Basic Info

Common NameEthylenethiourea(F05414)
2D Structure
Description

Ethylenethiourea is an organosulfur compound. It is an example of an N-substituted thiourea. This compound is be synthesized by treating ethylenediamine with carbon disulfide.

FRCD IDF05414
CAS Number96-45-7
PubChem CID2723650
FormulaC3H6N2S
IUPAC Name

imidazolidine-2-thione

InChI Key

PDQAZBWRQCGBEV-UHFFFAOYSA-N

InChI

InChI=1S/C3H6N2S/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)

Canonical SMILES

C1CNC(=S)N1

Isomeric SMILES

C1CNC(=S)N1

Synonyms
        
            ETHYLENE THIOUREA
        
            2-Imidazolidinethione
        
            imidazolidine-2-thione
        
            Ethylenethiourea
        
            96-45-7
        
            2-Mercaptoimidazoline
        
            N,N'-Ethylenethiourea
        
            Imidazolidinethione
        
            Mercazin I
        
            Warecure C
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassAzolidines
SubclassImidazolidines
Intermediate Tree NodesNot available
Direct ParentImidazolidines
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsImidazolidine - Thiourea - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as imidazolidines. These are organic compounds containing an imidazolidine ring, which is a saturated ring (derived from imidazole) with two nitrogen atoms at positions 1 and 3 respectively, and containing only single bonds.

Properties

Property NameProperty Value
Molecular Weight102.155
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity63.2
Monoisotopic Mass102.025
Exact Mass102.025
XLogP-0.7
Formal Charge0
Heavy Atom Count6
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9493
Human Intestinal AbsorptionHIA+0.5082
Caco-2 PermeabilityCaco2-0.5181
P-glycoprotein SubstrateSubstrate0.5000
P-glycoprotein InhibitorNon-inhibitor0.9440
Non-inhibitor0.9951
Renal Organic Cation TransporterNon-inhibitor0.6141
Distribution
Subcellular localizationLysosome0.6804
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8726
CYP450 2D6 SubstrateNon-substrate0.7219
CYP450 3A4 SubstrateNon-substrate0.8007
CYP450 1A2 InhibitorInhibitor0.6332
CYP450 2C9 InhibitorNon-inhibitor0.6968
CYP450 2D6 InhibitorNon-inhibitor0.5266
CYP450 2C19 InhibitorNon-inhibitor0.6330
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6674
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9154
Non-inhibitor0.9214
AMES ToxicityAMES toxic0.9108
CarcinogensNon-carcinogens0.9564
Fish ToxicityHigh FHMT0.5859
Tetrahymena Pyriformis ToxicityHigh TPT0.8189
Honey Bee ToxicityLow HBT0.5377
BiodegradationNot ready biodegradable0.9319
Acute Oral ToxicityIII0.8060
Carcinogenicity (Three-class)Danger0.7463

Model Value Unit
Absorption
Aqueous solubility-0.7724LogS
Caco-2 Permeability0.9373LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7774LD50, mol/kg
Fish Toxicity2.6993pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5409pIGC50, ug/L

References

TitleJournalDatePubmed ID
Rapid determination of polar pesticides and plant growth regulators in fruits andvegetables by liquid chromatography/tandem mass spectrometry.J Environ Sci Health B2018 May 22:1-1029787687
Iodine nutritional status and thyroid effects of exposure toethylenebisdithiocarbamates.Environ Res2017 Apr28073049
Effects of hydrochemistry variables on the half-life of mancozeb and on thehazard index associated to the sum of mancozeb and ethylenethiourea.Environ Res2017 Apr28110212
Phytoremediation of groundwater contaminated with pesticides using short-rotationwillow crops: A case study of an apple orchard.Int J Phytoremediation2016 Nov27196962
Combined determination and confirmation of ethylenethiourea and propylenethiourearesidues in fruits at low levels of detection.Food Chem2014 Feb 1524128576
High-throughput method for the analysis of ethylenethiourea with direct injectionof hydrolysed urine using online on-column extraction liquid chromatography andtriple quadrupole mass spectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2013 Sep 123896430
Reproductive toxicity and thyroid effects in Sprague Dawley rats exposed to lowdoses of ethylenethiourea.Food Chem Toxicol2013 Sep23774258
Kinetic and thermodynamic investigation of mancozeb degradation in tomato homogenate during thermal processing.J Sci Food Agric2012 Feb21953177
Effect of household and industrial processing on the levels of pesticide residuesand degradation products in melons.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222489844
Soil and water pollution in a banana production region in tropical Mexico.Bull Environ Contam Toxicol2010 Oct20734023
Liquid chromatographic analysis of maneb and its main degradation product,ethylenethiouera, in fruit juice.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2008Aug18608508
Determination of ethylenethiourea (ETU) and propylenethiourea (PTU) in foods byhigh performance liquid chromatography-atmospheric pressure chemicalionisation-medium-resolution mass spectrometry.Food Addit Contam2005 Mar16019792
Twenty-four-hour urinary excretion of ten pesticide metabolites in healthy adultsin two different areas of Italy (Florence and Ragusa).Sci Total Environ2004 Oct 115336892
Stability of the dithiocarbamate pesticide maneb in tomato homogenates during cold storage and thermal processing.Food Addit Contam2004 Nov15764337
Kinetics of maneb degradation during thermal treatment of tomatoes.J Agric Food Chem2004 Mar 1014995123
Determination of degradation products and pathways of mancozeb andethylenethiourea (ETU) in solutions due to ozone and chlorine dioxide treatments.J Agric Food Chem2003 Feb 2612590479
Chlorine and chlorine dioxide treatment to reduce or remove EBDCs and ETUresidues in a solution.J Agric Food Chem2002 Jul 3112137506
Ozone and hydrogen peroxyacetic acid treatment to reduce or remove EBDCs and ETU residues in a solution.J Agric Food Chem2001 Nov11714379
Postharvest treatments for the reduction of mancozeb in fresh apples.J Agric Food Chem2001 Jun11410019
Toxicity study of a rubber antioxidant, 2-mercaptobenzimidazole, by repeated oral administration to rats.J Toxicol Sci1998 Feb9513921

Targets

General Function:
Transferase activity
Specific Function:
Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:
CD38
Uniprot ID:
P28907
Molecular Weight:
34328.145 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]