Page last updated: 2024-11-07

acetylphenylalanyl-prolyl-boroarginine

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

Description

Ac-(D)Phe-Pro-boroArg-OH : A C-terminal boronic acid petide that is N-acetyl-D-phenylalanyl-L-prolyl-L-arginine in which the C-termnal carboxy group has been replaced by a borono (-B(OH)2) group. A thrombin (Factor IIa) inhibitor, thereby acting as an anticoagulant. [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]

DuP-714 : A hydrochloride resulting from the formal reaction of equimolar amounts of Ac-(D)Phe-Pro-boroArg-OH and hydrogen chloride. A thrombin (Factor IIa) inhibitor, thereby acting as an anticoagulant. [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 CID122296
CHEMBL ID290376
CHEBI ID42142
SCHEMBL ID4454615
MeSH IDM0181405

Synonyms (23)

Synonym
ac-(d)phe-pro-boroarg-oh
acetylphenylalanyl-prolyl-boroarginine
ac-phe-pro-boroarg-oh
l-prolinamide, n-acetyl-d-phenylalanyl-n-(4-((aminoiminomethyl)amino)-1-boronobutyl)-, (s)-
dup-714
dup 714
130982-43-3
CHEMBL290376 ,
[(1r)-1-[[(2s)-1-[(2r)-2-acetamido-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-4-(diaminomethylideneamino)butyl]boronic acid
1-(2-acetylamino-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid (1-dihydroxyboranyl-4-guanidino-butyl)-amide
bdbm50288406
dup714
gtpl8760
SCHEMBL4454615
bdbm50451005
DTXSID70156826
n-acetyl-d-phenylalanyl-n-[(1r)-4-carbamimidamido-1-(dihydroxyboranyl)butyl]-l-prolinamide
n-acetyl-d-phenylalanyl-n-[(1r)-1-borono-4-carbamimidamidobutyl]-l-prolinamide
CHEBI:42142
Q27077128
130982-43-3 (free base)
((r)-1-((s)-1-((r)-2-acetamido-3-phenylpropanoyl)pyrrolidine-2-carboxamido)-4-((diaminomethylene)amino)butyl)boronic acid
AKOS040748288

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Therefore, although bioavailability cannot be estimated, it is demonstrated that this peptide analog was absorbed by each of these routes."( Anticoagulant activity of a peptide boronic acid thrombin inhibitor by various routes of administration in rats.
Aungst, BJ; Hussain, MA; Kettner, C; Knabb, R,
)
0.13
" administration of DuP 714, as well as the percent bioavailability after oral administration of the agent."( Analysis of the thrombin inhibitor DuP 714 by an enzyme-linked immunosorbent assay.
Christ, DD; Farmer, AR; Knabb, RM; Mitchell, TJ; Reilly, TM, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
EC 3.4.21.5 (thrombin) inhibitorAn EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC 3.4.21.5).
anticoagulantAn agent that prevents blood clotting.
[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 (3)

ClassDescription
C-terminal boronic acid peptideA member of the class of boronic acids that is any peptide in which the carboxy group at the C-terminus has been replaced by a borono (-B(OH)2) group.
acetamidesCompounds with the general formula RNHC(=O)CH3.
guanidinesAny organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ProthrombinHomo sapiens (human)Ki0.00000.00000.78469.0000AID211182; AID211596; AID51156
Trypsin-1Homo sapiens (human)Ki0.00450.00001.76768.9000AID213343; AID215748
[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)
ProthrombinHomo sapiens (human)Kd0.00000.00000.01010.0387AID211568
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
positive regulation of protein phosphorylationProthrombinHomo sapiens (human)
proteolysisProthrombinHomo sapiens (human)
acute-phase responseProthrombinHomo sapiens (human)
cell surface receptor signaling pathwayProthrombinHomo sapiens (human)
G protein-coupled receptor signaling pathwayProthrombinHomo sapiens (human)
blood coagulationProthrombinHomo sapiens (human)
positive regulation of cell population proliferationProthrombinHomo sapiens (human)
regulation of cell shapeProthrombinHomo sapiens (human)
response to woundingProthrombinHomo sapiens (human)
negative regulation of platelet activationProthrombinHomo sapiens (human)
platelet activationProthrombinHomo sapiens (human)
regulation of blood coagulationProthrombinHomo sapiens (human)
positive regulation of blood coagulationProthrombinHomo sapiens (human)
positive regulation of cell growthProthrombinHomo sapiens (human)
positive regulation of insulin secretionProthrombinHomo sapiens (human)
positive regulation of collagen biosynthetic processProthrombinHomo sapiens (human)
fibrinolysisProthrombinHomo sapiens (human)
negative regulation of proteolysisProthrombinHomo sapiens (human)
positive regulation of receptor signaling pathway via JAK-STATProthrombinHomo sapiens (human)
negative regulation of astrocyte differentiationProthrombinHomo sapiens (human)
positive regulation of release of sequestered calcium ion into cytosolProthrombinHomo sapiens (human)
regulation of cytosolic calcium ion concentrationProthrombinHomo sapiens (human)
cytolysis by host of symbiont cellsProthrombinHomo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionProthrombinHomo sapiens (human)
negative regulation of fibrinolysisProthrombinHomo sapiens (human)
antimicrobial humoral immune response mediated by antimicrobial peptideProthrombinHomo sapiens (human)
neutrophil-mediated killing of gram-negative bacteriumProthrombinHomo sapiens (human)
positive regulation of lipid kinase activityProthrombinHomo sapiens (human)
negative regulation of cytokine production involved in inflammatory responseProthrombinHomo sapiens (human)
positive regulation of protein localization to nucleusProthrombinHomo sapiens (human)
positive regulation of phospholipase C-activating G protein-coupled receptor signaling pathwayProthrombinHomo sapiens (human)
ligand-gated ion channel signaling pathwayProthrombinHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processProthrombinHomo sapiens (human)
digestionTrypsin-1Homo sapiens (human)
extracellular matrix disassemblyTrypsin-1Homo sapiens (human)
proteolysisTrypsin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
lipopolysaccharide bindingProthrombinHomo sapiens (human)
serine-type endopeptidase activityProthrombinHomo sapiens (human)
signaling receptor bindingProthrombinHomo sapiens (human)
calcium ion bindingProthrombinHomo sapiens (human)
protein bindingProthrombinHomo sapiens (human)
growth factor activityProthrombinHomo sapiens (human)
heparin bindingProthrombinHomo sapiens (human)
thrombospondin receptor activityProthrombinHomo sapiens (human)
serine-type endopeptidase activityTrypsin-1Homo sapiens (human)
metal ion bindingTrypsin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
external side of plasma membraneProthrombinHomo sapiens (human)
collagen-containing extracellular matrixProthrombinHomo sapiens (human)
extracellular regionProthrombinHomo sapiens (human)
extracellular spaceProthrombinHomo sapiens (human)
endoplasmic reticulum lumenProthrombinHomo sapiens (human)
Golgi lumenProthrombinHomo sapiens (human)
plasma membraneProthrombinHomo sapiens (human)
extracellular exosomeProthrombinHomo sapiens (human)
blood microparticleProthrombinHomo sapiens (human)
collagen-containing extracellular matrixProthrombinHomo sapiens (human)
extracellular spaceProthrombinHomo sapiens (human)
extracellular regionTrypsin-1Homo sapiens (human)
collagen-containing extracellular matrixTrypsin-1Homo sapiens (human)
blood microparticleTrypsin-1Homo sapiens (human)
extracellular spaceTrypsin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID211568Binding affinity against Thrombin.2000Journal of medicinal chemistry, Feb-10, Volume: 43, Issue:3
Protease inhibitors: current status and future prospects.
AID51156Inhibition of Coagulation factor II1999Bioorganic & medicinal chemistry letters, Apr-05, Volume: 9, Issue:7
Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors.
AID213343Inhibitory activity against trypsin1999Bioorganic & medicinal chemistry letters, Apr-05, Volume: 9, Issue:7
Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors.
AID211596Inhibition of compound against thrombin mediated platelet activation and fibrinogen cleavage.2000Journal of medicinal chemistry, Feb-10, Volume: 43, Issue:3
Protease inhibitors: current status and future prospects.
AID182812Effect on thrombus weight in rat vena cava thrombosis model (iv administration)1999Bioorganic & medicinal chemistry letters, Apr-05, Volume: 9, Issue:7
Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors.
AID72518Inhibition of factor Xa1999Bioorganic & medicinal chemistry letters, Apr-05, Volume: 9, Issue:7
Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors.
AID215748Binding affinity against Trypsin2000Journal of medicinal chemistry, Feb-10, Volume: 43, Issue:3
Protease inhibitors: current status and future prospects.
AID211182Inhibition constant for binding with thrombin was determined1993Journal of medicinal chemistry, Jun-25, Volume: 36, Issue:13
The solution conformation of (D)Phe-Pro-containing peptides: implications on the activity of Ac-(D)Phe-Pro-boroArg-OH, a potent thrombin inhibitor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's25 (86.21)18.2507
2000's4 (13.79)29.6817
2010's0 (0.00)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: 10.71

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 Index10.71 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other27 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]