Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H9N3O2 |
| Molecular Weight | 131.1332 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=N)NCCC(O)=O
InChI
InChIKey=KMXXSJLYVJEBHI-UHFFFAOYSA-N
InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)
| Molecular Formula | C4H9N3O2 |
| Molecular Weight | 131.1332 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of creatine and β-guanidinopropionic acid and alterations in creatine transporter and creatine kinases expression in acute seizure and chronic epilepsy models. | 2010-10-28 |
|
| Impairment of PGC-1alpha expression, neuropathology and hepatic steatosis in a transgenic mouse model of Huntington's disease following chronic energy deprivation. | 2010-08-15 |
|
| Amino acid derivatives from Lucilia sericata excretions/secretions may contribute to the beneficial effects of maggot therapy via increased angiogenesis. | 2010-03 |
|
| Na(+)/Cl(-)/creatine transporter activity and expression in rat brain synaptosomes. | 2010-01-13 |
|
| Could early ischemic arrhythmia triggered by purinergic activation of the transient receptor potential channels be prevented by creatine? | 2010 |
|
| Guanidino acids act as rho1 GABA(C) receptor antagonists. | 2009-10 |
|
| Impaired PGC-1alpha function in muscle in Huntington's disease. | 2009-08-15 |
|
| Muscle-specific differences in the response of mitochondrial proteins to beta-GPA feeding: an evaluation of potential mechanisms. | 2009-06 |
|
| The orally active antihyperglycemic drug beta-guanidinopropionic acid is transported by the human proton-coupled amino acid transporter hPAT1. | 2009-04-11 |
|
| [Effects of creatine phosphokinase competitive inhibitor on system and tissue energy metabolism in rats in the norm and during unloading]. | 2009-01-15 |
|
| Decreasing intramuscular phosphagen content simultaneously increases plasma membrane FAT/CD36 and GLUT4 transporter abundance. | 2008-09 |
|
| Accumulation of methylguanidine and changes in guanidino compound levels in plasma, urine, and kidneys of furosemide-treated rats. | 2008-06 |
|
| LKB1 and AMPK and the regulation of skeletal muscle metabolism. | 2008-05 |
|
| Metabolic transformation of rabbit skeletal muscle cells in primary culture in response to low glucose. | 2008-05 |
|
| Arginine and glycine stimulate creatine synthesis in creatine transporter 1-deficient lymphoblasts. | 2008-04-01 |
|
| In vivo effects of myocardial creatine depletion on left ventricular function morphology and lipid metabolism: study in a mouse model. | 2008-03 |
|
| Cardiac structure and function during ageing in energetically compromised Guanidinoacetate N-methyltransferase (GAMT)-knockout mice - a one year longitudinal MRI study. | 2008-02-06 |
|
| Ontogeny up-regulates renal Na(+)/Cl(-)/creatine transporter in rat. | 2007-11 |
|
| BVT.3531 reduces body weight and activates K(ATP) channels in isolated arcuate neurons in rats. | 2007-06-07 |
|
| In vivo effects of myocardial creatine depletion on left ventricular function, morphology, and energy metabolism--consequences in acute myocardial infarction. | 2007-04 |
|
| Aging-associated reductions in AMP-activated protein kinase activity and mitochondrial biogenesis. | 2007-02 |
|
| Electrolysis stimulates creatine transport and transporter cell surface expression in incubated mouse skeletal muscle: potential role of ROS. | 2006-12 |
|
| The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds. | 2006-11-03 |
|
| Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds. | 2006-09-11 |
|
| Possible role of creatine concentrations in the brain in regulating appetite and weight. | 2006-07-26 |
|
| Overexpression of wild-type creatine transporter (SLC6A8) restores creatine uptake in primary SLC6A8-deficient fibroblasts. | 2006-06-10 |
|
| Increased resistance to fatigue in creatine kinase deficient muscle is not due to improved contractile economy. | 2006-06 |
|
| Increased guanidino species in murine and human succinate semialdehyde dehydrogenase (SSADH) deficiency. | 2006-04 |
|
| Pseudomonas aeruginosa PAO1 genes for 3-guanidinopropionate and 4-guanidinobutyrate utilization may be derived from a common ancestor. | 2005-12 |
|
| Novel parent structures for inhibitors of the murine GABA transporters mGAT3 and mGAT4. | 2005-09-05 |
|
| Activation of hypothalamic ATP-sensitive K+ channels by the aminoguanidine carboxylate BVT.12777. | 2005-04 |
|
| Possible involvement of glutamic and/or aspartic acid residue(s) and requirement of mitochondrial integrity for the protective effect of creatine against inhibition of cardiac mitochondrial respiration by methylglyoxal. | 2005-03 |
|
| Plasma protein aspartyl damage is increased in hemodialysis patients: studies on causes and consequences. | 2004-10 |
|
| The aminoguanidine carboxylate BVT.12777 activates ATP-sensitive K+ channels in the rat insulinoma cell line, CRI-G1. | 2004-08-24 |
|
| Taurine-induced long-lasting potentiation in the rat hippocampus shows a partial dissociation from total hippocampal taurine content and independence from activation of known taurine transporters. | 2004-06 |
|
| Functional characterization of sodium- and chloride-dependent taurine transport in human keratinocytes. | 2004-03 |
|
| Effect of muscle creatine content manipulation on contractile properties in mouse muscles. | 2004-03 |
|
| Stimulation of HSP72 expression following ATP depletion and short-term exercise training in fast-twitch muscle. | 2004-01 |
|
| Metabolic modulation of muscle fiber properties unrelated to mechanical stimuli. | 2003-12 |
|
| Anti-inflammatory activity of creatine supplementation in endothelial cells in vitro. | 2003-06 |
|
| Muscle creatine uptake and creatine transporter expression in response to creatine supplementation and depletion. | 2003-06 |
|
| Inhibition of the mitochondrial permeability transition by creatine kinase substrates. Requirement for microcompartmentation. | 2003-05-16 |
|
| A role for guanidino compounds in the brain. | 2003-02 |
|
| Creatine transporter activity and content in the rat heart supplemented by and depleted of creatine. | 2003-02 |
|
| AMP kinase is required for mitochondrial biogenesis in skeletal muscle in response to chronic energy deprivation. | 2002-12-10 |
|
| Effect of creatine manipulation on fast-twitch skeletal muscle of the mouse. | 2002-12 |
|
| Human, rat and chicken small intestinal Na+ - Cl- -creatine transporter: functional, molecular characterization and localization. | 2002-11-15 |
|
| The blood-brain barrier creatine transporter is a major pathway for supplying creatine to the brain. | 2002-11 |
|
| Effects of creatine loading and depletion on rat skeletal muscle contraction. | 2002-10 |
|
| Mitochondrial intermembrane inclusion bodies: the common denominator between human mitochondrial myopathies and creatine depletion, due to impairment of cellular energetics. | 1997-09 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:59:56 GMT 2025
by
admin
on
Mon Mar 31 17:59:56 GMT 2025
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| Record UNII |
UL1984YRKA
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| Record Status |
Validated (UNII)
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| Record Version |
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DSLD |
1758 (Number of products:1)
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12181
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67701
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DTXSID40188795
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Guanidinopropionic acid
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206-530-0
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C153354
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300000050177
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353-09-3
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UL1984YRKA
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LM-162
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