Page last updated: 2024-12-06

5-imidazolepropionic acid

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

Description

5-Imidazolepropionic acid (IPA) is a naturally occurring compound found in various organisms, including humans. It is a derivative of histidine and is involved in the metabolism of the neurotransmitter histamine. IPA is synthesized through the decarboxylation of histidine by the enzyme histidine decarboxylase. Research suggests that IPA may have potential therapeutic applications due to its diverse biological activities. For example, studies have shown that IPA can modulate the activity of certain enzymes, act as an antioxidant, and exhibit anti-inflammatory properties. Its role in the regulation of histamine levels and its potential influence on immune responses have made it a subject of ongoing scientific investigation. Additionally, some researchers are exploring the potential of IPA as a therapeutic agent for conditions such as allergies, inflammatory bowel disease, and cancer. However, further research is required to fully understand the mechanism of action, efficacy, and safety of IPA as a therapeutic.'

5-imidazolepropionic acid: competitive inhibitor of urocanase reaction which catalyzes conversion of urocanate into imidazolone propionate; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dihydrourocanic acid : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 3 has been replaced by an imidazol-4-yl group. [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]

Cross-References

ID SourceID
PubMed CID70630
CHEMBL ID84253
CHEBI ID73087
SCHEMBL ID216266
MeSH IDM0071044

Synonyms (64)

Synonym
chebi:73087 ,
CHEMBL84253 ,
deaminohistidine
imidazolylpropionic acid
1074-59-5
nsc66737
nsc-66737
URO ,
3-(1h-imidazol-4-yl)-propionic acid
imidazolepropionic acid
3-(1h-imidazol-5-yl)propanoic acid
3-(1h-imidazol-4-yl)propanoic acid
AKOS006229491
3-(1h-imidazol-4-yl)propionic acid
3-(imidazol-4-yl)propanoic acid
dihydrourocanic acid
AM802898
4-imidazolylpropanoic acid
4-imidazolylpropionic acid
unii-8b1241598d
einecs 214-045-0
1h-imidazole-4-propanoic acid
5-imidazolepropionic acid
nsc 66737
8b1241598d ,
3-(imidazol-4-yl)propionic acid
1h-imidazole-5-propanoicacid
C20522
AKOS015856228
SCHEMBL216266
PS-5123
3-(1h-imidazol-4-yl) propionic acid
desamino-histidine
3-(1h-4-imidazolyl)propanoic acid
(3-imidazol-4-yl)propionic acid
ZCKYOWGFRHAZIQ-UHFFFAOYSA-N
3-(4-imidazolyl)propionic acid
3-(1h-imidazol-5-yl)-propionic acid
mfcd00237415
3-(4-imidazolyl)propionsaure
W-204640
deamino-histidine
imidazole-4(or 5)-propionic acid
dihydrourocanoic acid
AC-25677
DTXSID30148040
5-imidazolylpropionate
imidazolepropionic acid, >=98.0% (gc)
bdbm50026404
1h-imidazole-4-propanoate
3-(imidazol-4-yl)propionate
5-imidazolepropionate
imidazolepropionate
imidazolylpropionate
3-(1h-imidazol-4-yl)-propionate
dihydrourocanic acid;3-(imidazol-4-yl)-propionic acid
CS-0038274
Q27140293
FT-0733120
deamino-his-oh
MWQ ,
3-(1~{h}-imidazol-5-yl)propanoic acid
3-(imidazol-4-yl)propionicacid
3-(1h-imidazol-4-yl)propanoicacid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
monocarboxylic acidAn oxoacid containing a single 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 (18)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.505710.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.497310.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.498810.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.504610.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Sodium- and chloride-dependent GABA transporter 2Mus musculus (house mouse)IC50 (µMol)645.65401.41255.26838.1283AID595474
Sodium- and chloride-dependent GABA transporter 3Mus musculus (house mouse)IC50 (µMol)22.90871.54883.67618.1283AID595475
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.506510.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.505710.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
GABA theta subunitRattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)IC50 (µMol)290.00000.00010.507510.0000AID72319
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1133935Inhibition of histidine decarboxylase in Sprague-Dawley rat stomach assessed as decrease in 14CO2 production using L-histidine-carboxyl-14C as substrate at 0.13 mM by scintillation counting analysis1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Inhibition of histidine decarboxylase. Derivatives of histidine.
AID595475Inhibition of mouse GAT3-mediated [3H]GABA uptake expressed in human HEK cells2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
AID595509Selectivity ratio of pIC50 for mouse GAT3 topIC50 for mouse GAT12011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
AID595476Inhibition of mouse GAT4-mediated [3H]GABA uptake expressed in human HEK cells2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
AID595482Selectivity ratio of pIC50 for mouse GAT3 to pIC50 for mouse GAT22011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
AID595474Inhibition of mouse GAT2-mediated [3H]GABA uptake expressed in human HEK cells2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
AID595477Inhibition of mouse GAT1-mediated [3H]GABA uptake expressed in human HEK cells assessed as specific binding remaining at 1 mM2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
AID598116Inhibition of Geotrichum candidum Histidinol dehydrogenase2010Bioorganic & medicinal chemistry letters, Jul-01, Volume: 20, Issue:13
Structure based design of novel inhibitors for histidinol dehydrogenase from Geotrichum candidum.
AID72319Inhibition of [3H]GABA binding to Gamma-aminobutyric acid A (GABA-A) receptor of rat brain membranes1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of gamma-aminobutyric acid acting as selective GABA-A antagonists.
AID595483Selectivity ratio of pIC50 for mouse GAT3 to pIC50 for mouse GAT42011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (25.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (16.67)24.3611
2020's14 (58.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.21

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 Index12.21 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (8.33%)5.53%
Reviews1 (4.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]