Basic Info

Common NameEthopabate(F06115)
2D Structure
FRCD IDF06115
CAS Number59-06-3
PubChem CID6034
FormulaC12H15NO4
IUPAC Name

methyl 4-acetamido-2-ethoxybenzoate

InChI Key

GOVWOKSKFSBNGD-UHFFFAOYSA-N

InChI

InChI=1S/C12H15NO4/c1-4-17-11-7-9(13-8(2)14)5-6-10(11)12(15)16-3/h5-7H,4H2,1-3H3,(H,13,14)

Canonical SMILES

CCOC1=C(C=CC(=C1)NC(=O)C)C(=O)OC

Isomeric SMILES

CCOC1=C(C=CC(=C1)NC(=O)C)C(=O)OC

Synonyms
        
            4-Acetamido-2-ethoxybenzoesaeuremethylester
        
            ETHOPABATE
        
            Methyl 4-acetamido-2-ethoxybenzoate
        
            59-06-3
        
            Ethopabat
        
            Benzoic acid, 4-(acetylamino)-2-ethoxy-, methyl ester
        
            UNII-F4X3L6068O
        
            Methyl 4-(acetylamino)-2-ethoxybenzoate
        
            Amprol Plus (veterinary)
        
            EINECS 200-414-3
        
Classifies
                

                  
                    Predicted: Fungal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzoic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentAcylaminobenzoic acid and derivatives
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAcylaminobenzoic acid or derivatives - Acetanilide - Benzoate ester - N-acetylarylamine - Anilide - Phenoxy compound - Benzoyl - Phenol ether - N-arylamide - Alkyl aryl ether - Acetamide - Methyl ester - Carboxamide group - Carboxylic acid ester - Secondary carboxylic acid amide - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Organopnictogen compound - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Properties

Property NameProperty Value
Molecular Weight237.255
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity280
Monoisotopic Mass237.1
Exact Mass237.1
XLogP1.2
Formal Charge0
Heavy Atom Count17
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+0.9236
Human Intestinal AbsorptionHIA+0.9415
Caco-2 PermeabilityCaco2+0.6477
P-glycoprotein SubstrateNon-substrate0.8281
P-glycoprotein InhibitorNon-inhibitor0.8477
Non-inhibitor0.8994
Renal Organic Cation TransporterNon-inhibitor0.9279
Distribution
Subcellular localizationMitochondria0.8782
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8162
CYP450 2D6 SubstrateNon-substrate0.7091
CYP450 3A4 SubstrateSubstrate0.5491
CYP450 1A2 InhibitorNon-inhibitor0.5470
CYP450 2C9 InhibitorNon-inhibitor0.5273
CYP450 2D6 InhibitorNon-inhibitor0.9115
CYP450 2C19 InhibitorInhibitor0.5564
CYP450 3A4 InhibitorNon-inhibitor0.8578
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7083
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9763
Non-inhibitor0.9469
AMES ToxicityNon AMES toxic0.6570
CarcinogensNon-carcinogens0.7561
Fish ToxicityHigh FHMT0.8615
Tetrahymena Pyriformis ToxicityHigh TPT0.9506
Honey Bee ToxicityLow HBT0.5891
BiodegradationReady biodegradable0.7202
Acute Oral ToxicityIII0.7388
Carcinogenicity (Three-class)Non-required0.6245

Model Value Unit
Absorption
Aqueous solubility-2.9728LogS
Caco-2 Permeability1.1241LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1226LD50, mol/kg
Fish Toxicity0.7338pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1400pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,FatJapan0.04ppm
Chicken,MuscleJapan0.04ppm
Muscle Of ChickensUnited States0.5ppm
Kidney Of ChickensUnited States1.5ppm
Liver Of ChickensUnited States1.5ppm
Chicken,Edible OffalJapan0.04ppm
Other Poultry Animals,KidneyJapan20ppm
Chicken,KidneyJapan0.04ppm
Other Poultry Animals,LiverJapan20ppm
Chicken,LiverJapan0.04ppm
Other Poultry Animals,Edible OffalJapan20ppm

References

TitleJournalDatePubmed ID
Spectrofluorimetric analysis of ethopabate in veterinary formulations with application to residue determination in chicken muscles and liver.Luminescence2014 Dec24817251
Anticoccidial drugs for preventive therapy in intensively reared pheasants.Vet Rec1981 Dec 197336544
The short-term toxicity of some feed additives to different freshwater organisms.Bull Environ Contam Toxicol1976 Jun938765