Zeranol

Basic Info

Common NameZeranol(F06109)
2D Structure
FRCD IDF06109
CAS Number26538-44-3
PubChem CID2999413
FormulaC18H26O5
IUPAC Name

(7R,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one

InChI Key

DWTTZBARDOXEAM-GXTWGEPZSA-N

InChI

InChI=1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1

Canonical SMILES

CC1CCCC(CCCCCC2=CC(=CC(=C2C(=O)O1)O)O)O

Isomeric SMILES

C[C@H]1CCC[C@@H](CCCCCC2=CC(=CC(=C2C(=O)O1)O)O)O

Synonyms
        
            Ralgro
        
            Ralone
        
            ZERANOL
        
            Zearalanol
        
            alpha-Zearalanol
        
            26538-44-3
        
            Ralabol
        
            Zearanol
        
            Zeranolum [INN-Latin]
        
            Zeranol [USAN:INN:BAN]
Classifies
                

                  
                    Veterinary Drug
                  
                    Illegal Additives
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassMacrolides and analogues
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentMacrolides and analogues
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsMacrolide - Dihydroxybenzoic acid - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Vinylogous acid - Carboxylic acid ester - Lactone - Secondary alcohol - Carboxylic acid derivative - Polyol - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Properties

Property NameProperty Value
Molecular Weight322.401
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Complexity372
Monoisotopic Mass322.178
Exact Mass322.178
XLogP4.3
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count2
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+0.5707
Human Intestinal AbsorptionHIA+0.9545
Caco-2 PermeabilityCaco2+0.6273
P-glycoprotein SubstrateSubstrate0.7397
P-glycoprotein InhibitorNon-inhibitor0.9899
Non-inhibitor0.9783
Renal Organic Cation TransporterNon-inhibitor0.9094
Distribution
Subcellular localizationMitochondria0.6668
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7324
CYP450 2D6 SubstrateNon-substrate0.8123
CYP450 3A4 SubstrateNon-substrate0.5000
CYP450 1A2 InhibitorInhibitor0.7088
CYP450 2C9 InhibitorNon-inhibitor0.8967
CYP450 2D6 InhibitorNon-inhibitor0.9136
CYP450 2C19 InhibitorNon-inhibitor0.7774
CYP450 3A4 InhibitorInhibitor0.6622
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9482
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9247
Non-inhibitor0.8175
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.9584
Fish ToxicityHigh FHMT0.9169
Tetrahymena Pyriformis ToxicityHigh TPT0.9887
Honey Bee ToxicityHigh HBT0.6724
BiodegradationReady biodegradable0.6900
Acute Oral ToxicityIII0.5274
Carcinogenicity (Three-class)Non-required0.6882
Model Value Unit
Absorption
Aqueous solubility-2.7888LogS
Caco-2 Permeability0.6767LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9841LD50, mol/kg
Fish Toxicity1.3346pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7286pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0.002ppm
Other Aquatic AnimalJapan0.002ppm
CrustaceansJapan0.002ppm
Shelled MolluscasJapan0.002ppm
Other FishJapan0.002ppm
PerciformesJapan0.002ppm
AnguilliformesJapan0.002ppm
SalmoniformesJapan0.002ppm
Chicken,EggsJapan0.002ppm
Other Poultry Animals,Edible OffalJapan0.002ppm
Chicken,Edible OffalJapan0.002ppm
Other Poultry Animals,KidneyJapan0.002ppm
Chicken,KidneyJapan0.002ppm
Other Poultry Animals,LiverJapan0.002ppm
Chicken,LiverJapan0.002ppm
Other Poultry Animals,FatJapan0.002ppm
Chicken,FatJapan0.002ppm
Other Poultry Animals,MuscleJapan0.002ppm
Chicken,MuscleJapan0.002ppm
MilkJapan0.002ppm

References

TitleJournalDatePubmed ID
Mycotoxins induce developmental toxicity and behavioural aberrations in zebrafish larvae.Environ Pollut2018 Nov30005262
Liquid chromatography - high resolution mass spectrometry method for monitoring of 17 mycotoxins in human plasma for exposure studies.J Chromatogr A2018 May 429576275
Preparation of a broad-spectrum anti-zearalenone and its primary analogues antibody and its application in an indirect competitive enzyme-linked immunosorbent assay.Food Chem2018 May 129277231
Estrogenic activity of zearalenone, α-zearalenol and β-zearalenol assessed using the E-screen assay in MCF-7 cells.Toxicol Mech Methods2018 May29057713
[Simultaneous determination of six zeranols in milk samples by immunoaffinity solid phase extraction coupled with ultra-performance convergence chromatography-tandem mass spectrometry].Se Pu2018 Jun 830136479
Measurement of urinary concentrations of the mycotoxins zearalenone and sterigmatocystin as biomarkers of exposure in mares.Reprod Domest Anim2018 Feb28921680
Multiresidue Determination of the Anabolic-Agent Residues Steroids, Stilbenes,and Resorcylic Acid Lactones in Bovine Urine by GC-MS/MS with Microwave-Assisted Derivatization.J Agric Food Chem2018 Aug 1530020779
Fluorescence Polarization Immunoassay Based on a New Monoclonal Antibody for the Detection of the Zearalenone Class of Mycotoxins in Maize.J Agric Food Chem2017 Mar 1528231710
Synergistic estrogenic effects of Fusarium and Alternaria mycotoxins in vitro.Arch Toxicol2017 Mar27401186
Core-shell poly(dopamine) magnetic nanoparticles for the extraction of estrogenic mycotoxins from milk and yogurt prior to LC-MS analysis.Food Chem2017 Jan 1527542487
Metabolism of Zearalenone and Its Major Modified Forms in Pigs.Toxins (Basel)2017 Feb 828208710
Reaction of zearalenone and α-zearalenol with allyl isothiocyanate, characterization of reaction products, their bioaccessibility and bioavailability in vitro.Food Chem2017 Feb 1527664682
Masked trichothecene and zearalenone mycotoxins withstand digestion and absorption in the upper GI tract but are efficiently hydrolyzed by human gut microbiota in vitro.Mol Nutr Food Res2017 Apr27921366
Zeranol induces COX-2 expression through TRPC-3 activation in the placental cells JEG-3.Toxicol In Vitro2016 Sep27224899
Cytotoxic effects of zearalenone and its metabolites and antioxidant cell defense in CHO-K1 cells.Food Chem Toxicol2016 Oct27465603
Application of multiwalled carbon nanotubes as sorbents for the extraction of mycotoxins in water samples and infant milk formula prior to high performance liquid chromatography mass spectrometry analysis.Electrophoresis2016 May26892029
Activation of ER stress and apoptosis by α- and β-zearalenol in HCT116 cells, protective role of Quercetin.Neurotoxicology2016 Mar26584763
Toxicological effects of fumonisin B1 alone and in combination with other fusariotoxins on bovine granulosa cells.Toxicon2016 Aug27108238
Fusarium toxin-contaminated maize in diets of growing bulls: effects on performance, slaughtering characteristics, and transfer into physiological liquids.Mycotoxin Res2016 Aug27083899
A simple sample pretreatment method for multi-mycotoxin determination in eggs by liquid chromatography tandem mass spectrometry.J Chromatogr A2015 Oct 2326385084