Carboxin (CHEM003443)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:39 UTC
Update Date2016-11-09 01:09:08 UTC
Accession NumberCHEM003443
Identification
Common NameCarboxin
ClassSmall Molecule
DescriptionCarboxin is a systemic fungicide used to control seed and seedling diseases (smut, rot, blight) on barley, beans, canola, corn, cotton, oats, onions, peanuts, rice, rye, safflower, sorghum, soybeans, triticale, and wheat. Carboxin has been shown to have low acute toxicity. Toxicity Categories, which range from I (most toxic) to IV (least toxic), were III for the oral route of exposure, IV for inhalation, and III for dermal. Carboxin is a slight eye irritant (Toxicity Category III), is not a skin irritant (Toxicity Category IV), and is negative for dermal sensitization. The mechanism of toxicity for carboxin has not been fully investigated; however the primary target organs appear to be the liver and kidney. In carcinogenicity studies in rats and mice, carboxin did not demonstrate any significant evidence of carcinogenic potential.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Fungicide
  • Fungicide, Industrial
  • Lachrymator
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiinChEBI
2,3-Dihydro-6-methyl-1,4-oxathiin-5-carboxanilideChEBI
2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiinChEBI
5,6-Dihydro-2-methyl-1,4-oxathiin-3-carboxanilideChEBI
5,6-Dihydro-2-methyl-3-carboxanilido-1,4-oxathiinChEBI
5,6-Dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamideChEBI
5-Carboxanilido-2,3-dihydro-6-methyl-1,4-oxathiinChEBI
CarbathiinChEBI
CarboxineChEBI
OxatinChEBI
VitavaxMeSH
Chemical FormulaC12H13NO2S
Average Molecular Mass235.302 g/mol
Monoisotopic Mass235.067 g/mol
CAS Registry Number5234-68-4
IUPAC Name2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
Traditional Namecarboxin
SMILESCC1=C(SCCO1)C(=O)NC1=CC=CC=C1
InChI IdentifierInChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14)
InChI KeyGYSSRZJIHXQEHQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • N-arylamide
  • 1,4-oxathiin
  • Vinylogous ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Thioenolether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrial Membrane
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Antifungal AgentsNot AvailableNot Available
Homologous recombinationNot Availablemap03440
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP1.65ALOGPS
logP1.51ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.24ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.1 m³·mol⁻¹ChemAxon
Polarizability24.87 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9330000000-8fb38949e792782c2d8dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-4901000000-ccaeb7005f3f1f68e10aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-4901000000-ccaeb7005f3f1f68e10aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0006-9500000000-8175760759481b4fc390Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0006-9200000000-321966ed4052e6513586Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-1900000000-be26bd3bd37b90b11be8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0006-4900000000-c5d1f9bffd8b2ba62544Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0910000000-38444f8b75fd3665c3ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000f-0950000000-ba5f28d04dd6509f0d93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-7190000000-0702aed90bcc1f8f6f9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-c50a7e27d2782423ff88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-529fd698e01daefc1d80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2970000000-d83ec37591aecd093fb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-9300000000-6f7e68dfb86c706359f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9300000000-54d156aabb4ef4bb3f57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-2980000000-63f3a7441814ee041c4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-8970000000-b9ce3d3832dca3ed5ad0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-d21a06c1826ec44e6c21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07d0-8980000000-733c27fdcb32495ac679Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-1488e39a56b22f10bcaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-8ada38a017b4218f9008Spectrum
MSMass Spectrum (Electron Ionization)splash10-000f-9620000000-9a851c11b79664d86a44Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04657
HMDB IDHMDB0249648
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD0-1366
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID20027
ChEBI ID3405
PubChem Compound ID21307
Kegg Compound IDC11255
YMDB IDNot Available
ECMDB IDECMDB20440
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21228470
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23047320
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23261124
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24119086
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24785712