Page last updated: 2024-12-05

4-carboxyphenylglycine

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

Description

4-Carboxyphenylglycine, also known as 4-CPA, is an organic compound that has been investigated for its potential therapeutic applications. It is a synthetic derivative of phenylglycine, a naturally occurring amino acid. 4-CPA has shown promising activity as an inhibitor of enzymes involved in the biosynthesis of porphyrins, which are essential components of heme. This property has led to research into its potential use in the treatment of porphyrias, a group of inherited disorders characterized by a deficiency in porphyrin metabolism. Additionally, 4-CPA has been explored for its potential anticancer effects, as it has been shown to inhibit the growth of certain tumor cell lines. The compound's mechanism of action in these contexts is related to its ability to interfere with the synthesis of heme, which is a crucial molecule involved in cellular respiration and other vital processes. Further research is ongoing to better understand the pharmacological properties and therapeutic potential of 4-CPA.'

4-carboxyphenylglycine: RN given for (+-)-isomer; RN for cpd without isomeric designation not available 3/93; glutamate receptor antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5115
CHEMBL ID328984
CHEBI ID178134
SCHEMBL ID2266884
MeSH IDM0213259

Synonyms (32)

Synonym
4-[amino(carboxy)methyl]benzoic acid
CHEMBL328984 ,
4-(amino-carboxy-methyl)-benzoic acid
4cpg
(r,s)-4-carboxy-3-hydroxyphenylglycine
4-(amino-carboxy-methyl)-benzoic acid(s-4cpg)
bdbm50030629
CHEBI:178134
7292-81-1
NCI60_015099
nsc644612
nsc-644612
benzeneacetic acid, alpha-amino-4-carboxy-, (+-)-
4-cpg
4-carboxylphenylglycine
4-carboxyphenylglycine
L001308
FT-0694231
AKOS023158559
4-(amino(carboxy)methyl)benzoic acid
SCHEMBL2266884
(rs)-4-carboxyphenylglycine
(rs)-4cpg
SR-01000597634-1
sr-01000597634
(+-)- alpha-amino-4-carboxy-benzeneacetic acid
mfcd00673852
(rs)-4-carboxyphenylglycine (h-dl-phg(4-co2h)-oh)
4-(amino(carboxy)methyl)benzoicacid
DTXSID70864035
F14594
(s)-4-carboxyphenylglycine;4cpg

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Further characterization of the dose-response effects of the compounds on quisqualate induced [Ca2+]i mobilization showed that although the magnitude of phenylglycine inhibition was reduced for both mGluR subtypes compared to those observed for stimulation of PI hydrolysis (except for 4C3HPG on mGluR1 alpha), similar differences in the relative potencies of the phenylglycines between mGluR1 alpha (IC50s: 40 +/- 10 microM for 4C3HPG: 300-1000 microM for 4CPG and M4CPG) and mGluR5a (IC50s: > 1000 microM) were evident."( Pharmacological analysis of 4-carboxyphenylglycine derivatives: comparison of effects on mGluR1 alpha and mGluR5a subtypes.
Burnett, JP; Kingston, AE; Lodge, D; Mayne, NG, 1995
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
alpha-amino acidAn amino acid in which the amino group is located on the carbon atom at the position alpha to the carboxy group.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Metabotropic glutamate receptor 1Homo sapiens (human)IC50 (µMol)65.00000.00052.01408.8000AID221522
Metabotropic glutamate receptor 2Homo sapiens (human)IC50 (µMol)577.00000.00290.46624.3000AID221660
Metabotropic glutamate receptor 4Homo sapiens (human)IC50 (µMol)1,000.00000.00510.00510.0051AID221681
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
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)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 4Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 4Homo sapiens (human)
neurotransmitter secretionMetabotropic glutamate receptor 4Homo sapiens (human)
positive regulation of MAPK cascadeMetabotropic glutamate receptor 4Homo sapiens (human)
regulation of neuron apoptotic processMetabotropic glutamate receptor 4Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 4Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
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)
G protein-coupled receptor activityMetabotropic glutamate receptor 4Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 4Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
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)
plasma membraneMetabotropic glutamate receptor 4Homo sapiens (human)
cytoplasmic vesicleMetabotropic glutamate receptor 4Homo sapiens (human)
presynapseMetabotropic glutamate receptor 4Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID221660Ability to inhibit mGluR2-alpha induced cAMP formation was determined at BHK cells at 100 Micro M Concentration1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
1-Aminoindan-1,5-dicarboxylic acid: a novel antagonist at phospholipase C-linked metabotropic glutamate receptors.
AID221681Ability to inhibit mGluR4-alpha induced cAMP formation was determined at BHK cells at 100 Micro M Concentration1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
1-Aminoindan-1,5-dicarboxylic acid: a novel antagonist at phospholipase C-linked metabotropic glutamate receptors.
AID221522Ability to inhibit mGluR1-alpha-mediated PI (phospho inositol) hydrolysis was determined at BHK cells at 100 Micro M Concentration1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
1-Aminoindan-1,5-dicarboxylic acid: a novel antagonist at phospholipase C-linked metabotropic glutamate receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (51)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's27 (52.94)18.2507
2000's13 (25.49)29.6817
2010's11 (21.57)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: 16.99

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

MetricThis Compound (vs All)
Research Demand Index16.99 (24.57)
Research Supply Index4.01 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.99)

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%
Other54 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]