Moxidectin (CHEM017493)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:23:57 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017493
Identification
Common NameMoxidectin
ClassSmall Molecule
DescriptionMoxidectin is an anthelmintic drug used in animals to prevent or control parasitic worms (helminths), such as heartworm and intestinal worms, in dogs, cats, horses, cattle and sheep. Moxidectin kills some of the most common internal and external parasites by selectively binding to a parasite's glutamate-gated chloride ion channels. These channels are vital to the function of invertebrate nerve and muscle cells; when moxidectin binds to the channels, it disrupts neurotransmission, resulting in paralysis and death of the parasite.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Milbemycin beta2MeSH
5-Hydroxymilbemycin beta7MeSH
MilbemectinMeSH
Milbemycin a4MeSH
MilbemycinMeSH
Milbemycin beta1MeSH
CydectinMeSH
Milbemycin alpha13MeSH
Milbemycin alpha6MeSH
Milbemycin DMeSH
MilbemycinsMeSH
Milbemycin alpha9MeSH
Milbemycin alpha14MeSH
Milbemycin alpha15MeSH
Milbemycin bMeSH
Milbemycin a3MeSH
Milbemycin alpha10MeSH
Milbemycin beta3MeSH
Milbemycin alpha4MeSH
Milbemycin alpha3MeSH
Milbemycin alpha2MeSH
Milbemycin beta12MeSH
Milbemycin alpha8MeSH
Milbemycin alpha5MeSH
Milbemycin alpha1MeSH
Milbemycin alpha7MeSH
Milbemycin alpha11MeSH
MoxidectinMeSH
Chemical FormulaC37H53NO8
Average Molecular Mass639.830 g/mol
Monoisotopic Mass639.377 g/mol
CAS Registry Number113507-06-5
IUPAC Name(1'R,2R,4Z,4'S,5S,6S,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-4-(methoxyimino)-5,11',13',22'-tetramethyl-6-[(2E)-4-methylpent-2-en-2-yl]-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one
Traditional Name(1'R,2R,4Z,4'S,5S,6S,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-4-(methoxyimino)-5,11',13',22'-tetramethyl-6-[(2E)-4-methylpent-2-en-2-yl]-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one
SMILES[H]\C(C(C)C)=C(\C)[C@@]1([H])O[C@]2(C\C(=N\OC)[C@]1([H])C)C[C@]1([H])C[C@@]([H])(C\C([H])=C(C)\C[C@@]([H])(C)\C([H])=C(/[H])\C(\[H])=C3/CO[C@]4([H])[C@]([H])(O)C(C)=C[C@@]([H])(C(=O)O1)[C@]34O)O2
InChI IdentifierInChI=1S/C37H53NO8/c1-21(2)14-25(6)33-26(7)31(38-42-8)19-36(46-33)18-29-17-28(45-36)13-12-23(4)15-22(3)10-9-11-27-20-43-34-32(39)24(5)16-30(35(40)44-29)37(27,34)41/h9-12,14,16,21-22,26,28-30,32-34,39,41H,13,15,17-20H2,1-8H3/b10-9+,23-12+,25-14+,27-11+,38-31-/t22-,26-,28+,29-,30-,32+,33+,34+,36-,37+/m0/s1
InChI KeyYZBLFMPOMVTDJY-CBYMMZEQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.g. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassMilbemycins
Direct ParentMilbemycins
Alternative Parents
Substituents
  • Milbemycin
  • Ketal
  • Oxane
  • Tertiary alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Oxime ether
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • 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 Solubility0.0052 g/LALOGPS
logP5.3ALOGPS
logP5.67ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)2.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.04 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity179.22 m³·mol⁻¹ChemAxon
Polarizability70.88 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1500049000-ba03db68bcb9efcf2e0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05is-3914022000-04966496827decd698daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w93-6921041000-c7894908aa4b8ff3d258Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-1901013000-f6beb131a2806ac91616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-3223869000-3b2b7b9284ea946972ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-024j-0519411000-6ba8184fcfa9d33850bfSpectrum
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 LinkMoxidectin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID16760141
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available