Page last updated: 2024-11-08

5-bromowillardiine

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Description

5-bromowillardiine: acts as a kainate-like agonist on chick EAA receptors expressed in Xenopus oocytes; RN given refers to (S)-isomer; RN for cpd without isomeric designation not avail 5/91 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID167842
CHEMBL ID333964
SCHEMBL ID4311549
MeSH IDM0187515

Synonyms (24)

Synonym
2-amino-3-(5-bromo-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-propionic acid
BWD ,
1MY3
1MQH
DB04000
1MXU
bromo-willardiine
5-bromowillardiine
CHEMBL333964 ,
3-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-l-alanine
19772-78-2
(s)-2-amino-3-(5-bromo-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-propionic acid
bdbm50060636
(s)-2-amino-3-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)propanoic acid
(2s)-2-amino-3-(5-bromo-2,4-dioxopyrimidin-1-yl)propanoic acid
unii-qgw9m0l9sj
qgw9m0l9sj ,
1(2h)-pyrimidinepropanoic acid, alpha-amino-5-bromo-3,4-dihydro-2,4-dioxo-, (s)-
SCHEMBL4311549
(2s)-2-amino-3-(5-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanoic acid
1(2h)-pyrimidinepropanoic acid, .alpha.-amino-5-bromo-3,4-dihydro-2,4-dioxo-, (.alpha.s)-
DTXSID00941545
5-bromo-s-willardiine
Q27094857
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (11)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)0.30000.02351.69454.7600AID977608
Chain A, glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)0.30000.02351.69454.7600AID977608
Chain A, glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)0.30000.02351.69454.7600AID977608
Chain A, glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)0.30000.02351.69454.7600AID977608
Chain A, Glutamate Receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)4.00004.00004.00004.0000AID977608
Chain A, Glutamate Receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)4.00004.00004.00004.0000AID977608
Glutamate receptor 1Homo sapiens (human)Ki0.09200.01472.50379.2000AID92951
Glutamate receptor 2Homo sapiens (human)Ki0.10100.01681.27725.0000AID92962
Glutamate receptor 4Homo sapiens (human)Ki0.45700.04001.23358.8500AID93111
Glutamate receptor ionotropic, kainate 5Homo sapiens (human)Ki0.00910.00800.71552.1440AID93254
[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)
Glutamate receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)2.80000.00411.89638.7000AID391448
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
regulation of receptor recyclingGlutamate receptor 1Homo sapiens (human)
signal transductionGlutamate receptor 1Homo sapiens (human)
chemical synaptic transmissionGlutamate receptor 1Homo sapiens (human)
synapse assemblyGlutamate receptor 1Homo sapiens (human)
long-term memoryGlutamate receptor 1Homo sapiens (human)
response to xenobiotic stimulusGlutamate receptor 1Homo sapiens (human)
response to lithium ionGlutamate receptor 1Homo sapiens (human)
positive regulation of gene expressionGlutamate receptor 1Homo sapiens (human)
neuronal action potentialGlutamate receptor 1Homo sapiens (human)
calcium-mediated signalingGlutamate receptor 1Homo sapiens (human)
spinal cord developmentGlutamate receptor 1Homo sapiens (human)
cerebral cortex developmentGlutamate receptor 1Homo sapiens (human)
receptor internalizationGlutamate receptor 1Homo sapiens (human)
response to estradiolGlutamate receptor 1Homo sapiens (human)
monoatomic ion transmembrane transportGlutamate receptor 1Homo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor 1Homo sapiens (human)
response to cocaineGlutamate receptor 1Homo sapiens (human)
positive regulation of membrane potentialGlutamate receptor 1Homo sapiens (human)
response to arsenic-containing substanceGlutamate receptor 1Homo sapiens (human)
response to electrical stimulusGlutamate receptor 1Homo sapiens (human)
regulation of postsynaptic membrane potentialGlutamate receptor 1Homo sapiens (human)
long-term synaptic potentiationGlutamate receptor 1Homo sapiens (human)
long-term synaptic depressionGlutamate receptor 1Homo sapiens (human)
response to fungicideGlutamate receptor 1Homo sapiens (human)
cellular response to amino acid stimulusGlutamate receptor 1Homo sapiens (human)
cellular response to ammonium ionGlutamate receptor 1Homo sapiens (human)
cellular response to dsRNAGlutamate receptor 1Homo sapiens (human)
cellular response to peptide hormone stimulusGlutamate receptor 1Homo sapiens (human)
cellular response to amine stimulusGlutamate receptor 1Homo sapiens (human)
regulation of presynaptic membrane potentialGlutamate receptor 1Homo sapiens (human)
regulation of postsynaptic cytosolic calcium ion concentrationGlutamate receptor 1Homo sapiens (human)
cellular response to brain-derived neurotrophic factor stimulusGlutamate receptor 1Homo sapiens (human)
modulation of chemical synaptic transmissionGlutamate receptor 1Homo sapiens (human)
synaptic transmission, glutamatergicGlutamate receptor 1Homo sapiens (human)
signal transductionGlutamate receptor 2Homo sapiens (human)
chemical synaptic transmissionGlutamate receptor 2Homo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor 2Homo sapiens (human)
synaptic transmission, glutamatergicGlutamate receptor 2Homo sapiens (human)
regulation of postsynaptic membrane potentialGlutamate receptor 2Homo sapiens (human)
monoatomic cation transmembrane transportGlutamate receptor 2Homo sapiens (human)
modulation of chemical synaptic transmissionGlutamate receptor 2Homo sapiens (human)
glutamate receptor signaling pathwayGlutamate receptor 4Homo sapiens (human)
monoatomic ion transmembrane transportGlutamate receptor 4Homo sapiens (human)
negative regulation of smooth muscle cell apoptotic processGlutamate receptor 4Homo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor 4Homo sapiens (human)
regulation of postsynaptic membrane potentialGlutamate receptor 4Homo sapiens (human)
regulation of presynaptic membrane potentialGlutamate receptor 4Homo sapiens (human)
modulation of chemical synaptic transmissionGlutamate receptor 4Homo sapiens (human)
synaptic transmission, glutamatergicGlutamate receptor 4Homo sapiens (human)
regulation of synaptic vesicle fusion to presynaptic active zone membraneGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
monoatomic ion transmembrane transportGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
excitatory postsynaptic potentialGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
regulation of presynaptic membrane potentialGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
synaptic transmission, glutamatergicGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
modulation of chemical synaptic transmissionGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
amyloid-beta bindingGlutamate receptor 1Homo sapiens (human)
G-protein alpha-subunit bindingGlutamate receptor 1Homo sapiens (human)
AMPA glutamate receptor activityGlutamate receptor 1Homo sapiens (human)
protein bindingGlutamate receptor 1Homo sapiens (human)
glutamate receptor activityGlutamate receptor 1Homo sapiens (human)
adenylate cyclase bindingGlutamate receptor 1Homo sapiens (human)
immunoglobulin bindingGlutamate receptor 1Homo sapiens (human)
protein kinase bindingGlutamate receptor 1Homo sapiens (human)
glutamate-gated calcium ion channel activityGlutamate receptor 1Homo sapiens (human)
PDZ domain bindingGlutamate receptor 1Homo sapiens (human)
small GTPase bindingGlutamate receptor 1Homo sapiens (human)
myosin V bindingGlutamate receptor 1Homo sapiens (human)
G-protein beta-subunit bindingGlutamate receptor 1Homo sapiens (human)
beta-2 adrenergic receptor bindingGlutamate receptor 1Homo sapiens (human)
glutamate receptor bindingGlutamate receptor 1Homo sapiens (human)
identical protein bindingGlutamate receptor 1Homo sapiens (human)
protein kinase A bindingGlutamate receptor 1Homo sapiens (human)
scaffold protein bindingGlutamate receptor 1Homo sapiens (human)
ligand-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potentialGlutamate receptor 1Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potentialGlutamate receptor 1Homo sapiens (human)
neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationGlutamate receptor 1Homo sapiens (human)
AMPA glutamate receptor activityGlutamate receptor 2Homo sapiens (human)
amyloid-beta bindingGlutamate receptor 2Homo sapiens (human)
glutamate-gated receptor activityGlutamate receptor 2Homo sapiens (human)
AMPA glutamate receptor activityGlutamate receptor 2Homo sapiens (human)
protein bindingGlutamate receptor 2Homo sapiens (human)
ligand-gated monoatomic cation channel activityGlutamate receptor 2Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potentialGlutamate receptor 2Homo sapiens (human)
amyloid-beta bindingGlutamate receptor 4Homo sapiens (human)
glutamate-gated receptor activityGlutamate receptor 4Homo sapiens (human)
AMPA glutamate receptor activityGlutamate receptor 4Homo sapiens (human)
ligand-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potentialGlutamate receptor 4Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potentialGlutamate receptor 4Homo sapiens (human)
glutamate-gated receptor activityGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
kainate selective glutamate receptor activityGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
ligand-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potentialGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potentialGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (41)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor 1Homo sapiens (human)
plasma membraneGlutamate receptor 1Homo sapiens (human)
cell-cell junctionGlutamate receptor 1Homo sapiens (human)
cell surfaceGlutamate receptor 1Homo sapiens (human)
ER to Golgi transport vesicle membraneGlutamate receptor 1Homo sapiens (human)
postsynaptic densityGlutamate receptor 1Homo sapiens (human)
dendriteGlutamate receptor 1Homo sapiens (human)
endocytic vesicle membraneGlutamate receptor 1Homo sapiens (human)
synaptic vesicle membraneGlutamate receptor 1Homo sapiens (human)
neuromuscular junctionGlutamate receptor 1Homo sapiens (human)
early endosome membraneGlutamate receptor 1Homo sapiens (human)
dendritic spine membraneGlutamate receptor 1Homo sapiens (human)
neuronal cell body membraneGlutamate receptor 1Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment membraneGlutamate receptor 1Homo sapiens (human)
neuronal cell bodyGlutamate receptor 1Homo sapiens (human)
dendritic spineGlutamate receptor 1Homo sapiens (human)
dendritic shaftGlutamate receptor 1Homo sapiens (human)
axonal spineGlutamate receptor 1Homo sapiens (human)
neuron spineGlutamate receptor 1Homo sapiens (human)
postsynaptic membraneGlutamate receptor 1Homo sapiens (human)
presynaptic active zone membraneGlutamate receptor 1Homo sapiens (human)
recycling endosomeGlutamate receptor 1Homo sapiens (human)
recycling endosome membraneGlutamate receptor 1Homo sapiens (human)
excitatory synapseGlutamate receptor 1Homo sapiens (human)
synaptic membraneGlutamate receptor 1Homo sapiens (human)
presynapseGlutamate receptor 1Homo sapiens (human)
postsynaptic density membraneGlutamate receptor 1Homo sapiens (human)
glutamatergic synapseGlutamate receptor 1Homo sapiens (human)
postsynaptic density, intracellular componentGlutamate receptor 1Homo sapiens (human)
perisynaptic spaceGlutamate receptor 1Homo sapiens (human)
AMPA glutamate receptor complexGlutamate receptor 1Homo sapiens (human)
plasma membraneGlutamate receptor 1Homo sapiens (human)
dendritic spineGlutamate receptor 1Homo sapiens (human)
postsynaptic density membraneGlutamate receptor 1Homo sapiens (human)
plasma membraneGlutamate receptor 2Homo sapiens (human)
external side of plasma membraneGlutamate receptor 2Homo sapiens (human)
postsynaptic densityGlutamate receptor 2Homo sapiens (human)
dendriteGlutamate receptor 2Homo sapiens (human)
endocytic vesicle membraneGlutamate receptor 2Homo sapiens (human)
asymmetric synapseGlutamate receptor 2Homo sapiens (human)
neuronal cell bodyGlutamate receptor 2Homo sapiens (human)
dendritic spineGlutamate receptor 2Homo sapiens (human)
excitatory synapseGlutamate receptor 2Homo sapiens (human)
postsynapseGlutamate receptor 2Homo sapiens (human)
postsynaptic endocytic zoneGlutamate receptor 2Homo sapiens (human)
AMPA glutamate receptor complexGlutamate receptor 2Homo sapiens (human)
plasma membraneGlutamate receptor 2Homo sapiens (human)
dendritic spineGlutamate receptor 2Homo sapiens (human)
postsynaptic density membraneGlutamate receptor 2Homo sapiens (human)
plasma membraneGlutamate receptor 4Homo sapiens (human)
dendriteGlutamate receptor 4Homo sapiens (human)
endocytic vesicle membraneGlutamate receptor 4Homo sapiens (human)
neuronal cell bodyGlutamate receptor 4Homo sapiens (human)
dendritic spineGlutamate receptor 4Homo sapiens (human)
extracellular vesicleGlutamate receptor 4Homo sapiens (human)
AMPA glutamate receptor complexGlutamate receptor 4Homo sapiens (human)
postsynaptic density membraneGlutamate receptor 4Homo sapiens (human)
plasma membraneGlutamate receptor 4Homo sapiens (human)
dendritic spineGlutamate receptor 4Homo sapiens (human)
plasma membraneGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
nucleoplasmGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
endoplasmic reticulumGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
plasma membraneGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
postsynaptic density membraneGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
presynaptic membraneGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
plasma membraneGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
kainate selective glutamate receptor complexGlutamate receptor ionotropic, kainate 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID391452Agonist activity at cyclothiazide-desensitized rat recombinant flop iGluR3 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method2008Journal of medicinal chemistry, Oct-23, Volume: 51, Issue:20
1H-cyclopentapyrimidine-2,4(1H,3H)-dione-related ionotropic glutamate receptors ligands. structure-activity relationships and identification of potent and Selective iGluR5 modulators.
AID391448Agonist activity at cyclothiazide-desensitized rat recombinant flop iGluR1 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method2008Journal of medicinal chemistry, Oct-23, Volume: 51, Issue:20
1H-cyclopentapyrimidine-2,4(1H,3H)-dione-related ionotropic glutamate receptors ligands. structure-activity relationships and identification of potent and Selective iGluR5 modulators.
AID92951Displacement of [3H]AMPA from human Ionotropic glutamate receptor AMPA 1 expressed in HEK293 cells1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis of willardiine and 6-azawillardiine analogs: pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes.
AID93254Displacement of [3H]kainate from human Ionotropic glutamate receptor ionotropic kainate 1 expressed in HEK293 cells1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis of willardiine and 6-azawillardiine analogs: pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes.
AID93111Displacement of [3H]AMPA from human Ionotropic glutamate receptor AMPA 4 expressed in HEK293 cells1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis of willardiine and 6-azawillardiine analogs: pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes.
AID92962Displacement of [3H]AMPA from human Ionotropic glutamate receptor AMPA 2 expressed in HEK293 cells1997Journal of medicinal chemistry, Oct-24, Volume: 40, Issue:22
Synthesis of willardiine and 6-azawillardiine analogs: pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes.
AID391450Agonist activity at cyclothiazide-desensitized rat recombinant flop iGluR2(Q) expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method2008Journal of medicinal chemistry, Oct-23, Volume: 51, Issue:20
1H-cyclopentapyrimidine-2,4(1H,3H)-dione-related ionotropic glutamate receptors ligands. structure-activity relationships and identification of potent and Selective iGluR5 modulators.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2003Biochemistry, May-13, Volume: 42, Issue:18
Probing the function, conformational plasticity, and dimer-dimer contacts of the GluR2 ligand-binding core: studies of 5-substituted willardiines and GluR2 S1S2 in the crystal.
AID1811Experimentally measured binding affinity data derived from PDB2003Biochemistry, May-13, Volume: 42, Issue:18
Probing the function, conformational plasticity, and dimer-dimer contacts of the GluR2 ligand-binding core: studies of 5-substituted willardiines and GluR2 S1S2 in the crystal.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2003Nature neuroscience, Aug, Volume: 6, Issue:8
Structural basis for partial agonist action at ionotropic glutamate receptors.
AID1811Experimentally measured binding affinity data derived from PDB2003Nature neuroscience, Aug, Volume: 6, Issue:8
Structural basis for partial agonist action at ionotropic glutamate receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (27.27)18.2507
2000's8 (72.73)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.16

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 Index12.16 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.16)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]