Avermectin B1B
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Basic Info
Common Name | Avermectin 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 ID | F04056 |
CAS Number | 65195-56-4 |
PubChem CID | 6858005 |
Formula | C47H70O14 |
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 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 | 859.063 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 14 |
Rotatable Bond Count | 7 |
Complexity | 1710 |
Monoisotopic Mass | 858.477 |
Exact Mass | 858.477 |
XLogP | 3.5 |
Formal Charge | 0 |
Heavy Atom Count | 61 |
Defined Atom Stereocenter Count | 19 |
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- | 0.8020 |
Human Intestinal Absorption | HIA+ | 0.8827 |
Caco-2 Permeability | Caco2- | 0.6878 |
P-glycoprotein Substrate | Substrate | 0.7547 |
P-glycoprotein Inhibitor | Inhibitor | 0.7023 |
Non-inhibitor | 0.5679 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7492 |
Distribution | ||
Subcellular localization | Mitochondria | 0.8128 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8662 |
CYP450 2D6 Substrate | Non-substrate | 0.8842 |
CYP450 3A4 Substrate | Substrate | 0.7400 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8545 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8702 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.8912 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8893 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9179 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7494 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9909 |
Non-inhibitor | 0.7943 | |
AMES Toxicity | Non AMES toxic | 0.6257 |
Carcinogens | Non-carcinogens | 0.9662 |
Fish Toxicity | High FHMT | 0.8518 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9782 |
Honey Bee Toxicity | High HBT | 0.8924 |
Biodegradation | Not ready biodegradable | 0.9591 |
Acute Oral Toxicity | III | 0.4355 |
Carcinogenicity (Three-class) | Non-required | 0.5501 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.6176 | LogS |
Caco-2 Permeability | 0.5930 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.4463 | LD50, mol/kg |
Fish Toxicity | 0.3769 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.6899 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Soy Bean | Australia | 0.002mg/kg |