Compound: monensin
SMILES: O=C(O)[C@H]([C@H](OC)[C@@H]([C@H]1O[C@]2(O[C@@]([C@@H]3O[C@@]([C@@H]4O[C@@H]([C@H]5O[C@](O)([C@H](C)C[C@@H]5C)CO)C[C@@H]4C)(CC)CC3)(C)CC2)C[C@@H]([C@H]1C)O)C)C
InChIKey: GAOZTHIDHYLHMS-KEOBGNEYSA-N
Synonyms: monensin, monensin A, Monensic acid, 17090-79-8, Monensina, Monensinum, Elancoban, Monelan, Rumensin 90, A 3823A, Coban (as sodium salt), Rumensin (as sodium salt), Lilly 673140, A-3823A, 906O0YJ6ZP, ATCC 15413, DTXSID4048561, CHEBI:27617, (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, 1,6-Dioxaspiro(4.5)decane-7-butyric acid, 2-(5-ethyltetrahydro-5-(tetrahydro-3-methyl-5-(tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl)-2-furyl)-2-furyl)-9-hydroxy-beta-methoxy-alpha,gamma,2,8-tetramethyl-, 4-(2-(2-ETHYL-3'-METHYL-5'-(TETRAHYDRO-6-HYDROXY-6-HYDROXYMETHYL-3,5-DIMETHYLPYRAN-2-YL)PERHYDRO-2,2'-BIFURAN-5-YL)-9-HYDROXY-2,8-DIMETHYL-1,6-DIOXASPIRO(4.5)DEC-7-YL)3-METHOXY-2-METHYLPENTANOIC ACID, Monensin Granulated, (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, (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, (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, Coxidin 90, Monovet 90, Coban 90, CycleGuard and Monovet, RefChem:57076, DTXCID7028190, monensin Type A medicated article, 241-154-0, Pasture Gainer Block 20 R350, Pasture Gainer Block 20 R350 No SE, Pasture Gainer Block 37 R350, Pasture Gainer Block 37 R350 No SE, Monensin (INN), MONENSIN [INN], Monensinum [INN-Latin], Monensina [INN-Spanish], UNII-906O0YJ6ZP, Monensine, HSDB 7031, Monensin [USAN:USP:INN:BAN], 2-(5-ETHYLTETRAHYDRO-5-(TETRAHYDRO-3-METHYL-5-(TETRAHYDRO-6-HYDROXY-6-(HYDROXYMETHYL)-3,5-DIMETHYL-2H-PYRAN-2-YL)-2-FURYL)-2-FURYL)-9-HYDROXY-.BETA.-METHOXY-.ALPHA.,.GAMMA.,2,8-TETRAMETHYL-1,6-DIOXASPIRO(4.5)DECANE-7-BUTYRIC ACID, 2-[5-Ethyltetrahydro-5-[tetrahydro-3-methyl-5-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-2-furyl]-2-furyl]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.,2,8-tetramethyl-1,6-dioxaspiro[4.5]decane-7-butyric acid, EINECS 241-154-0, MFCD00799192, MONENSIN [HSDB], MONENSIN [USAN], MONENSIN [MI], Prestwick3_000748, GlyTouCan:G49969XG, MONENSIN [MART.], SCHEMBL55367, BSPBio_000736, Elancoban [veterinary] (TN), MONENSIN [GREEN BOOK], BPBio1_000810, CHEMBL256105, orb1710412, MONENSIN [USP IMPURITY], MONENSIN [USP MONOGRAPH], GTPL14126, G49969XG, HY-N4302, T1033L, AKOS015964837, DB11430, FM31903, E714, Stereoisomer of 2-(2-ethyloctahydro-3'-methyl-5'-(tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl)(2,2'-bifuran-5-yl))-9-hydroxy-beta-methoxy-alpha,gamma,2,8-tetramethyl-1,6-dioxaspiro(4.5)decan-7-butanoic acid, SY248013, CS-0032703, NS00000169, C06693, D08228, Q3493048, SR-05000013702-2, BRD-K55375480-236-03-0, (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]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid, (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, (2S,3R,4S)-4-[(3S,5R,7S,8R,9S)-3-[(2R,5S)-5-ethyl-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-tetrahydropyran-2-yl]-3-methyl-tetrahydrofuran-2-yl]tetrahydrofuran-2-yl]-7-hydroxy-3,8-dimethyl-4,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methyl-pentanoic acid, 2-(2-ETHYLOCTAHYDRO-3'-METHYL-5'-(TETRAHYDRO-6-HYDROXY-6-(HYDROXYMETHYL)-3,5-DIMETHYL-2H-PYRAN-2-YL)(2,2'-BIFURAN-5-YL))-9-HYDROXY-.BETA.-METHOXY-.ALPHA.,.GAMMA.,2,8-TETRAMETHYL-1,6-DIOXASPIRO(4.5)DECAN-7-BUTANOIC ACID
Theoretical properties:
molecular_formula: C36H62O11
molecular_weight: 670.9 g/mol
exact_mass: 670.42921279 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 10
heavy_atom_count: 47
topological_polar_surface_area: 153 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
melting_point: MP: 103-105 °C /Monensin monohydrate/
solubility: Slightly soluble in water
Descriptions:
pubchem: Monensin A is 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. It has a role as an ionophore, an antifungal agent and a coccidiostat. It is a monocarboxylic acid, a polyether antibiotic, a cyclic hemiketal and a spiroketal.
chebi: A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by <em>Streptomyces cinnamonensis</em>. 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.
chembl: MONENSIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.