Monensin

Monensin A
Names
	Preferred 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-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
	Other names Monensic acid
Identifiers
CAS Number	17090-79-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27617 ;
ChEMBL	ChEMBL256105 ;
ChemSpider	389937 ;
ECHA InfoCard	100.037.398
E number	E714 (antibiotics)
KEGG	D08228 ;
PubChem CID	441145;
UNII	906O0YJ6ZP ;
CompTox Dashboard (EPA)	DTXSID4048561 ;
	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 Key: GAOZTHIDHYLHMS-KEOBGNEYSA-N ; InChI=1/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 Key: GAOZTHIDHYLHMS-KEOBGNEYBF;
	SMILES O=C(O)[C@@H](C)[C@H](OC)[C@H](C)[C@H]5O[C@]1(O[C@@](C)(CC1)[C@@H]2O[C@@](CC)(CC2)[C@@H]4O[C@@H]([C@H]3O[C@@](O)(CO)[C@@H](C[C@@H]3C)C)C[C@@H]4C)C[C@H](O)[C@H]5C;
Properties
Chemical formula	C36H62O11
Molar mass	670.871 g/mol
Appearance	solid state, white crystals
Melting point	104 °C (219 °F; 377 K)
Solubility in water	3x10−6 g/dm3 (20 °C)
Solubility	ethanol, acetone, diethyl ether, benzene
Pharmacology
ATCvet code	QA16QA06 (WHO) QP51BB03 (WHO)
Legal status	CA: ℞-only;
Related compounds
Related	antibiotics, ionophores
Related compounds	Monensin A methyl ester,
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Monensin is a polyether antibiotic isolated from Streptomyces cinnamonensis.^[2] It is widely used in ruminant animal feeds.^[2]^[3]

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.^[4]

^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
^ ^a ^b Daniel Łowicki and Adam Huczyński (2013). "Structure and Antimicrobial Properties of Monensin A and Its Derivatives: Summary of the Achievements". BioMed Research International. 2013: 1–14. doi:10.1155/2013/742149. PMC 3586448. PMID 23509771.
^ Butaye, P.; Devriese, L. A.; Haesebrouck, F. (2003). "Antimicrobial Growth Promoters Used in Animal Feed: Effects of Less Well Known Antibiotics on Gram-Positive Bacteria". Clinical Microbiology Reviews. 16 (2): 175–188. doi:10.1128/CMR.16.2.175-188.2003. PMC 153145. PMID 12692092.
^ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 185–187. ISBN 3-527-29284-5.

[1] "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.

[BMRI2013-2] Daniel Łowicki and Adam Huczyński (2013). "Structure and Antimicrobial Properties of Monensin A and Its Derivatives: Summary of the Achievements". BioMed Research International. 2013: 1–14. doi:10.1155/2013/742149. PMC 3586448. PMID 23509771.

[3] Butaye, P.; Devriese, L. A.; Haesebrouck, F. (2003). "Antimicrobial Growth Promoters Used in Animal Feed: Effects of Less Well Known Antibiotics on Gram-Positive Bacteria". Clinical Microbiology Reviews. 16 (2): 175–188. doi:10.1128/CMR.16.2.175-188.2003. PMC 153145. PMID 12692092.

[Nicolaou-4] Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 185–187. ISBN 3-527-29284-5.

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