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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-9100000000-351fe5459bc2aa982f1dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9700000000-8fa57b59d32757572966View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9000000000-4458e96907418a84d54bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-555c4102f4a65d8aed9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9400000000-202f65d00956e051d5b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-2ba68363493ccaf36edeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-9000000000-245d3980a77046e1db8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052f-9000000000-4659c75c5d7116058d41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0089-6900000000-23e0505168600ceb154dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03k9-9000000000-04ea2687312454f3f43bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900000000-d05e3c3a923d5ffaf398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-9200000000-6b780b0080ec3851a2a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fu-9000000000-585f46f520a38f066ad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9600000000-e7ba0696feae67ecd2c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059l-9000000000-1ad5c9a7f49f2b5eab63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-28676e3aacf9b4d8ea55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-d58857401b43d8ccc8b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9000000000-5900927063e733df75f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tc-7900000000-23251cef83c81d03c926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-9b84fcc1808b7ece8370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dd976c4f7e1faaec59fdView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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 ]