sterigmatocystin

CHEBI:18227 EXACT SEEDED cytotoxictoxin

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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.

Mechanism & Biosynthesis Overview

Bioactivities 9

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Assay	Result	Target enzyme	Source detail
CCRIS carcinogenicity studies	ACTIVE	Not recorded	pubchem.aid:1259411 assay CCRIS carcinogenicity studies evidence reference pubchem.aid:1259411 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1259411, deposited by 22070; assay type Other. call ACTIVE activity class TOXIN
CCRIS mutagenicity studies	ACTIVE	Not recorded	pubchem.aid:1259407 assay CCRIS mutagenicity studies evidence reference pubchem.aid:1259407 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1259407, deposited by 22070; assay type Other. call ACTIVE activity class TOXIN
GENE-TOX mutagenicity studies	ACTIVE	Not recorded	pubchem.aid:1259408 assay GENE-TOX mutagenicity studies evidence reference pubchem.aid:1259408 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1259408, deposited by 22071; assay type Other. call ACTIVE activity class TOXIN
NCI In Vivo Anticancer Drug Screen. Data for tumor model L1210 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice	ACTIVE	Not recorded	pubchem.aid:248 assay NCI In Vivo Anticancer Drug Screen. Data for tumor model L1210 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice evidence reference pubchem.aid:248 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 248, deposited by DTP/NCI; assay type Other. call ACTIVE activity class CYTOTOXIC
NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice	ACTIVE	Not recorded	pubchem.aid:328 assay NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice evidence reference pubchem.aid:328 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 328, deposited by DTP/NCI; assay type Other. call ACTIVE activity class CYTOTOXIC
NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in CD2F1 (CDF1) mice	ACTIVE	Not recorded	pubchem.aid:330 assay NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in CD2F1 (CDF1) mice evidence reference pubchem.aid:330 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 330, deposited by DTP/NCI; assay type Other. call ACTIVE activity class CYTOTOXIC
NCI human tumor cell line growth inhibition assay. Data for the MCF7 Breast cell line	ACTIVE	Not recorded	pubchem.aid:83 assay NCI human tumor cell line growth inhibition assay. Data for the MCF7 Breast cell line evidence reference pubchem.aid:83 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 83, deposited by DTP/NCI; assay type Confirmatory. call ACTIVE activity class CYTOTOXIC
NCI human tumor cell line growth inhibition assay. Data for the P388 Leukemia cell line	ACTIVE	Not recorded	pubchem.aid:111 assay NCI human tumor cell line growth inhibition assay. Data for the P388 Leukemia cell line evidence reference pubchem.aid:111 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 111, deposited by DTP/NCI; assay type Confirmatory. call ACTIVE activity class CYTOTOXIC
NCI human tumor cell line growth inhibition assay. Data for the P388/ADR Leukemia cell line	ACTIVE	Not recorded	pubchem.aid:117 assay NCI human tumor cell line growth inhibition assay. Data for the P388/ADR Leukemia cell line evidence reference pubchem.aid:117 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 117, deposited by DTP/NCI; assay type Confirmatory. call ACTIVE activity class CYTOTOXIC

Explore across X-Mech

AntibioticMech (sterigmatocystin) ↗ MediaIngredientMech (CHEBI:18227) ↗ TaxonMech: Aspergillus ochraceoroseus (NCBITaxon:138278) ↗ TaxonMech: Aspergillus nidulans (NCBITaxon:162425) ↗ PathwayMech (mibig:BGC0000011) ↗ PathwayMech (mibig:BGC0000152) ↗

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.