Page last updated: 2024-12-11

ampa, (r)-isomer

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

Cross-References

ID SourceID
PubMed CID6604707
CHEMBL ID14815
SCHEMBL ID13957590
SCHEMBL ID2458874
MeSH IDM0329160

Synonyms (34)

Synonym
HMS3266E07
NCGC00024516-01
tocris-0253
BPBIO1_001302
NCGC00024516-02
BIOMOL-NT_000215
CHEMBL14815 ,
bdbm50026947
(r)-2-ammonio-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoate
2-amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)-propionic acid(d-ampa)
(2r)-2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic acid
AKOS006272257
(r)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
(r)-ampa
ampa, d-
d-ampa
83654-13-1
unii-f45tj02el1
f45tj02el1 ,
4-isoxazolepropanoic acid, alpha-amino-2,3-dihydro-5-methyl-3-oxo-, (alphar)-
(-)-ampa
4-isoxazolepropanoic acid, .alpha.-amino-2,3-dihydro-5-methyl-3-oxo-, (.alpha.r)-
SCHEMBL13957590
SCHEMBL2458874
(r)-?-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
sr-01000597719
SR-01000597719-1
(r)-a-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
(r)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic acid
ampa-(rs)
Q27277614
(2r)-2-amino-3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)propanoic acid
AKOS040745324
PD071226
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (26)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency3.98110.631035.7641100.0000AID504339
phosphopantetheinyl transferaseBacillus subtilisPotency79.43280.141337.9142100.0000AID1490
USP1 protein, partialHomo sapiens (human)Potency100.00000.031637.5844354.8130AID504865
Microtubule-associated protein tauHomo sapiens (human)Potency8.91250.180013.557439.8107AID1468
Smad3Homo sapiens (human)Potency31.62280.00527.809829.0929AID588855
mitogen-activated protein kinase 1Homo sapiens (human)Potency0.02510.039816.784239.8107AID995
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
[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)
Glutamate receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)40.40000.00011.617910.0000AID92501; AID92505
Glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)40.40000.00011.700010.0000AID92501; AID92505
Glutamate receptor 3Rattus norvegicus (Norway rat)IC50 (µMol)40.40000.00011.700010.0000AID92501; AID92505
Glutamate receptor 4Rattus norvegicus (Norway rat)IC50 (µMol)40.40000.00011.700010.0000AID92501; AID92505
Glutamate receptor ionotropic, kainate 1Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00700.98217.0000AID93725
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.600310.0000AID145035; AID145036
Glutamate receptor ionotropic, kainate 2Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID93725
Glutamate receptor ionotropic, kainate 3Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID93725
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.630610.0000AID145035; AID145036
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00061.525710.0000AID145035; AID145036
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.747210.0000AID145035; AID145036
Glutamate receptor ionotropic, kainate 4Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID93725
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.741110.0000AID145035; AID145036
Glutamate receptor ionotropic, kainate 5Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID93725
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.741110.0000AID145035; AID145036
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.741110.0000AID145035; AID145036
[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)
Metabotropic glutamate receptor 6Homo sapiens (human)EC50 (µMol)1,000.00000.05502.27864.9000AID107254
Glutamate receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)580.00000.00411.89638.7000AID92195
Glutamate receptor 2Rattus norvegicus (Norway rat)EC50 (µMol)580.00000.00411.62517.6000AID92195
Glutamate receptor 3Rattus norvegicus (Norway rat)EC50 (µMol)580.00000.00411.17063.5000AID92195
Glutamate receptor 4Rattus norvegicus (Norway rat)EC50 (µMol)580.00000.00411.13393.5000AID92195
Metabotropic glutamate receptor 1Homo sapiens (human)EC50 (µMol)1,000.00000.20004.41009.3000AID108656
Metabotropic glutamate receptor 2Homo sapiens (human)EC50 (µMol)1,000.00000.00061.17848.5000AID109010
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 6Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 6Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 6Homo sapiens (human)
locomotory behaviorMetabotropic glutamate receptor 6Homo sapiens (human)
detection of visible lightMetabotropic glutamate receptor 6Homo sapiens (human)
detection of light stimulus involved in visual perceptionMetabotropic glutamate receptor 6Homo sapiens (human)
retina development in camera-type eyeMetabotropic glutamate receptor 6Homo sapiens (human)
positive regulation of calcium ion import across plasma membraneMetabotropic glutamate receptor 6Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 6Homo sapiens (human)
G protein-coupled receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
phospholipase C-activating G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 1Homo sapiens (human)
locomotory behaviorMetabotropic glutamate receptor 1Homo sapiens (human)
sensory perception of painMetabotropic glutamate receptor 1Homo sapiens (human)
positive regulation of MAPK cascadeMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of sensory perception of painMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 1Homo sapiens (human)
cellular response to electrical stimulusMetabotropic glutamate receptor 1Homo sapiens (human)
L-glutamate import across plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 1Homo sapiens (human)
negative regulation of adenylate cyclase activityMetabotropic glutamate receptor 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 2Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 2Homo sapiens (human)
gene expressionMetabotropic glutamate receptor 2Homo sapiens (human)
glutamate secretionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of glutamate secretionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of dopamine secretionMetabotropic glutamate receptor 2Homo sapiens (human)
behavioral response to nicotineMetabotropic glutamate receptor 2Homo sapiens (human)
response to cocaineMetabotropic glutamate receptor 2Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionMetabotropic glutamate receptor 2Homo sapiens (human)
long-term synaptic depressionMetabotropic glutamate receptor 2Homo sapiens (human)
intracellular glutamate homeostasisMetabotropic glutamate receptor 2Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of response to drugMetabotropic glutamate receptor 2Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityMetabotropic glutamate receptor 6Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 6Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 6Homo sapiens (human)
protein homodimerization activityMetabotropic glutamate receptor 6Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 6Homo sapiens (human)
G protein-coupled receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 1Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor activity involved in regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
calcium channel regulator activityMetabotropic glutamate receptor 2Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 2Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
scaffold protein bindingMetabotropic glutamate receptor 2Homo sapiens (human)
group II metabotropic glutamate receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
Golgi membraneMetabotropic glutamate receptor 6Homo sapiens (human)
endoplasmic reticulum membraneMetabotropic glutamate receptor 6Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 6Homo sapiens (human)
dendriteMetabotropic glutamate receptor 6Homo sapiens (human)
new growing cell tipMetabotropic glutamate receptor 6Homo sapiens (human)
synapseMetabotropic glutamate receptor 6Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 6Homo sapiens (human)
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
nucleusMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
dendriteMetabotropic glutamate receptor 1Homo sapiens (human)
Schaffer collateral - CA1 synapseMetabotropic glutamate receptor 1Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor dimeric complexMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor homodimeric complexMetabotropic glutamate receptor 1Homo sapiens (human)
postsynaptic density membraneMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 2Homo sapiens (human)
axonMetabotropic glutamate receptor 2Homo sapiens (human)
dendriteMetabotropic glutamate receptor 2Homo sapiens (human)
presynaptic membraneMetabotropic glutamate receptor 2Homo sapiens (human)
astrocyte projectionMetabotropic glutamate receptor 2Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 2Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 2Homo sapiens (human)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID92195The compound (AMPA agonist) was evaluated for agonist activity at Ionotropic glutamate receptor AMPA in cortical wedge.1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID179948Inhibition of [3H]AMPA binding in rat brain membrane was evaluated1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Ibotenic acid analogues. Synthesis, molecular flexibility, and in vitro activity of agonists and antagonists at central glutamic acid receptors.
AID145250NMDA Antagonist activity was evaluated; na means no activity1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Ibotenic acid analogues. Synthesis, molecular flexibility, and in vitro activity of agonists and antagonists at central glutamic acid receptors.
AID187288GDEE-sensitive neuronal excitant (Relative potency) was evaluated; +(+)1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Ibotenic acid analogues. Synthesis, molecular flexibility, and in vitro activity of agonists and antagonists at central glutamic acid receptors.
AID145035The compound was evaluated for agonist to competitive inhibition of radioligand ([3H]- CPP ) at Ionotropic Excitatory Amino acid receptors1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID92501Tested for inhibition of Specific DL-[H]Ionotropic glutamate receptor AMPA binding to rat brain membranes1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
Enzymic resolution and binding to rat brain membranes of the glutamic acid agonist alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid.
AID93725The compound was evaluated for agonist to competitive inhibition of radioligand ([3H]- kainic acid ) at Ionotropic glutamate receptor kainate1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID92505The compound was evaluated for agonist to competitive inhibition of radioligand ([3H]- AMPA ) at Ionotropic glutamate receptor AMPA1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID107254Agonist activity of the compound at Metabotropic Excitatory Amino acid Receptors Expressed in CHO cells. mGlu61996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID108656Agonist activity of the compound at Metabotropic Excitatory Amino acid Receptors Expressed in CHO cells. mGlu1-alpha1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID109482Agonist activity of the compound at Metabotropic Excitatory Amino acid Receptors Expressed in CHO cells. mGlu4a; No data1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID109010Agonist activity of the compound at Metabotropic Excitatory Amino acid Receptors Expressed in CHO cells. mGlu21996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID145036The compound was evaluated for agonist to competitive inhibition of radioligand ([3H]- MK -801) at Ionotropic Excitatory Amino acid receptors1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
[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-19902 (40.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.80

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 Index12.80 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.80)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]