kojic acid
CHEBI:43572 EXACT SEEDED cytotoxicenzyme inhibitor
A pyranone that is 4H-pyran substituted by a hydroxy group at position 5, a hydroxymethyl group at position 2 and an oxo group at position 4. It has been isolated from the fungus Aspergillus oryzae.
Structure
| Standard InChIKey | BEJNERDRQOWKJM-UHFFFAOYSA-N |
|---|---|
| SMILES | O=C1C=C(CO)OC=C1O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:3840, npatlas:NPA028615 |
Filing pathway
Polyketides — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Aspergillus oryzae RIB40 NCBITaxon:510516 |
SOURCE_ASSERTION | mibig:BGC0002195 | DOI:10.2174/1871520618666180402141714 |
Occurrences 15
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Thalassotalea NCBITaxon:1518149 |
LOTUS | DOI:10.1021/ACS.JNATPROD.5B00972 |
| Phaeosphaeria fuckelii NCBITaxon:178153 |
LOTUS | DOI:10.1021/ACS.JNATPROD.0C00046 |
| Marrubium cylleneum NCBITaxon:2291699 |
LOTUS | DOI:10.1016/J.BMC.2007.01.035 |
| Acronychia pedunculata NCBITaxon:354485 |
LOTUS | DOI:10.1021/NP030054X |
| Aspergillus terricola NCBITaxon:36642 |
LOTUS | DOI:10.1071/CH9682775 |
| Aspergillus candidus NCBITaxon:41067 |
LOTUS | DOI:10.1080/00021369.1979.10863620 |
| Aspergillus candidus NCBITaxon:41067 |
LOTUS | DOI:10.1271/BBB1961.43.1337 |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1016/J.FGB.2010.08.014 |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1016/S1389-1723(01)80133-X |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1039/CT9242500575 |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1080/14786419.2013.841687 |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1139/M82-200 |
| Aspergillus flavus NCBITaxon:5059 |
LOTUS | DOI:10.1248/CPB.59.1174 |
| Aspergillus oryzae NCBITaxon:5062 |
CHEBI | PMID:24116376 |
| Penicillium NCBITaxon:5073 |
LOTUS | DOI:10.1021/ACS.JNATPROD.0C00741 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002195 | Aspergillus oryzae RIB40 NCBITaxon:510516 |
CLUSTER_UNSTATED | genbank:BA000053.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Causal graph — bioactivity 3 nodes, 2 edges
Kojic acid inhibition of BindingDB-grounded Agaricus bisporus tyrosinase/polyphenol oxidase proteins.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| kojic acid | inhibits | Agaricus bisporus polyphenol oxidase 1 | DOI:10.3109/14756366.2010.482529 |
| kojic acid | inhibits | Agaricus bisporus polyphenol oxidase 2 | DOI:10.1080/14756360701810207 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Molecular targets 7
| Target | Assay organism | Measurement | Reference |
|---|---|---|---|
| Polyphenol oxidase 1 UniProtKB:Q00024 |
Agaricus bisporus NCBITaxon:5341 |
IC50 16670 nM | PMID:20476840 |
| Polyphenol oxidase 1 [61-568] UniProtKB:Q00024 |
Agaricus bisporus NCBITaxon:5341 |
IC50 23600 nM | PMID:27669118 |
| Polyphenol oxidase 1 [N65D,S176D,K211T,P277A,P406L] UniProtKB:Q00024 |
Agaricus bisporus var. bisporus (strain H97 / ATCC MYA-4626 / FGSC 10389) NCBITaxon:936046 |
KI 12200 nM | PMID:26496408 |
| Polyphenol oxidase 2 UniProtKB:O42713 |
Agaricus bisporus NCBITaxon:5341 |
IC50 12500 nM | PMID:18608767 |
| Polyphenol oxidase 2 UniProtKB:O42713 |
Agaricus bisporus NCBITaxon:5341 |
IC50 23000 nM | PMID:23461881 |
| Tyrosinase UniProtKB:P14679 |
Homo sapiens NCBITaxon:9606 |
IC50 16670 nM | PMID:16206837 |
| Uncharacterized protein YOR062C UniProtKB:P36025 |
Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NCBITaxon:559292 |
IC50 19000 nM | PMID:25916324 |
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 4.6109 uM | pubchem.aid:1963990 |
| Enzymatic Activity Assay from Article 10.1016/j.bioorg.2015.10.003: "Development of hydroxylated naphthylchalcones as polyphenol oxidase inhibitors: Synthesis, biochemistry and molecular docking studies." | KI 12.2 uM | PMID:26496408 |
| In Vitro Tyrosinase Inhibition Assay from Article 10.3109/14756366.2010.482529: "Tyrosinase inhibitory effect of benzoic acid derivatives and their structure-activity relationships." | IC50 16.67 uM | PMID:20476840 |
| Inhibition Assay from Article 10.1080/14756360500179333: "Tyrosinase inhibition: conformational analysis based studies on molecular dynamics calculations of bipiperidine based inhibitors." | IC50 16.67 uM | PMID:16206837 |
| Inhibition Assay from US Patent US9422261: "Heterocyclic resorcinol derivatives, preparation of same and cosmetic uses thereof" | IC50 15 uM | pubchem.aid:1803246 |
| Mushroom Tyrosinase Assay from US Patent US9682910: "Series of skin-whitening (lightening) compounds" | IC50 20 uM | pubchem.aid:1794918 |
| NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay | 0.1995 uM | PMID:36786055 |
| Primary qHTS for Inhibitors of N-terminal methyltransferase 1 (NTMT1): MTaseGlo Assay | 0.0447 uM | pubchem.aid:1645870 |
| Primary qHTS for Inhibitors of N-terminal methyltransferase 1 (NTMT1): MTaseGlo Assay | 0.0447 uM | pubchem.aid:1645870 |
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 0.0101 uM | pubchem.aid:1964107 |
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 11.0903 uM | pubchem.aid:1964107 |
| Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 8.9125 uM | PMID:33910017 |
| S16 Schwann cell PMP22 intronic element firefly luciferase assay | 16.1366 uM | pubchem.aid:624032 |
| Spectrophotometric Assay from Article 10.1111/cbdd.12126: "Microwave-assisted synthesis and tyrosinase inhibitory activity of chalcone derivatives." | IC50 23 uM | PMID:23461881 |
| Tyrosinase Activity Assay from Article 10.1016/j.bioorg.2016.09.007: "Molecular docking studies and biological evaluation of 1,3,4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors." | IC50 23.6 uM | PMID:27669118 |
| Tyrosinase Assay from Article 10.1080/14756360701810207: "Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz." | IC50 12.5 uM | PMID:18608767 |
| Tyrosinase Inhibition Assay from Article 10.1111/cbdd.12577: "Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4-triazole as potent tyrosinase inhibitors." | IC50 19 uM | PMID:25916324 |
| Tyrosinase Inhibition Assay from US Patent US10857082: "Diarylalkanes as potent inhibitors of binuclear enzymes" | IC50 29 uM | pubchem.aid:1805056 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus, Screen 2 blue channel | EC50 8.9125 uM | pubchem.aid:1117304 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus, Screen 2 green channel | EC50 0.7079 uM | pubchem.aid:1117298 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus, Screen 2 ratio channel | EC50 8.9125 uM | pubchem.aid:1117305 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus: Screen 2, blue channel | EC50 8.91251 uM | pubchem.aid:1117314 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus: Screen 2, green channel | EC50 0.707946 uM | pubchem.aid:1117310 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus: Screen2, ratio channel | EC50 8.91251 uM | pubchem.aid:1117312 |
| qHTS Assay for Inhibitors of Human Jumonji Domain Containing 2E (JMJD2E) | 25.1189 uM | pubchem.aid:2147 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002195 | MIBIG | 2 |
| CHEBI:43572 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/kojic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.