Carboxin

Identification

Name
Carboxin
Accession Number
DB04657
Type
Small Molecule
Groups
Experimental, Investigational
Description

A 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
International/Other Brands
Kisvax / Vitavax
Categories
UNII
5A8K850HDE
CAS number
5234-68-4
Weight
Average: 235.302
Monoisotopic: 235.066699355
Chemical Formula
C12H13NO2S
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USuccinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrialNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C11255
PubChem Compound
21307
PubChem Substance
46507275
ChemSpider
20027
ChEBI
3405
ChEMBL
CHEMBL1231667
HET
CBE
PDB Entries
2fbw / 2wdq / 2wp9 / 2wqy / 2ws3 / 2wu2 / 2wu5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentDepression, Bipolar1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)91.5 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-000f-9620000000-9a851c11b79664d86a44
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-4901000000-ccaeb7005f3f1f68e10a

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Anilides
Alternative Parents
N-arylamides / Oxathiins / Vinylogous esters / Thioenol ethers / Secondary carboxylic acid amides / Oxacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Anilide / N-arylamide / 1,4-oxathiin / Vinylogous ester / Carboxamide group / Secondary carboxylic acid amide / Thioenolether / Carboxylic acid derivative / Oxacycle / Organoheterocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
anilide (CHEBI:41412) / Amide fungicides (C11255) / an amide (CPD0-1366)

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 ...
Gene Name
SDHA
Uniprot ID
P31040
Uniprot Name
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
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]

Drug created on September 11, 2007 11:49 / Updated on December 01, 2017 15:30