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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:26 UTC
Update Date2019-07-23 06:09:30 UTC
HMDB IDHMDB0031782
Secondary Accession Numbers
  • HMDB31782
Metabolite Identification
Common NameEthiofencarb
DescriptionEthiofencarb, also known as croneton or arylmate, belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Ethiofencarb is a moderately basic compound (based on its pKa). Ethiofencarb is a potentially toxic compound. He developed a severe case of pulmonary edema within an hour of admission, and after three hours, he died and 26.4 mg/L ethiofencarb, along with 0/12 g/100 mL ethanol, 37.9 mg/L ethiofencarbsulfoxide and 0.9 mg/L ethiofencarbsulfone were found in his urine analysis. Carbamates are effective insecticides because of their ability to inhibit acetylcholinesterase (AChE) in the nervous system. Ethiofencarb could be transported from place to place in the environment through various natural waste pathways. This chemical is rapidly oxidized in the bodies of mammals, hydrolyzing to phenolic metabolites.
Structure
Data?1563862170
Synonyms
ValueSource
2-((Ethylthio)methyl)phenol methylcarbamateChEBI
2-((Ethylthio)methyl)phenyl methylcarbamateChEBI
alpha-(Ethylthio)-O-tolyl methylcarbamateChEBI
alpha-Ethylthio-O-tolyl methylcarbamateChEBI
CronetonChEBI
2-((Ethylthio)methyl)phenol methylcarbamic acidGenerator
2-((Ethylthio)methyl)phenyl methylcarbamic acidGenerator
a-(Ethylthio)-O-tolyl methylcarbamateGenerator
a-(Ethylthio)-O-tolyl methylcarbamic acidGenerator
alpha-(Ethylthio)-O-tolyl methylcarbamic acidGenerator
Α-(ethylthio)-O-tolyl methylcarbamateGenerator
Α-(ethylthio)-O-tolyl methylcarbamic acidGenerator
a-Ethylthio-O-tolyl methylcarbamateGenerator
a-Ethylthio-O-tolyl methylcarbamic acidGenerator
alpha-Ethylthio-O-tolyl methylcarbamic acidGenerator
Α-ethylthio-O-tolyl methylcarbamateGenerator
Α-ethylthio-O-tolyl methylcarbamic acidGenerator
(2-Ethylthiomethyl-phenyl)-N-methylcarbamateHMDB
2-(Ethylthiomethyl)phenyl methylcarbamate, 9ciHMDB
2-Ethyl-mercaptomethyl-phenyl-N-methylcarbamateHMDB
2-Ethylthiomethylphenyl N-methylcarbamateHMDB
2-[(Ethylsulfanyl)methyl]phenyl methylcarbamateHMDB
ArylmateHMDB
BAY-hox-1901HMDB
Carbamic acid, methyl-, 2-(ethylthiomethyl)phenyl esterHMDB
Carbamic acid, methyl-, alpha-(ethylthio)-O-tolyl esterHMDB
Croneton 500HMDB
EthiophencarbeHMDB
KronetoneHMDB
N-Methyl-O-(2-ethylthiomethyl) phenylcarbamateHMDB
Phenol, 2-((ethylthio)methyl)-, methylcarbamateHMDB
Phenol, 2-((ethylthio)methyl)-, methylcarbamate (9ci)HMDB
Phenol, 2-[(ethylthio)methyl]-, methylcarbamateHMDB
KronetonHMDB
Chemical FormulaC11H15NO2S
Average Molecular Weight225.307
Monoisotopic Molecular Weight225.082349419
IUPAC Name1-{2-[(ethylsulfanyl)methyl]phenoxy}-N-methylmethanimidic acid
Traditional Name1-2-[(ethylsulfanyl)methyl]phenoxy-N-methylmethanimidic acid
CAS Registry Number29973-13-5
SMILES
CCSCC1=CC=CC=C1OC(O)=NC
InChI Identifier
InChI=1S/C11H15NO2S/c1-3-15-8-9-6-4-5-7-10(9)14-11(13)12-2/h4-7H,3,8H2,1-2H3,(H,12,13)
InChI KeyHEZNVIYQEUHLNI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenyl methylcarbamates
Direct ParentPhenyl methylcarbamates
Alternative Parents
Substituents
  • Phenyl methylcarbamate
  • Phenoxy compound
  • Carbamic acid ester
  • Carbonic acid derivative
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.82 mg/mL at 20 °CNot Available
LogP2.04Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.76ALOGPS
logP3.13ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)2.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.82 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.58 m³·mol⁻¹ChemAxon
Polarizability23.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-5900000000-a0e811b07807c20dc226Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05d0-9450000000-a60b46f1581a965f9032Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02di-6930000000-f6673165e1a176b115dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-9600000000-b5a2082ff68df8b1e4e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9200000000-8ab2ca87a079db8a8838Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-9310000000-94bc3480b80e35059030Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-9300000000-153b9e9dba9bd6921897Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9200000000-58c7056048f6ab3a59dbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008455
KNApSAcK IDNot Available
Chemspider ID31991
KEGG Compound IDC18649
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthiofencarb
METLIN IDNot Available
PubChem Compound34766
PDB IDNot Available
ChEBI ID38483
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .