fumagillin
CHEBI:48635 EXACT SEEDED antibacterial
A meroterpenoid resulting from the formal condensation of the hydroxy group of fumagillol with the carboxylic acid group of (all-E)-deca-2,4,6,8-tetraenedioic acid. Originally isolated from the fungus Aspergillus fumigatus, it is used for the control of Nosema infection in honey bees.
Structure
| Standard InChIKey | NGGMYCMLYOUNGM-CSDLUJIJSA-N |
|---|---|
| SMILES | CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O)OC)C |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA010119 |
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, terpene, 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 fumigatus Af293 NCBITaxon:330879 |
BGC_CHARACTERIZED | mibig:BGC0001067 | DOI:10.1021/ja312503y |
Occurrences 4
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 terreus NCBITaxon:33178 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B01190 |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1021/JA01475A029 |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1021/JA312503Y |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1021/NP049893P |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001067 | Aspergillus fumigatus Af293 NCBITaxon:330879 |
CLUSTER_DEMONSTRATED | genbank:CM000176.1 |
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.
Elsewhere in the fleet
- AntibioticMech — CHEBI:48635 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001067 | MIBIG | 5 |
| CHEBI:48635 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/fumagillin.yaml, which is generated from the committed inventories. Neither is edited by hand.