Compounds > alanylpyrrolidine-boronic acid
Page last updated: 2024-11-12

alanylpyrrolidine-boronic acid

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

Cross-References

ID SourceID
PubMed CID10149048
CHEMBL ID63860
SCHEMBL ID8286523
MeSH IDM0280219

Synonyms (9)

Synonym
us8933056, ala-boropro
(r)-1-((s)-2-aminopropanoyl)pyrrolidin-2-ylboronic acid
bdbm50050525
alaninyl-l-boroproline
CHEMBL63860 ,
ala-boropro
SCHEMBL8286523
[(2r)-1-[(2s)-2-aminopropanoyl]pyrrolidin-2-yl]boronic acid
l-ala-l-boropro

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The adverse effects induced by boronic acid-based DPP-IV inhibitors are essentially limited to what has been observed previously for non-boronic acid inhibitors and attributed to cross-reactivity with DPP8/9."( Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
Bachovchin, WW; Chiluwal, AK; Connolly, BA; Dimare, MT; Healey, SE; Jin, Z; Lai, JH; Li, Y; Liu, Y; Maw, H; Peters, DE; Sanford, DG; Sudmeier, JL; Wu, W; Zhou, Y, 2008)		0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CPG DNA methylaseSpiroplasma monobiaeIC50 (µMol)0.00280.00280.55821.6000AID675170
Dipeptidyl peptidase 4Homo sapiens (human)IC50 (µMol)0.50280.00010.444410.0000AID287008; AID287009; AID56232; AID592141; AID592142; AID675168
Dipeptidyl peptidase 4Homo sapiens (human)Ki0.00080.00000.34142.2000AID287007; AID390968; AID393688
Prolyl endopeptidaseHomo sapiens (human)IC50 (µMol)1.00000.00111.98969.7500AID160222
Dipeptidyl peptidase 8Homo sapiens (human)IC50 (µMol)0.01300.00192.653210.0000AID675169
Dipeptidyl peptidase 8Homo sapiens (human)Ki0.00200.00150.46241.3420AID390967
Dipeptidyl peptidase 9Homo sapiens (human)IC50 (µMol)180.00140.00011.420710.0000AID390975; AID675170
Dipeptidyl peptidase 9Homo sapiens (human)Ki0.00050.00050.20621.3420AID390966
Dipeptidyl peptidase 2Homo sapiens (human)IC50 (µMol)0.06000.00020.93166.6000AID56223
Dipeptidyl peptidase 2Homo sapiens (human)Ki0.12500.00010.09380.1250AID393710
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
behavioral fear responseDipeptidyl peptidase 4Homo sapiens (human)
response to hypoxiaDipeptidyl peptidase 4Homo sapiens (human)
proteolysisDipeptidyl peptidase 4Homo sapiens (human)
cell adhesionDipeptidyl peptidase 4Homo sapiens (human)
positive regulation of cell population proliferationDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of extracellular matrix disassemblyDipeptidyl peptidase 4Homo sapiens (human)
peptide hormone processingDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated endocytosis of virus by host cellDipeptidyl peptidase 4Homo sapiens (human)
T cell costimulationDipeptidyl peptidase 4Homo sapiens (human)
regulation of cell-cell adhesion mediated by integrinDipeptidyl peptidase 4Homo sapiens (human)
locomotory exploration behaviorDipeptidyl peptidase 4Homo sapiens (human)
psychomotor behaviorDipeptidyl peptidase 4Homo sapiens (human)
T cell activationDipeptidyl peptidase 4Homo sapiens (human)
endothelial cell migrationDipeptidyl peptidase 4Homo sapiens (human)
symbiont entry into host cellDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated virion attachment to host cellDipeptidyl peptidase 4Homo sapiens (human)
negative chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
membrane fusionDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of neutrophil chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
glucagon processingDipeptidyl peptidase 4Homo sapiens (human)
proteolysisProlyl endopeptidaseHomo sapiens (human)
proteolysisDipeptidyl peptidase 8Homo sapiens (human)
apoptotic processDipeptidyl peptidase 8Homo sapiens (human)
immune responseDipeptidyl peptidase 8Homo sapiens (human)
negative regulation of programmed cell deathDipeptidyl peptidase 8Homo sapiens (human)
pyroptosisDipeptidyl peptidase 9Homo sapiens (human)
negative regulation of programmed cell deathDipeptidyl peptidase 9Homo sapiens (human)
proteolysisDipeptidyl peptidase 9Homo sapiens (human)
proteolysisDipeptidyl peptidase 2Homo sapiens (human)
lysosomal protein catabolic processDipeptidyl peptidase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
virus receptor activityDipeptidyl peptidase 4Homo sapiens (human)
protease bindingDipeptidyl peptidase 4Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
serine-type endopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
signaling receptor bindingDipeptidyl peptidase 4Homo sapiens (human)
protein bindingDipeptidyl peptidase 4Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 4Homo sapiens (human)
protein homodimerization activityDipeptidyl peptidase 4Homo sapiens (human)
chemorepellent activityDipeptidyl peptidase 4Homo sapiens (human)
serine-type endopeptidase activityProlyl endopeptidaseHomo sapiens (human)
protein bindingProlyl endopeptidaseHomo sapiens (human)
serine-type peptidase activityProlyl endopeptidaseHomo sapiens (human)
oligopeptidase activityProlyl endopeptidaseHomo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 8Homo sapiens (human)
protein bindingDipeptidyl peptidase 8Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 8Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 8Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 9Homo sapiens (human)
protein bindingDipeptidyl peptidase 9Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 9Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 9Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 9Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 2Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 2Homo sapiens (human)
serine-type exopeptidase activityDipeptidyl peptidase 2Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (22)

Processvia Protein(s)Taxonomy
extracellular regionDipeptidyl peptidase 4Homo sapiens (human)
lysosomal membraneDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
focal adhesionDipeptidyl peptidase 4Homo sapiens (human)
cell surfaceDipeptidyl peptidase 4Homo sapiens (human)
membraneDipeptidyl peptidase 4Homo sapiens (human)
apical plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
lamellipodiumDipeptidyl peptidase 4Homo sapiens (human)
endocytic vesicleDipeptidyl peptidase 4Homo sapiens (human)
lamellipodium membraneDipeptidyl peptidase 4Homo sapiens (human)
membrane raftDipeptidyl peptidase 4Homo sapiens (human)
intercellular canaliculusDipeptidyl peptidase 4Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
nucleusProlyl endopeptidaseHomo sapiens (human)
cytoplasmProlyl endopeptidaseHomo sapiens (human)
cytosolProlyl endopeptidaseHomo sapiens (human)
membraneProlyl endopeptidaseHomo sapiens (human)
cytosolProlyl endopeptidaseHomo sapiens (human)
cytoplasmDipeptidyl peptidase 8Homo sapiens (human)
cytoplasmDipeptidyl peptidase 8Homo sapiens (human)
cytosolDipeptidyl peptidase 8Homo sapiens (human)
cytosolDipeptidyl peptidase 9Homo sapiens (human)
nucleusDipeptidyl peptidase 9Homo sapiens (human)
cytosolDipeptidyl peptidase 9Homo sapiens (human)
microtubuleDipeptidyl peptidase 9Homo sapiens (human)
cell leading edgeDipeptidyl peptidase 9Homo sapiens (human)
extracellular regionDipeptidyl peptidase 2Homo sapiens (human)
Golgi apparatusDipeptidyl peptidase 2Homo sapiens (human)
azurophil granule lumenDipeptidyl peptidase 2Homo sapiens (human)
intracellular membrane-bounded organelleDipeptidyl peptidase 2Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 2Homo sapiens (human)
vesicleDipeptidyl peptidase 2Homo sapiens (human)
vesicleDipeptidyl peptidase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID390970Selectivity ratio of Ki for human recombinant DPP9 to Ki for human placental DPP42008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390976Inhibition of human recombinant DPP9 expressed in intact HEK293T cells after 2 hrs relative to Val-boroPro2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390978Reduction of glucose level in po dosed C57BL/6 mouse assessed as drug level causing maximal reduction of glucose AUC by oral glucose tolerance test2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID287009Inhibition of human placental DPP4 at pH 82007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Synthesis and characterization of constrained peptidomimetic dipeptidyl peptidase IV inhibitors: amino-lactam boroalanines.
AID390980Inhibition of human recombinant DPP9 expressed in intact HEK293T cells assessed as residual enzyme activity at 100 uM2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390975Inhibition of human recombinant DPP9 expressed in intact HEK293T cells after 2 hrs2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID675169Inhibition of human DPP8 expressed in HEK293 cells using Ala-Pro-p-nitroanilide hydrochloride salt as substrate preincubated for 10 mins prior to addition of substrate measured after 30 mins2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
4-Substituted boro-proline dipeptides: synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities.
AID390966Inhibition of human recombinant DPP9 expressed in HEK293T cells2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID675170Inhibition of human DPP9 expressed in HEK293 cells using Ala-Pro-p-nitroanilide hydrochloride salt as substrate preincubated for 10 mins prior to addition of substrate measured after 30 mins2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
4-Substituted boro-proline dipeptides: synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities.
AID592142Inhibition of DDP4 at pH 7.4 preincubated for 10 mins2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Pro-soft Val-boroPro: a strategy for enhancing in vivo performance of boronic acid inhibitors of serine proteases.
AID390973Inhibition of DPP4 in po dosed Sprague-Dawley rat plasma after 24 hrs2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID287008Inhibition of human placental DPP4 at pH 22007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Synthesis and characterization of constrained peptidomimetic dipeptidyl peptidase IV inhibitors: amino-lactam boroalanines.
AID393710Inhibition of QPP2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.
AID160222Compound was tested in vitro for inhibition of Prolyl endopeptidase1996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Structure-activity relationships of boronic acid inhibitors of dipeptidyl peptidase IV. 1. Variation of the P2 position of Xaa-boroPro dipeptides.
AID390968Inhibition of human placental DPP42008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390984Inhibition of human recombinant DPP9 expressed in HEK293T cells relative to Ala-boroPro2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID56232In vitro for inhibition of Dipeptidylpeptidase IV.1996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Structure-activity relationships of boronic acid inhibitors of dipeptidyl peptidase IV. 1. Variation of the P2 position of Xaa-boroPro dipeptides.
AID390971Reduction of glucose level in po dosed C57BL/6 mouse by oral glucose tolerance test2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390982Inhibition of human recombinant DPP9 expressed in intact HEK293T cells assessed as residual enzyme activity at 1 uM2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID287007Inhibition of human placental DPP42007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Synthesis and characterization of constrained peptidomimetic dipeptidyl peptidase IV inhibitors: amino-lactam boroalanines.
AID390979Toxicity in po dosed Sprague-Dawley rat assessed as maximum tolerated dose2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID592141Inhibition of DDP4 at pH 2 preincubated for 10 mins2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Pro-soft Val-boroPro: a strategy for enhancing in vivo performance of boronic acid inhibitors of serine proteases.
AID287010Ratio of IC50 for human placental DPP4 at pH 2 to IC50 for human placental DPP4 at pH 82007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Synthesis and characterization of constrained peptidomimetic dipeptidyl peptidase IV inhibitors: amino-lactam boroalanines.
AID675168Inhibition of human DPP4 expressed in HEK293 cells using Ala-Pro-p-nitroanilide hydrochloride salt as substrate preincubated for 10 mins prior to addition of substrate measured after 30 mins2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
4-Substituted boro-proline dipeptides: synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities.
AID393688Inhibition of DPP42009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.
AID390967Inhibition of human recombinant DPP8 expressed in HEK293T cells2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390981Inhibition of human recombinant DPP9 expressed in intact HEK293T cells assessed as residual enzyme activity at 10 uM2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390983Inhibition of human placental DPP4 after 2 hrs relative to Ala-boroPro2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390986Therapeutic index, ratio of MTD to drug level causing maximal reduction of glucose AUC in po dosed Sprague-Dawley rat2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390985Toxicity in po dosed Sprague-Dawley rat assessed as maximum tolerated dose relative to Val-boroPro2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID56223Compound was tested in vitro for inhibition of Dipeptidylpeptidase II1996Journal of medicinal chemistry, May-10, Volume: 39, Issue:10
Structure-activity relationships of boronic acid inhibitors of dipeptidyl peptidase IV. 1. Variation of the P2 position of Xaa-boroPro dipeptides.
AID390969Selectivity ratio of Ki for human recombinant DPP8 to Ki for human placental DPP42008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
AID390977Inhibition of human recombinant DPP9 expressed in intact HEK293T cells assessed as residual enzyme activity at 1 mM2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potency and in vivo efficacy and safety.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's3 (50.00)29.6817
2010's2 (33.33)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: 12.79

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 Index12.79 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
vildagliptin
[no description available]		3.1410amino acid amide
talabostat
talabostat: an antineoplastic agent; structure in first source		2.9440
nvp-dpp728
[no description available]		3.1410
bms 477118
[no description available]		3.1410adamantanes;
azabicycloalkane;
monocarboxylic acid amide;
nitrile;
tertiary alcohol		EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
hypoglycemic agent
ConditionIndicatedRelationship StrengthStudiesTrials
Adverse Drug Event
[description not available]		02.0410
Drug-Related Side Effects and Adverse Reactions
Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.		02.0410
Diabetes Mellitus, Adult-Onset
[description not available]		03.3820
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		03.3820