Compounds > n-(n-(phenyl)butyryl-l-prolyl)pyrrolidine
Page last updated: 2024-11-10

n-(n-(phenyl)butyryl-l-prolyl)pyrrolidine

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Description

N-(N-(phenyl)butyryl-L-prolyl)pyrrolidine: inhibits prolyl endopeptidase; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3081017
CHEMBL ID289651
SCHEMBL ID6285952
MeSH IDM0200716

Synonyms (15)

Synonym
n-(n-(phenyl)butyryl-l-prolyl)pyrrolidine
112603-82-4
pyrrolidine, 1-(1-oxo-4-phenylbutyl)-2-(1-pyrolidinylcarbonyl)-, (s)-
4-phenyl-1-[2-(pyrrolidine-1-carbonyl)-pyrrolidin-1-yl]-butan-1-one
(s)-4-phenyl-1-(2-(pyrrolidine-1-carbonyl)pyrrolidin-1-yl)butan-1-one
4-phenyl-1-[(s)-2-(pyrrolidine-1-carbonyl)-pyrrolidin-1-yl]-butan-1-one
bdbm50051539
suam 1221
suam-1221
CHEMBL289651 ,
4-phenyl-1-[(2s)-2-(pyrrolidine-1-carbonyl)pyrrolidin-1-yl]butan-1-one
HDRSLHFTJYMQIL-KRWDZBQOSA-N
n-[n-(gamma-phenyl)butyryl-l-prolyl]pyrrolidine
SCHEMBL6285952
DTXSID40150119
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prolyl endopeptidaseRattus norvegicus (Norway rat)IC50 (µMol)0.00720.00010.12430.3000AID481658
Metabotropic glutamate receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)0.13000.00020.58878.9900AID709198
Prolyl endopeptidaseSus scrofa (pig)IC50 (µMol)0.02970.00020.01050.1300AID160360; AID1611788; AID242814; AID481396; AID709198
Prolyl endopeptidaseHomo sapiens (human)IC50 (µMol)0.08470.00111.98969.7500AID160210; AID160213; AID161118
Prolyl endopeptidaseHomo sapiens (human)Ki0.00100.00000.00200.0080AID1127417
Prolyl endopeptidase FAPMus musculus (house mouse)IC50 (µMol)100.00000.06600.18840.3700AID709197
Prolyl endopeptidaseMus musculus (house mouse)IC50 (µMol)0.00470.00030.00250.0047AID481397
Prolyl endopeptidaseBos taurus (cattle)IC50 (µMol)2.10002.10002.10002.1000AID481395
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
proteolysisProlyl endopeptidaseHomo sapiens (human)
proteolysisProlyl endopeptidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityProlyl endopeptidaseHomo sapiens (human)
protein bindingProlyl endopeptidaseHomo sapiens (human)
serine-type peptidase activityProlyl endopeptidaseHomo sapiens (human)
oligopeptidase activityProlyl endopeptidaseHomo sapiens (human)
serine-type endopeptidase activityProlyl endopeptidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneMetabotropic glutamate receptor 1Rattus norvegicus (Norway rat)
nucleusProlyl endopeptidaseHomo sapiens (human)
cytoplasmProlyl endopeptidaseHomo sapiens (human)
cytosolProlyl endopeptidaseHomo sapiens (human)
membraneProlyl endopeptidaseHomo sapiens (human)
cytosolProlyl endopeptidaseHomo sapiens (human)
cytoplasmProlyl endopeptidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1127417Inhibition of prolyl oligopeptidase (unknown origin)2014European journal of medicinal chemistry, May-22, Volume: 79Synthesis and biological evaluation of novel (123)I-labeled 4-(4-iodophenyl)butanoyl-L-prolyl-(2S)-pyrrolidines for imaging prolyl oligopeptidase in vivo.
AID161118Inhibitory activity was evaluated against Post-proline cleaving enzyme from bovine brain1996Journal of medicinal chemistry, Jun-07, Volume: 39, Issue:12
New prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives.
AID481412Inhibition of dog POP2010Journal of medicinal chemistry, May-13, Volume: 53, Issue:9
Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.
AID481395Inhibition of bovine brain POP2010Journal of medicinal chemistry, May-13, Volume: 53, Issue:9
Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.
AID241048Inhibitory activity against prolyl oligopeptidase of porcine brain homogenate2004Journal of medicinal chemistry, Nov-04, Volume: 47, Issue:23
A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors.
AID709195Inhibition of human seminal plasma DPP2 assessed as pNA release from Lys-Ala-p-nitroanilide substrate pre-incubated with enzyme for 15 min prior to substrate addition by fluorescence technique2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.
AID160213In vitro inhibitory activity against purified prolyl endopeptidase (PEP) from canine brain.1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
New potent prolyl endopeptidase inhibitors: synthesis and structure-activity relationships of indan and tetralin derivatives and their analogues.
AID709194Inhibition of bovine testes DPP9 assessed as pNA release from Ala-Pro- p-nitroanilide substrate pre-incubated with enzyme for 15 min prior to substrate addition by fluorescence technique2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.
AID276013Partition co-efficient, log P by shake-flask method2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors.
AID709196Inhibition of human seminal plasma DPP4 assessed as pNA release from Gly-Pro-p-nitroanilide substrate pre-incubated with enzyme for 15 min prior to substrate addition by fluorescence technique2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.
AID276015Solubility in phosphate buffer at pH 7.42006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors.
AID709197Inhibition of mouse recombinant FAP expressed in HEK293 cells assessed as pNA release from Ala-Pro-p-nitroanilide pre-incubated with enzyme for 15 mins prior to substrate addition by fluorescence technique2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.
AID481396Inhibition of pig brain POP2010Journal of medicinal chemistry, May-13, Volume: 53, Issue:9
Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.
AID481397Inhibition of mouse brain POP2010Journal of medicinal chemistry, May-13, Volume: 53, Issue:9
Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.
AID347183Inhibition of POP in Sprague-Dawley rat brain homogenates2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Prolyl oligopeptidase inhibition by N-acyl-pro-pyrrolidine-type molecules.
AID237428Partition coefficient (logP) determined in a 1-octanol-phosphate buffer system2004Journal of medicinal chemistry, Nov-04, Volume: 47, Issue:23
A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors.
AID709198Inhibition of pig PREP expressed in Escherichia coli using Z-Gly-Pro-p-nitroanilide substrate2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.
AID160360In vitro inhibitory activity against prolyl oligopeptidase (POP) from pig brain; value ranges from (1.9-2.5)2002Journal of medicinal chemistry, Sep-26, Volume: 45, Issue:20
Dicarboxylic acid bis(L-prolyl-pyrrolidine) amides as prolyl oligopeptidase inhibitors.
AID160210Inhibition of Prolyl endopeptidase1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Automated parallel synthesis of a tetrahydroisoquinolin-based library: potential prolyl endopeptidase inhibitors.
AID481658Inhibition of rat brain POP2010Journal of medicinal chemistry, May-13, Volume: 53, Issue:9
Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.
AID276012Inhibition of POP in pig brain2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors.
AID242814In vitro inhibitory activity against porcine prolyl oligopeptidase by using 4 mM Suc-Gly-Pro-7-amido-4-methylcoumarin as substrate (pH 7.0) at 30 degree C for 60 min2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Dicarboxylic acid azacycle l-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions.
AID1611788Inhibition of recombinant porcine brain PREP expressed in Escherichia coli assessed as formation of 7-amido-4-methylcoumarin using Suc-Gly-Pro-amido-4-methylcoumarin as substrate preincubated for 30 mins followed by substrate addition measured after 60 mi2019ACS medicinal chemistry letters, Dec-12, Volume: 10, Issue:12
Tetrazole as a Replacement of the Electrophilic Group in Characteristic Prolyl Oligopeptidase Inhibitors.
AID709193Inhibition of PREP in human SH-SY5Y cells assessed as reduction in enzyme residual activity at 1 to 100 uM incubated for 24 hrs using Z-Gly-Pro-p-nitroanilide substrate by colorogenic activity assay2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
P2-substituted N-acylprolylpyrrolidine inhibitors of prolyl oligopeptidase: biochemical evaluation, binding mode determination, and assessment in a cellular model of synucleinopathy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (35.29)18.2507
2000's7 (41.18)29.6817
2010's4 (23.53)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: 11.46

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 Index11.46 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		3.3870pyrrole;
secondary amine
Berberine chloride (TN)
[no description available]		3.1510organic molecular entity
baicalin
[no description available]		3.1510dihydroxyflavone;
glucosiduronic acid;
glycosyloxyflavone;
monosaccharide derivative		antiatherosclerotic agent;
antibacterial agent;
anticoronaviral agent;
antineoplastic agent;
antioxidant;
cardioprotective agent;
EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
ferroptosis inhibitor;
neuroprotective agent;
non-steroidal anti-inflammatory drug;
plant metabolite;
prodrug
prolinal
[no description available]		1.9810pyrrolidines
n-benzyloxycarbonylprolylprolinal
N-benzyloxycarbonylprolylprolinal: inhibitor of prolyl endopeptidase		4.250
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		2.420amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
jtp 4819
JTP 4819: a prolyl endopeptidase inhibitor; structure given in first source		4.0340
(2s,3as,7as)-1-(((r,r)-2-phenylcyclopropyl)carbonyl)-2-((thiazolidin-3-yl)carbonyl)octahydro-1h-indole
S 17092-1: structure in first source; inhibits proline endopeptidase		3.1510
kyp 2047
[no description available]		4.4160
scopolamine hydrobromide
[no description available]		2.3920
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Confusional Senile Dementia
[description not available]		01.9910
Amnesia-Memory Loss
[description not available]		01.9910
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		01.9910
Amnesia
Pathologic partial or complete loss of the ability to recall past experiences (AMNESIA, RETROGRADE) or to form new memories (AMNESIA, ANTEROGRADE). This condition may be of organic or psychologic origin. Organic forms of amnesia are usually associated with dysfunction of the DIENCEPHALON or HIPPOCAMPUS. (From Adams et al., Principles of Neurology, 6th ed, pp426-7)		01.9910
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.0710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.110