Page last updated: 2024-12-11

phenylalanylglycine

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

Description

phenylalanylglycine: RN given refers to (DL)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Phe-Gly : A dipeptide formed from L-phenylalanine and glycine residues. [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]

FloraRankFlora DefinitionFamilyFamily Definition
GlycinegenusA non-essential amino acid. It is found primarily in gelatin and silk fibroin and used therapeutically as a nutrient. It is also a fast inhibitory neurotransmitter.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID6992304
CHEMBL ID417979
CHEBI ID73635
SCHEMBL ID1329817
MeSH IDM0120582

Synonyms (38)

Synonym
721-90-4
((s)-2-amino-3-phenyl-propionylamino)-acetic acid
bdbm50139894
((s)-3-amino-2-oxo-4-phenyl-butylamino)-acetic acid
(2-amino-3-phenyl-propionylamino)-acetic acid
phenylalanylglycine
phe-gly
chebi:73635 ,
(s)-phenylalanylglycine
CHEMBL417979 ,
l-phenylalanylglycine
h-phe-gly-oh
fg
SCHEMBL1329817
phe-gly hydrate
f-g
l-phe-gly
l-phenylalanyl-glycine
n-(l-phenylalanyl)glycine
{[(2s)-2-amino-3-phenylpropanoyl]amino}acetic acid
mfcd00021728
l-phenylalanyl-l-glycine
fg dipeptide
phenylalanine-glycine dipeptide
f-g dipeptide
phenylalanine glycine dipeptide
phenylalanyl-glycine
Q27142685
CS-0201727
(s)-2-(2-amino-3-phenylpropanamido)acetic acid
2-[[(2s)-2-amino-3-phenylpropanoyl]amino]acetic acid
AT16962
BS-29332
DTXSID901315619
2-[(2s)-2-amino-3-phenylpropanamido]acetic acid
EN300-151353
PD119121
HY-W141936
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (1)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 15 member 1Homo sapiens (human)IC50 (µMol)85.10000.18000.19000.2000AID266249; AID92024
Solute carrier family 15 member 1Homo sapiens (human)Ki0.20000.18003.39339.8000AID92025
Mu-type opioid receptorCavia porcellus (domestic guinea pig)IC50 (µMol)170.00000.00020.660310.0000AID266249
Solute carrier family 15 member 2Homo sapiens (human)Ki14.06270.79434.22108.0000AID612540
Solute carrier family 15 member 2Rattus norvegicus (Norway rat)Ki7.00003.00006.47788.5000AID681124
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
peptide amidationPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
response to zinc ionPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
fatty acid primary amide biosynthetic processPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
monoatomic ion transportSolute carrier family 15 member 1Homo sapiens (human)
protein transportSolute carrier family 15 member 1Homo sapiens (human)
peptide transportSolute carrier family 15 member 1Homo sapiens (human)
dipeptide import across plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
tripeptide import across plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
proton transmembrane transportSolute carrier family 15 member 1Homo sapiens (human)
monoatomic ion transportSolute carrier family 15 member 2Homo sapiens (human)
protein transportSolute carrier family 15 member 2Homo sapiens (human)
peptide transportSolute carrier family 15 member 2Homo sapiens (human)
peptidoglycan transportSolute carrier family 15 member 2Homo sapiens (human)
xenobiotic transportSolute carrier family 15 member 2Homo sapiens (human)
dipeptide transportSolute carrier family 15 member 2Homo sapiens (human)
renal absorptionSolute carrier family 15 member 2Homo sapiens (human)
regulation of nucleotide-binding domain, leucine rich repeat containing receptor signaling pathwaySolute carrier family 15 member 2Homo sapiens (human)
dipeptide import across plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
tripeptide import across plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
antibacterial innate immune responseSolute carrier family 15 member 2Homo sapiens (human)
transport across blood-brain barrierSolute carrier family 15 member 2Homo sapiens (human)
proton transmembrane transportSolute carrier family 15 member 2Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
peptidylglycine monooxygenase activityPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
peptidylamidoglycolate lyase activityPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
copper ion bindingPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
calcium ion bindingPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
protein bindingPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
zinc ion bindingPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
L-ascorbic acid bindingPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
proton-dependent oligopeptide secondary active transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
peptide:proton symporter activitySolute carrier family 15 member 1Homo sapiens (human)
tripeptide transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
dipeptide transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
protein bindingSolute carrier family 15 member 2Homo sapiens (human)
peptide:proton symporter activitySolute carrier family 15 member 2Homo sapiens (human)
tripeptide transmembrane transporter activitySolute carrier family 15 member 2Homo sapiens (human)
dipeptide transmembrane transporter activitySolute carrier family 15 member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
membranePeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
transport vesicle membranePeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
secretory granule membranePeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
extracellular exosomePeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
extracellular regionPeptidyl-glycine alpha-amidating monooxygenaseHomo sapiens (human)
plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
brush borderSolute carrier family 15 member 1Homo sapiens (human)
membraneSolute carrier family 15 member 1Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
phagocytic vesicle membraneSolute carrier family 15 member 2Homo sapiens (human)
plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
membraneSolute carrier family 15 member 2Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
extracellular exosomeSolute carrier family 15 member 2Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
plasma membraneSolute carrier family 15 member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID228722Bitter tasting threshold was expressed as log 1/T.1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Amino acid side chain descriptors for quantitative structure-activity relationship studies of peptide analogues.
AID195438Affinity against Renal peptide transporter PepT2 in SKPT cells was measured by the inhibition of [14C]Gly-Sar uptake2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: synthesis and biological investigations.
AID92025Affinity fo the compound against human Intestinal peptide transporter PepT1 in Caco-2 cells was measured as inhibition of [14C]Gly-Sar uptake2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: synthesis and biological investigations.
AID266249Binding affinity to human PEPT1 assessed as inhibition of [14C]Gly-Sar uptake in MDCK cells2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID195437Concentration required to inhibit the maximum [14C]Gly-Sar uptake by Renal peptide transporter PepT2 in SKPT cells2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: synthesis and biological investigations.
AID500816Inhibition of nitrogen-starved wild type sigma1278b yeast Gap1-mediated amino acid uptake at 5 mM after 60 secs relative to L-citrulline2009Nature chemical biology, Jan, Volume: 5, Issue:1
Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.
AID612540Binding affinity to human PepT2 in SKTP cells2011Bioorganic & medicinal chemistry, Aug-01, Volume: 19, Issue:15
Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping.
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.
AID717275Binding affinity to secreted PAM in human DMS53 cell culture medium after 2 hrs by HPLC analysis2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Prohormone-substrate peptide sequence recognition by peptidylglycine α-amidating monooxygenase and its reflection in increased glycolate inhibitor potency.
AID266248Ratio of %GSmax to EC50 for human PEPT1 activation2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID717276Binding affinity to PAM in human DMS53 cells after 2 hrs by HPLC analysis2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Prohormone-substrate peptide sequence recognition by peptidylglycine α-amidating monooxygenase and its reflection in increased glycolate inhibitor potency.
AID681125TP_TRANSPORTER: inhibition of Gly-Sar uptake in PEPT1-expressing LLC-PK1 cells2000Pflugers Archiv : European journal of physiology, Sep, Volume: 440, Issue:5
Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2.
AID92024Concentration required to inhibit the maximum [14C]Gly-Sar uptake by human Intestinal peptide transporter PepT1 in Caco-2 cells2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: synthesis and biological investigations.
AID266247Activation of human PEPT1 expressed in MDCK cells relative to Gly-Sar2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID681124TP_TRANSPORTER: inhibition of Gly-Sar uptake in PEPT2-expressing LLC-PK1 cells2000Pflugers Archiv : European journal of physiology, Sep, Volume: 440, Issue:5
Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2.
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.
AID266246Activation of human PEPT1 expressed in MDCK cells2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (15.63)18.7374
1990's5 (15.63)18.2507
2000's9 (28.13)29.6817
2010's12 (37.50)24.3611
2020's1 (3.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.86

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 Index18.86 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.86)

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%
Other32 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]