natamycin
CHEBI:7488 EXACT SEEDED antifungal
A macrolide antibiotic that has formula C33H47NO13, produced by several Streptomyces species including Streptomyces natalensis. It exhibits broad spectrum antifungal activity and used in eye drops, and as a food preservative, and also as a postharvest biofungicide for citrus and other fruit crops.
Structure
| Standard InChIKey | NCXMLFZGDNKEPB-FFPOYIOWSA-N |
|---|---|
| SMILES | C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:5284447 |
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 |
|---|---|---|---|
| Streptomyces natalensis NCBITaxon:68242 |
SOURCE_ASSERTION | mibig:BGC0000125 | PMID:11094342 |
| Streptomyces gilvosporeus NCBITaxon:553510 |
SOURCE_ASSERTION | mibig:BGC0001690 | PMID:27746324 |
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 |
|---|---|---|
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.7164/ANTIBIOTICS.53.623 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1002/BTPR.1659 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S00203-019-01710-3 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S00253-013-4786-0 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S00253-013-5455-Z |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S00253-017-8440-0 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S00253-019-10131-7 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S10295-013-1370-7 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S11274-013-1561-4 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1007/S12275-013-2321-8 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1016/J.BIORTECH.2018.11.009 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1016/J.ENZMICTEC.2007.08.012 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1016/J.FEBSLET.2014.07.010 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1080/10826068.2017.1365244 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1111/MMI.13583 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1128/AEM.00099-13 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1128/AEM.01849-14 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1128/GENOMEA.01402-17 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1186/S12896-019-0546-2 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.1186/S12934-019-1055-7 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.3389/FMICB.2018.00316 |
| Streptomyces lydicus NCBITaxon:47763 |
LOTUS | DOI:10.4014/JMB.1505.05033 |
| Streptomyces chattanoogensis NCBITaxon:66876 |
LOTUS | DOI:10.1002/BTPR.1659 |
| Streptomyces chattanoogensis NCBITaxon:66876 |
LOTUS | DOI:10.1007/S00203-019-01710-3 |
| Streptomyces chattanoogensis NCBITaxon:66876 |
LOTUS | DOI:10.1007/S00253-013-4786-0 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000125 | Streptomyces natalensis NCBITaxon:68242 |
CLUSTER_UNSTATED | genbank:AJ278573.1 |
| mibig:BGC0001690 | Streptomyces gilvosporeus NCBITaxon:553510 |
CLUSTER_UNSTATED | genbank:KX458106.1 |
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 4
| Assay | Result | Reference |
|---|---|---|
| qHTS assay for small molecule agonists of the p53 signaling pathway - cell viability | 29.8493 uM | pubchem.aid:651633 |
| qHTS assay to identify aromatase inhibitors | 33.4915 uM | pubchem.aid:743083 |
| qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line | 8.4127 uM | pubchem.aid:743042 |
| DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database | ACTIVE | pubchem.aid:1195 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:7488 (same structure, same inchikey)
Open questions 2
name-disagreement — ChEBI calls this structure 'natamycin' and MIBiG calls it 'pimaricin'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000125, BGC0001690. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000125 | MIBIG | 5 |
| BGC0001690 | MIBIG | 5 |
| CHEBI:7488 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/natamycin.yaml, which is generated from the committed inventories. Neither is edited by hand.