CHEBI:133915 - N-hydroxy-MeIQx

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ChEBI Name N-hydroxy-MeIQx
ChEBI ID CHEBI:133915
ChEBI ASCII Name N-hydroxy-MeIQx
Definition An imidazoquinoxaline that is 3H-imidazo[4,5-f]quinoxaline substituted at positions 3 and 8 by methyl groups and at position 2 by a hydroxyamino group. The active metabolite of the dietary carcinogen MeIQx.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C11H11N5O
Net Charge 0
Average Mass 229.238
Monoisotopic Mass 229.09636
InChI InChI=1S/C11H11N5O/c1-6-5-12-7-3-4-8-10(9(7)13-6)14-11(15-17)16(8)2/h3-5,17H,1-2H3,(H,14,15)
InChIKey FVNCCTJGBOTWTM-UHFFFAOYSA-N
SMILES C=1(C=NC=2C(N1)=C3C(=CC2)N(C(=N3)NO)C)C
Metabolite of Species Details
Rattus norvegicus (NCBI:txid10116) See: PubMed
Apis cerana (NCBI:txid7461) See: MetaboLights Study
Homo Sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: PubMed
Roles Classification
Chemical Role(s): nitric oxide donor
An agent, with unique chemical structure and biochemical requirements, which generates nitric oxide.
(via hydroxylamine )
nucleophilic reagent
A reagent that forms a bond to its reaction partner (the electrophile) by donating both bonding electrons.
(via hydroxylamine )
Biological Role(s): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
genotoxin
A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
rat metabolite
Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
bacterial xenobiotic metabolite
Any bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria.
(via hydroxylamine )
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
(via hydroxylamine )
EC 1.1.3.13 (alcohol oxidase) inhibitor
An EC 1.1.3.* (oxidoreductase acting on donor CH-OH group, oxygen as acceptor) inhibitor that interferes with the action of alcohol oxidase (EC 1.1.3.13).
(via hydroxylamine )
EC 4.2.1.22 (cystathionine beta-synthase) inhibitor
An EC 4.2.1.* (hydro-lyases) inhibitor that interferes with the action of cystathionine beta-synthase (EC 4.2.1.22).
(via hydroxylamine )
EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
An EC 4.3.1.* (ammonia-lyase) inhibitor that interferes with the action of serine-sulfate ammonia-lyase (EC 4.3.1.10).
(via hydroxylamine )
Application(s): nucleophilic reagent
A reagent that forms a bond to its reaction partner (the electrophile) by donating both bonding electrons.
(via hydroxylamine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-hydroxy-MeIQx (CHEBI:133915) has functional parent MeIQx (CHEBI:76604)
N-hydroxy-MeIQx (CHEBI:133915) has role carcinogenic agent (CHEBI:50903)
N-hydroxy-MeIQx (CHEBI:133915) has role genotoxin (CHEBI:50902)
N-hydroxy-MeIQx (CHEBI:133915) has role human urinary metabolite (CHEBI:84087)
N-hydroxy-MeIQx (CHEBI:133915) has role human xenobiotic metabolite (CHEBI:76967)
N-hydroxy-MeIQx (CHEBI:133915) has role mutagen (CHEBI:25435)
N-hydroxy-MeIQx (CHEBI:133915) has role rat metabolite (CHEBI:86264)
N-hydroxy-MeIQx (CHEBI:133915) is a hydroxylamine (CHEBI:15429)
N-hydroxy-MeIQx (CHEBI:133915) is a imidazoquinoxaline (CHEBI:76605)
IUPAC Name
N-(3,8-dimethyl-1,3-dihydro-2H-imidazo[4,5-f]quinoxalin-2-ylidene)hydroxylamine
Synonyms Sources
2-hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline ChEBI
3,8-dimethyl-1,3-dihydro-2H-imidazo(4,5-f)quinoxalin-2-one oxime ChemIDplus
N-hydroxy-methyl-IQX ChemIDplus
N-OH-MeIQx ChEBI
Manual Xref Database
C20291 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
115044-41-2 CAS Registry Number ChemIDplus
8146608 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10503894 PubMed citation Europe PMC
11258970 PubMed citation Europe PMC
11453738 PubMed citation Europe PMC
12351158 PubMed citation Europe PMC
1473228 PubMed citation Europe PMC
17627018 PubMed citation Europe PMC
19449459 PubMed citation Europe PMC
21194225 PubMed citation Europe PMC
21456541 PubMed citation Europe PMC
2462668 PubMed citation Europe PMC
7788858 PubMed citation Europe PMC
Last Modified
20 April 2017