naringenin
CHEBI:50202 EXACT SEEDED antiviralcytotoxicenzyme inhibitor
A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4'.
Structure
| Standard InChIKey | FTVWIRXFELQLPI-UHFFFAOYSA-N |
|---|---|
| SMILES | C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O |
| Stereochemistry | undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers |
| Cross-references | pubchem:932 |
Filing pathway
Shikimates and phenylpropanoids — 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 pks, 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 |
|---|---|---|---|
| Streptomyces clavuligerus ATCC 27064 NCBITaxon:1901 |
SOURCE_ASSERTION | mibig:BGC0001310 | PMID:26553209 |
Occurrences 25
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 |
|---|---|---|
| Prunus mume NCBITaxon:102107 |
LOTUS | DOI:10.1021/JF980936F |
| Helichrysum cephaloideum NCBITaxon:112358 |
LOTUS | DOI:10.1002/CBER.19731060432 |
| Helichrysum cephaloideum NCBITaxon:112358 |
LOTUS | DOI:10.1515/ZNC-1983-11-1201 |
| Dendrobium fimbriatum NCBITaxon:117953 |
LOTUS | DOI:10.1016/S0031-9422(01)00168-6 |
| Dendrobium loddigesii NCBITaxon:117954 |
LOTUS | DOI:10.1016/S0031-9422(01)00168-6 |
| Prunus lycioides NCBITaxon:1284230 |
LOTUS | DOI:10.3390/MOLECULES17021665 |
| Dalbergia parviflora NCBITaxon:1353466 |
LOTUS | DOI:10.1039/P19730001737 |
| Prunus campanulata NCBITaxon:136465 |
LOTUS | DOI:10.1021/JA01650A088 |
| Rhynchosia beddomei NCBITaxon:1378005 |
LOTUS | DOI:10.1016/0031-9422(80)83211-0 |
| Dendrobium moniliforme NCBITaxon:142614 |
LOTUS | DOI:10.1016/S0031-9422(01)00168-6 |
| Dendrobium officinale NCBITaxon:142615 |
LOTUS | DOI:10.1155/2017/7436259 |
| Prunus davidiana NCBITaxon:151430 |
LOTUS | DOI:10.1021/JF980936F |
| Dendrobium chrysanthum NCBITaxon:154291 |
LOTUS | DOI:10.1016/S0031-9422(01)00168-6 |
| Dendrobium chrysotoxum NCBITaxon:161865 |
LOTUS | DOI:10.1016/S0031-9422(01)00168-6 |
| Intsia NCBITaxon:162811 |
LOTUS | DOI:10.1016/0031-9422(73)80461-3 |
| Brosimum acutifolium NCBITaxon:1835378 |
LOTUS | DOI:10.1021/NP010389J |
| Maclura cochinchinensis NCBITaxon:194324 |
LOTUS | DOI:10.1021/NP030127C |
| Maclura tricuspidata NCBITaxon:210328 |
LOTUS | DOI:10.1016/0031-9422(95)00277-E |
| Maclura tricuspidata NCBITaxon:210328 |
LOTUS | DOI:10.1021/NP030127C |
| Dendrobium longicornu NCBITaxon:257357 |
LOTUS | DOI:10.1055/S-2008-1074492 |
| Dendrobium trigonopus NCBITaxon:257360 |
LOTUS | DOI:10.1080/10286020802133605 |
| Helichrysum arenarium NCBITaxon:261776 |
LOTUS | DOI:10.1002/CBER.19731060432 |
| Helichrysum arenarium NCBITaxon:261776 |
LOTUS | DOI:10.1515/ZNC-1983-11-1201 |
| Ageratina havanensis NCBITaxon:2773069 |
LOTUS | DOI:10.1021/NP50048A063 |
| Senecio adenophyllus NCBITaxon:2841764 |
LOTUS | DOI:10.1016/0031-9422(77)83033-1 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001310 | Streptomyces clavuligerus ATCC 27064 NCBITaxon:1901 |
CLUSTER_UNSTATED | genbank:CM000913.1 |
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 6 nodes, 5 edges
Naringenin inhibits human and bovine carbonic anhydrase isoenzymes.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| naringenin | inhibits | human carbonic anhydrase 1 | DOI:10.3109/14756366.2011.651464 |
| naringenin | inhibits | human carbonic anhydrase 2 | DOI:10.3109/14756366.2011.651464 |
| naringenin | inhibits | bovine carbonic anhydrase 3 | DOI:10.3109/14756366.2011.651464 |
| naringenin | inhibits | human carbonic anhydrase 4 | DOI:10.3109/14756366.2011.651464 |
| naringenin | inhibits | human carbonic anhydrase 6 | DOI:10.3109/14756366.2011.651464 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — bioactivity 2 nodes, 1 edges
Naringenin inhibits human aromatase.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| naringenin | inhibits | human aromatase | DOI:10.1111/j.1747-0285.2012.01439.x |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Molecular targets 9
| Target | Assay organism | Measurement | Reference |
|---|---|---|---|
| Aldehyde oxidase 1 UniProtKB:H9TB17 |
Cavia porcellus NCBITaxon:10141 |
KI 148000 nM | PMID:26722818 |
| Aromatase UniProtKB:P11511 |
Homo sapiens NCBITaxon:9606 |
KI 0.00109662 nM | PMID:22726671 |
| Carbonic anhydrase 1 UniProtKB:P00915 |
Homo sapiens NCBITaxon:9606 |
KI 970 nM | PMID:22299585 |
| Carbonic anhydrase 2 UniProtKB:P00918 |
Homo sapiens NCBITaxon:9606 |
KI 113 nM | PMID:22299585 |
| Carbonic anhydrase 3 UniProtKB:Q3SZX4 |
Bos taurus NCBITaxon:9913 |
KI 2210 nM | PMID:22299585 |
| Carbonic anhydrase 4 UniProtKB:P22748 |
Homo sapiens NCBITaxon:9606 |
KI 1120 nM | PMID:22299585 |
| Carbonic anhydrase 6 UniProtKB:P23280 |
Homo sapiens NCBITaxon:9606 |
KI 1490 nM | PMID:22299585 |
| Estrogen receptor UniProtKB:P03372 |
Homo sapiens NCBITaxon:9606 |
IC50 72302 nM | PMID:17149865 |
| Estrogen receptor beta UniProtKB:Q92731 |
Homo sapiens NCBITaxon:9606 |
IC50 13473 nM | PMID:17149865 |
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 2.5119 uM | pubchem.aid:624297 |
| AO Enzyme Assay from Article 10.1016/j.bioorg.2015.12.004: "Inhibition of guinea pig aldehyde oxidase activity by different flavonoid compounds: An in vitro study." | KI 148 uM | PMID:26722818 |
| Aromatase Assay from Article 10.1111/j.1747-0285.2012.01439.x: "Neoflavonoids and Tetrahydroquinolones as Possible Cancer Chemopreventive Agents." | KI 1.09662e-06 uM | PMID:22726671 |
| Competition-Based Ligand Binding Assay. from Article 10.1021/jm060692n: "Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alpha and beta." | IC50 72.302 uM | PMID:17149865 |
| Competition-Based Ligand Binding Assay. from Article 10.1021/jm060692n: "Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alpha and beta." | IC50 13.473 uM | PMID:17149865 |
| Esterase Activity Assay from Article 10.3109/14756366.2011.651464: "Analysis of saponins and phenolic compounds as inhibitors of a-carbonic anhydrase isoenzymes." | KI 0.97 uM | PMID:22299585 |
| Esterase Activity Assay from Article 10.3109/14756366.2011.651464: "Analysis of saponins and phenolic compounds as inhibitors of a-carbonic anhydrase isoenzymes." | KI 0.113 uM | PMID:22299585 |
| Esterase Activity Assay from Article 10.3109/14756366.2011.651464: "Analysis of saponins and phenolic compounds as inhibitors of a-carbonic anhydrase isoenzymes." | KI 1.12 uM | PMID:22299585 |
| Esterase Activity Assay from Article 10.3109/14756366.2011.651464: "Analysis of saponins and phenolic compounds as inhibitors of a-carbonic anhydrase isoenzymes." | KI 1.49 uM | PMID:22299585 |
| Esterase Activity Assay from Article 10.3109/14756366.2011.651464: "Analysis of saponins and phenolic compounds as inhibitors of a-carbonic anhydrase isoenzymes." | KI 2.21 uM | PMID:22299585 |
| High Throughput Screening for Foot and Mouth Disease Virus Antivirals | 14.1254 uM | pubchem.aid:1159524 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 44.6684 uM | pubchem.aid:1671190 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 44.6684 uM | pubchem.aid:1671190 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation | 2.6169 uM | pubchem.aid:504832 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | 6.5733 uM | pubchem.aid:504834 |
| qHTS Assay for Activators of Cytochrome P450 3A4 | 10 uM | pubchem.aid:885 |
| qHTS Assay for Activators of Cytochrome P450 3A4 | 12.5893 uM | pubchem.aid:885 |
| qHTS Assay for Compounds that Induce Erasure of Genomic Imprints | 12.5893 uM | pubchem.aid:1948 |
| qHTS Assay for Compounds that Induce Erasure of Genomic Imprints | 15.8489 uM | pubchem.aid:1948 |
| qHTS Assay for Identification of Novel General Anesthetics | 28.1838 uM | pubchem.aid:485281 |
| qHTS Assay for Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Texas Red Labeled MLL-derived Mutant Peptide | 25.1189 uM | pubchem.aid:1768 |
| qHTS Assay for Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Texas Red Labeled MLL-derived Mutant Peptide | 25.1189 uM | pubchem.aid:1768 |
| qHTS Assay for Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Texas Red Labeled MLL-derived Mutant Peptide | 39.8107 uM | pubchem.aid:1768 |
| qHTS Assay for Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Texas Red Labeled MLL-derived Mutant Peptide | 39.8107 uM | pubchem.aid:1768 |
| qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease | 11.2202 uM | pubchem.aid:2101 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001310 | MIBIG | 5 |
| CHEBI:50202 | CHEBI | 3-star |
This page is generated from data/natural_products/shikimates_and_phenylpropanoids/naringenin.yaml, which is generated from the committed inventories. Neither is edited by hand.