Page last updated: 2024-12-08

1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone

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

1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone is a synthetic compound with the chemical formula C16H21NO3. It is a **potent and selective inhibitor of monoamine oxidase A (MAO-A)**.

Here's why it's important for research:

* **MAO-A Inhibition:** MAO-A is an enzyme that breaks down neurotransmitters like serotonin, norepinephrine, and dopamine. Inhibiting MAO-A increases the levels of these neurotransmitters in the brain, which can be beneficial in treating conditions like depression, anxiety, and Parkinson's disease.
* **Potential Therapeutic Applications:** This compound's selective MAO-A inhibition makes it a promising lead compound for developing new drugs for these conditions.
* **Research Tool:** Researchers use 1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone as a tool to study the role of MAO-A in various biological processes.
* **Understanding Neurotransmission:** Research with this compound contributes to our understanding of how neurotransmitters are regulated and how this regulation impacts brain function.

**It's important to note:** This compound is not a drug and is currently only used for research purposes. Further research is needed to evaluate its safety and efficacy in humans before it can be considered for therapeutic use.

**Here are some additional points to consider:**

* The compound's structure and activity can be further modified to improve its properties like selectivity, potency, and pharmacokinetic profile.
* Research is ongoing to investigate the potential side effects and long-term consequences of inhibiting MAO-A.

Overall, 1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone is a valuable research tool with potential therapeutic applications in the treatment of neuropsychiatric disorders.

Cross-References

ID SourceID
PubMed CID147354
CHEMBL ID1606959
CHEBI ID123280

Synonyms (36)

Synonym
smr000140746
1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone
MLS000533308 ,
OPREA1_513022
OPREA1_140269
3',4'-(methylenedioxy)-3-piperidinopropiophenone
propiophenone, 3',4'-(methylenedioxy)-3-piperidino-
safrole ii
brn 0259941
1-propanone, 1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-
3-piperidino-1-(3,4-methylenedioxyphenyl)-1-propanone
CHEBI:123280
safrol ii
1-(1,3-benzodioxol-5-yl)-3-piperidin-1-ylpropan-1-one
NCGC00245608-01
30418-51-0
5-20-03-00462 (beilstein handbook reference)
HMS2170I18
CHEMBL1606959
HMS3316J15
AKOS022134367
STL329150
1-(1,3-benzodioxol-5-yl)-3-(piperidin-1-yl)propan-1-one
AB00096990-01
propan-1-one, 1-(benzo[d]1,3-dioxolan-5-yl)-3-(4-piperidyl)-
1-(1,3-benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone #
DJXZMJWCDITTEO-UHFFFAOYSA-N
cambridge id 5789934
bdbm89881
cid_147354
1-(1,3-benzodioxol-5-yl)-3-piperidino-propan-1-one
1-(1,3-benzodioxol-5-yl)-3-piperidin-1-yl-propan-1-one
Q27212986
DTXSID50184506
SR-01000219861-1
sr-01000219861
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzodioxoles
[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]

Protein Targets (22)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nrf2Homo sapiens (human)Potency25.11890.09208.222223.1093AID624171
thioredoxin reductaseRattus norvegicus (Norway rat)Potency0.31620.100020.879379.4328AID588453
WRNHomo sapiens (human)Potency50.11870.168331.2583100.0000AID651768
phosphopantetheinyl transferaseBacillus subtilisPotency56.23410.141337.9142100.0000AID1490
TDP1 proteinHomo sapiens (human)Potency8.81520.000811.382244.6684AID686978; AID686979
thioredoxin glutathione reductaseSchistosoma mansoniPotency0.28180.100022.9075100.0000AID485364
Smad3Homo sapiens (human)Potency11.22020.00527.809829.0929AID588855
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency0.02510.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency44.66840.531815.435837.6858AID504845
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency7.94330.035520.977089.1251AID504332
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency44.66840.016525.307841.3999AID602332
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency35.48130.001815.663839.8107AID894
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency44.66840.354828.065989.1251AID504847
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency21.19230.168316.404067.0158AID720504
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency7.87580.00798.23321,122.0200AID2546; AID2551
gemininHomo sapiens (human)Potency31.62280.004611.374133.4983AID624296
VprHuman immunodeficiency virus 1Potency7.94331.584919.626463.0957AID651644
Glycoprotein hormones alpha chainHomo sapiens (human)Potency5.62344.46688.344810.0000AID624291
[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)
corticotropin-releasing hormone receptor 2Homo sapiens (human)IC50 (µMol)47.10000.36807.095518.0000AID602180
corticotropin releasing factor-binding proteinHomo sapiens (human)IC50 (µMol)47.10000.36807.095518.0000AID602180
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)100.00000.00002.37899.7700AID718839
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)3.43000.00001.89149.5700AID718838
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
corticotropin-releasing hormone receptor 2Homo sapiens (human)EC50 (µMol)53.00001.120011.561736.8000AID602473
corticotropin releasing factor-binding proteinHomo sapiens (human)EC50 (µMol)53.00001.120011.561736.8000AID602473
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (29)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

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.
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.
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.
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
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
AID718839Inhibition of MAO-A assessed as inhibition of kyneuramine conversion to 4-hydroxyquinoline after 20 mins by fluorescence assay2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease.
AID718838Inhibition of MAO-B assessed as inhibition of kyneuramine conversion to 4-hydroxyquinoline after 20 mins by fluorescence assay2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Inhibition of monoamine oxidase by derivatives of piperine, an alkaloid from the pepper plant Piper nigrum, for possible use in Parkinson's disease.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (11.11)29.6817
2010's6 (66.67)24.3611
2020's2 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.14

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.14 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.14)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]