natamycin

CHEBI:7488 EXACT SEEDED antifungal

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

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.

Mechanism & Biosynthesis Overview

Bioactivities 4

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
qHTS assay for small molecule agonists of the p53 signaling pathway - cell viability	OTHER 29.8493 uM; INACTIVE	Not recorded	pubchem.aid:651633 assay qHTS assay for small molecule agonists of the p53 signaling pathway - cell viability evidence reference pubchem.aid:651633 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 651633, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call INACTIVE measurement type OTHER value 29.8493 units uM
qHTS assay to identify aromatase inhibitors	OTHER 33.4915 uM; INACTIVE	Not recorded	pubchem.aid:743083 assay qHTS assay to identify aromatase inhibitors evidence reference pubchem.aid:743083 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 743083, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession EAW77416 was left ungrounded because PubChem did not provide a UniProtKB accession. call INACTIVE measurement type OTHER value 33.4915 units uM
qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line	OTHER 8.4127 uM; NOT_DETERMINED	Not recorded	pubchem.aid:743042 assay qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line evidence reference pubchem.aid:743042 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 743042, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAI32976 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 8.4127 units uM
DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database	ACTIVE	Not recorded	pubchem.aid:1195 assay DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database evidence reference pubchem.aid:1195 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1195, deposited by EPA DSSTox; assay type Other. call ACTIVE

Elsewhere in the fleet

AntibioticMech — CHEBI:7488 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (natamycin) ↗ MediaIngredientMech (CHEBI:7488) ↗ TaxonMech: Streptomyces natalensis (NCBITaxon:68242) ↗ TaxonMech: Streptomyces gilvosporeus (NCBITaxon:553510) ↗ PathwayMech (mibig:BGC0000125) ↗ PathwayMech (mibig:BGC0001690) ↗

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.