Guanidinopropionic acid

Guanidinopropionic acid
Names
	IUPAC name 3-Carbamimidamidopropanoic acid
	Other names 3-(Diaminomethylideneamino)propanoic acid[citation needed]
Identifiers
CAS Number	353-09-3 ;
3D model (JSmol)	Interactive image;
3DMet	B00534;
Beilstein Reference	1705262
ChEBI	CHEBI:15968 ;
ChEMBL	ChEMBL20489 ;
ChemSpider	61020 ;
ECHA InfoCard	100.005.937
EC Number	206-530-0;
KEGG	C03065 ;
MeSH	guanidopropionic+acid
PubChem CID	67701;
RTECS number	AY3157500;
UNII	UL1984YRKA ;
CompTox Dashboard (EPA)	DTXSID40188795 ;
	InChI InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7) Key: KMXXSJLYVJEBHI-UHFFFAOYSA-N ;
	SMILES NC(=N)NCCC(O)=O;
Properties
Chemical formula	C4H9N3O2
Molar mass	131.135 g·mol−1
Appearance	White crystals
Odor	Odourless
log P	−1.472
Acidity (pKa)	4.219
Basicity (pKb)	9.778
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Related compounds
Related alkanoic acids	Sarcosine; Dimethylglycine; Glycocyamine; Creatine; N-Methyl-D-aspartic acid; beta-Methylamino-L-alanine; Arginine;
Related compounds	Dimethylacetamide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

β-Guanidinopropionic acid, also referred to as guanidinopropionic acid, beta-guanidinopropionic acid or β-GPA, is a dietary supplement.

β-Guanidinopropionic acid, also known as Ompenaclid (RGX-202), is being investigated in colorectal cancer by Inspirna and Merck^[2]

β-Guanidinopropionic acid is a white crystalline powder soluble in water (50 mg/ml-clear, colorless solution).^[3]

Studies on animals (rats, monkeys, hamsters) show that acidic guanidine derivatives such as β-GPA can ameliorate hyperglycemia in animal models of noninsulin-dependent diabetes.^[4]

Though the oral availability of β-GPA is well established, the basic uptake mechanism has not been studied yet.^[5]

References

^ "3-guanidinopropanoic acid (CHEBI:15968)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 20 July 2010. Main. Retrieved 26 April 2012.
^ "Pipeline – Inspirna". inspirna.com. Retrieved 2024-11-12.
^ Bergeron, R.; Ren, J. M.; Cadman, K. S.; Moore, I. K.; Perret, P.; Pypaert, M.; Young, L. H.; Semenkovich, C. F.; Shulman, G. I. (2001). "Chronic Activation of AMP Kinase Results in NRF-1 Activation and Mitochondrial Biogenesis". American Journal of Physiology. Endocrinology and Metabolism. 281 (6): E1340–E1346. doi:10.1152/ajpendo.2001.281.6.e1340. PMID 11701451. S2CID 21577702.
^ Meglasson, M. D.; Wilson, J. M.; Yu, J. H.; Robinson, D. D.; Wyse, B. M.; de Souza, C. J. (September 1993). "Antihyperglycemic Action of Guanidinoalkanoic Acids: 3-Guanidinopropionic Acid Ameliorates Hyperglycemia in Diabetic KKAy and C57BL6Job/ob Mice and Increases Glucose Disappearance in Rhesus Monkeys". The Journal of Pharmacology and Experimental Therapeutics. 266 (3): 1454–1462. PMID 8371149.
^ Metzner, L.; Dorn, M.; Markwardt, F.; Brandsch, M. (April 2009). "The Orally Active Antihyperglycemic Drug β-Guanidinopropionic Acid is Transported by the Human Proton-Coupled Amino Acid Transporter hPAT1". Molecular Pharmaceutics. 6 (3): 1006–1011. doi:10.1021/mp9000684. PMID 19358571.

[1] "3-guanidinopropanoic acid (CHEBI:15968)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 20 July 2010. Main. Retrieved 26 April 2012.

[2] "Pipeline – Inspirna". inspirna.com. Retrieved 2024-11-12.

[3] Bergeron, R.; Ren, J. M.; Cadman, K. S.; Moore, I. K.; Perret, P.; Pypaert, M.; Young, L. H.; Semenkovich, C. F.; Shulman, G. I. (2001). "Chronic Activation of AMP Kinase Results in NRF-1 Activation and Mitochondrial Biogenesis". American Journal of Physiology. Endocrinology and Metabolism. 281 (6): E1340–E1346. doi:10.1152/ajpendo.2001.281.6.e1340. PMID 11701451. S2CID 21577702.

[4] Meglasson, M. D.; Wilson, J. M.; Yu, J. H.; Robinson, D. D.; Wyse, B. M.; de Souza, C. J. (September 1993). "Antihyperglycemic Action of Guanidinoalkanoic Acids: 3-Guanidinopropionic Acid Ameliorates Hyperglycemia in Diabetic KKAy and C57BL6Job/ob Mice and Increases Glucose Disappearance in Rhesus Monkeys". The Journal of Pharmacology and Experimental Therapeutics. 266 (3): 1454–1462. PMID 8371149.

[5] Metzner, L.; Dorn, M.; Markwardt, F.; Brandsch, M. (April 2009). "The Orally Active Antihyperglycemic Drug β-Guanidinopropionic Acid is Transported by the Human Proton-Coupled Amino Acid Transporter hPAT1". Molecular Pharmaceutics. 6 (3): 1006–1011. doi:10.1021/mp9000684. PMID 19358571.

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Names

IUPAC name 3-Carbamimidamidopropanoic acid^[1]
Other names 3-(Diaminomethylideneamino)propanoic acid^{[citation needed]}
Identifiers
CAS Number	353-09-3^Y
3D model (JSmol)	Interactive image
3DMet	B00534
Beilstein Reference	1705262
ChEBI	CHEBI:15968^N
ChEMBL	ChEMBL20489^N
ChemSpider	61020^N
ECHA InfoCard	100.005.937
EC Number	206-530-0
KEGG	C03065^N
MeSH	guanidopropionic+acid
PubChem CID	67701
RTECS number	AY3157500
UNII	UL1984YRKA^Y
CompTox Dashboard (EPA)	DTXSID40188795
InChI InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)^N Key: KMXXSJLYVJEBHI-UHFFFAOYSA-N^N
SMILES NC(=N)NCCC(O)=O
Properties
Chemical formula	C₄H₉N₃O₂
Molar mass	131.135 g·mol⁻¹
Appearance	White crystals
Odor	Odourless
log P	−1.472
Acidity (pK_a)	4.219
Basicity (pK_b)	9.778
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Related compounds
Related alkanoic acids	Sarcosine Dimethylglycine Glycocyamine Creatine N-Methyl-D-aspartic acid beta-Methylamino-L-alanine Arginine
Related compounds	Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references