Basic Info

Common NameSalinomycin(F05891)
2D Structure
FRCD IDF05891
CAS Number53003-10-4
PubChem CID3085092
FormulaC42H70O11
IUPAC Name

(2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.5^{7}.3^{5}]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid

InChI Key

KQXDHUJYNAXLNZ-XQSDOZFQSA-N

InChI

InChI=1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1

Canonical SMILES

CCC(C1CCC(C(O1)C(C)C(C(C)C(=O)C(CC)C2C(CC(C3(O2)C=CC(C4(O3)CCC(O4)(C)C5CCC(C(O5)C)(CC)O)O)C)C)O)C)C(=O)O

Isomeric SMILES

CC[C@H]([C@H]1CC[C@@H]([C@@H](O1)[C@@H](C)[C@@H]([C@H](C)C(=O)[C@H](CC)[C@@H]2[C@H](C[C@H]([C@]3(O2)C=C[C@H]([C@@]4(O3)CC[C@@](O4)(C)[C@H]5CC[C@@]([C@@H](O5)C)(CC)O)O)C)C)O)C)C(=O)O

Synonyms
        
            salinomycin
        
            Salinomycine [INN-French]
        
            Coxistac
        
            Bio-cox
        
            Procoxacin
        
            53003-10-4
        
            UNII-62UXS86T64
        
            CHEBI:80025
        
            62UXS86T64
        
            Salinomycinum [INN-Latin]
        
Classifies
                

                  
                    Veterinary Drug
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassTerpene glycosides
Intermediate Tree NodesNot available
Direct ParentDiterpene glycosides
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsDiterpene glycoside - Diterpenoid - Fatty alcohol - Ketal - Branched fatty acid - Heterocyclic fatty acid - Hydroxy fatty acid - Beta-hydroxy ketone - Fatty acyl - Pyran - Oxane - Tetrahydrofuran - Tertiary alcohol - Secondary alcohol - Ketone - Acetal - Organoheterocyclic compound - Ether - Oxacycle - Dialkyl ether - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Alcohol - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Properties

Property NameProperty Value
Molecular Weight751.011
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count12
Complexity1320
Monoisotopic Mass750.492
Exact Mass750.492
XLogP5.7
Formal Charge0
Heavy Atom Count53
Defined Atom Stereocenter Count18
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+0.8288
Human Intestinal AbsorptionHIA+0.9739
Caco-2 PermeabilityCaco2-0.7343
P-glycoprotein SubstrateSubstrate0.7685
P-glycoprotein InhibitorInhibitor0.5292
Inhibitor0.8616
Renal Organic Cation TransporterNon-inhibitor0.8958
Distribution
Subcellular localizationMitochondria0.7936
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8153
CYP450 2D6 SubstrateNon-substrate0.8928
CYP450 3A4 SubstrateSubstrate0.6441
CYP450 1A2 InhibitorNon-inhibitor0.9336
CYP450 2C9 InhibitorNon-inhibitor0.9195
CYP450 2D6 InhibitorNon-inhibitor0.9624
CYP450 2C19 InhibitorNon-inhibitor0.8875
CYP450 3A4 InhibitorNon-inhibitor0.5747
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9527
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9780
Non-inhibitor0.7271
AMES ToxicityNon AMES toxic0.7878
CarcinogensNon-carcinogens0.9403
Fish ToxicityHigh FHMT0.9940
Tetrahymena Pyriformis ToxicityHigh TPT0.9998
Honey Bee ToxicityHigh HBT0.6948
BiodegradationNot ready biodegradable0.9928
Acute Oral ToxicityI0.7721
Carcinogenicity (Three-class)Non-required0.5187

Model Value Unit
Absorption
Aqueous solubility-3.7676LogS
Caco-2 Permeability0.5114LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.5855LD50, mol/kg
Fish Toxicity1.1716pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0958pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,Edible OffalJapan0.5ppm
Other Poultry,EggsJapan0.02ppm
Chicken,EggsJapan0.02ppm
Other Poultry Animals,Edible OffalJapan0.5ppm
Other Poultry Animals,KidneyJapan0.5ppm
Chicken,KidneyJapan0.5ppm
Other Poultry Animals,LiverJapan0.5ppm
Chicken,LiverJapan0.5ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.4ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
Pig,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.5ppm
Pig,KidneyJapan0.1ppm
Cattle,KidneyJapan0.5ppm
Pig,LiverJapan0.2ppm
Cattle,LiverJapan0.4ppm
Pig,FatJapan0.1ppm
Cattle,FatJapan0.02ppm

References

TitleJournalDatePubmed ID
Evaluation of PCR and DNA sequencing for direct detection of Clostridium perfringens in the intestinal tract of broilers.Avian Dis2009 Sep19848086
Pathotype and antibiotic resistance gene distributions of Escherichia coli isolates from broiler chickens raised on antimicrobial-supplemented diets.Appl Environ Microbiol2009 Nov19749070
An integrated sample preparation to determine coccidiostats and emerging Fusarium-mycotoxins in various poultry tissues with LC-MS/MS.Mol Nutr Food Res2007 May17440994
A new method for in vitro detection of microbially produced mitochondrial toxins.Toxicol In Vitro2003 Oct-Dec14599472
Effects of dietary fat source and subtherapeutic levels of antibiotic on the bacterial community in the ileum of broiler chickens at various ages.Appl Environ Microbiol2002 Dec12450811
Salinomycin-induced polyneuropathy in cats: morphologic and epidemiologic data.Vet Pathol1999 Mar10098644
A chronic cardiomyopathy in feedlot cattle attributed to toxic levels of salinomycin in the feed.J S Afr Vet Assoc1996 Mar8786618
Lipolysis and biohydrogenation of soybean oil in the rumen in vitro: inhibition by antimicrobials.J Dairy Sci1995 Dec8675762