Page last updated: 2024-11-07

1-(aminoethyl)phosphonic acid

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

Description

1-(Aminoethyl)phosphonic acid (AEP) is a synthetic amino acid analog that has attracted attention for its potential biological activity and potential applications. AEP is structurally similar to the naturally occurring amino acid alanine, but with a phosphonic acid group replacing the carboxylic acid group. Its synthesis involves a multi-step process typically starting from commercially available reagents. One common approach involves the reaction of diethyl phosphite with acetaldehyde followed by an amination step using ammonia. AEP has been shown to exhibit biological activity in various areas, including its potential as an enzyme inhibitor. It has been studied as an inhibitor of various enzymes, such as carboxypeptidases and aminotransferases. The unique structural features of AEP, with the presence of the phosphonic acid group, allow it to interact with the active sites of enzymes, leading to inhibition. AEP's ability to mimic the structure of natural amino acids while possessing a different functional group, makes it a valuable tool for studying enzyme mechanisms and developing new therapeutic agents. Additionally, AEP has been investigated for its potential applications in various fields, including agriculture, where it may be used as a plant growth regulator or pesticide. The study of AEP continues to be an active area of research, with ongoing efforts to further understand its biological activity and potential applications.'

1-(aminoethyl)phosphonic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID97709
CHEMBL ID296494
CHEBI ID183822
SCHEMBL ID242135
MeSH IDM0137489

Synonyms (37)

Synonym
phosphonic acid, (1-aminoethyl)-
nsc-30077
6323-97-3
nsc30077
(1-aminoethyl)phosphonic acid
A1071
CHEMBL296494 ,
1-ammonium-ethanephosphonic acid anion
inchi=1/c2h8no3p/c1-2(3)7(4,5)6/h2h,3h2,1h3,(h2,4,5,6)
uiqskedqpsegau-uhfffaoysa-
1-aminoethylphosphonic acid
CHEBI:183822
(1-amino-ethyl)-phosphonic acid
bdbm50017377
AKOS003614588
w5p74040w1 ,
1-(aminoethyl)phosphonic acid
unii-w5p74040w1
nsc 30077
SCHEMBL242135
dl-1-aminoethylphosphonic acid
.alpha.-aminoethanephosphonic acid
phosphonic acid, p-(1-aminoethyl)-
(+/-)-1-aminoethylphosphonic acid
(1r,s)-1-aminoethyl-phosphonic acid
J81.190D ,
mfcd00008068
dl-1-(aminoethyl)phosphonic acid
alpha-amino-ethyl phosphonic acid
4-(acetamido)benzoicacid,compoundwith2-(dimethylamino)ethanol(1:1)
Q27292350
T71158
A851544
(s)-(+)-(1-aminoethyl)phosphonicacid
(r)-(-)-1-aminoethyl-phosphonicacid
SB75371
DTXSID101346480
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phosphonoacetic acidA member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl 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)
Aminopeptidase NSus scrofa (pig)IC50 (µMol)42.00000.00053.53548.9000AID472434
Cytosol aminopeptidaseHomo sapiens (human)Ki240.00000.00060.16010.4200AID101210
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
proteolysisCytosol aminopeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
aminopeptidase activityCytosol aminopeptidaseHomo sapiens (human)
carboxypeptidase activityCytosol aminopeptidaseHomo sapiens (human)
protein bindingCytosol aminopeptidaseHomo sapiens (human)
metalloexopeptidase activityCytosol aminopeptidaseHomo sapiens (human)
manganese ion bindingCytosol aminopeptidaseHomo sapiens (human)
metalloaminopeptidase activityCytosol aminopeptidaseHomo sapiens (human)
peptidase activityCytosol aminopeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
nucleusCytosol aminopeptidaseHomo sapiens (human)
trans-Golgi networkCytosol aminopeptidaseHomo sapiens (human)
focal adhesionCytosol aminopeptidaseHomo sapiens (human)
extracellular exosomeCytosol aminopeptidaseHomo sapiens (human)
cytoplasmCytosol aminopeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID74840ATP dependent inhibition of glutamine synthetase after 4 hours at 10000 uM concentration; none1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Phosphinic acid inhibitors of D-alanyl-D-alanine ligase.
AID101210Inhibition of Leucine aminopeptidase isolated from porcine kidney.1987Journal of medicinal chemistry, Sep, Volume: 30, Issue:9
Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase.
AID74838ATP dependent inhibition of glutamine synthetase after 24 hours at 10000 uM concentration; none1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Phosphinic acid inhibitors of D-alanyl-D-alanine ligase.
AID55425Antibacterial activity against D-alanyl-D-alanine ligase from Streptococcus faecalis (ATCC 8043)1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Phosphinic acid inhibitors of D-alanyl-D-alanine ligase.
AID55619Compound was tested for its inhibitory activity against DAla-DAla Ligase1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Synthesis of an analogue of tabtoxinine as a potential inhibitor of D-alanine:D-alanine ligase (ADP forming).
AID472434Inhibition of pig kidney aminopeptidase N using Leu-AMC as substrate2010Bioorganic & medicinal chemistry, Apr-15, Volume: 18, Issue:8
New aromatic monoesters of alpha-aminoaralkylphosphonic acids as inhibitors of aminopeptidase N/CD13.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (62.50)18.7374
1990's2 (25.00)18.2507
2000's0 (0.00)29.6817
2010's1 (12.50)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: 11.91

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 Index11.91 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.11 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.91)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]