Showing metabocard for Beta-Guanidinopropionic acid (BMDB0096043)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-10 17:00:16 UTC
Update Date2026-03-26 16:20:27 UTC
BMDB IDBMDB0096043
Secondary Accession Numbers
  • BMDB96043
Metabolite Identification
Common NameBeta-Guanidinopropionic acid
DescriptionGuanidinopropionic 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-GuanidinopropanoateChEBI
beta-GPAChEBI
N-[Amino(imino)methyl]-beta-alanineChEBI
Guanidinopropionic acidKegg
3-Guanidinopropanoic acidGenerator
b-GPAGenerator
Β-gpaGenerator
N-[Amino(imino)methyl]-b-alanineGenerator
N-[Amino(imino)methyl]-β-alanineGenerator
GuanidinopropionateGenerator
b-GuanidinopropionateGenerator
b-Guanidinopropionic acidGenerator
beta-GuanidinopropionateGenerator
Β-guanidinopropionateGenerator
Β-guanidinopropionic acidGenerator
3-Guanidinopropionic acidHMDB
beta-GuanadinopropionateHMDB
beta-Guanidinopropionic acid.HMDB
beta-Guanidine propionic acidMeSH, HMDB
Guanidine propionateMeSH, HMDB
beta-Guanidinopropionic acidChEBI
Amidino beta-alanineMeSH
Chemical FormulaC4H9N3O2
Average Molecular Weight131.1332
Monoisotopic Molecular Weight131.069476547
IUPAC Name3-carbamimidamidopropanoic acid
Traditional Name3-guanidinopropanoic acid
CAS Registry NumberNot Available
SMILES
NC(=N)NCCC(O)=O
InChI Identifier
InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)
InChI KeyKMXXSJLYVJEBHI-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative Parents
Substituents
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.7ALOGPS
logP-2.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)12.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.2 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.42 m³·mol⁻¹ChemAxon
Polarizability12.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0013222
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029341
KNApSAcK IDNot Available
Chemspider ID61020
KEGG Compound IDC03065
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanidinopropionic_acid
METLIN IDNot Available
PubChem Compound67701
PDB IDNot Available
ChEBI ID15968
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thomas G, Ramwell PW: Identification of guanidino succinate as a putative endogenous source of the endothelium derived relaxing factor. Biochem Biophys Res Commun. 1992 Mar 16;183(2):584-9. doi: 10.1016/0006-291x(92)90522-m. [PubMed:1312834 ]
  2. Dorigatti JD, Thyne KM, Ginsburg BC, Salmon AB: Beta-guanidinopropionic acid has age-specific effects on markers of health and function in mice. Geroscience. 2021 Jun;43(3):1497-1511. doi: 10.1007/s11357-021-00372-8. Epub 2021 Apr 23. [PubMed:33890206 ]
  3. Gurreri G, Ghiggeri G, Salvidio G, Garibotto G, Robaudo C, Deferrari G: Effects of hemodialysis on guanidinopropionic acid metabolism. Nephron. 1986;42(4):295-7. doi: 10.1159/000183691. [PubMed:3960241 ]