CHEBI:7488 - natamycin

ChEBI IDCHEBI:7488
ChEBI Namenatamycin
Stars
DefinitionA 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.
Last Modified13 October 2021
DownloadsMolfile
FormulaC33H47NO13
Net Charge0
Average Mass665.733
Monoisotopic Mass665.30474
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
InChIInChI=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
InChIKeyNCXMLFZGDNKEPB-FFPOYIOWSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces natalensis (ncbitaxon:68242) - PubMed (31311527)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
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).
antifungal agrochemical  Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
natamicinaWHO MedNet
natamycinWHO MedNet
natamycineWHO MedNet
natamycinumWHO MedNet
Synonyms  Source
antibiotic A-5283ChemIDplus
CL 12,625ChemIDplus
CL 12625ChemIDplus
E 235ChEBI
E-235ChEBI
pimaricinKEGG COMPOUND
Brand Names  Source
DelvocidChemIDplus
DelvolanChemIDplus
DelvoposChemIDplus
MycophytChemIDplus
MyprozineChemIDplus
MyuprozineDrugCentral
Manual XrefsDatabases
10468784ChemSpider
1885DrugCentral
2062BPDB
C08073KEGG COMPOUND
CPD-17213MetaCyc
D00884KEGG DRUG
DB00826DrugBank
FDB002337FooDB
HMDB0014964HMDB
natamycinAlan Wood's Pesticides
NatamycinWikipedia
Registry NumbersSources
CAS:7681-93-8ChemIDplus
Citations