CHEBI:133971 - nigerloxin

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ChEBI Name nigerloxin
ChEBI ID CHEBI:133971
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information ZINC000085560803
Download Molfile XML SDF
Formula C13H15NO5
Net Charge 0
Average Mass 265.262
Monoisotopic Mass 265.09502
InChI InChI=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+
InChIKey UOIRNFVLBXIGKH-SNAWJCMRSA-N
SMILES C=1(C(=C(C(=C(C1O)/C=C/C)C)OC)C(O)=O)C(=O)N
Metabolite of Species Details
Aspergillus niger (NCBI:txid5061) of strain CFR-W-105 See: PubMed
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
9342829 Reaxys Registry Number Reaxys
Citations Types Sources
12458767 PubMed citation Europe PMC
15134145 PubMed citation Europe PMC
19504138 PubMed citation Europe PMC
22423974 PubMed citation Europe PMC
23458199 PubMed citation Europe PMC
23767695 PubMed citation Europe PMC
24915992 PubMed citation Europe PMC
25507780 PubMed citation Europe PMC
Last Modified
17 November 2016