1.0 2011-09-21 01:54:16 UTC 2026-03-26 16:26:23 UTC FDB029341 beta-Guanidinopropionic acid Guanidinopropionic acid (GPA), also known as guanidinopropionate or 3-guanidinopropionic acid or beta-guanidinopropionic acid, belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. GPA (C₄H₉N₃O₂) is structurally related to creatine that has been detected at low levels in mammalian tissues including blood, brain, liver, kidney, and urine, suggesting a minor endogenous origin possibly arising through transamidination reactions between arginine and β-alanine occurring in the kidney (PMID: 1312834; PMID: 33890206). Functionally, GPA acts as a competitive inhibitor of creatine transport, entering cells via the creatine transporter and reducing intracellular creatine and phosphocreatine levels, thereby disrupting the creatine kinase energy-buffering system. This induces a state of cellular energy stress, activating adaptive pathways such as AMP-activated protein kinase and promoting shifts toward oxidative metabolism, which has led to its widespread use as an experimental tool to study muscle energetics, mitochondrial function, and metabolic regulation (PMID: 33890206). In animal models, GPA administration has been associated with decreased phosphocreatine levels in muscle and heart, improved insulin sensitivity, reduced adiposity, and alterations in brown adipose tissue metabolism, although chronic exposure can impair growth and muscle function. GPA is typically synthesized chemically through reactions that introduce a guanidino group onto a propionic acid backbone using guanidine derivatives and activated intermediates. While GPA does not play a major essential physiological role in humans, it is increasingly recognized as a guanidino compound that can accumulate under conditions of impaired renal function, where it may contribute to the pool of uremic toxins (PMID: 3960241). In this context, elevated GPA levels may exacerbate metabolic disturbances by interfering with cellular energy homeostasis and contributing to mitochondrial dysfunction, highlighting its potential relevance in chronic kidney disease and related metabolic complications. 3-Guanidinopropanoate 3-Guanidinopropanoic acid 3-Guanidinopropionic acid b-GPA b-Guanidinopropionate b-Guanidinopropionic acid beta-GPA beta-Guanadinopropionate beta-Guanidinopropionate beta-Guanidinopropionic acid beta-Guanidinopropionic acid. Guanidinopropionic acid N-[amino(Imino)methyl]-b-alanine N-[amino(Imino)methyl]-beta-alanine N-[amino(Imino)methyl]-β-alanine β-gpa β-guanidinopropionate β-guanidinopropionic acid C4H9N3O2 131.1332 131.069476547 3-carbamimidamidopropanoic acid 3-guanidinopropanoic acid 353-09-3 NC(=N)NCCC(O)=O InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7) KMXXSJLYVJEBHI-UHFFFAOYSA-N belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. Guanidines Organic compounds Organic nitrogen compounds Organonitrogen compounds Guanidines Aliphatic acyclic compounds Carbonyl compounds Carboximidamides Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Carbonyl group Carboximidamide Carboxylic acid Carboxylic acid derivative Guanidine Hydrocarbon derivative Monocarboxylic acid or derivatives Organic 1,3-dipolar compound Organic oxide Organic oxygen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound guanidines Solid logp -1.70 ALOGPS logs -1.59 ALOGPS solubility 3.39e+00 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 3.98 ChemAxon pka_strongest_basic 12.62 ChemAxon iupac 3-carbamimidamidopropanoic acid ChemAxon average_mass 131.1332 ChemAxon mono_mass 131.069476547 ChemAxon smiles NC(=N)NCCC(O)=O ChemAxon formula C4H9N3O2 ChemAxon inchi InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7) ChemAxon inchikey KMXXSJLYVJEBHI-UHFFFAOYSA-N ChemAxon polar_surface_area 99.2 ChemAxon refractivity 41.42 ChemAxon polarizability 12.49 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20496 Specdb::CMs 40089 Specdb::CMs 146168 Specdb::MsIr 2871 Specdb::MsIr 2872 Specdb::MsIr 2873 Specdb::NmrOneD 99258 Specdb::NmrOneD 99259 Specdb::NmrOneD 99260 Specdb::NmrOneD 99261 Specdb::NmrOneD 99262 Specdb::NmrOneD 99263 Specdb::NmrOneD 99264 Specdb::NmrOneD 99265 Specdb::NmrOneD 99266 Specdb::NmrOneD 99267 Specdb::NmrOneD 99268 Specdb::NmrOneD 99269 Specdb::NmrOneD 99270 Specdb::NmrOneD 99271 Specdb::NmrOneD 99272 Specdb::NmrOneD 99273 Specdb::NmrOneD 99274 Specdb::NmrOneD 99275 Specdb::NmrOneD 99276 Specdb::NmrOneD 99277 Specdb::MsMs 311635 Specdb::MsMs 311636 Specdb::MsMs 311637 Specdb::MsMs 356689 Specdb::MsMs 356690 Specdb::MsMs 356691 Specdb::MsMs 439126 Specdb::MsMs 446211 Specdb::MsMs 446212 Specdb::MsMs 446213 Specdb::MsMs 446214 Specdb::MsMs 446215 Specdb::MsMs 448076 Specdb::MsMs 2245522 Specdb::MsMs 2763451 Specdb::MsMs 2763452 Specdb::MsMs 2763453 Specdb::MsMs 2942446 Specdb::MsMs 2942447 Specdb::MsMs 2942448 HMDB13222