CHEBI:7569 - nigericin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name nigericin
ChEBI ID CHEBI:7569
Definition A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:530451
Supplier Information ChemicalBook:CB9752065, eMolecules:491943
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C40H68O11
Net Charge 0
Average Mass 724.96130
Monoisotopic Mass 724.47616
InChI InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1
InChIKey DANUORFCFTYTSZ-SJSJOXFOSA-N
SMILES [H][C@@]1(CC[C@H](C)[C@@]([H])(O1)[C@@H](C)C(O)=O)C[C@@H]1C[C@@H](OC)[C@@H](C)[C@]2(O1)O[C@@](C)(C[C@H]2C)[C@@]1([H])CC[C@](C)(O1)[C@]1([H])O[C@]([H])(C[C@@H]1C)[C@@]1([H])O[C@@](O)(CO)[C@H](C)C[C@@H]1C
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
potassium ionophore
Any ionophore capable of transportation of potassium ions across membranes.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nigericin (CHEBI:7569) has role antibacterial agent (CHEBI:33282)
nigericin (CHEBI:7569) has role antimicrobial agent (CHEBI:33281)
nigericin (CHEBI:7569) has role bacterial metabolite (CHEBI:76969)
nigericin (CHEBI:7569) has role potassium ionophore (CHEBI:88227)
nigericin (CHEBI:7569) is a polycyclic ether (CHEBI:36468)
IUPAC Name
(2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methyltetrahydro-2H-pyran-2-yl]propanoic acid
Synonyms Sources
Azalomycin M ChemIDplus
Helixin C ChemIDplus
Polyetherin A ChemIDplus
Manual Xrefs Databases
2572 VSDB
C00018750 KNApSAcK
C11609 KEGG COMPOUND
Nigericin Wikipedia
US3555150 Patent
View more database links
Registry Numbers Types Sources
28380-24-7 CAS Registry Number KEGG COMPOUND
28380-24-7 CAS Registry Number ChemIDplus
74670 Reaxys Registry Number Reaxys
Citations Types Sources
10341035 PubMed citation Europe PMC
10516103 PubMed citation Europe PMC
10996433 PubMed citation Europe PMC
15595852 PubMed citation Europe PMC
17618633 PubMed citation Europe PMC
20678563 PubMed citation Europe PMC
20709811 PubMed citation Europe PMC
20951746 PubMed citation Europe PMC
21257734 PubMed citation Europe PMC
22327078 PubMed citation Europe PMC
22493436 PubMed citation Europe PMC
7592045 PubMed citation Europe PMC
7638257 PubMed citation Europe PMC
7829226 PubMed citation Europe PMC
8010949 PubMed citation Europe PMC
8076364 PubMed citation Europe PMC
8717427 PubMed citation Europe PMC
8895841 PubMed citation Europe PMC
8913333 PubMed citation Europe PMC
9018148 PubMed citation Europe PMC
9178132 PubMed citation Europe PMC
9770325 PubMed citation Europe PMC
Last Modified
15 October 2015