Monensin, monosodium salt (CHEM011008)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:31:27 UTC
Update Date2016-11-09 01:14:18 UTC
Accession NumberCHEM011008
Identification
Common NameMonensin, monosodium salt
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • HPV EPA Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Monensic acidChEBI
MonensinaChEBI
MonensinumChEBI
Monensin aKegg
ElancobanKegg
MonensateGenerator
MonensinChEBI
(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-methylpentanoateGenerator
Monensin monosodium saltMeSH
Monensin-a-sodium complexMeSH
Monensin a sodium complexMeSH
CobanMeSH
Monensin sodiumMeSH
RumensinMeSH
Chemical FormulaC36H62O11
Average Molecular Mass670.881 g/mol
Monoisotopic Mass670.429 g/mol
CAS Registry Number22373-78-0
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'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-3-methoxy-2-methylpentanoic acid
Traditional 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'-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-KEOBGNEYSA-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 Descriptors
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
Polarizability73.16 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, Positivesplash10-1070-0912028000-1fcd631aec73c60a847eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-2926273000-fa32b603be22d8197c3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3901000000-973bda8772a48bea9a0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0920004000-0f5c82b46780bb06737eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7a-2202829000-85f75cdb54c472efcce5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n0-4930000000-1985c91614a2a2cf82a2Spectrum
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 IDDB11430
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 ID27617
PubChem Compound ID441145
Kegg Compound IDC06693
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21215424