Emamectin B1b (CHEM000901)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (11)XML
Record Information
Version1.0
Creation Date2009-06-18 20:15:07 UTC
Update Date2026-04-06 04:20:18 UTC
Accession NumberCHEM000901
Identification
Common NameEmamectin B1b
ClassSmall Molecule
DescriptionThe avermectins are a series of macrocyclic lactone derivatives with potent anthelmintic properties. A commonly used therapy in recent times has been based on oral or parenteral administration of avermectins, which are macrocyclic lactones produced by fermentation of various, carefully prepared laboratory broths using the soil micro-organism Streptomyces avermitilis. They show activity against a broad range of nematodes and arthropod parasites of domestic animals at dose rates of 300 microgram/kg or less. Unlike the macrolide or polyene antibiotics, they lack significant antibacterial or antifungal activity. (1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Avermectin
  • Bacterial Toxin
  • Ester
  • Ether
  • Lachrymator
  • Natural Compound
  • Organic Compound
  • Pesticide
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2AE,4E,5's,6S,6'r,7S,8E,11R,13S,15S,17ar,20R,20ar,20BS)-20,20b-dihydroxy-6'-isopropyl-5',6,8,19-tetramethyl-17-oxo-5',6,6',10,11,14,15,17,17a,20,20a,20b-dodecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-PQ][2,6]benzodioxacyclooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-3-O-methyl-4-O-[2,4,6-trideoxy-3-O-methyl-4-(methylamino)-alpha-L-arabino-hexopyranosyl]-alpha-L-arabino-hexopyranosideChEBI
(2AE,4E,5's,6S,6'r,7S,8E,11R,13S,15S,17ar,20R,20ar,20BS)-20,20b-dihydroxy-6'-isopropyl-5',6,8,19-tetramethyl-17-oxo-5',6,6',10,11,14,15,17,17a,20,20a,20b-dodecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-PQ][2,6]benzodioxacyclooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-3-O-methyl-4-O-[2,4,6-trideoxy-3-O-methyl-4-(methylamino)-a-L-arabino-hexopyranosyl]-a-L-arabino-hexopyranosideGenerator
(2AE,4E,5's,6S,6'r,7S,8E,11R,13S,15S,17ar,20R,20ar,20BS)-20,20b-dihydroxy-6'-isopropyl-5',6,8,19-tetramethyl-17-oxo-5',6,6',10,11,14,15,17,17a,20,20a,20b-dodecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-PQ][2,6]benzodioxacyclooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-3-O-methyl-4-O-[2,4,6-trideoxy-3-O-methyl-4-(methylamino)-α-L-arabino-hexopyranosyl]-α-L-arabino-hexopyranosideGenerator
Chemical FormulaC48H73NO13
Average Molecular Mass872.092 g/mol
Monoisotopic Mass871.508 g/mol
CAS Registry Number121424-52-0
IUPAC Name(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)-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-4-methoxy-5-{[(2S,4S,5S,6S)-4-methoxy-6-methyl-5-(methylamino)oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-6-(propan-2-yl)-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'-one
Traditional Nameemamectin B1b
SMILESCN[C@H]1[C@H](C)O[C@H](C[C@@H]1OC)O[C@H]1[C@H](C)O[C@H](C[C@@H]1OC)O[C@H]1[C@@H](C)\C=C\C=C2/CO[C@@H]3[C@H](O)C(C)=C[C@@H](C(=O)O[C@H]4C[C@@H](C\C=C1/C)O[C@@]1(C=C[C@H](C)[C@@H](C(C)C)O1)C4)[C@]23O
InChI IdentifierInChI=1S/C48H73NO13/c1-25(2)42-28(5)17-18-47(62-42)23-34-20-33(61-47)16-15-27(4)43(26(3)13-12-14-32-24-55-45-41(50)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-11)44(31(8)57-39)60-38-21-36(53-10)40(49-9)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,16,20-24H2,1-11H3/b13-12+,27-15+,32-14+/t26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40-,41+,42+,43-,44-,45+,47+,48+/m0/s1
InChI KeyDXIOOXFZLKCVHK-UTAOKEBVSA-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
  • Ketal
  • Monosaccharide
  • Oxane
  • Pyran
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Amino acid or derivatives
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Organoheterocyclic compound
  • Secondary amine
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen 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 Solubility0.007 g/LALOGPS
logP3.92ALOGPS
logP5.73ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area161.86 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity233.01 m³·mol⁻¹ChemAxon
Polarizability96 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0fk9-5200072290-45c733b8d2de914241c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-6810091210-03ee612dd943af5bd5abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9420010000-4d9e5de51abe20a6cc56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900010130-ebd988a6206da25843baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gbd-0300091340-01afa09f628f62f6cabfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-6800391000-11cfc2fb9fb8a06a66d0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityIt has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. (3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesActive ingredient in some commercial ant bait traps. (1)
Minimum Risk LevelNot Available
Health EffectsAvermectins are neurotoxic and have reproductive and developmental effects. (2)
SymptomsAvermectins cause irritation of skin and eyes, central nervous system depression (incoordination, tremors, lethargy, excitation, pupil dilation, coma), vomiting, convulsions and/or tremors, and respiratory failure at high doses. (2)
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 ID39232
PubChem Compound ID16722138
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available