nigericin

CHEBI:7569 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

ionophore with antibiotic activityARO:3005163

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:36468
ionophore with antibiotic activity ARO:3005163

Chemical structure

Computed structure properties
Molecular formula	C40H68O11
Charge	0
Average mass	724.973 Da
Monoisotopic mass	724.47616 Da
Source	ChEBI
InChIKey	DANUORFCFTYTSZ-SJSJOXFOSA-N

SMILES

[H][C@]1(C[C@@H]2C[C@@H](OC)[C@@H](C)[C@]3(O2)O[C@](C)([C@@]2([H])CC[C@@](C)([C@]4([H])O[C@@]([H])([C@@]5([H])O[C@@](O)(CO)[C@H](C)C[C@@H]5C)C[C@@H]4C)O2)C[C@H]3C)CC[C@H](C)[C@]([H])([C@@H](C)C(=O)O)O1

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

Also called

(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 (EXACT_SYNONYM)— chebi
Azalomycin M (EXACT_SYNONYM)— chebi
Helixin C (EXACT_SYNONYM)— chebi
Polyetherin A (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.

Patents and articles

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

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial agent CHEBI:33282

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
ARO	`ARO:3007485`	nigericin	`antibioticmech:aro-0aff72adb5`	2026-08-30
CHEBI	`CHEBI:7569`	nigericin	`antibioticmech:chebi-9c7c4af4e8`	2026-08-30

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Streptomyces violaceusniger NCBITaxon:68280	BGC0000114	Gene expression correlated with compound production compound specific	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'nigericin' joined by exact Standard InChIKey.	PMID:17584617 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)
Streptomyces sp. NCBITaxon:2583819 strain DASNCL29	BGC0002038	Enzymatic assays compound specific	MIBIG 4.0.1 (entry 2)	questionable	MIBiG active entry; compound 'nigericin' joined by exact Standard InChIKey.	PMID:35514935 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · 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).

Explore across X-Mech: MediaIngredientMech (nigericin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces violaceusniger)