Page last updated: 2024-11-09

phenylalanine methyl ester

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

Description

phenylalanine methyl ester: RN given refers to (L)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methyl L-phenylalaninate : An alpha-amino acid ester that is the methyl ester of L-phenylalanine. [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 CID736234
CHEMBL ID51969
CHEBI ID49339
SCHEMBL ID74888
MeSH IDM0106349

Synonyms (48)

Synonym
10at497i17 ,
ai3-28811
einecs 219-934-7
2577-90-4
unii-10at497i17
l-phenylalanine, methyl ester
(s)-2-amino-3-phenyl-propionic acid methyl ester
AKOS000302179
phenylalanine methyl ester
DB06838
methyl 3-phenyl-l-alaninate
methyl l-phenylalaninate
(s)-phenylalanine methyl ester
chebi:49339 ,
(s)-phenylalanine methylester
CHEMBL51969
l-phenylalanine methyl ester
methyl (2s)-2-amino-3-phenylpropanoate
0a9 ,
AKOS010397234
(s)-methyl 2-amino-3-phenylpropanoate
SCHEMBL74888
methyl-2(s)-amino-3-phenylpropionate
h-phe-och3
phe-ome
(2s)-amino-3-phenyl propionic acid methyl ester
l-phe-ome
methyl (s)-2-amino-3-phenylpropanoate
(l)-phenylalanine methyl ester
h-phe-ome
(s) -phenylalanine methyl ester
l-.beta.-phenylalanine methyl ester
methyl 2-amino-3-phenylpropanoate #
alanine, phenyl-, methyl ester, l-
mfcd00800359
l-phenylalanine methyl ester (h-l-phe-ome)
(+)-l-phenylalanine methyl ester
(s)-2-amino-3-phenylpropionic acid methyl ester
l-phenylalanine,methyl ester
DS-4635
(s)-methyl2-amino-3-phenylpropanoate
Q27095740
N12401
(s)-methyl2-amino-3-phenylpropanoate hcl
s-phenylalanine methyl ester
A925631
CS-0010907
EN300-1719688

Research Excerpts

Overview

Phenylalanine methyl ester (PM) is a decomposition product of the sweetening agent aspartame.

ExcerptReferenceRelevance
"Phenylalanine methyl ester (PM) is a decomposition product of the sweetening agent aspartame. "( Absorption by the rhesus monkey of phenylalanine methyl ester and species differences in its metabolism by blood, plasma and intestinal mucosa.
Burton, EG; Dal Monte, P; Frank, P; Oppermann, JA; Spears, C, 1984
)
1.99

Bioavailability

ExcerptReferenceRelevance
" Our results suggest that L-valine is a desirable L-amino acid for the esterification of poorly permeable drugs to enhance their oral bioavailability targeting intestinal PEPT1."( Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2.
Hashimoto, Y; Inui, KI; Saito, H; Sawada, K; Terada, T, 1999
)
0.3

Dosage Studied

ExcerptRelevanceReference
" Rats were acutely dosed with vortioxetine, ondansetron (5-HT3 receptor antagonist) or flesinoxan (5-HT1A receptor agonist)."( Vortioxetine dose-dependently reverses 5-HT depletion-induced deficits in spatial working and object recognition memory: a potential role for 5-HT1A receptor agonism and 5-HT3 receptor antagonism.
du Jardin, KG; Jensen, JB; Pehrson, AL; Sanchez, C, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
alpha-amino acid esterThe amino acid ester derivative obtained the formal condensation of an alpha-amino acid with an alcohol.
L-phenylalanine derivativeA proteinogenic amino acid derivative resulting from reaction of L-phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-phenylalanine by a heteroatom.
[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]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1090826Antifeedant activity against Hylobius abietis (pine weevil ) in compound pre-treated Scots pine twig at 50 mM measured after 24 hr by two-choice laboratory bioassay2007Journal of agricultural and food chemistry, Nov-14, Volume: 55, Issue:23
Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach.
AID681161TP_TRANSPORTER: inhibition of L-tryptophan uptake in Xenopus laevis oocytes2002Genomics, Jan, Volume: 79, Issue:1
The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location.
AID353103Displacement of [3H]MK801 from NMDA receptor in rat brain neuronal membrane2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.
AID678875TP_TRANSPORTER: inhibition of Gly-Sar uptake (Gly-Sar: 20 uM, Phe-OMe: 10000 uM) in PEPT2-expressing LLC-PK1 cells1999The Journal of pharmacology and experimental therapeutics, Nov, Volume: 291, Issue:2
Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2.
AID679858TP_TRANSPORTER: inhibition of Gly-Sar uptake (Gly-Sar: 20 uM, Phe-OMe: 10000 uM) in PEPT1-expressing LLC-PK1 cells1999The Journal of pharmacology and experimental therapeutics, Nov, Volume: 291, Issue:2
Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2.
AID494525Cytotoxicity against human PBMC at 2 times IC50 concentration after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID494522Antileishmanial activity against Leishmania donovani amastigotes after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID353104Ratio of Ki for rat brain NMDA receptor in presence of 100 uM spermine to Ki for rat brain NMDA receptor in absence of spermine2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.
AID681113TP_TRANSPORTER: inhibition of L-tryptophan uptake in Xenopus laevis oocytes2001The Journal of biological chemistry, May-18, Volume: 276, Issue:20
Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters.
AID26797Partition coefficient (logP)1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
AID494524Cytotoxicity against human PBMC at IC50 concentration after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID233318Bitter threshold value1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
AID494523Antileishmanial activity against Leishmania donovani promastigotes after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (54)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (16.67)18.7374
1990's21 (38.89)18.2507
2000's11 (20.37)29.6817
2010's13 (24.07)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: 42.82

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

MetricThis Compound (vs All)
Research Demand Index42.82 (24.57)
Research Supply Index4.13 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index61.87 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (42.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (3.39%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other57 (96.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]