Emamectin benzoate (CHEM002792)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (40)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:51 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002792
Identification
Common NameEmamectin benzoate
ClassSmall Molecule
DescriptionEmamectin benzoate (Proclaim) is an avermectin class insecticide developed for the control of lepidopteron insects. This class of pesticide consists of homologous semi-synthetic macrolides that are derived from the natural fermentation products of Streptomyces bacteria. It kills insects by disrupting neurotransmitters, causing irreversible paralysis. It is more effective when ingested, but it also somewhat effective on contact. When sprayed to foliage, emamectin benzoate penetrates the leaf tissue and forms reservoir within treated leaves, which provides residual activity against pests that ingest the substance when feeding. Emamectin is widely used in the US and Canada as an insecticide because of its chloride channel activation properties. It is approved by the EPA for use in prevention of emerald ash borer in ash trees. Emamectin has also shown promising applications in the eradication of fish lice and in fish farming.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Insecticide
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Emamectin benzoic acidGenerator
4''-Deoxy-4''-epi-N-methylaminoavermectin b1 benzoateMeSH
Chemical FormulaC56H81NO15
Average Molecular Mass1008.240 g/mol
Monoisotopic Mass1007.561 g/mol
CAS Registry Number155569-91-8
IUPAC Name(2S,3S,4S,6S)-6-{[(2S,3S,4S,6R)-6-[(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-oneoxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-N,2-dimethyloxan-3-aminium benzoate
Traditional Name(2S,3S,4S,6S)-6-{[(2S,3S,4S,6R)-6-[(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-oneoxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-N,2-dimethyloxan-3-aminium benzoate
SMILES[O-]C(=O)C1=CC=CC=C1.[H][C@](C)(CC)[C@@]1([H])O[C@@]2(C[C@@H]3C[C@@]([H])(C\C=C(C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H]([NH2+]C)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C4/CO[C@]5([H])[C@H](O)C(C)=C[C@@]([H])(C(=O)O3)[C@]45O)O2)C=C[C@@H]1C
InChI IdentifierInChI=1S/C49H75NO13.C7H6O2/c1-12-26(2)44-29(5)18-19-48(63-44)24-35-21-34(62-48)17-16-28(4)43(27(3)14-13-15-33-25-56-46-42(51)30(6)20-36(47(52)59-35)49(33,46)53)60-40-23-38(55-11)45(32(8)58-40)61-39-22-37(54-10)41(50-9)31(7)57-39;8-7(9)6-4-2-1-3-5-6/h13-16,18-20,26-27,29,31-32,34-46,50-51,53H,12,17,21-25H2,1-11H3;1-5H,(H,8,9)/b14-13+,28-16+,33-15+;/t26-,27-,29-,31-,32-,34+,35-,36-,37-,38-,39-,40-,41-,42+,43-,44+,45-,46+,48+,49+;/m0./s1
InChI KeyGCKZANITAMOIAR-XWVCPFKXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Ketal
  • Benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Tetrahydrofuran
  • Tertiary alcohol
  • Amino acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Secondary amine
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
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 Solubility0.0014 g/LALOGPS
logP5.55ALOGPS
logP6.17ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area166.44 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity249.03 m³·mol⁻¹ChemAxon
Polarizability99.35 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-0a4i-9000000000-59be3ae3b24c8cbd6bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-59be3ae3b24c8cbd6bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-59be3ae3b24c8cbd6bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-70b44bba6aa0336bce93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-70b44bba6aa0336bce93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-70b44bba6aa0336bce93Spectrum
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 LinkEmamectin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11650986
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available