Basic Info

Common NameSulfocarbathione(F04028)
2D Structure
Description

Sulfocarbathione is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

FRCD IDF04028
CAS Number114654-31-8
PubChem CID2770187
FormulaC5H9NO2S3
IUPAC Name

(1,1-dioxothiolan-3-yl)carbamodithioic acid

InChI Key

UEKOYEYXLALUCZ-UHFFFAOYSA-N

InChI

InChI=1S/C5H9NO2S3/c7-11(8)2-1-4(3-11)6-5(9)10/h4H,1-3H2,(H2,6,9,10)

Canonical SMILES

C1CS(=O)(=O)CC1NC(=S)S

Isomeric SMILES

C1CS(=O)(=O)CC1NC(=S)S

Synonyms
        
            Sulfocarbathion
        
            (1,1-dioxothiolan-3-yl)carbamodithioic acid
        
            Sulfocarbathione
        
            Sulfocarbathion K
        
            114654-31-8
        
            Enamine_000156
        
            AC1MCI46
        
            STL483786
        
            LS-147949
        
            3-[Mercapto(thiocarbonyl)amino]thiolane 1,1-dioxide
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassThiolanes
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentThiolanes
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsThiolane - Sulfone - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as thiolanes. These are organic compounds containing thiolane, a five-member saturated ring containing four carbon atoms and a sulfur atom.

Properties

Property NameProperty Value
Molecular Weight211.312
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Complexity253
Monoisotopic Mass210.98
Exact Mass210.98
XLogP0.3
Formal Charge0
Heavy Atom Count11
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+0.9488
Human Intestinal AbsorptionHIA+0.7113
Caco-2 PermeabilityCaco2-0.6239
P-glycoprotein SubstrateNon-substrate0.6448
P-glycoprotein InhibitorNon-inhibitor0.8502
Non-inhibitor0.9961
Renal Organic Cation TransporterNon-inhibitor0.7802
Distribution
Subcellular localizationLysosome0.5915
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6382
CYP450 2D6 SubstrateNon-substrate0.8017
CYP450 3A4 SubstrateNon-substrate0.6019
CYP450 1A2 InhibitorNon-inhibitor0.6584
CYP450 2C9 InhibitorNon-inhibitor0.7825
CYP450 2D6 InhibitorNon-inhibitor0.9011
CYP450 2C19 InhibitorNon-inhibitor0.6659
CYP450 3A4 InhibitorNon-inhibitor0.8634
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8934
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7282
Non-inhibitor0.7950
AMES ToxicityNon AMES toxic0.6543
CarcinogensNon-carcinogens0.8758
Fish ToxicityLow FHMT0.6682
Tetrahymena Pyriformis ToxicityLow TPT0.6752
Honey Bee ToxicityHigh HBT0.5080
BiodegradationReady biodegradable0.9343
Acute Oral ToxicityIII0.5453
Carcinogenicity (Three-class)Non-required0.5702

Model Value Unit
Absorption
Aqueous solubility-2.1250LogS
Caco-2 Permeability0.4853LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7775LD50, mol/kg
Fish Toxicity2.3116pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1087pIGC50, ug/L

Targets

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088