Basic Info

Common NameNarasin(F05946)
2D Structure
FRCD IDF05946
CAS Number
PubChem CID65452
FormulaC43H72O11
IUPAC Name

(2R)-2-[(2R,3S,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]-3,5-dimethyloxan-2-yl]butanoic acid

InChI Key

VHKXXVVRRDYCIK-CWCPJSEDSA-N

InChI

InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)/t23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,36+,37+,38-,40-,41+,42-,43-/m0/s1

Canonical SMILES

CCC(C1C(CC(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)C(=O)O

Isomeric SMILES

CC[C@H]([C@H]1[C@H](C[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)C(=O)O

Synonyms
        
            Narasin A
        
            Narasine [INN-French]
        
            narasin
        
            Monteban
        
            Compound 79891
        
            Antibiotic C 7819B
        
            Antibiotic A 28086A
        
            Narasinum [INN-Latin]
        
            Narasino [INN-Spanish]
        
            UNII-DZY9VU539P
        
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 Weight765.038
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count12
Complexity1360
Monoisotopic Mass764.507
Exact Mass764.507
XLogP6.2
Formal Charge0
Heavy Atom Count54
Defined Atom Stereocenter Count19
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
Other Poultry Animals,Edible OffalJapan0.3ppm
Chicken,Edible OffalJapan0.3ppm
Other Poultry Animals,KidneyJapan0.3ppm
Chicken,KidneyJapan0.3ppm
Other Poultry Animals,LiverJapan0.3ppm
Chicken,LiverJapan0.3ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.5ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
Cattle,Edible OffalJapan0.05ppm
Cattle,KidneyJapan0.05ppm
Cattle,LiverJapan0.05ppm
Cattle,FatJapan0.05ppm
Cattle,MuscleJapan0.05ppm

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
Determination of the residue levels of nicarbazin and combinationnicarbazin-narasin in broiler chickens after oral administration.PLoS One2017 Jul 2728750013
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
Transformation of ionophore antimicrobials in poultry litter during pilot-scalecomposting.Environ Pollut2016 May26874321
Determination of Narasin in Chicken Fat: A Bridging Study Comparing theBioautographic Method (FSIS CLG Method R22) to a Liquid Chromatography withTandem Mass Spectrometry Method (AOAC Method 2011.24).J AOAC Int2016 Mar-Apr26961063
Evaluation of ionophore sensitivity of Eimeria acervulina and Eimeria maximaisolated from the Algerian to Jijel province poultry farms.Vet Parasitol2016 Jul 1527270394
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
Comparison of fatty acid profile in the chicken meat after feeding with narasin, nicarbazin and salinomycin sodium and phyto-additive substances.J Environ Sci Health B201626950416
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
Detection and quantification of ionophore antibiotics in runoff, soil and poultrylitter.J Chromatogr A2013 Oct 1824028934
Single-laboratory validation of a multiplex flow cytometric immunoassay for thesimultaneous detection of coccidiostats in eggs and feed.Anal Bioanal Chem2013 Nov24081566
Determination and confirmation of narasin and monensin in chicken, swine, andbovine tissues by LC/MS/MS: Final Action 2011.24.J AOAC Int2013 Jul-Aug24000767
Risk assessment of coccidostatics during feed cross-contamination: animal andhuman health aspects.Toxicol Appl Pharmacol2013 Aug 121215766
Development of a five-plex flow cytometric immunoassay for the simultaneousdetection of six coccidiostats in feed and eggs.Anal Bioanal Chem2012 Sep22850895
Detection and quantitative analysis of 21 veterinary drugs in river water usinghigh-pressure liquid chromatography coupled to tandem mass spectrometry.Environ Sci Pollut Res Int2012 Sep22392691
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
Quantification of ionophores in aged poultry litter using liquid chromatographytandem mass spectrometry.J Environ Sci Health B201222938580
Non-soluble fibres and narasin reduce spontaneous gizzard erosion and ulceration in broiler chickens.Avian Pathol201222515541