Page last updated: 2024-11-11

valyl-prolyl-proline

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

Description

Val-Pro-Pro : A tripeptide composed of L-valine and two L-proline units joined by peptide linkages. [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 CID9818200
CHEMBL ID190414
CHEBI ID73696
SCHEMBL ID1644894
MeSH IDM0471978

Synonyms (27)

Synonym
bdbm50169128
(s)-1-[(s)-1-((s)-2-amino-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid
chebi:73696 ,
CHEMBL190414 ,
l-val-l-pro-l-pro
v-p-p
l-valyl-l-prolyl-l-proline
val-pro-pro
h-val-pro-pro-oh
58872-39-2
AKOS016014020
valine-proline-proline
l-proline, l-valyl-l-prolyl-
vpp peptide
l-proline, 1-(1-l-valyl-l-prolyl)-
2u1r84870f ,
unii-2u1r84870f
SCHEMBL1644894
c15h25n3o4
(s)-1-((s)-1-((s)-2-amino-3-methylbutanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid
mfcd08458654
(2s)-1-[(2s)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
valyl-prolyl-proline
Q27143860
HY-114161
CS-0077520
l-valyl-l-prolyl-l-proline; l-proline,1-(1-l-valyl-l-prolyl)-

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" These studies showed that there were no adverse effects of treatment at the highest doses tested."( A 90-day subchronic toxicity study and reproductive toxicity studies on ACE-inhibiting lactotripeptide.
Braun, WH; Dent, MP; Marburger, A; O'Hagan, S; Schaetti, P; Vogel, O, 2007
)
0.34

Pharmacokinetics

ExcerptReferenceRelevance
" The aim of this study was to characterize the pharmacokinetic behavior of IPP, LPP, and VPP in a conscious pig model."( Pharmacokinetics of proline-rich tripeptides in the pig.
Deutz, NE; Duchateau, GS; Kies, AK; Ten Have, GA; van der Pijl, PC, 2008
)
0.35

Bioavailability

ExcerptReferenceRelevance
"The utilization of the membrane transport protein PEPT1 as a drug delivery system is a promising strategy to enhance the oral bioavailability of drugs."( Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1.
Biegel, A; Brandsch, M; Gebauer, S; Hartrodt, B; Neubert, K; Thondorf, I, 2005
)
0.33
"VPP peptide did not prevent ovariectomy-induced bone loss, which could be due to the poor bioavailability of VPP from water solution."( Effects of bioactive peptide, valyl-prolyl-proline (VPP), and lactobacillus helveticus fermented milk containing VPP on bone loss in ovariectomized rats.
Halleen, J; Korpela, R; Narva, M; Rissanen, J; Väänänen, K; Vapaatalo, H, 2007
)
0.63
"IPP and VPP were poorly absorbed and rapidly eliminated."( The lactotripeptides isoleucine-proline-proline and valine-proline-proline do not inhibit the N-terminal or C-terminal angiotensin converting enzyme active sites in humans.
Azizi, M; Blanchard, A; Lalanne, F; Peyrard, S; Wuerzner, G, 2009
)
0.35
" CasH prolonged portal bioavailability with 18 min (absorption half-life, synthetic XPP: 15 ± 2 min, CasH: 33 ± 3 min, p<0."( Enhanced Lacto-Tri-Peptide Bio-Availability by Co-Ingestion of Macronutrients.
Deutz, NE; Kies, AK; Ten Have, GA; van der Pijl, PC, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" Similarly, ophthalmic changes (lenticular clouding) were observed in both control and dosed animals."( Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyl-L-proline): V. A 13-week toxicity study of tripeptides-containing casein hydrolysate in male and female rats.
Bernard, BK; Matsuura, K; Mennear, JH; Mizuno, S, 2005
)
0.33
" This study included direct dosing of the neonates, and was designed specifically to investigate renal development and to ensure that the bioactive peptides were not associated with the same type of fetopathy exhibited by ACE inhibiting drugs."( A 90-day subchronic toxicity study and reproductive toxicity studies on ACE-inhibiting lactotripeptide.
Braun, WH; Dent, MP; Marburger, A; O'Hagan, S; Schaetti, P; Vogel, O, 2007
)
0.34
" The present study was designed as a randomized, double-blind, parallel-group, dose-response trial: 166 subjects (>140/90 mmHg) received placebo during a 2-week run-in, 8-weeks intervention followed by a 2-week washout."( Dose-dependent lowering of blood pressure by dairy peptides in mildly hypertensive subjects.
de Leeuw, PW; Koning, MM; Kroon, AA; Rennenberg, RM; van der Zander, K, 2009
)
0.35
"In a double-blind parallel group intervention study, 89 hypertensive subjects received daily peptide milk containing a low dose of tripeptides (5 mg/day) for 12 weeks and a high dose (50 mg/day) for the following 12 weeks, or a placebo milk drink to titrate the dose-response effect."( Long-term intervention with Lactobacillus helveticus fermented milk reduces augmentation index in hypertensive subjects.
Groop, PH; Jauhiainen, T; Kautiainen, H; Korpela, R; Rönnback, M; Vapaatalo, H; Wuolle, K, 2010
)
0.36
" The authors recently evaluated BP response using 24-hour ambulatory BP monitoring and office BP monitoring of lactotripeptides dosed twice daily in 91 previously treated and treatment-naive patients with stage 1 and stage 2 hypertension."( The impact of lactotripeptides on blood pressure response in stage 1 and stage 2 hypertensives.
Germino, FW; Hendler, SS; Neutel, J; Nonaka, M, 2010
)
0.36
" Their acute effects on BP and vascular function, important for daily dosing scheme, were studied in a placebo-controlled double-blind crossover study using a single oral dose of a fermented milk product containing Ile-Pro-Pro and Val-Pro-Pro as well as plant sterols."( Ile-Pro-Pro and Val-Pro-Pro tripeptide-containing milk product has acute blood pressure lowering effects in mildly hypertensive subjects.
Ehlers, PI; Filler, I; Jähnchen, E; Järvenpää, S; Kivimäki, AS; Korpela, R; Turpeinen, AM; Vapaatalo, H; Wagner, F; Wiegert, E, 2011
)
0.37
[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
tripeptideAny oligopeptide that consists of three 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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Angiotensin-converting enzymeOryctolagus cuniculus (rabbit)IC50 (µMol)9.00000.00001.612910.0000AID608775
Solute carrier family 15 member 1Homo sapiens (human)Ki100.00000.18003.39339.8000AID238858
Solute carrier family 15 member 2Homo sapiens (human)Ki22.95440.79434.22108.0000AID612540
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
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 (5)

Processvia Protein(s)Taxonomy
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 (6)

Processvia Protein(s)Taxonomy
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 (3)

Assay IDTitleYearJournalArticle
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.
AID608775Inhibition of rabbit lung ACE preincubated for 5 mins by spectrophotometric assay2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Angiotensin-I-converting enzyme inhibitory peptides: Chemical feature based pharmacophore generation.
AID238858Binding affinity against membrane transport protein PEPT1 in human Caco-2 cells2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (84)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's38 (45.24)29.6817
2010's43 (51.19)24.3611
2020's3 (3.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.16

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 Index22.16 (24.57)
Research Supply Index4.70 (2.92)
Research Growth Index4.49 (4.65)
Search Engine Demand Index17.79 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials24 (28.24%)5.53%
Reviews7 (8.24%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other54 (63.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]