Basic Info

Common NameSemduramicin(F05854)
2D Structure
FRCD IDF05854
CAS Number113378-31-7
PubChem CID71327
FormulaC45H76O16
IUPAC Name

2-[(2R,3S,4S,5R,6S)-2,4-dihydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-3-methyloxan-2-yl]acetic acid

InChI Key

WINSLRIENGBHSH-ASZYJFLUSA-N

InChI

InChI=1S/C45H76O16/c1-22-18-23(2)43(9,50)58-36(22)30-19-31(55-34-13-12-29(52-10)27(6)54-34)40(56-30)42(8)15-14-32(57-42)41(7)16-17-44(61-41)20-28(46)24(3)37(59-44)25(4)38-39(53-11)35(49)26(5)45(51,60-38)21-33(47)48/h22-32,34-40,46,49-51H,12-21H2,1-11H3,(H,47,48)/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31-,32+,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+/m0/s1

Canonical SMILES

CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C6C(C(C(C(O6)(CC(=O)O)O)C)O)OC)C)O)C)C)OC7CCC(C(O7)C)OC)(C)O)C

Isomeric SMILES

C[C@H]1C[C@H]([C@@](O[C@@H]1[C@H]2C[C@@H]([C@@H](O2)[C@@]3(CC[C@@H](O3)[C@@]4(CC[C@@]5(O4)C[C@@H]([C@H]([C@H](O5)[C@@H](C)[C@H]6[C@@H]([C@H]([C@@H]([C@](O6)(CC(=O)O)O)C)O)OC)C)O)C)C)O[C@H]7CC[C@@H]([C@H](O7)C)OC)(C)O)C

Synonyms
        
            Semduramicine
        
            Aviax
        
            Semduramicinum [INN-Latin]
        
            Semduramicin
        
            UNII-P6VXL377WL
        
            P6VXL377WL
        
            113378-31-7
        
            Semduramicina
        
            Semduramicinum
        
            Semduramicine [INN-French]
        
Classifies
                

                  
                    Predicted: Veterinary Drug
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesGlycosyl compounds
Direct ParentC-glycosyl compounds
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsC-glycosyl compound - Ketal - Monosaccharide - Oxane - Tetrahydrofuran - Hemiacetal - Secondary alcohol - Acetal - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Ether - Organoheterocyclic compound - Oxacycle - Monocarboxylic acid or derivatives - Carbonyl group - Hydrocarbon derivative - Alcohol - Organic oxide - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Properties

Property NameProperty Value
Molecular Weight873.087
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count16
Rotatable Bond Count11
Complexity1540
Monoisotopic Mass872.513
Exact Mass872.513
XLogP3.8
Formal Charge0
Heavy Atom Count61
Defined Atom Stereocenter Count23
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.5062
Human Intestinal AbsorptionHIA+0.7051
Caco-2 PermeabilityCaco2-0.7441
P-glycoprotein SubstrateSubstrate0.7465
P-glycoprotein InhibitorInhibitor0.5569
Inhibitor0.9479
Renal Organic Cation TransporterNon-inhibitor0.8545
Distribution
Subcellular localizationMitochondria0.7334
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8051
CYP450 2D6 SubstrateNon-substrate0.8689
CYP450 3A4 SubstrateSubstrate0.6747
CYP450 1A2 InhibitorNon-inhibitor0.9383
CYP450 2C9 InhibitorNon-inhibitor0.8561
CYP450 2D6 InhibitorNon-inhibitor0.9443
CYP450 2C19 InhibitorNon-inhibitor0.8986
CYP450 3A4 InhibitorNon-inhibitor0.8595
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9304
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9839
Non-inhibitor0.6163
AMES ToxicityNon AMES toxic0.7690
CarcinogensNon-carcinogens0.9553
Fish ToxicityHigh FHMT0.9036
Tetrahymena Pyriformis ToxicityHigh TPT0.9984
Honey Bee ToxicityHigh HBT0.7362
BiodegradationNot ready biodegradable0.9842
Acute Oral ToxicityI0.6882
Carcinogenicity (Three-class)Non-required0.6269

Model Value Unit
Absorption
Aqueous solubility-3.0320LogS
Caco-2 Permeability0.3455LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.9596LD50, mol/kg
Fish Toxicity1.4577pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.1784pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle Of Broiler ChickensUnited States130ppb
Liver Of Broiler ChickensUnited States400ppb
Other Poultry Animals,Edible OffalJapan0.5ppm
Chicken,Edible OffalJapan0.03ppm
Other Poultry Animals,KidneyJapan0.5ppm
Chicken,KidneyJapan0.2ppm
Other Poultry Animals,LiverJapan0.5ppm
Chicken,LiverJapan0.5ppm
Other Poultry Animals,FatJapan0.5ppm
Chicken,FatJapan0.5ppm
Other Poultry Animals,MuscleJapan0.09ppm
Chicken,MuscleJapan0.09ppm

References

TitleJournalDatePubmed ID
Validation of a liquid chromatography-electrospray ionization tandem massspectrometric method to determine six polyether ionophores in raw, UHT,pasteurized and powdered milk.Food Chem2016 Apr 126593474
Semduramicin in eggs--the incompatibility of feed and food maximum levels.Food Chem2014 Apr 1524295692
Distribution of semduramicin in hen eggs and tissues after administration ofcross-contaminated feed.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201424856255
The determination of six ionophore coccidiostats in feed by liquid chromatographywith postcolumn derivatisation and spectrofotometric/fluorescence detection.ScientificWorldJournal2013 Oct 2924288505
Determination of semduramicin in poultry feed additive, premixture and compoundfeed by liquid chromatography and UV spectrophotometric detection afterpost-column derivatisation.J Pharm Biomed Anal2012 Mar 522169468
Inter-laboratory comparison of an analytical method for the determination of the feed additive semduramicin in poultry feed at authorised level by liquidchromatography single quadrupole mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Jan21240826
The efficacy of anticoccidial products against Eimeria spp. in northernbobwhites.Avian Dis2011 Mar21500637
Simultaneous determination of polyether ionophores, macrolides and lincosamidesin hen eggs by liquid chromatography-electrospray ionization tandem massspectrometry using a simple solvent extraction.Anal Chim Acta2010 Dec 321056719
Determination of semduramicin in poultry feed at authorized level by liquidchromatography single quadrupole mass spectrometry.J Pharm Biomed Anal2010 Dec 120619995
The activity and compatibility of the antibiotic tiamulin with other drugs inpoultry medicine--A review.Poult Sci2009 Nov19834086
[Development of monoclonal-based enzyme-linked immunosorbent assay andimmunochromatographic assay for lasalocid and semduramicin].Shokuhin Eiseigaku Zasshi2004 Jun15468928
Phenotypic and genotypic changes in Salmonella enterica subsp. enterica serotype typhimurium during passage in intestines of broiler chickens fed on diets thatincluded ionophore anticoccidial supplements.J Clin Microbiol2004 Aug15297474
Effects of the ionophore anticoccidial semduramicin on broiler breeders.Poult Sci2001 Mar11261553