ochratoxin A
CHEBI:7719 EXACT SEEDED cytotoxicenzyme inhibitor
A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin α). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.
Structure
| Standard InChIKey | RWQKHEORZBHNRI-BMIGLBTASA-N |
|---|---|
| SMILES | [H][C@@](CC1=CC=CC=C1)(NC(=O)C1=C(O)C2=C(C[C@@]([H])(C)OC2=O)C(Cl)=C1)C(O)=O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:442530, npatlas:NPA016066 |
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 nrps, pks, from MIBiG.
Producer organisms 7
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 |
|---|---|---|---|
| Penicillium nordicum NCBITaxon:229535 |
SOURCE_ASSERTION | mibig:BGC0001030 | DOI:10.1016/j.fct.2015.11.018 |
| Aspergillus westerdijkiae NCBITaxon:357447 |
SOURCE_ASSERTION | mibig:BGC0002598 | PMID:33652337 |
| Aspergillus carbonarius NCBITaxon:40993 |
SOURCE_ASSERTION | mibig:BGC0002605 | PMID:29324288 |
| Aspergillus niger NCBITaxon:5061 |
SOURCE_ASSERTION | mibig:BGC0002606 | PMID:29324288 |
| Aspergillus westerdijkiae NCBITaxon:357447 |
SOURCE_ASSERTION | mibig:BGC0002607 | PMID:29324288 |
| Aspergillus steynii NCBITaxon:306088 |
SOURCE_ASSERTION | mibig:BGC0002608 | PMID:29324288 |
| Aspergillus welwitschiae NCBITaxon:1341132 |
SOURCE_ASSERTION | mibig:BGC0002609 | PMID:27667988 |
Occurrences 11
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 |
|---|---|---|
| Aspergillus melleus NCBITaxon:138277 |
LOTUS | DOI:10.1007/S10295-003-0048-Y |
| Aspergillus ochraceus NCBITaxon:40380 |
LOTUS | DOI:10.1016/S0031-9422(01)00316-8 |
| Aspergillus ochraceus NCBITaxon:40380 |
LOTUS | DOI:10.1038/171524B0 |
| Aspergillus ochraceus NCBITaxon:40380 |
LOTUS | DOI:10.1039/J39700000278 |
| Aspergillus ochraceus NCBITaxon:40380 |
LOTUS | DOI:10.1039/JR9650007083 |
| Penicillium verrucosum NCBITaxon:60171 |
LOTUS | DOI:10.1016/S0953-7562(10)80017-6 |
| Glycyrrhiza uralensis NCBITaxon:74613 |
LOTUS | DOI:10.1016/J.FOODCONT.2012.11.028 |
| Penicillium nordicum NCBITaxon:229535 |
LOTUS | DOI:10.1016/J.SYAPM.2005.03.008 |
| Aspergillus westerdijkiae NCBITaxon:357447 |
LOTUS | DOI:10.1016/J.IJFOODMICRO.2021.109113 |
| Aspergillus niger NCBITaxon:5061 |
LOTUS | DOI:10.1128/AEM.60.7.2650-2652.1994 |
| Aspergillus niger NCBITaxon:5061 |
LOTUS | DOI:10.3389/FMICB.2016.01412 |
Biosynthetic gene clusters 7
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001030 | Penicillium nordicum NCBITaxon:229535 |
CLUSTER_UNSTATED | genbank:MG701895.1 |
| mibig:BGC0002598 | Aspergillus westerdijkiae NCBITaxon:357447 |
CLUSTER_UNSTATED | genbank:MW526246.1 |
| mibig:BGC0002605 | Aspergillus carbonarius NCBITaxon:40993 |
CLUSTER_UNSTATED | genbank:MG701890.1 |
| mibig:BGC0002606 | Aspergillus niger NCBITaxon:5061 |
CLUSTER_UNSTATED | genbank:MG701892.1 |
| mibig:BGC0002607 | Aspergillus westerdijkiae NCBITaxon:357447 |
CLUSTER_UNSTATED | genbank:MG701896.1 |
| mibig:BGC0002608 | Aspergillus steynii NCBITaxon:306088 |
CLUSTER_UNSTATED | genbank:MG701897.1 |
| mibig:BGC0002609 | Aspergillus welwitschiae NCBITaxon:1341132 |
CLUSTER_UNSTATED | genbank:KX267735.1 |
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.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 11.3762 uM | PMID:31515284 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 1 (GPX1) | 22.2073 uM | pubchem.aid:1845191 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 1 (GPX1) | 22.2073 uM | pubchem.aid:1845191 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 12.4881 uM | pubchem.aid:1845192 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 12.4881 uM | pubchem.aid:1845192 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 6.3586 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 6.3586 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 8.9817 uM | pubchem.aid:1645876 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 8.9817 uM | pubchem.aid:1645876 |
| Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells. | 26.2496 uM | pubchem.aid:2060322 |
| Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells. | 26.2496 uM | pubchem.aid:2060322 |
| Primary qHTS to identify anti-liver cancer compounds using libraries of approved drugs and bioactive compounds | 3.5481 uM | pubchem.aid:2202548 |
| VP16 counterscreen qHTS for inhibitors of ROR gamma transcriptional activity | 22.3872 uM | pubchem.aid:2546 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 0.2858 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 0.2858 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 0.7178 uM | pubchem.aid:1963823 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 0.7178 uM | pubchem.aid:1963823 |
| qHTS Assay for Identification of Novel General Anesthetics | 25.1189 uM | pubchem.aid:485281 |
| qHTS Assay for Identifying the Cell-Membrane Permeable IMPase Inhibitors: Potentiation with Lithium | 17.7828 uM | pubchem.aid:1457 |
| qHTS Assay for Inhibitors and Activators of Human alpha-Galactosidase From Spleen Homogenate | 35.4813 uM | pubchem.aid:2107 |
| qHTS Assay for Inhibitors and Activators of Human alpha-Glucosidase From Spleen Homogenate | 35.4813 uM | pubchem.aid:2112 |
| qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease | 31.6228 uM | pubchem.aid:2101 |
| qHTS Assay for Inhibitors of Aldehyde Dehydrogenase 1 (ALDH1A1) | 31.6228 uM | pubchem.aid:1030 |
| qHTS Assay for Inhibitors of HPGD (15-Hydroxyprostaglandin Dehydrogenase) | 28.1838 uM | pubchem.aid:894 |
| qHTS Assay for Inhibitors of Human alpha-Galactosidase at pH 4.5. | 19.9526 uM | pubchem.aid:1467 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0001030, BGC0002598, BGC0002605, BGC0002606, BGC0002607, BGC0002608, BGC0002609. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001030 | MIBIG | 3 |
| BGC0002598 | MIBIG | 2 |
| BGC0002605 | MIBIG | 2 |
| BGC0002606 | MIBIG | 2 |
| BGC0002607 | MIBIG | 2 |
| BGC0002608 | MIBIG | 2 |
| BGC0002609 | MIBIG | 2 |
| CHEBI:7719 | CHEBI | 3-star |
This page is generated from data/natural_products/shikimates_and_phenylpropanoids/ochratoxin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.