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CHEBI:27617 - monensin A

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:
ionophore  A compound which can carry specific ions through membranes of cells or organelles.
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.
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
monensinumChemIDplus
monensinaChemIDplus
monensinChemIDplus
Synonyms  Source
MonensinKEGG COMPOUND
monensic acidChemIDplus
Monensin AKEGG COMPOUND
Manual XrefsDatabases
C06693KEGG COMPOUND
D08228KEGG DRUG
LSM-5659LINCS
Registry NumbersSources
Reaxys:1633130Reaxys
CAS:17090-79-8KEGG COMPOUND
Citations