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CHEBI:133971 - nigerloxin

ChEBI IDCHEBI:133971
ChEBI Namenigerloxin
Stars
DefinitionA member of the class of benzoic acids that is benzoic acid which is substituted at positions 2, 3, 4, 5, and 6 by carbamoyl, hydroxy, E)-prop-1-en-1-yl, methyl, and methoxy groups, respectively. Obtained from solid-state fermentation of Aspergillus niger CFR-W-105, it inhibits soy bean lipoxygenase-1 (LOX-1) and rat lens aldose reductase (RLAR). It also shows free radical scavenging activity.
Last Modified17 November 2016
SubmitterJubra
DownloadsMolfile
FormulaC13H15NO5
Net Charge0
Average Mass265.265
Monoisotopic Mass265.09502
SMILESC/C=C/c1c(C)c(OC)c(C(=O)O)c(C(N)=O)c1O
InChIInChI=1S/C13H15NO5/c1-4-5-7-6(2)11(19-3)9(13(17)18)8(10(7)15)12(14)16/h4-5,15H,1-3H3,(H2,14,16)(H,17,18)/b5-4+
InChIKeyUOIRNFVLBXIGKH-SNAWJCMRSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger (ncbitaxon:5061) - PubMed (12458767) Strain: CFR-W-105
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
lipoxygenase inhibitor  A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
EC 1.1.1.21 (aldehyde reductase) inhibitor  An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).
ChEBI Ontology
Outgoing Relation(s)
nigerloxin (CHEBI:133971) has role Aspergillus metabolite (CHEBI:76956)
nigerloxin (CHEBI:133971) has role antioxidant (CHEBI:22586)
nigerloxin (CHEBI:133971) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
nigerloxin (CHEBI:133971) has role lipoxygenase inhibitor (CHEBI:35856)
nigerloxin (CHEBI:133971) has role radical scavenger (CHEBI:48578)
nigerloxin (CHEBI:133971) is a aromatic ether (CHEBI:35618)
nigerloxin (CHEBI:133971) is a benzamides (CHEBI:22702)
nigerloxin (CHEBI:133971) is a benzoic acids (CHEBI:22723)
nigerloxin (CHEBI:133971) is a phenols (CHEBI:33853)
nigerloxin (CHEBI:133971) is a styrenes (CHEBI:26799)
IUPAC Name 
2-carbamoyl-3-hydroxy-6-methoxy-5-methyl-4-[(1E)-prop-1-en-1-yl]benzoic acid
Registry NumbersSources
Reaxys:9342829Reaxys
Citations