Basic information
- CAS
352-97-6- Standard SMILES
NC(N)=NCC(=O)O- InChIKey
BPMFZUMJYQTVII-UHFFFAOYSA-N- Molecular formula
- C3H7N3O2
- Average molar mass
- 117.11 g/mol
Overview
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.
Names & identifiers
- Preferred name
- Guanidinoacetic Acid
- IUPAC
- 2-(diaminomethylideneamino)acetic acid
- English name
- Guanidineacetic acid
- Molecular formula
- C3H7N3O2
- Molecular weight
- 117.11
Names & synonyms
glycocyamineguanidinoacetic acid352-97-6Guanidineacetic acidGuanidoacetic acidN-amidinoglycineGuanyl glycineBetacyamineBetasyamineguanidinoacetateGuanidylacetic acidglycine, N-(aminoiminomethyl)-
Show more names
NSC 1901NSC 26360NSC 227847GLYCOYAMINEGlycocyaminglucocyamine
GLYCINE, N-AMIDINO-Guanidine, (carboxymethyl)-amidinoglycine2-(diaminomethylideneamino)acetic acid2-carbamimidamidoacetic acidAcetic acid, ((aminoiminomethyl)amino)-N-(aminoiminomethyl)-glycineGO52O1A04E
Database identifiers
- CAS
352-97-6- PubChem CID
- 763
- DTXSID
DTXSID50861885- ChEMBL
CHEMBL281593- ChEBI
CHEBI:16344- UNII
- GO52O1A04E
- EC Number
- 206-529-5
- Nikkaji
- J4.504G
Properties
Computed structural properties
- XLogP
- -1.6
- Topological polar surface area
- 102 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 116
Experimental & physicochemical properties
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]+
Physicochemical properties
- Melting point
- 300 °C · 300 °C(lit.)
- Boiling point
- 218.88 °C · 218.88°C (rough estimate)
- Density
- 1.402 · 1.4020 (rough estimate)
- refractive index
- 1.49 · 1.4900 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- 6 M · 6 M NaOH : 50 mg/mL, clear, colorless
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
Regulatory InformationRegulation (EC) No 1831/2003 (amended)
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)
Toxicology
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.
Chemistry & industry
Pharmacology
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
Uses & manufacturing
UsesNaturally produced by the body (endogenous). Is used as a supplement to enhance athletic performance.
Applications
UsesGuanidinoacetic Acid is an important marker for renal failure, in kidney transplantation, and for the renal metabolic activity.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
Loading…