Basic Info

Common NameAvermectin B1A(F04055)
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 IDF04055
CAS Number65195-55-3
PubChem CID6434889
FormulaC48H72O14
IUPAC Name

None

InChI Key

RRZXIRBKKLTSOM-XPNPUAGNSA-N

InChI

InChI=1S/C48H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1

Canonical SMILES

CCC(C)C1C(C=CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C

Isomeric SMILES

CC[C@H](C)[C@@H]1[C@H](C=C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)C

Synonyms
        
            Abamectina [Spanish]
        
            AVERMECTIN B1A
        
            65195-55-3
        
            abamectin component B1a
        
            Avermectin B(1)a
        
            Abamectine [French]
        
            Abamectinum [Latin]
        
            Caswell No. 063AB
        
            Antibiotic C 076B1a
        
            Abamectin komponente B1a
        
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 Weight873.09
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count14
Rotatable Bond Count8
Complexity1730
Monoisotopic Mass872.492
Exact Mass872.492
XLogP3.8
Formal Charge0
Heavy Atom Count62
Defined Atom Stereocenter Count20
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-0.5357
Human Intestinal AbsorptionHIA+0.9304
Caco-2 PermeabilityCaco2-0.7309
P-glycoprotein SubstrateSubstrate0.7786
P-glycoprotein InhibitorInhibitor0.7556
Inhibitor0.5991
Renal Organic Cation TransporterNon-inhibitor0.7851
Distribution
Subcellular localizationMitochondria0.7163
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8826
CYP450 2D6 SubstrateNon-substrate0.8852
CYP450 3A4 SubstrateSubstrate0.7327
CYP450 1A2 InhibitorNon-inhibitor0.9031
CYP450 2C9 InhibitorNon-inhibitor0.8963
CYP450 2D6 InhibitorNon-inhibitor0.9272
CYP450 2C19 InhibitorNon-inhibitor0.9035
CYP450 3A4 InhibitorNon-inhibitor0.8310
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6033
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9836
Non-inhibitor0.7368
AMES ToxicityNon AMES toxic0.6292
CarcinogensNon-carcinogens0.9645
Fish ToxicityHigh FHMT0.8893
Tetrahymena Pyriformis ToxicityHigh TPT0.9980
Honey Bee ToxicityHigh HBT0.8934
BiodegradationNot ready biodegradable0.9675
Acute Oral ToxicityIII0.4164
Carcinogenicity (Three-class)Non-required0.5518

Model Value Unit
Absorption
Aqueous solubility-3.8519LogS
Caco-2 Permeability0.4503LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.6336LD50, mol/kg
Fish Toxicity0.4500pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9235pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Rose hips0154050European Union0.01*05/06/2018
Citrus fruits0110000European Union0.01505/06/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01505/06/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01505/06/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01505/06/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01505/06/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01505/06/2018
Others (2)0110990European Union0.01505/06/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.0205/06/2018
Brazil nuts0120020European Union0.01*05/06/2018
Cashew nuts0120030European Union0.01*05/06/2018
Chestnuts0120040European Union0.01*05/06/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*05/06/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.0205/06/2018
Macadamias0120070European Union0.01*05/06/2018
Pecans (Hickory nuts,)0120080European Union0.01*05/06/2018
Pistachios0120100European Union0.01*05/06/2018
Walnuts0120110European Union0.0205/06/2018
Others (2)0120990European Union0.01*05/06/2018
Pome fruits0130000European Union0.0305/06/2018