Page last updated: 2024-12-06

guanidinopropionic acid

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

Description

Guanidinopropionic acid (GPA) is a naturally occurring amino acid that has been shown to have a variety of biological effects. It is a precursor to creatine, an important molecule for muscle energy production. GPA has been studied for its potential therapeutic benefits in conditions such as muscle wasting, heart failure, and neurodegenerative diseases. The synthesis of GPA involves the reaction of guanidine with propionic acid. Research into GPA is ongoing, with focus on its potential as a therapeutic agent and its role in cellular metabolism.'

guanidinopropionic acid: alters creatine metabolism; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-guanidinopropanoic acid : A guanidine compound bearing an N-(2-carboxyethyl) substituent. It is a creatine analogue that has been found to decreases plasma glucose levels [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 CID67701
CHEMBL ID20489
CHEBI ID15968
SCHEMBL ID33761
MeSH IDM0047544

Synonyms (68)

Synonym
einecs 206-530-0
3-carbamimidamidopropanoic acid
CHEBI:15968 ,
beta-gpa
3-guanidinopropanoic acid
n-[amino(imino)methyl]-beta-alanine
beta-guanidinopropionic acid
PDSP2_000137
353-09-3
C03065
guanidinopropionic acid
3-guanidinopropanoate
beta-guanadinopropionate
3-guanidinopropionic acid
PDSP1_000138
3-guanidino-propionic acid
CHEMBL20489 ,
3-(diaminomethylideneamino)propanoic acid
bdbm50021610
guanidinoproprionic-beta
pnu-10483
EN300-61035
unii-ul1984yrka
ul1984yrka ,
AKOS006223011
n-(aminomethyl)-beta-alanine
FT-0602540
gtpl4707
3-[(diaminomethylidene)amino]propanoic acid
SCHEMBL33761
ss--guanidinopropionic acid
W-106675
n-[amino(imino)methyl]-beta-alanine #
dl-.beta.-guanidino propionic acid
.beta.-alanine, n-(aminoiminomethyl)-
.beta.-guanidinopropionic acid
3-(carbamimidoylamino)propanoic acid
rgx 202 [who-dd]
oristar gpa
amidino beta-alanine [inci]
ompenaclid
amidino .beta.-alanine
n-carbamimidoyl-beta-alanine
ompenaclid [inn]
mfcd00045939
DTXSID40188795
GS-6269
3-guanidinopropionic acid, puriss., >=99.0% (nt)
beta-guanidinopropionic acid.
Q5613765
guanidino propionic acid
AMY22177
3-guanidinopropanoicacid
guanidinopropionic-acid
b-gpa
b-alanine, n-(aminoiminomethyl)-
H10255
SY066704
rgx-202; 3-guanidinopropionic acid
CS-W016544
HY-W015828
rgx-202
guanidinopropionicacid
n-amidino-beta-alanin
guanidinepropanoicacid
n-(aminoiminomethyl)-beta-alanin
n-(aminoiminomethyl)beta-alanine
Z959165114

Research Excerpts

Overview

beta-guanidinopropionic acid (GPA) is a creatine analog suggested as a treatment for hypertension, diabetes, and obesity. It has been shown to promote an AMPK-dependent increase in fatty acid utilization and aerobic capacity in mammals.

ExcerptReferenceRelevance
"Beta-guanidinopropionic acid (GPA) is a creatine analog suggested as a treatment for hypertension, diabetes, and obesity, which manifest primarily in older adults. "( Age- and time-dependent mitochondrial genotoxic and myopathic effects of beta-guanidinopropionic acid, a creatine analog, on rodent skeletal muscles.
Aiken, JM; Choi, S; Gushue, D; Herbst, A; Hoang, AN; Kim, C; McKenzie, D; Moore, TM; Wanagat, J; Zhou, J, 2023
)
1.65
"β-Guanidinopropionic acid (GPA) is an endogenous AMPK activator previously shown to improve metabolic function in young and obese mice."( Beta-guanidinopropionic acid has age-specific effects on markers of health and function in mice.
Dorigatti, JD; Ginsburg, BC; Salmon, AB; Thyne, KM, 2021
)
1.69
"β-guanidinopropionic acid (βGPA) is a commercially available dietary supplement that has been shown to promote an AMPK-dependent increase in fatty acid utilization and aerobic capacity in mammals by compromising creatine kinase function."( Dietary supplementation of β-guanidinopropionic acid (βGPA) reduces whole-body and skeletal muscle growth in young CD-1 mice.
Baumgarner, BL; Farmer, AE; Kinsey, ST; Nagle, AM; Quinn, MR, 2015
)
1.27

Effects

3-Guanidinopropionic acid has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue. It has been used in mammalian models to reduce intracellular phosphocreatine (PCr) concentration, which in turn lowers the energetic state of cells.

ExcerptReferenceRelevance
"3-Guanidinopropionic acid (1) has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue in animal models of non-insulin-dependent diabetes mellitus (NIDDM). "( Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
Burr, JE; Connell, MA; Cudahy, MM; Evans, BR; Fisher, PV; Larsen, SD; May, PD; Meglasson, MD; Robinson, DD; Stevens, FC; Tanis, SP; Tucker, JA; Vaillancourt, VA; Vidmar, TJ; Yu, JH, 2001
)
1.24
"β-guanidinopropionic acid (β-GPA) has been used in mammalian models to reduce intracellular phosphocreatine (PCr) concentration, which in turn lowers the energetic state of cells. "( The effects of dietary β-guanidinopropionic acid on growth and muscle fiber development in juvenile red porgy, Pagrus pagrus.
Alam, MS; Baumgarner, BL; Kinsey, ST; Watanabe, WO; White, DP, 2018
)
1.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
hypoglycemic agentA drug which lowers the blood glucose level.
[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 (2)

ClassDescription
zwitterionA neutral compound having formal unit electrical charges of opposite sign on non-adjacent atoms. Sometimes referred to as inner salts, dipolar ions (a misnomer).
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 (17)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.505710.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.497310.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.498810.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.504610.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.506510.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.505710.0000AID72319
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
GABA theta subunitRattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)IC50 (µMol)1.80000.00010.507510.0000AID72319
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
monoatomic ion transportProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid transportProton-coupled amino acid transporter 1Homo sapiens (human)
taurine transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
proline transportProton-coupled amino acid transporter 1Homo sapiens (human)
alanine transportProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid import across plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
glycine transportProton-coupled amino acid transporter 1Homo sapiens (human)
proline transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
proton transmembrane transportProton-coupled amino acid transporter 1Homo sapiens (human)
L-alanine transportProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
amino acid:proton symporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
proline:proton symporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
taurine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
protein bindingProton-coupled amino acid transporter 1Homo sapiens (human)
amino acid transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
alanine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
L-alanine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
L-proline transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
glycine transmembrane transporter activityProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
lysosomal membraneProton-coupled amino acid transporter 1Homo sapiens (human)
endoplasmic reticulumProton-coupled amino acid transporter 1Homo sapiens (human)
plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
apical plasma membraneProton-coupled amino acid transporter 1Homo sapiens (human)
vacuolar membraneProton-coupled amino acid transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID227430Inhibition of creatine transport was assessed from Percent inhibition of [C14] creatine uptake2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID140722Average daily dose was determined in ob/ob mice(0)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID630741Inhibition of human PAT1-mediated L-[3H]proline uptake in human Caco2 cells after 10 mins by liquid scintillation counting2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1).
AID139919Terminal body weight was determined in ob/ob mice after oral administration for two weeks (control = 53+/-1)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID139920Terminal fat body weight was determined in ob/ob mice after oral administration for two weeks (control = 28+/-0.9)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID139921Terminal lean body weight was determined in ob/ob mice after oral administration for two weeks (control = 25+/-1)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID139918Initial body weight was determined in ob/ob mice (control=55+/-1)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID9784In vitro [14C]- creatine uptake (1 mM) was determined in rat A10 smooth muscle cells at a concentration of (1 mM)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.
AID139916Initial blood glucose level was determined in ob/ob mice (control=228+/-19)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID72319Inhibition of [3H]GABA binding to Gamma-aminobutyric acid A (GABA-A) receptor of rat brain membranes1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of gamma-aminobutyric acid acting as selective GABA-A antagonists.
AID220042In vitro kinase activity (phosphorylation) of creatine kinase was determined2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.
AID139917Terminal blood glucose level was determined in ob/ob mice after oral administration for two weeks (control = 226+/-29)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID243684Percentage inhibition against tryptase at 10 uM2005Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6
Combinatorial approaches towards the discovery of new tryptase inhibitors.
AID94677In vivo blood glucose was determined in obese, hyperglycemic, hyperinsulinemic, insulin-resistant KKA mice after a dose of 500 mg/kg for 4 days2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.
AID54680Reaction rate of creatine kinase activity is determined at 100 mM concentration (relative to creatine)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
AID138250Average daily food consumption was determined in ob/ob mice after oral administration for two weeks (control = 90+/-3)2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (152)

TimeframeStudies, This Drug (%)All Drugs %
pre-199037 (24.34)18.7374
1990's60 (39.47)18.2507
2000's31 (20.39)29.6817
2010's21 (13.82)24.3611
2020's3 (1.97)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.74

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index46.74 (24.57)
Research Supply Index5.09 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index72.65 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (46.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.25%)5.53%
Reviews3 (1.88%)6.00%
Case Studies1 (0.63%)4.05%
Observational0 (0.00%)0.25%
Other154 (96.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]