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Identification
NameCarboxin
Accession NumberDB04657
TypeSmall Molecule
GroupsExperimental
DescriptionA systemic agricultural fungicide and seed treatment agent.
Structure
Thumb
Synonyms
2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin
2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin
Carbathiin
Carbathiine
Carboxine
CBX
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
KisvaxNot Available
VitavaxNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII5A8K850HDE
CAS number5234-68-4
WeightAverage: 235.302
Monoisotopic: 235.066699355
Chemical FormulaC12H13NO2S
InChI KeyInChIKey=GYSSRZJIHXQEHQ-UHFFFAOYSA-N
InChI
InChI=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)
IUPAC Name
2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
SMILES
CC1=C(SCCO1)C(=O)NC1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassN-arylamides
Sub ClassNot Available
Direct ParentN-arylamides
Alternative Parents
Substituents
  • N-arylamide
  • Anilide
  • Benzenoid
  • 1,4-oxathiin
  • Monocyclic benzene moiety
  • Vinylogous ester
  • Thioenolether
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Thioether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9794
Blood Brain Barrier+0.9764
Caco-2 permeable+0.6035
P-glycoprotein substrateNon-substrate0.6547
P-glycoprotein inhibitor IInhibitor0.5183
P-glycoprotein inhibitor IINon-inhibitor0.9174
Renal organic cation transporterNon-inhibitor0.7344
CYP450 2C9 substrateNon-substrate0.655
CYP450 2D6 substrateNon-substrate0.7929
CYP450 3A4 substrateSubstrate0.5503
CYP450 1A2 substrateInhibitor0.6498
CYP450 2C9 inhibitorInhibitor0.5784
CYP450 2D6 inhibitorNon-inhibitor0.8963
CYP450 2C19 inhibitorInhibitor0.7341
CYP450 3A4 inhibitorNon-inhibitor0.8503
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8491
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8705
BiodegradationReady biodegradable0.6897
Rat acute toxicity2.7064 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9405
hERG inhibition (predictor II)Non-inhibitor0.8196
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point91.5 °CPhysProp
water solubility147 mg/L (at 20 °C)TOMLIN,C (2003)
logP2.14HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.536 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.1 m3·mol-1ChemAxon
Polarizability24.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-000f-9620000000-9a851c11b79664d86a44View in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Succinate dehydrogenase activity
Specific Function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:
SDHA
Uniprot ID:
P31040
Molecular Weight:
72690.975 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24