Basic Info

Common NameOfurace(F06022)
2D Structure
FRCD IDF06022
CAS Number58810-48-3
PubChem CID42850
FormulaC14H16ClNO3
IUPAC Name

2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxooxolan-3-yl)acetamide

InChI Key

OWDLFBLNMPCXSD-UHFFFAOYSA-N

InChI

InChI=1S/C14H16ClNO3/c1-9-4-3-5-10(2)13(9)16(12(17)8-15)11-6-7-19-14(11)18/h3-5,11H,6-8H2,1-2H3

Canonical SMILES

CC1=C(C(=CC=C1)C)N(C2CCOC2=O)C(=O)CCl

Isomeric SMILES

CC1=C(C(=CC=C1)C)N(C2CCOC2=O)C(=O)CCl

Synonyms
        
            Ofurace [ANSI:BSI:ISO]
        
            Acetamide, 2-chloro-N-(2,6-dimethylphenyl)-N-(tetrahydro-2-oxo-3-furanyl)-
        
            Ofurace
        
            58810-48-3
        
            Milfuram
        
            Ortho 20615
        
            Chevron 20615
        
            RE 20615
        
            EINECS 261-451-9
        
            BRN 1653655
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentAlpha amino acid esters
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAlpha-amino acid ester - Anilide - M-xylene - Xylene - Monocyclic benzene moiety - Gamma butyrolactone - Benzenoid - Chloroacetamide - Tetrahydrofuran - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Lactone - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Alkyl chloride - Organochloride - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Properties

Property NameProperty Value
Molecular Weight281.736
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity351
Monoisotopic Mass281.082
Exact Mass281.082
XLogP2.7
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9001
Human Intestinal AbsorptionHIA+0.9736
Caco-2 PermeabilityCaco2+0.6221
P-glycoprotein SubstrateNon-substrate0.8677
P-glycoprotein InhibitorNon-inhibitor0.8786
Non-inhibitor0.8292
Renal Organic Cation TransporterNon-inhibitor0.7814
Distribution
Subcellular localizationMitochondria0.7724
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6361
CYP450 2D6 SubstrateNon-substrate0.8458
CYP450 3A4 SubstrateSubstrate0.6104
CYP450 1A2 InhibitorInhibitor0.6042
CYP450 2C9 InhibitorNon-inhibitor0.6470
CYP450 2D6 InhibitorNon-inhibitor0.9239
CYP450 2C19 InhibitorInhibitor0.7356
CYP450 3A4 InhibitorNon-inhibitor0.5576
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5517
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9087
Non-inhibitor0.9297
AMES ToxicityNon AMES toxic0.5502
CarcinogensNon-carcinogens0.8255
Fish ToxicityHigh FHMT0.8455
Tetrahymena Pyriformis ToxicityHigh TPT0.9273
Honey Bee ToxicityLow HBT0.8908
BiodegradationNot ready biodegradable0.9492
Acute Oral ToxicityIII0.7783
Carcinogenicity (Three-class)Non-required0.6251

Model Value Unit
Absorption
Aqueous solubility-3.1634LogS
Caco-2 Permeability1.1741LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0664LD50, mol/kg
Fish Toxicity0.7538pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0347pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
TomatoKorea2ppm

References

TitleJournalDatePubmed ID
A sensitive and selective method for the determination of selected pesticides in fruit by gas chromatography/mass spectrometry with negative chemical ionization.J Chromatogr A2012 Nov 1623058941