Lasalocid

Basic Info

Common NameLasalocid(F06167)
2D Structure
FRCD IDF06167
CAS Number25999-31-9
PubChem CID5360807
FormulaC34H54O8
IUPAC Name

6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid

InChI Key

BBMULGJBVDDDNI-OWKLGTHSSA-N

InChI

InChI=1S/C34H54O8/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39)/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+/m1/s1

Canonical SMILES

CCC(C1C(CC(O1)(CC)C2CCC(C(O2)C)(CC)O)C)C(=O)C(C)C(C(C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O

Isomeric SMILES

CC[C@H]([C@@H]1[C@H](C[C@@](O1)(CC)[C@H]2CC[C@@]([C@@H](O2)C)(CC)O)C)C(=O)[C@@H](C)[C@H]([C@H](C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O

Synonyms
        
            Lasalocid A
        
            Lasalocide A
        
            lasalocid
        
            Avatec
        
            Lasalocide
        
            25999-31-9
        
            Ionophore X 537A
        
            Antibiotic X 537A
        
            UNII-W7V2ZZ2FWB
        
            Lasalocide [INN-French]
Classifies
                

                  
                    Predicted: 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 FrameworkAromatic heteromonocyclic compounds
SubstituentsDiterpene glycoside - Diterpenoid - Hydroxybenzoic acid - Salicylic acid or derivatives - Salicylic acid - Fatty alcohol - Benzoic acid or derivatives - Benzoic acid - Benzoyl - O-cresol - 1-hydroxy-4-unsubstituted benzenoid - Toluene - Phenol - Monocyclic benzene moiety - Fatty acyl - Beta-hydroxy ketone - Benzenoid - Oxane - Vinylogous acid - Tetrahydrofuran - Tertiary alcohol - Ketone - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Monocarboxylic acid or derivatives - Ether - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aromatic heteromonocyclic 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 Weight590.798
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count13
Complexity910
Monoisotopic Mass590.382
Exact Mass590.382
XLogP6.4
Formal Charge0
Heavy Atom Count42
Defined Atom Stereocenter Count10
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+0.6193
Human Intestinal AbsorptionHIA+0.9291
Caco-2 PermeabilityCaco2-0.7353
P-glycoprotein SubstrateSubstrate0.7926
P-glycoprotein InhibitorNon-inhibitor0.7732
Inhibitor0.8388
Renal Organic Cation TransporterNon-inhibitor0.9154
Distribution
Subcellular localizationMitochondria0.7955
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7823
CYP450 2D6 SubstrateNon-substrate0.8469
CYP450 3A4 SubstrateSubstrate0.6174
CYP450 1A2 InhibitorNon-inhibitor0.8276
CYP450 2C9 InhibitorNon-inhibitor0.7950
CYP450 2D6 InhibitorNon-inhibitor0.9403
CYP450 2C19 InhibitorNon-inhibitor0.8424
CYP450 3A4 InhibitorInhibitor0.5600
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8474
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9789
Non-inhibitor0.6467
AMES ToxicityNon AMES toxic0.7919
CarcinogensNon-carcinogens0.9183
Fish ToxicityHigh FHMT0.9969
Tetrahymena Pyriformis ToxicityHigh TPT0.9998
Honey Bee ToxicityHigh HBT0.5558
BiodegradationNot ready biodegradable0.9935
Acute Oral ToxicityII0.7428
Carcinogenicity (Three-class)Non-required0.6164
Model Value Unit
Absorption
Aqueous solubility-3.5447LogS
Caco-2 Permeability0.3745LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.7165LD50, mol/kg
Fish Toxicity0.9915pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.3145pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Liver Of SheepUnited States1.0ppm
Liver Of RabbitsUnited States0.7ppm
Skin (With Adhering Fat) Of TurkeysUnited States0.4ppm
Liver Of TurkeysUnited States0.4ppm
Liver Of ChickensUnited States0.4ppm
Skin (With Adhering Fat) Of ChickensUnited States1.2ppm
Liver Of CattleUnited States0.7ppm
CrustaceansJapan0.005ppm
Shelled MolluscasJapan0.005ppm
Other FishJapan0.005ppm
PerciformesJapan0.005ppm
AnguilliformesJapan0.005ppm
SalmoniformesJapan0.005ppm
Other Poultry,EggsJapan0.05ppm
Chicken,EggsJapan0.005ppm
Other Poultry Animals,Edible OffalJapan0.4ppm
Chicken,Edible OffalJapan0.01ppm
Other Poultry Animals,KidneyJapan0.4ppm
Chicken,KidneyJapan0.01ppm
Other Poultry Animals,LiverJapan0.3ppm

References

TitleJournalDatePubmed ID
Magnetic solid-phase extraction based on carbon nanotubes for the determinationof polyether antibiotic and s-triazine drug residues in animal food withLC-MS/MS.J Sep Sci2017 Jun28402029
A multi-residue method for 17 anticoccidial drugs and ractopamine in animaltissues by liquid chromatography-tandem mass spectrometry and time-of-flight massspectrometry.Drug Test Anal2016 May27443201
Evaluation of ionophore sensitivity of Eimeria acervulina and Eimeria maximaisolated from the Algerian to Jijel province poultry farms.Vet Parasitol2016 Jul 1527270394
The effect of composting on the persistence of four ionophores in dairy manureand poultry litter.Waste Manag2016 Aug27189139
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
Determination of six polyether antibiotic residues in foods of animal origin bysolid phase extraction combined with liquid chromatography-tandem massspectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2016 Apr 126990733
Degradation and dissipation of the veterinary ionophore lasalocid in manure andsoil.Chemosphere2015 Nov25556006
Development of intramammary delivery systems containing lasalocid for thetreatment of bovine mastitis: impact of solubility improvement on safety,efficacy, and milk distribution in dairy cattle.Drug Des Devel Ther2015 Jan 2225653501
Effect of distillers feedstuffs and lasalocid on Campylobacter carriage infeedlot cattle.J Food Prot2014 Nov25364932
Effects of Artemisia annua and Foeniculum vulgare on chickens highly infectedwith Eimeria tenella (phylum Apicomplexa).Acta Vet Scand2014 Apr 1524731599
Assessment of probiotics supplementation via feed or water on the growthperformance, intestinal morphology and microflora of chickens after experimental infection with Eimeria acervulina, Eimeria maxima and Eimeria tenella.Avian Pathol201424601749
Quantification of four ionophores in soil, sediment and manure using pressurised liquid extraction.J Chromatogr A2013 Sep 1323890553
The determination of six ionophore coccidiostats in feed by liquid chromatographywith postcolumn derivatisation and spectrofotometric/fluorescence detection.ScientificWorldJournal2013 Oct 2924288505
Single-laboratory validation of a multiplex flow cytometric immunoassay for thesimultaneous detection of coccidiostats in eggs and feed.Anal Bioanal Chem2013 Nov24081566
Effects of lasalocid and intermittent feeding of chlortetracycline on the growth of prepubertal dairy heifers.J Dairy Sci2013 Jul23684035
Application of Tb(4)O(7) nanoparticles for lasalocid and salicylate determinationin food analysis.J Agric Food Chem2012 Nov 2823140477
Rapid method for the simultaneous determination of six ionophores in feed byliquid chromatography/mass spectrometry.J AOAC Int2012 Jul-Aug22970566
Determination of narasin and monensin in bovine, swine, and chicken tissues byliquid chromatography with tandem mass spectrometry: first action 2011.24.J AOAC Int2012 Jul-Aug22970563
Multiclass screening method based on solvent extraction and liquid chromatography-tandem mass spectrometry for the determination of antimicrobials and mycotoxins in egg.J Chromatogr A2012 Dec 1423141710
Assessment of dietary supplementation with probiotics on performance, intestinal morphology and microflora of chickens infected with Eimeria tenella.Vet Parasitol2012 Aug 1322459110