Grundinformationen
- CAS
352-97-6- Standard-SMILES
NC(N)=NCC(=O)O- InChIKey
BPMFZUMJYQTVII-UHFFFAOYSA-N- Summenformel
- C3H7N3O2
- Durchschnittliche Molmasse
- 117,11 g/mol
Überblick
Guanidinoacetic acid is the N-amidino derivative of glycine. It has a role as a nutraceutical, a mouse metabolite, a bacterial metabolite, a human metabolite and a rat metabolite. It is a conjugate acid of a guanidinoacetate. It is a tautomer of a guanidinoacetic acid zwitterion.
Namen und Bezeichner
- Bevorzugter Name
- Guanidinoacetic Acid
- IUPAC
- 2-(diaminomethylideneamino)acetic acid
- Lokaler Name
- Guanidinoessigsure
- Englischer Name
- Guanidineacetic acid
- Summenformel
- C3H7N3O2
- Molmasse
- 117.11
Namen und Synonyme
glycocyamineguanidinoacetic acid352-97-6Guanidineacetic acidGuanidoacetic acidN-amidinoglycineGuanyl glycineBetacyamineBetasyamineguanidinoacetateGuanidylacetic acidglycine, N-(aminoiminomethyl)-
Weitere Namen anzeigen
NSC 1901NSC 26360NSC 227847GLYCOYAMINEGlycocyaminglucocyamine
GLYCINE, N-AMIDINO-Guanidine, (carboxymethyl)-amidinoglycine2-(diaminomethylideneamino)acetic acid2-carbamimidamidoacetic acidAcetic acid, ((aminoiminomethyl)amino)-N-(aminoiminomethyl)-glycineGO52O1A04E
Datenbank-Bezeichner
- CAS
352-97-6- PubChem CID
- 763
- DTXSID
DTXSID50861885- ChEMBL
CHEMBL281593- ChEBI
CHEBI:16344- UNII
- GO52O1A04E
- EC Number
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,6
- Polarare Oberfläche (TPSA)
- 102 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 116
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Solubility3.6 mg/mL at 15 °C
Physical DescriptionSolid
Collision Cross Section
134.6 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
124.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
126.88 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
134.4 Ų [M+Na]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 300 °C · 300 °C(lit.)
- Siedepunkt
- 218.88 °C · 218.88°C (rough estimate)
- Dichte
- 1.402 · 1.4020 (rough estimate)
- Brechungsindex
- 1.49 · 1.4900 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- Löslichkeit
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (1 of 46) of reports.
Warning
H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationRegulation (EC) No 1831/2003 (amended)
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)
Toxikologische Informationen
Treatment
Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
Health Effects
Acute exposure to guanidoacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of guanidoacetic acid are associated with at least 4 inborn errors of metabolism including: Argininemia, Guanidinoacetate methyltransferase deficiency, Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) and S-Adenosylhomocysteine (SAH) Hydrolase Deficiency.
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Guanidino acetic acid (GAA) is synthesized in the liver and kidney from Arg and Gly and subsequently methylated by S-adenosylmethionine to form creatine. The conversion of guaniodacetate to creatinine in the liver causes a depletion of methyl groups. This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems.
MeSH Pharmacological Classification
Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Verwendung und Herstellung
UsesNaturally produced by the body (endogenous). Is used as a supplement to enhance athletic performance.
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