Structure via PubChem · Public domain (PubChem)
monensin
Sign in to saveAlso known as monensic acid, monensin A, polyether antibiotic monensin
Monensin is a polyether antibiotic isolated from Streptomyces cinnamonensis. It is widely used in ruminant animal feeds.
Chemical data
- Formula
- C36H62O11
- Molecular weight
- 670.9 g/mol
- IUPAC name
- (2S,3R,4S)-4-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-ethyl-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoic acid
- SMILES
- CC[C@]1(CC[C@@H](O1)[C@@]2(CC[C@@]3(O2)C[C@@H]([C@H]([C@H](O3)[C@@H](C)[C@H]([C@H](C)C(=O)O)OC)C)O)C)[C@H]4[C@H](C[C@@H](O4)[C@@H]5[C@H](C[C@H]([C@@](O5)(CO)O)C)C)C
- InChIKey
- GAOZTHIDHYLHMS-KEOBGNEYSA-N
- XLogP
- 4.2
- Polar surface area
- 153 Ų
- H-bond donors
- 4
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
5,522 papers- Monensin toxicity in cattle.Journal of animal science · 1984
- Effects of monensin supplementation on lactation performance of dairy cows: a systematic review and dose-response meta‑analysis.Scientific reports · 2023
- Monensin induces secretory granule-mediated cell death in eosinophils.The Journal of allergy and clinical immunology · 2023
- Effects of monensin supplementation on rumen fermentation, methane emissions, nitrogen balance, and metabolic responses of dairy cows: A systematic review and dose-response meta-analysis.Journal of dairy science · 2024
- Influence of monensin on the performance of cattle.Journal of animal science · 1984
via PubMed
Wikidata facts
- Mass
- 670.429213
Show 4 more facts
- chemical formula
- C₃₆H₆₂O₁₁
- isomeric SMILES
- CC[C@]1(CC[C@@H](O1)[C@@]2(CC[C@@]3(O2)C[C@@H]([C@H]([C@H](O3)[C@@H](C)[C@H]([C@H](C)C(=O)O)OC)C)O)C)[C@H]4[C@H](C[C@@H](O4)[C@@H]5[C@H](C[C@H]([C@@](O5)(CO)O)C)C)C
- canonical SMILES
- CCC1(CCC(O1)C2(CCC3(O2)CC(C(C(O3)C(C)C(C(C)C(=O)O)OC)C)O)C)C4C(CC(O4)C5C(CC(C(O5)(CO)O)C)C)C
- World Health Organisation international non-proprietary name
- monensin
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Mechanism of action
- Uses
- Toxicity
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 408764013 | Name = Monensin A | ImageFile = Monensin A.svg | ImageClass = skin-invert-image | ImageSize = | PIN = (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-dimethyloxan-2-yl]-3′-methyl[2,2′-bioxolan]-5-yl}-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid | OtherNames = Monensic acid |Section1= |Section2= | Section6 = |Section8= }} Monensin is a polyether antibiotic isolated from Streptomyces cinnamonensis. It is widely used in ruminant animal feeds.
The structure of monensin was first described by Agtarap et al. in 1967, and was the first polyether antibiotic to have its structure elucidated in this way. The first total synthesis of monensin was reported in 1979 by Kishi et al.
Excerpted from Wikipedia’s “monensin” article, available under the CC BY-SA 4.0 licence.