Avermectin B1A
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Basic Info
Common Name | Avermectin 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 ID | F04055 |
CAS Number | 65195-55-3 |
PubChem CID | 6434889 |
Formula | C48H72O14 |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Phenylpropanoids and polyketides |
Class | Macrolides and analogues |
Subclass | Not available |
Intermediate Tree Nodes | Not available |
Direct Parent | Macrolides and analogues |
Alternative Parents | |
Molecular Framework | Aliphatic heteropolycyclic compounds |
Substituents | Macrolide - 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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 873.09 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 14 |
Rotatable Bond Count | 8 |
Complexity | 1730 |
Monoisotopic Mass | 872.492 |
Exact Mass | 872.492 |
XLogP | 3.8 |
Formal Charge | 0 |
Heavy Atom Count | 62 |
Defined Atom Stereocenter Count | 20 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 3 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.5357 |
Human Intestinal Absorption | HIA+ | 0.9304 |
Caco-2 Permeability | Caco2- | 0.7309 |
P-glycoprotein Substrate | Substrate | 0.7786 |
P-glycoprotein Inhibitor | Inhibitor | 0.7556 |
Inhibitor | 0.5991 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7851 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7163 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8826 |
CYP450 2D6 Substrate | Non-substrate | 0.8852 |
CYP450 3A4 Substrate | Substrate | 0.7327 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9031 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8963 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9272 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9035 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6033 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9836 |
Non-inhibitor | 0.7368 | |
AMES Toxicity | Non AMES toxic | 0.6292 |
Carcinogens | Non-carcinogens | 0.9645 |
Fish Toxicity | High FHMT | 0.8893 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9980 |
Honey Bee Toxicity | High HBT | 0.8934 |
Biodegradation | Not ready biodegradable | 0.9675 |
Acute Oral Toxicity | III | 0.4164 |
Carcinogenicity (Three-class) | Non-required | 0.5518 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.8519 | LogS |
Caco-2 Permeability | 0.4503 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.6336 | LD50, mol/kg |
Fish Toxicity | 0.4500 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.9235 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Rose hips | 0154050 | European Union | 0.01* | 05/06/2018 | |
Citrus fruits | 0110000 | European Union | 0.015 | 05/06/2018 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.015 | 05/06/2018 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.015 | 05/06/2018 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.015 | 05/06/2018 | |
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.015 | 05/06/2018 | |
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.015 | 05/06/2018 | |
Others (2) | 0110990 | European Union | 0.015 | 05/06/2018 | |
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02 | 05/06/2018 | |
Brazil nuts | 0120020 | European Union | 0.01* | 05/06/2018 | |
Cashew nuts | 0120030 | European Union | 0.01* | 05/06/2018 | |
Chestnuts | 0120040 | European Union | 0.01* | 05/06/2018 | |
Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 05/06/2018 | |
Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02 | 05/06/2018 | |
Macadamias | 0120070 | European Union | 0.01* | 05/06/2018 | |
Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 05/06/2018 | |
Pistachios | 0120100 | European Union | 0.01* | 05/06/2018 | |
Walnuts | 0120110 | European Union | 0.02 | 05/06/2018 | |
Others (2) | 0120990 | European Union | 0.01* | 05/06/2018 | |
Pome fruits | 0130000 | European Union | 0.03 | 05/06/2018 |