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CHEBI:27617 - monensin A

Default Structure
ChEBI IDCHEBI:27617
ChEBI Namemonensin A
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:6973, CHEBI:25376
Last Modified25 February 2016
DownloadsMolfile
FormulaC36H62O11
Net Charge0
Average Mass670.881
Monoisotopic Mass670.42921
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
InChIInChI=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
InChIKeyGAOZTHIDHYLHMS-KEOBGNEYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
coccidiostat  An agent useful in the treatment or prevention of coccidiosis in man or animals.
ionophore  A compound which can carry specific ions through membranes of cells or organelles.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
coccidiostat  An agent useful in the treatment or prevention of coccidiosis in man or animals.
ChEBI Ontology
Outgoing Relation(s)
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  Source
monensinChemIDplus
monensinaChemIDplus
monensinumChemIDplus
Synonyms  Source
monensic acidChemIDplus
MonensinKEGG COMPOUND
Monensin AKEGG COMPOUND
Manual XrefsDatabases
C06693KEGG COMPOUND
D08228KEGG DRUG
LSM-5659LINCS
Registry NumbersSources
Reaxys:1633130Reaxys
CAS:17090-79-8KEGG COMPOUND
Citations