monensin A

CHEBI:27617 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle. — 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:25384
Label unavailable CHEBI:26179
Label unavailable CHEBI:59780
Label unavailable CHEBI:72600
ionophore with antibiotic activity ARO:3005163

Chemical structure

Computed structure properties
Molecular formula	C36H62O11
Charge	0
Average mass	670.881 Da
Monoisotopic mass	670.42921 Da
Source	ChEBI
InChIKey	GAOZTHIDHYLHMS-KEOBGNEYSA-N

SMILES

[H][C@]1([C@@H](C)[C@@H](OC)[C@H](C)C(=O)O)O[C@@]2(CC[C@@](C)([C@@]3([H])CC[C@@](CC)([C@]4([H])O[C@@]([H])([C@@]5([H])O[C@@](O)(CO)[C@H](C)C[C@@H]5C)C[C@@H]4C)O3)O2)C[C@H](O)[C@H]1C

InChI

InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1

Also called

monensin (INN)— chebi
monensina (INN)— chebi
monensinum (INN)— chebi
(2S,3R,4S)-4-[(2S,5R,7S,8R,9S)-2-{(2S,2'R,3'S,5R,5'R)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-3'-methyloctahydro-2,2'-bifuran-5-yl}-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]dec-7-yl]-3-methoxy-2-methylpentanoic acid (EXACT_SYNONYM)— chebi
Monensin (EXACT_SYNONYM)— chebi
Monensin A (EXACT_SYNONYM)— chebi
monensic acid (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.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

kegg.drug:D08228

Activity roles

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

antimicrobial agent CHEBI:33281
antifungal agent CHEBI:35718
coccidiostat CHEBI:35818

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:3007484`	monensin	`antibioticmech:aro-63950f6285`	2026-08-30
CHEBI	`CHEBI:27617`	monensin A	`antibioticmech:chebi-dd38701fcb`	2026-08-30

Mechanism summary

Mode of action: MEMBRANE_DISRUPTION host shared target — Assigned from ChEBI role CHEBI:24869 (ionophore). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

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 2026-09-10 · 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 (monensin A) · CultureMech · NaturalProductMech · PathwayMech · TraitMech