monensin (CHEM043971)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:30:05 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043971
Identification
Common Namemonensin
ClassSmall Molecule
DescriptionMonensin 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.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Monensin-a-sodium complexMeSH
RumensinMeSH
Monensin a sodium complexMeSH
Monensin monosodium saltMeSH
MonensinMeSH
Monensin sodiumMeSH
Chemical FormulaC36H62O11
Average Molecular Mass670.881 g/mol
Monoisotopic Mass670.429 g/mol
CAS Registry Number17090-79-8
IUPAC Name(2R,3S,4R)-4-[(2R,5R,7S,8R,9S)-2-[(2S,2'S,3'R,5R,5'S)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid
Traditional Name(2R,3S,4R)-4-[(2R,5R,7S,8R,9S)-2-[(2S,2'S,3'R,5R,5'S)-2-ethyl-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl-[2,2'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid
SMILES[H][C@](C)(C(O)=O)[C@@]([H])(OC)[C@@]([H])(C)[C@@]1([H])O[C@@]2(CC[C@@](C)(O2)[C@@]2([H])CC[C@](CC)(O2)[C@@]2([H])O[C@@]([H])(C[C@@]2([H])C)[C@@]2([H])O[C@@](O)(CO)[C@]([H])(C)C[C@]2([H])C)C[C@]([H])(O)[C@@]1([H])C
InChI IdentifierInChI=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
InChI KeyGAOZTHIDHYLHMS-GDMSFIFLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHeterocyclic fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Ketal
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Oxane
  • Tetrahydrofuran
  • Hemiacetal
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP2.7ALOGPS
logP4.82ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area153.37 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity172.38 m³·mol⁻¹ChemAxon
Polarizability73.78 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0911018000-2000451e1321518d02fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbd-2916283000-4564796f13a29238d166Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3901000000-5aaa9f062dd52b9814f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0920004000-80275a635e366bef8eaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uds-2201619000-28c026f4b02caef284dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n0-4930000000-24988509267f02eec985Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMonensin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID28263
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available