Compound: Aminooxyacetic acid
SMILES: O=C(O)CON
InChIKey: NQRKYASMKDDGHT-UHFFFAOYSA-N
Synonyms: Aminooxyacetic acid, 645-88-5, 2-(Aminooxy)acetic acid, (aminooxy)acetic acid, AOAA, aminoxyacetic acid, 2-aminooxyacetic acid, Carboxymethoxyamine, (Carboxymethoxy)amine, ACETIC ACID, (AMINOOXY)-, (o-Carboxymethyl)hydroxylamine, u-7524, 14I68GI3OQ, CHEBI:40823, DTXSID50214756, Acid, Aminooxyacetic, RefChem:112056, DTXCID80137247, Aminooxy-acetic acid, carboxymethoxylamine, Acetic acid,2-(aminooxy)-, AOA hemihydrochloride, AOA, Hydroxylamine, O-(carboxymethyl)-, AOA; AOAA; U 7524; alpha-Aminooxyacetic acid, BRN 0878238, UNII-14I68GI3OQ, U 7524, aminoxy-acetic acid, amino-oxyacetic acid, 2-aminooxyethanoic acid, 2-(Aminooxy)aceticacid, Acetic acid, aminooxy-, 2-(aminoxy)acetic acid, hydroxylamine acetic acid, Lopac-A-4508, Methoxyamine, 1-carboxy-, Lopac0_000007, SCHEMBL98144, Aminooxyacetic acid hydrochoride, CHEMBL347862, GTPL5136, orb1699080, SCHEMBL1091691, SCHEMBL8782152, SCHEMBL9185924, EBC-48195, EX-A11789, STL197511, AKOS015919037, AT14480, CCG-204103, DB02079, FA01375, HY-107994A, SB38109, SDCCGSBI-0049996.P002, NCGC00015058-01, NCGC00015058-02, NCGC00015058-03, NCGC00015058-04, NCGC00162041-01, DB-346235, AOA; AOAA; U 7524; -Aminooxyacetic acid, CS-0031154, NS00069916, EN300-40734, AB00172543-06, SR-01000075676, Q4746466, SR-01000075676-1, 396FBBC5-D28E-448C-A696-BF9163EA8B1A, Carboxymethoxylamine hemihydrochloride,Aminooxyacetate hemihydrochloride
Theoretical properties:
molecular_formula: C2H5NO3
molecular_weight: 91.07 g/mol
exact_mass: 91.026943022 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 6
topological_polar_surface_area: 72.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "(aminooxy)acetic acid is a member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity in vivo, resulting in increased levels of gamma-aminobutyric acid in tissues. It has a role as an anticonvulsant, an EC 4.2.1.22 (cystathionine beta-synthase) inhibitor, an EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor and a nootropic agent. It is a member of hydroxylamines, a monocarboxylic acid and an amino acid. It is a conjugate acid of an (aminooxy)acetate.", "chebi": "A member of the class of hydroxylamines that is acetic acid substituted at postion 2 by an aminooxy group. It is a compound which inhibits aminobutyrate aminotransferase activity <em>in vivo</em>, resulting in increased levels of \u03b3-aminobutyric acid in tissues.", "chembl": "CARBOXYMETHOXYLAMINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Aminooxyacetic acid, often abbreviated AOA or AOAA, is a compound that inhibits 4-aminobutyrate aminotransferase (GABA-T) activity in vitro and in vivo, leading to less gamma-aminobutyric acid (GABA) being broken down. Subsequently, the level of GABA  is increased in tissues. At concentrations high enough to fully inhibit 4-aminobutyrate aminotransferase activity, aminooxyacetic acid is indicated as a useful tool to study regional GABA turnover in rats.\nAminooxyacetic acid is a general inhibitor of pyridoxal phosphate (PLP)-dependent enzymes (this includes GABA-T). It functions as an inhibitor by attacking the Schiff base linkage between PLP and the enzyme, forming oxime type complexes.\nAminooxyacetic acid inhibits aspartate aminotransferase, another PLP-dependent enzyme, which is an essential part of the malate-aspartate shuttle. The inhibition of the malate-aspartate shuttle prevents the reoxidation of cytosolic NADH by the mitochondria in nerve terminals. Also in the nerve terminals, aminooxyacetic acid prevents the mitochondria from utilizing pyruvate generated from glycolysis, thus leading to a bioenergetic state similar to that of hypoglycemia. Aminooxyacetic acid has been shown to cause excitotoxic lesions of the striatum, similar to Huntington's disease, potentially due to its impairment of mitochondrial energy metabolism. Aminooxyacetic acid was previously used in a clinical trial to reduce symptoms of Huntington's disease by increasing GABA levels in the brain. However, the patients who received the aminooxyacetic acid treatment failed to show clinical improvement and suffered from side effects such as drowsiness, ataxia, seizures, and psychosis when the dosage was increased beyond 2 mg per kilogram per day. Also, the inhibition of aspartate aminotransferase by aminooxyacetic acid has clinical implications for the treatment of breast cancer, since a decrease in glycolysis disrupts breast adenocarcinoma cells more than normal cells.\nAminooxyacetic acid has been studied as a treatment for tinnitus. One study showed that about 20% of patients with tinnitus had a decrease in its severity when treated with aminooxyacetic acid. However, about 70% of those patients reported side effects, mostly nausea and disequilibrium. Thus, the investigators of the study concluded that the incidence of the side effects makes aminooxyacetic acid unsuitable to treat tinnitus.\nAminooxyacetic acid also has anticonvulsant properties. At high dosages, it can act as a convulsant agent in mice and rats.\nAminooxyacetic acid can also inhibit 1-aminocyclopropane-1-carboxylate synthase preventing ethylene synthesis, which can increase the vase life of cut flowers."}