CHEBI:7488 - natamycin

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ChEBI Name natamycin
ChEBI ID CHEBI:7488
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C33H47NO13
Net Charge 0
Average Mass 665.733
Monoisotopic Mass 665.30474
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
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
Metabolite of Species Details
Streptomyces natalensis (NCBI:txid68242) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via macrolide antibiotic )
(via polyene antibiotic )
Application(s): antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
ophthalmology drug
Any compound used for the treatment of eye conditions or eye diseases.
antifungal agrochemical
Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing natamycin (CHEBI:7488) has role antifungal agrochemical (CHEBI:86328)
natamycin (CHEBI:7488) has role antimicrobial food preservative (CHEBI:65256)
natamycin (CHEBI:7488) has role apoptosis inducer (CHEBI:68495)
natamycin (CHEBI:7488) has role bacterial metabolite (CHEBI:76969)
natamycin (CHEBI:7488) has role ophthalmology drug (CHEBI:66981)
natamycin (CHEBI:7488) is a antibiotic antifungal drug (CHEBI:87113)
natamycin (CHEBI:7488) is a dicarboxylic acid monoester (CHEBI:36244)
natamycin (CHEBI:7488) is a epoxide (CHEBI:32955)
natamycin (CHEBI:7488) is a macrolide antibiotic (CHEBI:25105)
natamycin (CHEBI:7488) is a monosaccharide derivative (CHEBI:63367)
natamycin (CHEBI:7488) is a polyene antibiotic (CHEBI:26177)
IUPAC Name
(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
INNs Sources
natamicina WHO MedNet
natamycin WHO MedNet
natamycine WHO MedNet
natamycinum WHO MedNet
Synonyms Sources
antibiotic A-5283 ChemIDplus
CL 12,625 ChemIDplus
CL 12625 ChemIDplus
E 235 ChEBI
E-235 ChEBI
pimaricin KEGG COMPOUND
pimaricine ChemIDplus
Pimarizin ChemIDplus
tennecetin DrugCentral
Brand Names Sources
Delvocid ChemIDplus
Delvolan ChemIDplus
Delvopos ChemIDplus
Mycophyt ChemIDplus
Myprozine ChemIDplus
Myuprozine DrugCentral
Natacyn ChEBI
Natajen ChEBI
Natamatrix ChEBI
Natamax ChEBI
Pimafucin ChemIDplus
Synogil ChemIDplus
Manual Xrefs Databases
10468784 ChemSpider
1885 DrugCentral
2062 BPDB
C08073 KEGG COMPOUND
CPD-17213 MetaCyc
D00884 KEGG DRUG
DB00826 DrugBank
FDB002337 FooDB
HMDB0014964 HMDB
natamycin Alan Wood's Pesticides
Natamycin Wikipedia
View more database links
Registry Number Type Source
7681-93-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18165687 PubMed citation Europe PMC
30562337 PubMed citation Europe PMC
31311527 PubMed citation Europe PMC
32382679 PubMed citation Europe PMC
32650062 PubMed citation Europe PMC
32891143 PubMed citation Europe PMC
33306429 PubMed citation Europe PMC
33320038 PubMed citation Europe PMC
33653522 PubMed citation Europe PMC
33737097 PubMed citation Europe PMC
33748084 PubMed citation Europe PMC
33822660 PubMed citation Europe PMC
33882328 PubMed citation Europe PMC
33973428 PubMed citation Europe PMC
34085850 PubMed citation Europe PMC
34311233 PubMed citation Europe PMC
34428517 PubMed citation Europe PMC
34515597 PubMed citation Europe PMC
34571612 PubMed citation Europe PMC
34574183 PubMed citation Europe PMC
IND607246306 Agricola citation Europe PMC
IND607253996 Agricola citation Europe PMC
Last Modified
13 October 2021