AntibioticMech

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

Classification

ionophore with antibiotic activityARO:3005163

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:36468 CHEBI:36468
• ARO:3005163 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

Equivalent identifiers for this same structure in other resources.

• ARO:3007485
• cas:28380-24-7
• kegg.compound:C11609
• knapsack:C00018750
• patent:US3555150
• reaxys:74670
• vsdb:2572
• wikipedia.en:Nigericin
• chembl:CHEMBL405862
• pubchem.compound:34230

Activity roles

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

• CHEBI:33281 CHEBI:33281
• CHEBI:33282 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

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · 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.