Structure via PubChem · Public domain (PubChem)
nigericin
Sign in to saveAlso known as Polyetherin A, Azalomycin M, Helixin C
Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation from soil from Nigeria was described in the 1950s, by R.L Harned (et. al), and in 1968 the structure could be elucidated by X-ray crystallography. The structure and properties of nigericin are similar to the antibiotic monensin. Commercially it is obtained as a byproduct, or contaminant, at the fermentation of geldanamycin. It is also called polyetherin A, azalomycin M, helixin C, antibiotic K178, and antibiotic X-464.
Chemical data
- Formula
- C40H68O11
- Molecular weight
- 725 g/mol
- IUPAC name
- (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid
- SMILES
- C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC
- InChIKey
- DANUORFCFTYTSZ-SJSJOXFOSA-N
- XLogP
- 5.5
- Polar surface area
- 142 Ų
- H-bond donors
- 3
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,756 papers- Evidence of nigericin as a potential therapeutic candidate for cancers: A review.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2021
- Nigericin treatment activates endoplasmic reticulum apoptosis pathway in goldfish kidney leukocytes.Fish & shellfish immunology · 2023
- Nigericin exerts anticancer effects through inhibition of the SRC/STAT3/BCL-2 in osteosarcoma.Biochemical pharmacology · 2022
- Nigericin is effective against multidrug resistant gram-positive bacteria, persisters, and biofilms.Frontiers in cellular and infection microbiology · 2022
- Nigericin Induces Paraptosis-Like Cell Death Instead of Pyroptosis in Corneal Keratocytes.FASEB journal : official publication of the Federation of American Societies for Experimental Biology · 2025
via PubMed
Wikidata facts
- Mass
- 724.476163
Show 5 more facts
- chemical formula
- C₄₀H₆₈O₁₁
- canonical SMILES
- CC1CCC(OC1C(C)C(=O)O)CC2CC(C(C3(O2)C(CC(O3)(C)C4CCC(O4)(C)C5C(CC(O5)C6C(CC(C(O6)(CO)O)C)C)C)C)C)OC
- isomeric SMILES
- C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC
- found in taxon
- Streptomyces hygroscopicus
- subject has role
- ionophore
via Wikidata · CC0
~2 min read
Encyclopedic overview
1 sectionsContents
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462260648 | ImageFile = Nigericin correct structure.svg | ImageClass = skin-invert-image | ImageSize=300 | PIN=(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-dimethyloxan-2-yl]-2,3′-dimethyl[2,2′-bioxolan]-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoic acid | OtherNames=Polyetherin A, Azalomycin M, Helixin C, Helix C |Section1= |Section2= |Section3= }}
Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation from soil from Nigeria was described in the 1950s, by R.L Harned (et. al), and in 1968 the structure could be elucidated by X-ray crystallography. The structure and properties of nigericin are similar to the antibiotic monensin. Commercially it is obtained as a byproduct, or contaminant, at the fermentation of geldanamycin. It is also called polyetherin A, azalomycin M, helixin C, antibiotic K178, and antibiotic X-464.
Excerpted from Wikipedia’s “nigericin” article, available under the CC BY-SA 4.0 licence.