CHEBI:27617 - monensin A

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ChEBI Name monensin A
ChEBI ID CHEBI:27617
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6973, CHEBI:25376
Supplier Information
Download Molfile XML SDF
Formula C36H62O11
Net Charge 0
Average Mass 670.87090
Monoisotopic Mass 670.429
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
InChIKey GAOZTHIDHYLHMS-KEOBGNEYSA-N
SMILES [H][C@@]1(C[C@H](C)[C@@]([H])(O1)[C@]1(CC)CC[C@@]([H])(O1)[C@]1(C)CC[C@]2(C[C@H](O)[C@@H](C)[C@]([H])(O2)[C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O1)[C@@]1([H])O[C@@](O)(CO)[C@H](C)C[C@@H]1C
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ionophore
A compound which can carry specific ions through membranes of cells or organelles.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing monensin A (CHEBI:27617) has role antifungal agent (CHEBI:35718)
monensin A (CHEBI:27617) has role coccidiostat (CHEBI:35818)
monensin A (CHEBI:27617) has role ionophore (CHEBI:24869)
monensin A (CHEBI:27617) is a cyclic hemiketal (CHEBI:59780)
monensin A (CHEBI:27617) is a monocarboxylic acid (CHEBI:25384)
monensin A (CHEBI:27617) is a polyether antibiotic (CHEBI:26179)
monensin A (CHEBI:27617) is a spiroketal (CHEBI:72600)
IUPAC Name
(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
INNs Sources
monensin ChemIDplus
monensina ChemIDplus
monensinum ChemIDplus
Synonyms Sources
monensic acid ChemIDplus
Monensin KEGG COMPOUND
Monensin A KEGG COMPOUND
Database Links Databases
C06693 KEGG COMPOUND
D08228 KEGG DRUG
LSM-5659 LINCS
View more database links
Registry Numbers Types Sources
1633130 Reaxys Registry Number Reaxys
17090-79-8 CAS Registry Number KEGG COMPOUND
Citation Waiting for Citations Type Source
21215424 PubMed citation Europe PMC
Last Modified
25 February 2016