Isocyanurate

Basic Info

Common NameIsocyanurate(F05763)
2D Structure
FRCD IDF05763
CAS Number108-80-5
PubChem CID7956
FormulaC3H3N3O3
IUPAC Name

1,3,5-triazinane-2,4,6-trione

InChI Key

ZFSLODLOARCGLH-UHFFFAOYSA-N

InChI

InChI=1S/C3H3N3O3/c7-1-4-2(8)6-3(9)5-1/h(H3,4,5,6,7,8,9)

Canonical SMILES

C1(=O)NC(=O)NC(=O)N1

Isomeric SMILES

C1(=O)NC(=O)NC(=O)N1

Synonyms
        
            sym-Triazinetriol
        
            CYANURIC ACID
        
            108-80-5
        
            Isocyanuric acid
        
            1,3,5-Triazine-2,4,6-triol
        
            Trihydroxycyanidine
        
            Tricyanic acid
        
            s-Triazinetriol
        
            1,3,5-Triazine-2,4,6(1H,3H,5H)-trione
        
            Pseudocyanuric acid
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTriazines
Subclass1,3,5-triazines
Intermediate Tree NodesNot available
Direct Parent1,3,5-triazines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents1,3,5-triazine - Heteroaromatic compound - Azacycle - Polyol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 1,3,5-triazines. These are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 3, and 5.

Properties

Property NameProperty Value
Molecular Weight129.075
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Complexity136
Monoisotopic Mass129.017
Exact Mass129.017
XLogP-1.2
Formal Charge0
Heavy Atom Count9
Defined Atom Stereocenter Count0
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+0.9730
Human Intestinal AbsorptionHIA+0.9558
Caco-2 PermeabilityCaco2-0.8624
P-glycoprotein SubstrateNon-substrate0.7483
P-glycoprotein InhibitorNon-inhibitor0.9663
Non-inhibitor0.9970
Renal Organic Cation TransporterNon-inhibitor0.9162
Distribution
Subcellular localizationMitochondria0.6842
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7507
CYP450 2D6 SubstrateNon-substrate0.8460
CYP450 3A4 SubstrateNon-substrate0.8172
CYP450 1A2 InhibitorNon-inhibitor0.7204
CYP450 2C9 InhibitorNon-inhibitor0.9742
CYP450 2D6 InhibitorNon-inhibitor0.9685
CYP450 2C19 InhibitorNon-inhibitor0.9772
CYP450 3A4 InhibitorNon-inhibitor0.9306
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9916
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9569
Non-inhibitor0.9761
AMES ToxicityNon AMES toxic0.9158
CarcinogensNon-carcinogens0.9424
Fish ToxicityLow FHMT0.7122
Tetrahymena Pyriformis ToxicityHigh TPT0.6266
Honey Bee ToxicityLow HBT0.7391
BiodegradationNot ready biodegradable0.6696
Acute Oral ToxicityIV0.6256
Carcinogenicity (Three-class)Non-required0.5381
Model Value Unit
Absorption
Aqueous solubility-1.3734LogS
Caco-2 Permeability0.6647LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.2554LD50, mol/kg
Fish Toxicity2.5268pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1917pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,EggsJapan0.8ppm
Chicken,Edible OffalJapan2ppm
Chicken,KidneyJapan0.8ppm
Chicken,LiverJapan0.8ppm
Chicken,FatJapan0.8ppm
Chicken,MuscleJapan0.8ppm
MilkJapan0.8ppm
Other Terrestrial Mammals,Edible OffalJapan0.8ppm
Pig,Edible OffalJapan0.8ppm
Cattle,Edible OffalJapan0.8ppm
Other Terrestrial Mammals,KidneyJapan0.8ppm
Pig,KidneyJapan0.8ppm
Cattle,KidneyJapan0.8ppm
Other Terrestrial Mammals,LiverJapan0.8ppm
Pig,LiverJapan0.8ppm
Cattle,LiverJapan0.8ppm
Other Terrestrial Mammals,FatJapan0.8ppm
Pig,FatJapan0.8ppm
Cattle,FatJapan0.8ppm
Other Terrestrial Mammals,MuscleJapan0.8ppm

References

TitleJournalDatePubmed ID
Polymeric substances for the removal of ochratoxin A from red wine followed by computational modeling of the complexes formed.Food Chem2018 Nov 129884367
Removal of fumonisin B<sub>1</sub> and B<sub>2</sub> from model solutions and red wine using polymeric substances.Food Chem2017 Jun 128159257
Novel hydrolytic de-methylthiolation of the s-triazine herbicide prometryn byLeucobacter sp. JW-1.Sci Total Environ2017 Feb 127866738
Melamine and cyanuric acid co-exposure causes renal dysfunction and structuraldamage via MAPKs and mitochondrial signaling.Food Chem Toxicol2016 Oct27523292
Determination of emerging nitrogenous economic adulterants in milk proteins byhigh-performance liquid chromatography/compact mass spectrometry.Rapid Commun Mass Spectrom2016 Jun 1527173108
The effects of melamine on humoral immunity with or without cyanuric acid in mice.Res Vet Sci2016 Apr27033911
Continuous temperature-dependent Raman spectroscopy of melamine and structuralanalog detection in milk powder.Appl Spectrosc2015 Mar25664966
Toxicity of new emerging pollutant tris-(2,3-dibromopropyl) isocyanurate on BALB/c mice.J Appl Toxicol2015 Apr25042629
Reproductive toxicity in rats with crystal nephropathy following high doses oforal melamine or cyanuric acid.Food Chem Toxicol2014 Jun24582682
An evaluation of genotoxicity and cytotoxicity of melamine in combination with cyanuric acid at three mass ratios.Biomed Environ Sci2014 Aug25189612
Effects of melamine and cyanuric acid on embryo-fetal development in rats.Birth Defects Res B Dev Reprod Toxicol2013 Oct24323939
Rapid detection of economic adulterants in fresh milk by liquidchromatography-tandem mass spectrometry.J Chromatogr A2013 May 323540766
Effect on morphology, oxidative stress and energy metabolism enzymes in thetestes of mice after a 13-week oral administration of melamine and cyanuric acid combination.Regul Toxicol Pharmacol2013 Mar23220542
Depletion of melamine and cyanuric acid in kidney of catfish Ictalurus punctatus and trout Oncorhynchus mykiss.J Vet Pharmacol Ther2013 Dec23682764
Recent advances in the risk assessment of melamine and cyanuric acid in animalfeed.Toxicol Appl Pharmacol2013 Aug 122306862
Depletion of melamine and cyanuric acid in serum from catfish Ictalurus punctatusand rainbow trout Onchorhynchus mykiss.Food Chem Toxicol2012 Oct22889901
Biodegradation of melamine and its hydroxy derivatives by a bacterial consortium containing a novel Nocardioides species.Appl Microbiol Biotechnol2012 Jun22105542
Effects of water uptake on melamine renal stone formation in mice.Nephrol Dial Transplant2012 Jun21987538
The Pathological Effects of Melamine and Cyanuric Acid in the Diet of Walking Catfish (Clarius batrachus).J Comp Pathol2012 Aug-Oct22316434
Migration of melamine from can coatings cross-linked with melamine-based resins, into food simulants and foods.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Feb21181594