Milbemectin (mixture) (CHEM002848)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (23)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002848
Identification
Common NameMilbemectin (mixture)
ClassSmall Molecule
DescriptionMilbemectin is a mixture of milbemycin A3 and milbemycin A4 in a ratio of 3:7. It is an active acaricide produced from fermentation products of Streptomyces subspecies. It is highly active on various phytophagous mites that live on tea plants, pome fruits, stone fruits, citrus, watermelon, strawberry and egg plants. It is also an insecticide that is active against aphids, cutworms, leafrollers and thrips. It appears to stimulate the release of gamma-aminobutyric acid (GABA) which affects the chloride channels of the central nervous system.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Insecticide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Hydroxymilbemycin beta7MeSH
Milbemycin alpha7MeSH
Milbemycin alpha2MeSH
Milbemycin alpha9MeSH
MoxidectinMeSH
Milbemycin alpha13MeSH
Milbemycin beta3MeSH
Milbemycin bMeSH
Milbemycin beta12MeSH
Milbemycin DMeSH
Milbemycin alpha3MeSH
Milbemycin alpha6MeSH
MilbemycinsMeSH
MilbemectinMeSH
MilbemycinMeSH
Milbemycin alpha8MeSH
Milbemycin beta2MeSH
Milbemycin alpha11MeSH
Milbemycin alpha1MeSH
Milbemycin alpha5MeSH
Milbemycin beta1MeSH
Milbemycin a3MeSH
Milbemycin alpha4MeSH
Milbemycin alpha10MeSH
CydectinMeSH
Milbemycin alpha14MeSH
Milbemycin alpha15MeSH
Milbemycin a4MeSH
Chemical FormulaC32H46O7
Average Molecular Mass542.703 g/mol
Monoisotopic Mass542.324 g/mol
CAS Registry Number51596-11-3
IUPAC Name(1'R,2R,4'S,5S,6R,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-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,4'S,5S,6R,8'R,10'E,13'R,14'E,20'R,21'R,24'S)-6-ethyl-21',24'-dihydroxy-5,11',13',22'-tetramethyl-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@@]12OC\C3=C/C=C/[C@H](C)C\C(C)=C\C[C@]4([H])C[C@@H](C[C@]5(CC[C@H](C)[C@@H](CC)O5)O4)OC(=O)[C@]([H])(C=C(C)[C@H]1O)[C@@]23O
InChI IdentifierInChI=1S/C32H46O7/c1-6-27-21(4)12-13-31(39-27)17-25-16-24(38-31)11-10-20(3)14-19(2)8-7-9-23-18-36-29-28(33)22(5)15-26(30(34)37-25)32(23,29)35/h7-10,15,19,21,24-29,33,35H,6,11-14,16-18H2,1-5H3/b8-7+,20-10+,23-9+/t19-,21-,24+,25-,26-,27+,28+,29+,31+,32+/m0/s1
InChI KeyVOZIAWLUULBIPN-LRBNAKOISA-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
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.48ALOGPS
logP4.53ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity151.6 m³·mol⁻¹ChemAxon
Polarizability61.24 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0006-3100290000-c0537502ba618e2d28d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9222020000-1bfbe716b5d7338aefb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003g-9121200000-0db3aa9765bd3fe72effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2003290000-d7f9b77aec3f53771d73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-0346950000-f6325e67be278daaa209Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kka-4019310000-0a312399e60dfbdb402bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
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 LinkNot Available
Chemspider IDNot Available
ChEBI ID39229
PubChem Compound ID9959038
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available