Isoprothiolane

Basic Info

Common NameIsoprothiolane(F05687)
2D Structure
FRCD IDF05687
CAS Number50512-35-1
PubChem CID39681
FormulaC12H18O4S2
IUPAC Name

dipropan-2-yl 2-(1,3-dithiolan-2-ylidene)propanedioate

InChI Key

UFHLMYOGRXOCSL-UHFFFAOYSA-N

InChI

InChI=1S/C12H18O4S2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8H,5-6H2,1-4H3

Canonical SMILES

CC(C)OC(=O)C(=C1SCCS1)C(=O)OC(C)C

Isomeric SMILES

CC(C)OC(=O)C(=C1SCCS1)C(=O)OC(C)C

Synonyms
        
            ISOPROTHIOLANE
        
            Diisopropyl 2-(1,3-dithiolan-2-ylidene)malonate
        
            50512-35-1
        
            Fudiolan
        
            Fujione
        
            IPT (pesticide)
        
            Fuji 1
        
            NKK 100
        
            Di-isopropyl 1,3-dithiolane-2-ylidenemalonate
        
            Isoprothiolane [BSI:ISO]
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassDicarboxylic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsVinylogous thioester - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - 1,3-dithiolane - Dithiolane - Ketene acetal or derivatives - Carboxylic acid ester - Organoheterocyclic compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Properties

Property NameProperty Value
Molecular Weight290.392
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Complexity329
Monoisotopic Mass290.065
Exact Mass290.065
XLogP3.3
Formal Charge0
Heavy Atom Count18
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+0.8092
Human Intestinal AbsorptionHIA+0.9757
Caco-2 PermeabilityCaco2-0.5421
P-glycoprotein SubstrateNon-substrate0.5712
P-glycoprotein InhibitorInhibitor0.5133
Non-inhibitor0.8080
Renal Organic Cation TransporterNon-inhibitor0.8441
Distribution
Subcellular localizationMitochondria0.7948
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8304
CYP450 2D6 SubstrateNon-substrate0.8512
CYP450 3A4 SubstrateNon-substrate0.5407
CYP450 1A2 InhibitorNon-inhibitor0.6455
CYP450 2C9 InhibitorNon-inhibitor0.6219
CYP450 2D6 InhibitorNon-inhibitor0.8658
CYP450 2C19 InhibitorInhibitor0.5080
CYP450 3A4 InhibitorNon-inhibitor0.8047
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5671
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9700
Non-inhibitor0.9407
AMES ToxicityNon AMES toxic0.6028
CarcinogensNon-carcinogens0.7616
Fish ToxicityHigh FHMT0.7662
Tetrahymena Pyriformis ToxicityHigh TPT0.8011
Honey Bee ToxicityHigh HBT0.8626
BiodegradationReady biodegradable0.8250
Acute Oral ToxicityIII0.7954
Carcinogenicity (Three-class)Non-required0.5435
Model Value Unit
Absorption
Aqueous solubility-2.4776LogS
Caco-2 Permeability0.9856LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3556LD50, mol/kg
Fish Toxicity0.9085pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1686pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
BlueberryJapan0.1ppm
BlackberryJapan0.1ppm
RaspberryJapan0.1ppm
StrawberryJapan0.1ppm
CherryJapan0.1ppm
Mume PlumJapan0.1ppm
(d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark...0639000European Union0.01*30/07/2014
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.01*30/07/2014
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.01*30/07/2014
Celeries0270030European Union0.01*30/07/2014
Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba...0243020European Union0.01*30/07/2014
Others (2)0243990European Union0.01*30/07/2014
(d) kohlrabies0244000European Union0.01*30/07/2014
Leaf vegetables, herbs and edible flowers0250000European Union0.01*30/07/2014
(a) lettuces and salad plants0251000European Union0.01*30/07/2014
Lamb's lettuces/corn salads (Italian corn salads,)0251010European Union0.01*30/07/2014
Lettuces (Crisp lettuces/iceberg lettuces, Cutting lettuces, Head lettuces/cabbage lettuces, Romaines/cos lettuces/lollo bionda/lollo rosso,)0251020European Union0.01*30/07/2014
Escaroles/broad-leaved endives (Curly endives/ frisée endives, Dandelions, Puntarelle, Radicchio/red-leaved chicories, Sugar loaf chicories, Wild chicories/common chicories,)0251030European Union0.01*30/07/2014
Land cresses0251050European Union0.01*30/07/2014
Roman rocket/rucola (Wall rocket,)0251060European Union0.01*30/07/2014

References

TitleJournalDatePubmed ID
Combretastatin A-4 and Derivatives: Potential Fungicides Targeting FungalTubulin.J Agric Food Chem2016 Feb 326711170
Pesticide pollution of multiple drinking water sources in the Mekong Delta,Vietnam: evidence from two provinces.Environ Sci Pollut Res Int2015 Jun25572267
Evaluation of the performance of 57 Japanese participating laboratories by twotypes of z-scores in proficiency test for the quantification of pesticideresidues in brown rice.Anal Bioanal Chem2014 Nov25258285
Detection of isoprothiolane in food, soil, and water samples by immunosorbentassay using avian antibodies.J Immunoassay Immunochem201323537300
Pesticide residues in soils, sediments, and vegetables in the Red River Delta,northern Vietnam.Environ Monit Assess2010 Oct19757109
A multiresidue method for the analysis of pesticide residues in polished rice(Oryza sativa L.) using accelerated solvent extraction and gas chromatography andconfirmation by mass spectrometry.Biomed Chromatogr2007 Jun17385804
Simple one-step extraction and cleanup by pressurized liquid extraction for gaschromatographic-mass spectrometric determination of pesticides in green leafyvegetables.J Chromatogr A2007 Dec 2117996881
Seasonal and spatial studies on pesticide residues in surface waters of theShinano river in Japan.J Agric Food Chem2001 Aug11513677
Kinetics of growth and accumulation of aflatoxin B(1) by Aspergillus parasiticus in the presence of butylated hydroxyanisole, isoprothiolane, and nystatin.Biotechnol Bioeng1984 Jan18551578