Journal of natural products, Oct, Volume: 61, Issue:10
Growth-inhibitory activities of benzofuran and chromene derivatives toward Tenebrio molitor.
AID614438Antiangiogenic activity in 3-day-old embryonated chicken eggs at 300 ng/CAM measured on 7th embryonic day by CAM assay2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID614391Inhibition of HIF1-dependent GLUT1 mRNA expression in human HCT116 cells under hypoxic condition at 50 uM after 24 hrs by RT-PCR analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID614380Cytotoxicity against human HCT116 cells assessed as cell viability under hypoxic condition at 200 uM after 7 days by clonogenic assay2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID1752498Cytotoxicity against human MCF-10A cells assessed as cell viability for 72 hrs by MTT assay2021Bioorganic & medicinal chemistry, 10-01, Volume: 47Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.
AID377976Antimutagenic activity in Salmonella Typhimurium TA100 assessed as inhibition of ethyl methanesulfonate-induced mutation at 7.8 uM treated for 30 mins and measured after 2 days by modified Ames test1999Journal of natural products, Jan, Volume: 62, Issue:1
Structure-antimutagenic activity relationship study of plicatin B.
AID664544Inhibition of human recombinant GST-tagged AKR1C1 expressed in Escherichia coli using S-tetralol as substrate at 100 uM by fluorometry2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
AID614379Cytotoxicity against human HCT116 cells assessed as cell viability under normoxic condition at 200 uM after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
AID664563Inhibition of AKR1C3-mediated [14C]farnesal metabolism in human MCF7 cells at 100 uM incubated for 2 hrs prior to substrate addition measured after 6 hrs2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.
AID641085Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis2012European journal of medicinal chemistry, Feb, Volume: 48Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.
AID1630031Inhibition of recombinant AKR1C3 (unknown origin) assessed as reduction in S-tetralol catalyzed oxidation in presence of NADPH by fluorescence assay2016ACS medicinal chemistry letters, Aug-11, Volume: 7, Issue:8
Selective AKR1C3 Inhibitors Potentiate Chemotherapeutic Activity in Multiple Acute Myeloid Leukemia (AML) Cell Lines.
AID456268Antiallergic activity in Ca(2+)-stimulated differentiated human HeLa cells assessed as inhibition of cys-leukotriene release after 6 days by ELISA2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes.
AID1752494Antiproliferative activity against human MCF7 cells assessed as cell viability for 72 hrs by MTT assay2021Bioorganic & medicinal chemistry, 10-01, Volume: 47Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.
AID1645794Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 (D3) using S-tetralol as substrate in presence of NADP+ by UV-spectrophotometric method2019Journal of medicinal chemistry, 04-11, Volume: 62, Issue:7
Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (16.67)18.2507
2000's0 (0.00)29.6817
2010's8 (66.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.10

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 Index22.10 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.44 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.10)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]