Basic Info

Common NameAvilamycin(F05734)
2D Structure
FRCD IDF05734
CAS Number
PubChem CID71674
FormulaC61H88Cl2O32
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 DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesNot available
Direct ParentOligosaccharides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsOligosaccharide - 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
DescriptionThis 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 NameProperty Value
Molecular Weight1404.243
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count32
Rotatable Bond Count20
Complexity2660
Monoisotopic Mass1402.464
Exact Mass1402.464
XLogP0.6
Formal Charge0
Heavy Atom Count95
Defined Atom Stereocenter Count29
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.6977
Human Intestinal AbsorptionHIA+0.9418
Caco-2 PermeabilityCaco2-0.5662
P-glycoprotein SubstrateSubstrate0.8169
P-glycoprotein InhibitorInhibitor0.5316
Inhibitor0.6498
Renal Organic Cation TransporterNon-inhibitor0.8486
Distribution
Subcellular localizationMitochondria0.5982
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8702
CYP450 2D6 SubstrateNon-substrate0.8284
CYP450 3A4 SubstrateSubstrate0.6948
CYP450 1A2 InhibitorNon-inhibitor0.7569
CYP450 2C9 InhibitorNon-inhibitor0.6791
CYP450 2D6 InhibitorNon-inhibitor0.8206
CYP450 2C19 InhibitorNon-inhibitor0.6556
CYP450 3A4 InhibitorInhibitor0.5893
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5211
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8901
Non-inhibitor0.8138
AMES ToxicityNon AMES toxic0.7108
CarcinogensNon-carcinogens0.8650
Fish ToxicityHigh FHMT0.9942
Tetrahymena Pyriformis ToxicityHigh TPT0.9991
Honey Bee ToxicityHigh HBT0.6400
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.4944
Carcinogenicity (Three-class)Danger0.4251

Model Value Unit
Absorption
Aqueous solubility-4.1450LogS
Caco-2 Permeability0.7736LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.0059LD50, mol/kg
Fish Toxicity0.6276pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0563pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,Edible OffalJapan0.05ppm
Chicken,Edible OffalJapan0.03ppm
Other Poultry Animals,KidneyJapan0.05ppm
Chicken,KidneyJapan0.03ppm
Other Poultry Animals,LiverJapan0.05ppm
Chicken,LiverJapan0.03ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.03ppm
Other Poultry Animals,MuscleJapan0.05ppm
Chicken,MuscleJapan0.03ppm
Pig,Edible OffalJapan0.03ppm
Pig,KidneyJapan0.03ppm
Pig,LiverJapan0.03ppm
Pig,FatJapan0.03ppm
Pig,MuscleJapan0.03ppm

References

TitleJournalDatePubmed ID
Determination of total avilamycin residues as dichloroisoeverninic acid inporcine muscle, fat, and liver by LC-MS/MS.Food Chem2018 May 3029407936
Understanding the mechanisms of zinc bacitracin and avilamycin on animalproduction: linking gut microbiota and growth performance in chickens.Appl Microbiol Biotechnol2017 Jun28243710
Improved antimicrobial activity of Pediococcus acidilactici against SalmonellaGallinarum by UV mutagenesis and genome shuffling.Appl Microbiol Biotechnol2017 Jul28470335
Different antibiotic growth promoters induce specific changes in the cecalmicrobiota membership of broiler chicken.PLoS One2017 Feb 2128222110
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 Sci2017 Aug 128339792
Use of Bacillus Subtilis PB6 as a potential antibiotic growth promoterreplacement in improving performance of broiler birds.Poult Sci2017 Aug 128482065
Efficacy of avilamycin for the prevention of necrotic enteritis caused by apathogenic strain of Clostridium perfringens in broiler chickens.Avian Pathol2016 Jun26981841
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 Int2016 Dec27646442
Effect of different doses of coated butyric acid on growth performance and energyutilization in broilers.Poult Sci2016 Apr26740137
Hydrolyzable and condensed tannins resistance in Clostridium perfringens.Anaerobe2015 Aug26037239
Effects of herbal essential oil mixture as a dietary supplement on egg productionin quail.ScientificWorldJournal2014 Jan 2324587729
Determination of avilamycin as dichloroisoeverninic acid in poultry and porcinemuscles by isotope dilution liquid chromatography-tandem mass spectrometry.Anal Bioanal Chem2013 Oct23975084
Genome shuffling of Streptomyces viridochromogenes for improved production ofavilamycin.Appl Microbiol Biotechnol2013 Jan22911092
Use of rosemary, oregano, and a commercial blend of essential oils in broilerchickens: in vitro antimicrobial activities and effects on growth performance.J Anim Sci2012 Mar22064737
Modulation of intestinal mucin composition and mucosal morphology by dietaryphytogenic inclusion level in broilers.Animal2012 Jul23031464
Dietary probiotic inclusion level modulates intestinal mucin composition andmucosal morphology in broilers.Poult Sci2012 Aug22802179
Effects of pitamin on growth performance, carcass characteristics and cecalmicroflora of broiler chicken.J Environ Biol2011 Sep22319873
Antimicrobial and heavy metal resistance in commensal enterococci isolated frompigs.Vet Microbiol2011 Mar 2420951513
Effect of dietary prebiotic supplementation on the performance, intestinalmicroflora, and immune response of broilers.Poult Sci2011 Jan21177446
The Effect of Various Probiotic Strains or Avilamycin Feed Additive on ImmuneDefense Markers and Acute-Phase Response to Salmonella Infection in Chickens.Probiotics Antimicrob Proteins2010 Oct26781240