Avilamycin
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Basic Info
Common Name | Avilamycin(F05734) |
2D Structure | |
FRCD ID | F05734 |
CAS Number | |
PubChem CID | 71674 |
Formula | C61H88Cl2O32 |
IUPAC Name | [(2R,3S,4R,6S)-6-[(2'R,3'S,3aR,4R,4'R,6S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(2R,3aS,3'aR,6'R,7R,7'S,7aR,7'aR)-7'-acetyl-7'-hydroxy-6'-methyl-7-(2-methylpropanoyloxy)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4'-hydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-hydroxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate |
InChI Key | XIRGHRXBGGPPKY-OTPQUNEMSA-N |
InChI | InChI=1S/C61H88Cl2O32/c1-21(2)53(70)87-49-45-32(92-61(93-45)52-51(78-20-79-52)60(72,27(8)64)28(9)91-61)19-77-56(49)89-57-48(76-14)39(68)44(31(83-57)18-73-11)88-55-40(69)47(43(74-12)24(5)82-55)85-34-17-58(10)50(26(7)81-34)94-59(95-58)16-30(66)42(25(6)90-59)84-33-15-29(65)41(23(4)80-33)86-54(71)35-22(3)36(62)38(67)37(63)46(35)75-13/h21,23-26,28-34,39-45,47-52,55-57,65-69,72H,15-20H2,1-14H3/t23-,24-,25-,26-,28-,29-,30-,31-,32+,33+,34+,39+,40-,41-,42-,43+,44-,45-,47-,48+,49-,50-,51-,52-,55+,56?,57+,58-,59?,60+,61-/m1/s1 |
Canonical SMILES | CC1C(C(CC(O1)OC2C(OC3(CC2O)OC4C(OC(CC4(O3)C)OC5C(C(OC(C5OC)C)OC6C(OC(C(C6O)OC)OC7C(C8C(CO7)OC9(O8)C1C(C(C(O9)C)(C(=O)C)O)OCO1)OC(=O)C(C)C)COC)O)C)C)O)OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C |
Isomeric SMILES | C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](OC3(C[C@H]2O)O[C@@H]4[C@H](O[C@H](C[C@]4(O3)C)O[C@@H]5[C@H]([C@@H](O[C@@H]([C@@H]5OC)C)O[C@@H]6[C@H](O[C@H]([C@H]([C@H]6O)OC)OC7[C@@H]([C@H]8[C@H](CO7)O[C@@]9(O8)[C@H]1[C@H]([C@@]([C@H](O9)C)(C(=O)C)O)OCO1)OC(=O)C(C)C)COC)O)C)C)O)OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C |
Synonyms | Avilamycin Surmax Avilamycine [INN-French] Avilamycinum [INN-Latin] Avilamycina [INN-Spanish] HSDB 7029 LY 048740 LY 048 740 Avilamycina Avilamycine |
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 | Not available |
Direct Parent | Oligosaccharides |
Alternative Parents |
|
Molecular Framework | Aromatic heteropolycyclic compounds |
Substituents | Oligosaccharide - Glycosyl compound - P-hydroxybenzoic acid alkyl ester - P-hydroxybenzoic acid ester - O-glycosyl compound - O-methoxybenzoic acid or derivatives - Benzoate ester - Methoxyphenol - 3-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Dioxolopyran - Benzoic acid or derivatives - Methoxybenzene - M-cresol - Anisole - 1,3-dichlorobenzene - 2-chlorophenol - Phenol ether - Benzoyl - 2-halophenol - Phenoxy compound - Halobenzene - Alkyl aryl ether - Ortho ester - Phenol - Carboxylic acid orthoester - Toluene - Chlorobenzene - Dicarboxylic acid or derivatives - Benzenoid - Aryl chloride - Monocyclic benzene moiety - Aryl halide - Oxane - Tertiary alcohol - Alpha-hydroxy ketone - Meta-dioxolane - Secondary alcohol - Orthocarboxylic acid derivative - Ketone - Carboxylic acid ester - Ether - Acetal - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Dialkyl ether - Alcohol - Organohalogen compound - Organochloride - Organic oxide - Carbonyl group - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
Description | This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 1404.243 |
Hydrogen Bond Donor Count | 6 |
Hydrogen Bond Acceptor Count | 32 |
Rotatable Bond Count | 20 |
Complexity | 2660 |
Monoisotopic Mass | 1402.464 |
Exact Mass | 1402.464 |
XLogP | 0.6 |
Formal Charge | 0 |
Heavy Atom Count | 95 |
Defined Atom Stereocenter Count | 29 |
Undefined Atom Stereocenter Count | 2 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.6977 |
Human Intestinal Absorption | HIA+ | 0.9418 |
Caco-2 Permeability | Caco2- | 0.5662 |
P-glycoprotein Substrate | Substrate | 0.8169 |
P-glycoprotein Inhibitor | Inhibitor | 0.5316 |
Inhibitor | 0.6498 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8486 |
Distribution | ||
Subcellular localization | Mitochondria | 0.5982 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8702 |
CYP450 2D6 Substrate | Non-substrate | 0.8284 |
CYP450 3A4 Substrate | Substrate | 0.6948 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.7569 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.6791 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.8206 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.6556 |
CYP450 3A4 Inhibitor | Inhibitor | 0.5893 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5211 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8901 |
Non-inhibitor | 0.8138 | |
AMES Toxicity | Non AMES toxic | 0.7108 |
Carcinogens | Non-carcinogens | 0.8650 |
Fish Toxicity | High FHMT | 0.9942 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9991 |
Honey Bee Toxicity | High HBT | 0.6400 |
Biodegradation | Not ready biodegradable | 1.0000 |
Acute Oral Toxicity | III | 0.4944 |
Carcinogenicity (Three-class) | Danger | 0.4251 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -4.1450 | LogS |
Caco-2 Permeability | 0.7736 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.0059 | LD50, mol/kg |
Fish Toxicity | 0.6276 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 1.0563 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Other Poultry Animals,Edible Offal | Japan | 0.05ppm | |||
Chicken,Edible Offal | Japan | 0.03ppm | |||
Other Poultry Animals,Kidney | Japan | 0.05ppm | |||
Chicken,Kidney | Japan | 0.03ppm | |||
Other Poultry Animals,Liver | Japan | 0.05ppm | |||
Chicken,Liver | Japan | 0.03ppm | |||
Other Poultry Animals,Fat | Japan | 0.05ppm | |||
Chicken,Fat | Japan | 0.03ppm | |||
Other Poultry Animals,Muscle | Japan | 0.05ppm | |||
Chicken,Muscle | Japan | 0.03ppm | |||
Pig,Edible Offal | Japan | 0.03ppm | |||
Pig,Kidney | Japan | 0.03ppm | |||
Pig,Liver | Japan | 0.03ppm | |||
Pig,Fat | Japan | 0.03ppm | |||
Pig,Muscle | Japan | 0.03ppm |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Determination of total avilamycin residues as dichloroisoeverninic acid inporcine muscle, fat, and liver by LC-MS/MS. | Food Chem | 2018 May 30 | 29407936 |
Understanding the mechanisms of zinc bacitracin and avilamycin on animalproduction: linking gut microbiota and growth performance in chickens. | Appl Microbiol Biotechnol | 2017 Jun | 28243710 |
Improved antimicrobial activity of Pediococcus acidilactici against SalmonellaGallinarum by UV mutagenesis and genome shuffling. | Appl Microbiol Biotechnol | 2017 Jul | 28470335 |
Different antibiotic growth promoters induce specific changes in the cecalmicrobiota membership of broiler chicken. | PLoS One | 2017 Feb 21 | 28222110 |
Interference of age and supplementation of direct-fed microbial and essential oilin the activity of digestive enzymes and expression of genes related to transportand digestion of carbohydrates and proteins in the small intestine of broilers. | Poult Sci | 2017 Aug 1 | 28339792 |
Use of Bacillus Subtilis PB6 as a potential antibiotic growth promoterreplacement in improving performance of broiler birds. | Poult Sci | 2017 Aug 1 | 28482065 |
Efficacy of avilamycin for the prevention of necrotic enteritis caused by apathogenic strain of Clostridium perfringens in broiler chickens. | Avian Pathol | 2016 Jun | 26981841 |
The effect of phytogenic feed additives to substitute in-feed antibiotics ongrowth traits and blood biochemical parameters in broiler chicks challenged with Salmonella typhimurium. | Environ Sci Pollut Res Int | 2016 Dec | 27646442 |
Effect of different doses of coated butyric acid on growth performance and energyutilization in broilers. | Poult Sci | 2016 Apr | 26740137 |
Hydrolyzable and condensed tannins resistance in Clostridium perfringens. | Anaerobe | 2015 Aug | 26037239 |
Effects of herbal essential oil mixture as a dietary supplement on egg productionin quail. | ScientificWorldJournal | 2014 Jan 23 | 24587729 |
Determination of avilamycin as dichloroisoeverninic acid in poultry and porcinemuscles by isotope dilution liquid chromatography-tandem mass spectrometry. | Anal Bioanal Chem | 2013 Oct | 23975084 |
Genome shuffling of Streptomyces viridochromogenes for improved production ofavilamycin. | Appl Microbiol Biotechnol | 2013 Jan | 22911092 |
Use of rosemary, oregano, and a commercial blend of essential oils in broilerchickens: in vitro antimicrobial activities and effects on growth performance. | J Anim Sci | 2012 Mar | 22064737 |
Modulation of intestinal mucin composition and mucosal morphology by dietaryphytogenic inclusion level in broilers. | Animal | 2012 Jul | 23031464 |
Dietary probiotic inclusion level modulates intestinal mucin composition andmucosal morphology in broilers. | Poult Sci | 2012 Aug | 22802179 |
Effects of pitamin on growth performance, carcass characteristics and cecalmicroflora of broiler chicken. | J Environ Biol | 2011 Sep | 22319873 |
Antimicrobial and heavy metal resistance in commensal enterococci isolated frompigs. | Vet Microbiol | 2011 Mar 24 | 20951513 |
Effect of dietary prebiotic supplementation on the performance, intestinalmicroflora, and immune response of broilers. | Poult Sci | 2011 Jan | 21177446 |
The Effect of Various Probiotic Strains or Avilamycin Feed Additive on ImmuneDefense Markers and Acute-Phase Response to Salmonella Infection in Chickens. | Probiotics Antimicrob Proteins | 2010 Oct | 26781240 |