Basic Info

Common NameAvermectin B1B(F04056)
2D Structure
Description

The 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. (L829)

FRCD IDF04056
CAS Number65195-56-4
PubChem CID6858005
FormulaC47H70O14
IUPAC Name

None

InChI Key

ZFUKERYTFURFGA-PVVXTEPVSA-N

InChI

InChI=1S/C47H70O14/c1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h11-14,16-18,24-25,27,29-30,32-44,48-49,51H,15,19-23H2,1-10H3/b12-11+,26-14+,31-13+/t25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m0/s1

Canonical SMILES

CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)O)OC)OC)C)OC7(C4)C=CC(C(O7)C(C)C)C)O

Isomeric SMILES

C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(/[C@H]1O[C@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O)OC)OC)\C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C(C)C)C)O

Synonyms
        
            Avermectin A1a, 5-O-demethyl-25-de(1-methylpropyl)-25-(1-methylethyl)-
        
            Avermectin B1b
        
            65195-56-4
        
            abamectin component B1b
        
            UNII-W8DT67027W
        
            CHEBI:29537
        
            W8DT67027W
        
            Abamectin komponente B1b
        
            Antibiotic C 076B(sub 1b)
        
            EINECS 265-611-9
        
Classifies
                

                  
                    Pesticide
                  
                    Bacterial Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassMacrolides and analogues
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentMacrolides and analogues
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsMacrolide - Disaccharide - Glycosyl compound - O-glycosyl compound - Ketal - Oxane - Pyran - Tetrahydrofuran - Tertiary alcohol - Secondary alcohol - Carboxylic acid ester - Lactone - Acetal - Carboxylic acid derivative - Organoheterocyclic compound - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organic oxygen compound - Alcohol - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Properties

Property NameProperty Value
Molecular Weight859.063
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Complexity1710
Monoisotopic Mass858.477
Exact Mass858.477
XLogP3.5
Formal Charge0
Heavy Atom Count61
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.8020
Human Intestinal AbsorptionHIA+0.8827
Caco-2 PermeabilityCaco2-0.6878
P-glycoprotein SubstrateSubstrate0.7547
P-glycoprotein InhibitorInhibitor0.7023
Non-inhibitor0.5679
Renal Organic Cation TransporterNon-inhibitor0.7492
Distribution
Subcellular localizationMitochondria0.8128
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8662
CYP450 2D6 SubstrateNon-substrate0.8842
CYP450 3A4 SubstrateSubstrate0.7400
CYP450 1A2 InhibitorNon-inhibitor0.8545
CYP450 2C9 InhibitorNon-inhibitor0.8702
CYP450 2D6 InhibitorNon-inhibitor0.8912
CYP450 2C19 InhibitorNon-inhibitor0.8893
CYP450 3A4 InhibitorNon-inhibitor0.9179
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7494
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9909
Non-inhibitor0.7943
AMES ToxicityNon AMES toxic0.6257
CarcinogensNon-carcinogens0.9662
Fish ToxicityHigh FHMT0.8518
Tetrahymena Pyriformis ToxicityHigh TPT0.9782
Honey Bee ToxicityHigh HBT0.8924
BiodegradationNot ready biodegradable0.9591
Acute Oral ToxicityIII0.4355
Carcinogenicity (Three-class)Non-required0.5501

Model Value Unit
Absorption
Aqueous solubility-3.6176LogS
Caco-2 Permeability0.5930LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.4463LD50, mol/kg
Fish Toxicity0.3769pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6899pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Soy BeanAustralia0.002mg/kg