Tylosin
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Basic Info
Common Name | Tylosin(F05882) |
2D Structure | |
FRCD ID | F05882 |
CAS Number | |
PubChem CID | 5280440 |
Formula | C46H77NO17 |
IUPAC Name | 2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde |
InChI Key | WBPYTXDJUQJLPQ-VMXQISHHSA-N |
InChI | InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+/t24-,25+,26-,27-,28+,29+,30-,32-,33-,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46-/m1/s1 |
Canonical SMILES | CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC |
Isomeric SMILES | CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC |
Synonyms | Tylan Fradizine Tylosin Tilosina Tylosinum UNII-YEF4JXN031 Tylocine Tylosine Tylosin A YEF4JXN031 |
Classifies | Veterinary Drug |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic oxygen compounds |
Class | Organooxygen compounds |
Subclass | Carbohydrates and carbohydrate conjugates |
Intermediate Tree Nodes | Aminosaccharides |
Direct Parent | Aminoglycosides |
Alternative Parents |
|
Molecular Framework | Aliphatic heteromonocyclic compounds |
Substituents | Aminoglycoside core - Macrolide - Disaccharide - Glycosyl compound - O-glycosyl compound - Oxane - Alpha-hydrogen aldehyde - Tertiary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Ketone - Lactone - Cyclic ketone - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Acetal - Organoheterocyclic compound - Ether - Monocarboxylic acid or derivatives - Dialkyl ether - Oxacycle - Carboxylic acid derivative - Organopnictogen compound - Carbonyl group - Alcohol - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Organic nitrogen compound - Amine - Aldehyde - Aliphatic heteromonocyclic compound |
Description | This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 916.112 |
Hydrogen Bond Donor Count | 5 |
Hydrogen Bond Acceptor Count | 18 |
Rotatable Bond Count | 13 |
Complexity | 1560 |
Monoisotopic Mass | 915.519 |
Exact Mass | 915.519 |
XLogP | 1 |
Formal Charge | 0 |
Heavy Atom Count | 64 |
Defined Atom Stereocenter Count | 21 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 2 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.9910 |
Human Intestinal Absorption | HIA+ | 0.5414 |
Caco-2 Permeability | Caco2- | 0.7275 |
P-glycoprotein Substrate | Substrate | 0.8267 |
P-glycoprotein Inhibitor | Inhibitor | 0.9174 |
Non-inhibitor | 0.5836 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9209 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6271 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8680 |
CYP450 2D6 Substrate | Non-substrate | 0.9027 |
CYP450 3A4 Substrate | Substrate | 0.6348 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8952 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9055 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9240 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8891 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9643 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9743 |
Non-inhibitor | 0.7947 | |
AMES Toxicity | Non AMES toxic | 0.7971 |
Carcinogens | Non-carcinogens | 0.9286 |
Fish Toxicity | High FHMT | 0.9852 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9966 |
Honey Bee Toxicity | High HBT | 0.5817 |
Biodegradation | Not ready biodegradable | 0.9675 |
Acute Oral Toxicity | III | 0.7906 |
Carcinogenicity (Three-class) | Non-required | 0.5168 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.8665 | LogS |
Caco-2 Permeability | 0.3985 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.2943 | LD50, mol/kg |
Fish Toxicity | 1.1082 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.6462 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Other Poultry Animals,Kidney | Japan | 0.2ppm | |||
Other Terrestrial Mammals,Edible Offal | Japan | 0.1ppm | |||
Chicken,Kidney | Japan | 0.05ppm | |||
Other Poultry Animals,Liver | Japan | 0.2ppm | |||
Chicken,Liver | Japan | 0.05ppm | |||
Other Poultry Animals,Fat | Japan | 0.2ppm | |||
Chicken,Fat | Japan | 0.05ppm | |||
Other Poultry Animals,Muscle | Japan | 0.2ppm | |||
Chicken,Muscle | Japan | 0.05ppm | |||
Milk | Japan | 0.05ppm | |||
Pig,Edible Offal | Japan | 0.05ppm | |||
Cattle,Edible Offal | Japan | 0.05ppm | |||
Other Terrestrial Mammals,Kidney | Japan | 0.1ppm | |||
Pig,Kidney | Japan | 0.05ppm | |||
Cattle,Kidney | Japan | 0.05ppm | |||
Other Terrestrial Mammals,Liver | Japan | 0.1ppm | |||
Pig,Liver | Japan | 0.05ppm | |||
Cattle,Liver | Japan | 0.05ppm | |||
Other Terrestrial Mammals,Fat | Japan | 0.1ppm | |||
Pig,Fat | Japan | 0.05ppm |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Development and validation of multi-residue and multi-class method forantibacterial substances analysis in non-target feed by liquid chromatography -tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Mar | 29219766 |
In vitro model to assess the adsorption of oral veterinary drugs to mycotoxin binders in a feed- and aflatoxin B1-containing buffered matrix. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Sep | 30016205 |
Characterization and biological activity of PVA hydrogel containingchitooligosaccharides conjugated with gallic acid. | Carbohydr Polym | 2018 Oct 15 | 30092991 |
The use of antibiotics in cattle in North-East Benin: pharmaceutical inventoryand risk practices of cattle breeders. | Trop Anim Health Prod | 2018 May 7 | 29732489 |
Biotransformation of macrolide antibiotics using enriched activated sludgeculture: Kinetics, transformation routes and ecotoxicological evaluation. | J Hazard Mater | 2018 May 5 | 29414746 |
Mobile macrolide resistance genes in staphylococci. | Plasmid | 2018 May 26 | 29807043 |
Combined Effects and Cross-Interactions of Different Antibiotics and Polypeptidesin Salmonella bredeney. | Microb Drug Resist | 2018 May 24 | 29792562 |
Studying the Phenotypic and Genotypic Expression of Antibiotic Resistance inCampylobacter jejuni under Stress Conditions. | Bull Exp Biol Med | 2018 Mar | 29504101 |
Multi-drug UPLC-MS/MS method to quantify antimicrobials in feedingstuffs atcarry-over level. | Rapid Commun Mass Spectrom | 2018 Jun 25 | 29943476 |
Draft genome sequences of extended-spectrum β-lactamase-producing Enterobacteraerogenes isolated from swine and human. | J Glob Antimicrob Resist | 2018 Jun 20 | 29935332 |
Draft genome sequence of an extended-spectrum β-lactamase (CTX-M-15)-producingEscherichia coli ST10 isolated from a nasal sample of an abattoir worker inCameroon. | J Glob Antimicrob Resist | 2018 Jun 19 | 29933117 |
Occurrence and distribution of antibiotics in mariculture farms, estuaries andthe coast of the Beibu Gulf, China: Bioconcentration and diet safety of seafood. | Ecotoxicol Environ Saf | 2018 Jun 15 | 29454268 |
Enterococci from ready-to-eat food - horizontal gene transfer of antibioticresistance genes and genotypic characterization by PCR Melting Profile. | J Sci Food Agric | 2018 Jul 25 | 30047163 |
A frameshift mutation in the rRNA large subunit methyltransferase gene rlmAIIdetermines the susceptibility of a honey bee pathogen Melissococcus plutonius to mirosamicin. | Environ Microbiol | 2018 Jul 24 | 30043554 |
Quick Multi-Class Determination of Residues of Antimicrobial Veterinary Drugs in Animal Muscle by LC-MS/MS. | Molecules | 2018 Jul 16 | 30012996 |
Functional Repertoire of Antibiotic Resistance Genes in Antibiotic Manufacturing Effluents and Receiving Freshwater Sediments. | Front Microbiol | 2018 Jan 17 | 29387045 |
Comparison of antimicrobial resistance genes in feedlots and urban wastewater. | Can J Vet Res | 2018 Jan | 29382966 |
Antimicrobial residues and resistance against critically important antimicrobialsin non-typhoidal Salmonella from meat sold at wet markets and supermarkets inVietnam. | Int J Food Microbiol | 2018 Feb 2 | 29275223 |
Occurrence and fate of most prescribed antibiotics in different waterenvironments of Tehran, Iran. | Sci Total Environ | 2018 Apr 1 | 29156265 |
Antimicrobial Resistance in Campylobacter spp. | Microbiol Spectr | 2018 Apr | 29623873 |