sterigmatocystin
CHEBI:18227 EXACT SEEDED cytotoxictoxin
An organic heteropentacyclic compound whose skeleton comprises a xanthene ring system ortho-fused to a dihydrofuranofuran moiety. The parent of the class of sterigmatocystins.
Structure
| Standard InChIKey | UTSVPXMQSFGQTM-DCXZOGHSSA-N |
|---|---|
| SMILES | COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=C(C2=O)C(=CC=C5)O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA005925, pubchem:5280389 |
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 pks, from MIBiG.
Producer organisms 2
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 ochraceoroseus NCBITaxon:138278 |
SOURCE_ASSERTION | mibig:BGC0000011 | DOI:10.1080/15572536.2006.11832818 |
| Aspergillus nidulans NCBITaxon:162425 |
SOURCE_ASSERTION | mibig:BGC0000152 | PMID:8643646 |
Occurrences 22
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 stellatus NCBITaxon:1549217 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus chevalieri NCBITaxon:182096 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Botryotrichum NCBITaxon:1934360 |
LOTUS | DOI:10.1021/NP070610D |
| Collariella virescens NCBITaxon:1934374 |
LOTUS | DOI:10.1248/CPB.28.2428 |
| Monocillium nordinii NCBITaxon:3412472 |
LOTUS | DOI:10.1016/S0031-9422(00)81811-7 |
| Aspergillus ruber NCBITaxon:396024 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus unguis NCBITaxon:40381 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus ustus NCBITaxon:40382 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus quadrilineatus NCBITaxon:41735 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus quadrilineatus NCBITaxon:41735 |
LOTUS | DOI:10.1515/ZNB-1985-0230 |
| Aspergillus multicolor NCBITaxon:41759 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus multicolor NCBITaxon:41759 |
LOTUS | DOI:10.1271/BBB1961.44.1149 |
| Bipolaris sorokiniana NCBITaxon:45130 |
LOTUS | DOI:10.1039/P19840001137 |
| Bipolaris sorokiniana NCBITaxon:45130 |
LOTUS | DOI:10.1039/P19850002489 |
| Aspergillus versicolor NCBITaxon:46472 |
LOTUS | DOI:10.1021/NP800777F |
| Aspergillus versicolor NCBITaxon:46472 |
LOTUS | DOI:10.1039/C39820000890 |
| Aspergillus striatus NCBITaxon:469280 |
LOTUS | DOI:10.1039/P19860000109 |
| Aspergillus amstelodami NCBITaxon:5054 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus ochraceoroseus NCBITaxon:138278 |
LOTUS | DOI:10.3852/08-173 |
| Aspergillus nidulans NCBITaxon:162425 |
LOTUS | DOI:10.1016/B978-0-12-179760-7.50023-1 |
| Aspergillus nidulans NCBITaxon:162425 |
LOTUS | DOI:10.1021/NP050454F |
| Aspergillus nidulans NCBITaxon:162425 |
LOTUS | DOI:10.1073/PNAS.93.4.1418 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000011 | Aspergillus ochraceoroseus NCBITaxon:138278 |
CLUSTER_UNSTATED | genbank:AY092402.3 |
| mibig:BGC0000152 | Aspergillus nidulans NCBITaxon:162425 |
CLUSTER_UNSTATED | genbank:U34740.1 |
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 9
| Assay | Result | Reference |
|---|---|---|
| CCRIS carcinogenicity studies | ACTIVE | pubchem.aid:1259411 |
| CCRIS mutagenicity studies | ACTIVE | pubchem.aid:1259407 |
| GENE-TOX mutagenicity studies | ACTIVE | pubchem.aid:1259408 |
| NCI In Vivo Anticancer Drug Screen. Data for tumor model L1210 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice | ACTIVE | pubchem.aid:248 |
| NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice | ACTIVE | pubchem.aid:328 |
| NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in CD2F1 (CDF1) mice | ACTIVE | pubchem.aid:330 |
| NCI human tumor cell line growth inhibition assay. Data for the MCF7 Breast cell line | ACTIVE | pubchem.aid:83 |
| NCI human tumor cell line growth inhibition assay. Data for the P388 Leukemia cell line | ACTIVE | pubchem.aid:111 |
| NCI human tumor cell line growth inhibition assay. Data for the P388/ADR Leukemia cell line | ACTIVE | pubchem.aid:117 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000011, BGC0000152. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000011 | MIBIG | 3 |
| BGC0000152 | MIBIG | 3 |
| CHEBI:18227 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/sterigmatocystin.yaml, which is generated from the committed inventories. Neither is edited by hand.