Compounds > 3',4'-dimethoxy-alpha-naphthoflavone
Page last updated: 2024-09-27

3',4'-dimethoxy-alpha-naphthoflavone

Description

3',4'-dimethoxy-alpha-naphthoflavone: activated Ah receptor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID276138
CHEMBL ID2420083
SCHEMBL ID4650074
MeSH IDM0556867

Synonyms (24)

Synonym
EU-0082241
nsc123391
14756-24-2
nsc-123391
2-(3,4-dimethoxyphenyl)-4h-benzo[h]chromen-4-one
2-(3,4-dimethoxyphenyl)benzo[h]chromen-4-one
AKOS001683486
CCG-23502
3',4'-dimethoxy-alpha-naphthoflavone
dimnf
4h-naphtho[1,2-b]pyran-4-one, 2-(3,4-dimethoxyphenyl)-
chembl2420083 ,
bdbm50439845
SCHEMBL4650074
DTXSID5058690
2-(3,4-dimethoxyphenyl)-4h-naphtho[1,2-b]pyran-4-one
3',4'-dimethoxy-.alpha.-naphthoflavone
QDZQDIUUJDAORK-UHFFFAOYSA-N
dimnf, >=98% (hplc)
3',4'-dimethoxy-|a-naphthoflavone
MS-25000
CS-0025313
HY-103222
E98636

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATP-dependent translocase ABCB1Homo sapiens (human)IC50 (µMol)4.00000.00022.318510.0000AID768684
Aryl hydrocarbon receptorMus musculus (house mouse)IC50 (µMol)0.02100.02100.02300.0250AID1527834
Multidrug resistance-associated protein 1 Homo sapiens (human)IC50 (µMol)1.76000.00153.71109.6600AID768683
Broad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)IC50 (µMol)1.18000.00401.966610.0000AID768689; AID768691
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
G2/M transition of mitotic cell cycleATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic metabolic processATP-dependent translocase ABCB1Homo sapiens (human)
response to xenobiotic stimulusATP-dependent translocase ABCB1Homo sapiens (human)
phospholipid translocationATP-dependent translocase ABCB1Homo sapiens (human)
terpenoid transportATP-dependent translocase ABCB1Homo sapiens (human)
regulation of response to osmotic stressATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
transepithelial transportATP-dependent translocase ABCB1Homo sapiens (human)
stem cell proliferationATP-dependent translocase ABCB1Homo sapiens (human)
ceramide translocationATP-dependent translocase ABCB1Homo sapiens (human)
export across plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
positive regulation of anion channel activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
regulation of chloride transportATP-dependent translocase ABCB1Homo sapiens (human)
leukotriene metabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic metabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
response to xenobiotic stimulusMultidrug resistance-associated protein 1 Homo sapiens (human)
cobalamin transportMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid biosynthetic processMultidrug resistance-associated protein 1 Homo sapiens (human)
cellular response to oxidative stressMultidrug resistance-associated protein 1 Homo sapiens (human)
heme catabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transportMultidrug resistance-associated protein 1 Homo sapiens (human)
phospholipid translocationMultidrug resistance-associated protein 1 Homo sapiens (human)
positive regulation of inflammatory responseMultidrug resistance-associated protein 1 Homo sapiens (human)
transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
cell chemotaxisMultidrug resistance-associated protein 1 Homo sapiens (human)
transepithelial transportMultidrug resistance-associated protein 1 Homo sapiens (human)
cyclic nucleotide transportMultidrug resistance-associated protein 1 Homo sapiens (human)
leukotriene transportMultidrug resistance-associated protein 1 Homo sapiens (human)
monoatomic anion transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid translocationMultidrug resistance-associated protein 1 Homo sapiens (human)
export across plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
transport across blood-brain barrierMultidrug resistance-associated protein 1 Homo sapiens (human)
cellular response to amyloid-betaMultidrug resistance-associated protein 1 Homo sapiens (human)
carboxylic acid transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transport across blood-brain barrierMultidrug resistance-associated protein 1 Homo sapiens (human)
glutathione transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
lipid transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid biosynthetic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate metabolic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transmembrane transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transepithelial transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
renal urate salt excretionBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
export across plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
cellular detoxificationBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (27)

Processvia Protein(s)Taxonomy
protein bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingATP-dependent translocase ABCB1Homo sapiens (human)
ABC-type xenobiotic transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
efflux transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP hydrolysis activityATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ubiquitin protein ligase bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylcholine floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylethanolamine flippase activityATP-dependent translocase ABCB1Homo sapiens (human)
ceramide floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type vitamin B12 transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
efflux transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATP hydrolysis activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled lipid transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
glutathione transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
carboxylic acid transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type xenobiotic transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ABC-type xenobiotic transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
efflux transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP hydrolysis activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATPase-coupled transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
identical protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
protein homodimerization activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
cytoplasmATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
cell surfaceATP-dependent translocase ABCB1Homo sapiens (human)
membraneATP-dependent translocase ABCB1Homo sapiens (human)
apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
extracellular exosomeATP-dependent translocase ABCB1Homo sapiens (human)
external side of apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
basal plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
apical plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
lateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
extracellular exosomeMultidrug resistance-associated protein 1 Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
nucleoplasmBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
brush border membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
mitochondrial membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
membrane raftBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
external side of apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID768691Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Hoechst 33342 preincubated for 30 mins before Hoechst 33342 addition measured after 120 mins by fluorescence assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID768684Inhibition of p-glycoprotein (unknown origin) expressed in human A2780Adr cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1527834Displacement of 2-azido-3-[125I]7,8-dibromodibenzo-pdioxin from C57BL/6J mouse liver AhR incubated for 20 mins by gamma counting based autoradiography2020European journal of medicinal chemistry, Jan-01, Volume: 185Targeting Aryl hydrocarbon receptor for next-generation immunotherapies: Selective modulators (SAhRMs) versus rapidly metabolized ligands (RMAhRLs).
AID768683Inhibition of MRP1 (unknown origin) expressed in human 2008 cells assessed as calcein-AM accumulation preincubated for 30 mins before calcein-AM addition measured up to 90 mins by fluorescence assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1437049Inhibition of porcine cholesterol esterase at 10 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1437050Inhibition of porcine cholesterol esterase at 25 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1437047Inhibition of porcine cholesterol esterase at 1 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID768689Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of pheophorbide-A preincubated for 30 mins before pheophorbide-A addition measured after 120 mins by flow cytometry2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1437048Inhibition of porcine cholesterol esterase at 5 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1437051Inhibition of porcine cholesterol esterase at 50 nM using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method relative to control2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
AID1437052Inhibition of porcine cholesterol esterase using para-nitrophenyl butyrate as substrate after 5 mins in presence of sodium taurocholate by spectrophotometric method2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (80.00)24.3611
2020's1 (20.00)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%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
beta-naphthoflavone[no description available]medium20extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist
3-hydroxyflavone[no description available]medium10flavonols;
monohydroxyflavone
alpha-naphthoflavone[no description available]medium40extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist;
aryl hydrocarbon receptor antagonist;
EC 1.14.14.14 (aromatase) inhibitor
3,5,7,3',4'-pentamethoxyflavone[no description available]medium10
3-methoxyflavone[no description available]medium10
cyclosporine[no description available]medium10homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite
5-hydroxy-3,3',4',7-tetramethoxyflavone[no description available]medium103'-methoxyflavones;
monohydroxyflavone;
tetramethoxyflavone		plant metabolite
ko 143[no description available]medium10beta-carbolines;
tert-butyl ester
3,3'-diindolylmethane[no description available]medium10indolesantineoplastic agent;
P450 inhibitor
6-methyl-1,3,8-trichlorodibenzofuran[no description available]medium10
kynurenine[no description available]medium10amino acid zwitterion;
kynurenine;
non-proteinogenic L-alpha-amino acid		human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Acute-Phase Reaction0low10
Acute-Phase State0low10
Diseases of Immune System0low10
Immune Diseases0low10
Immune Disorders0low10
Immune System Diseases0low10
Immune System Disorders0low10
Immunologic Diseases0low10
Immunological Diseases0low10
Inflammation0low10
Innate Inflammatory Response0low10
Reaction, Acute-Phase0low10
Response, Acute-Phase0low10