Record Information |
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Version | 2.0 |
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Creation Date | 2009-06-18 20:15:07 UTC |
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Update Date | 2014-12-24 20:23:05 UTC |
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Accession Number | T3D1044 |
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Identification |
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Common Name | Emamectin B1b |
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Class | Small Molecule |
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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. (2) |
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Compound Type | - Amine
- Avermectin
- Bacterial Toxin
- Ester
- Ether
- Lachrymator
- Natural Compound
- Organic Compound
- Pesticide
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Chemical Structure | |
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Synonyms | Synonym | emamectin B1b | Emamectin b1b |
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Chemical Formula | C48H73NO13 |
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Average Molecular Mass | 872.092 g/mol |
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Monoisotopic Mass | 871.508 g/mol |
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CAS Registry Number | 121424-52-0 |
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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 |
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Traditional Name | emamectin B1b |
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SMILES | CN[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 |
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InChI Identifier | InChI=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 |
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InChI Key | InChIKey=DXIOOXFZLKCVHK-UTAOKEBVSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Aminoglycosides |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fk9-5200072290-45c733b8d2de914241c6 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0g4i-6810091210-03ee612dd943af5bd5ab | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9420010000-4d9e5de51abe20a6cc56 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2900010130-ebd988a6206da25843ba | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gbd-0300091340-01afa09f628f62f6cabf | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kb-6800391000-11cfc2fb9fb8a06a66d0 | 2016-08-04 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | It has low solubility in water and extensive non-specific binding. It opens GABA-insensitive chloride channels, reducing membrane resistance and increasing conductance inward. (1) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not listed by IARC. |
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Uses/Sources | Active ingredient in some commercial ant bait traps. (2) |
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Minimum Risk Level | Not Available |
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Health Effects | Avermectins are neurotoxic and have reproductive and developmental effects. (3) |
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Symptoms | Avermectins 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. (3) |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 16722138 |
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ChEMBL ID | Not Available |
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ChemSpider ID | 16738623 |
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KEGG ID | Not Available |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 39232 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Emamectin B1b |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D1044.pdf |
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General References | - Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
- Wikipedia. Avermectin. Last Updated 8 June 2009. ht [Link]
- PAN Pesticides Database (2009). Avermectin. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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