CHEBI:78741 - oxidopamine

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name oxidopamine ChEBI ID CHEBI:78741 Definition A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease). Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ZINC000004096188 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Glucobrassicin is a type of glucosinolate that can be found in almost all cruciferous plants, such as cabbages, broccoli, mustards, and woad. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are indole-3-carbinol and thiocyanate ion (plus glucose, sulfate, and hydrogen ion), which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants. Glucobrassicin is also known to be a highly active egg-laying stimulant of cabbage white butterflies such as the small white (Pieris rapae) and the large white (Pieris brassicae). Several derivatives of glucobrassicin are known. The compound itself was first isolated from Brassica plants, hence the ending of the name. When a second, similar natural product was discovered, it was named neoglucobrassicin. When further derivatives were discovered, a more systematic nomenclature was used. Currently, the following six derivatives are known from plants: 1-Methoxyglucobrassicin (neoglucobrassicin) 4-Hydroxyglucobrassicin 4-Methoxyglucobrassicin 1,4-Dimethoxyglucobrassicin 1-Sulfoglucobrassicin 6′-Isoferuloylglucobrassicin The three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. The additional three derivatives appear to be rare in nature. 4-methoxyglucobrassicin was recently reported to be a signal molecule involved in plant defence against bacteria and fungi. Read full article at Wikipedia Formula C8H11NO3 Net Charge 0 Average Mass 169.17780 Monoisotopic Mass 169.07389 InChI InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2 InChIKey DIVDFFZHCJEHGG-UHFFFAOYSA-N SMILES NCCc1cc(O)c(O)cc1O Roles Classification Chemical Role(s): Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Biological Role(s): neurotoxin A poison that interferes with the functions of the nervous system. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). drug metabolite molecular messenger (via monoamine molecular messenger ) View more via ChEBI Ontology ChEBI Ontology Outgoing oxidopamine (CHEBI:78741) has functional parent dopamine (CHEBI:18243) oxidopamine (CHEBI:78741) has role drug metabolite (CHEBI:49103) oxidopamine (CHEBI:78741) has role human metabolite (CHEBI:77746) oxidopamine (CHEBI:78741) has role neurotoxin (CHEBI:50910) oxidopamine (CHEBI:78741) is a benzenetriol (CHEBI:22707) oxidopamine (CHEBI:78741) is a catecholamine (CHEBI:33567) oxidopamine (CHEBI:78741) is a primary amino compound (CHEBI:50994) IUPAC Name 5-(2-aminoethyl)benzene-1,2,4-triol INNs Sources oxidopamina ChemIDplus oxidopamine WHO MedNet oxidopamine ChemIDplus oxidopaminum ChemIDplus Synonyms Sources 2,4,5-trihydroxyphenethylamine ChemIDplus 6-hydroxydopamine ChemIDplus 6-OHDA ChemIDplus hydroxydopamine MetaCyc topamine ChEBI Manual Xrefs Databases CPD-7666 MetaCyc D05294 KEGG DRUG HMDB0001537 HMDB LSM-37081 LINCS Oxidopamine Wikipedia View more database links Registry Number Type Source 2211011 Reaxys Registry Number Reaxys Citations Types Sources 12486162 PubMed citation Europe PMC 22789904 PubMed citation Europe PMC 23358137 PubMed citation Europe PMC 23670213 PubMed citation Europe PMC 23959789 PubMed citation Europe PMC 24277157 PubMed citation Europe PMC 24333330 PubMed citation Europe PMC 24885281 PubMed citation Europe PMC 8255370 PubMed citation Europe PMC Last Modified 26 February 2016