natamycin

CHEBI:7488 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

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. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

macrolide antibiotic CHEBI:25105
polyene antibiotic CHEBI:26177
Label unavailable CHEBI:32955
Label unavailable CHEBI:36244
Label unavailable CHEBI:63367
antibiotic antifungal drug CHEBI:87113

Chemical structure

Computed structure properties
Molecular formula	C33H47NO13
Charge	0
Average mass	665.733 Da
Monoisotopic mass	665.30474 Da
Source	ChEBI
InChIKey	NCXMLFZGDNKEPB-FFPOYIOWSA-N

SMILES

[H][C@@]12C[C@H](O)C[C@]3(O)C[C@H](O)[C@@H](C(=O)O)[C@]([H])(C[C@@H](O[C@@H]4O[C@H](C)[C@@H](O)[C@H](N)[C@@H]4O)/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]1O2)O3

InChI

InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1

Also called

Delvocid (BRAND_NAME)— chebi
Delvolan (BRAND_NAME)— chebi
Delvopos (BRAND_NAME)— chebi
Mycophyt (BRAND_NAME)— chebi
Myprozine (BRAND_NAME)— chebi
Myuprozine (BRAND_NAME)— chebi
Natacyn (BRAND_NAME)— chebi
Natajen (BRAND_NAME)— chebi
Natamatrix (BRAND_NAME)— chebi
Natamax (BRAND_NAME)— chebi
Pimafucin (BRAND_NAME)— chebi
Synogil (BRAND_NAME)— chebi
natamicina (INN)— chebi
natamycine (INN)— chebi
natamycinum (INN)— chebi
(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid (EXACT_SYNONYM)— chebi
CL 12,625 (EXACT_SYNONYM)— chebi
CL 12625 (EXACT_SYNONYM)— chebi
E 235 (EXACT_SYNONYM)— chebi
E-235 (EXACT_SYNONYM)— chebi
Pimarizin (EXACT_SYNONYM)— chebi
antibiotic A-5283 (EXACT_SYNONYM)— chebi
pimaricin (EXACT_SYNONYM)— chebi
pimaricine (EXACT_SYNONYM)— chebi
tennecetin (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Natamycin

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antimicrobial agent CHEBI:33281
antifungal agent CHEBI:35718
antimicrobial food preservative CHEBI:65256
antifungal drug CHEBI:86327
antifungal agrochemical CHEBI:86328

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:7488`	natamycin	`antibioticmech:chebi-8ad2a743b5`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

ergosterol in the fungal plasma membrane MEMBRANE DIRECT_BINDING_TARGET

CHEBI:16933

Direct binding and isothermal titration calorimetry in ergosterol-containing model membranes, complemented by yeast sterol-biosynthesis mutants and membrane-permeability assays. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2008-04 (retrieved 2026-09-02).

PMID:18165687 (Compound-specific binding and growth study; supports ergosterol binding but not membrane permeabilization.)

Mechanism summary

Mode of action: ERGOSTEROL_PATHWAY_INHIBITION microbial target — CURATOR: PMID:18165687 established specific binding to ergosterol in model membranes and a sterol-dependent block of fungal growth. Under growth-inhibiting conditions natamycin did not permeabilize yeast or ergosterol-containing model membranes, so this record does not assign the pore-forming mechanism of other polyenes.
Clinical status: APPROVED

Record-level evidence

PMID:18165687 (Primary experimental mode-of-action and target study.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified the ChEBI-grounded identity, structure, and antifungal class; added the primary-evidence ergosterol target and a curator-owned mode of action that explicitly excludes membrane permeabilization.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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