Page last updated: 2024-12-07

2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid

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Description

2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid: RN refers to (R-)-isomer; structure in first source; AMPA receptor antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID127884
CHEMBL ID315203
SCHEMBL ID8129370
MeSH IDM0229855

Synonyms (13)

Synonym
CHEMBL315203 ,
(r)-2-amino-3-(3-hydroxy-5-phenyl-isoxazol-4-yl)-propionic acid
bdbm50030114
2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid
(2r)-2-amino-3-(3-oxo-5-phenyl-1,2-oxazol-4-yl)propanoic acid
4-isoxazolepropanoic acid, alpha-amino-2,3-dihydro-3-oxo-5-phenyl-, (r)-
appa-(r,s)
(r)-alpha-amino-2,3-dihydro-3-oxo-5-phenyl-4-isoxazolepropanoic acid
154420-28-7
SCHEMBL8129370
3-(3-hydroxy-5-phenyl-1,2-oxazol-4-yl)alanine
DTXSID90934986
(r)-2-amino-3-(3-oxo-5-phenyl-2,3-dihydroisoxazol-4-yl)propanoic acid

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Using the rat cortical wedge preparation, the latter series of experiments showed the expected rightward parallel shifts of the dose-response curves."( Functional partial agonism at ionotropic excitatory amino acid receptors.
Ebert, B; Krogsgaard-Larsen, P; Madsen, U; Søby, KK, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (16)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.617910.0000AID31459
Glutamate receptor 1Rattus norvegicus (Norway rat)Ki286.00000.00000.41052.7800AID31607
Glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.700010.0000AID31459
Glutamate receptor 2Rattus norvegicus (Norway rat)Ki286.00000.00000.68536.3000AID31607
Glutamate receptor 3Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.700010.0000AID31459
Glutamate receptor 3Rattus norvegicus (Norway rat)Ki286.00000.00000.71777.4000AID31607
Glutamate receptor 4Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.700010.0000AID31459
Glutamate receptor 4Rattus norvegicus (Norway rat)Ki286.00000.00000.52773.5700AID31607
Glutamate receptor ionotropic, kainate 1Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00700.98217.0000AID95528
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.600310.0000AID144838; AID144839; AID145264
Glutamate receptor ionotropic, kainate 2Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID95528
Glutamate receptor ionotropic, kainate 3Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID95528
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.630610.0000AID144838; AID144839
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00061.525710.0000AID144838; AID144839
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.747210.0000AID144838; AID144839
Glutamate receptor ionotropic, kainate 4Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID95528
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.741110.0000AID144838; AID144839
Glutamate receptor ionotropic, kainate 5Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00701.01327.0000AID95528
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.741110.0000AID144838; AID144839
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)100.00000.00071.741110.0000AID144838; AID144839
[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)286.00000.00411.89638.7000AID92794
Glutamate receptor 2Rattus norvegicus (Norway rat)EC50 (µMol)286.00000.00411.62517.6000AID92794
Glutamate receptor 3Rattus norvegicus (Norway rat)EC50 (µMol)286.00000.00411.17063.5000AID92794
Glutamate receptor 4Rattus norvegicus (Norway rat)EC50 (µMol)286.00000.00411.13393.5000AID92794
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
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)
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 (10)

Assay IDTitleYearJournalArticle
AID144459Ability to inhibit the binding of [3H]CPP radioligand to N-methyl-D-aspartate glutamate receptor in rat brain membranes.1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships.
AID92794Agonist effect for Ionotropic glutamate receptor AMPA was determined from in vitro electrophysiology studies using rat cortical wedge preparation.1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships.
AID92795Ability to inhibit the binding of [3H]AMPA radioligand to Ionotropic glutamate receptor AMPA in rat brain membranes.1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships.
AID31459Compound was evaluated for the inhibition of binding of [3H]AMPA to the AMPA receptor1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA].
AID144838Compound was evaluated for the inhibition of binding of [3H]- CPP to NMDA receptor1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA].
AID95528Compound was evaluated for the inhibition of binding of [3H]-Kainic acid to kianic acid receptor1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA].
AID144839Compound was evaluated for the inhibition of binding of [3H]- MK-801 to NMDA receptor1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA].
AID93554Ability to inhibit the binding of [3H]-kainic acid radioligand to Ionotropic glutamate receptor kainate in rat brain membranes.1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships.
AID31607Compound was evaluated for the antagonist activity on AMPA receptor in rat cortical wedge preparation1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA].
AID145264Compound was evaluated for the inhibition of binding of [3H]glycine to NMDA receptor1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-(-)-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic acid [(R,S)-APPA].
[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's5 (100.00)18.2507
2000's0 (0.00)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: 12.66

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 Index12.66 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.66)

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]