Bithionol (CED0010834)

Record Information
Version1.0
Creation Date2016-05-22 03:31:16 UTC
Update Date2026-08-18 21:18:04 UTC
Accession NumberCHEM016424
Identification
Common NameBithionol
ClassSmall Molecule
Description
Bithionol is an organic compound with the chemical formula C12H6Cl4O2S and an average molecular weight of 356.05 g/mol. Bithionol belongs to the aryl thioethers, a subclass of thioethers within the organic compounds. This compound is associated with 11 recorded sources across several sectors. Within healthcare, pharmaceuticals, and veterinary products, it is found in antibiotics. In the realm of household cleaning and consumer products, it is present in soap detergents, bleaching agents, and perfumes within detergents and soaps. Its use in food, food processing, and cookware includes food preservation, processing meats, and fermentation processes for beer. Additionally, it is released from electrical and electronic equipment, specifically electrodes, radio transmission systems, amplifiers, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for this substance include oral and inhalation. At the molecular level, bithionol acts on four recorded protein targets. It functions as an inhibitor of the estrogen receptor (ESR1), the estrogen receptor beta (ESR2), the calpain-2 catalytic subunit (CAPN2), and the induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulfideChEBI
2,2'-Thiobis(4,6-dichlorophenol)ChEBI
2-Hydroxy-3,5-dichlorophenyl sulfideChEBI
Bis(3,5-dichloro-2-hydroxyphenyl) sulfideChEBI
BithinChEBI
Bithionol sulfideChEBI
2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulphideGenerator
2-Hydroxy-3,5-dichlorophenyl sulphideGenerator
Bis(3,5-dichloro-2-hydroxyphenyl) sulphideGenerator
Bithionol sulphideGenerator
BitinMeSH
Chemical FormulaC12H6Cl4O2S
Average Molecular Mass356.052 g/mol
Monoisotopic Mass353.884 g/mol
CAS Registry Number97-18-7
IUPAC Name2,4-dichloro-6-[(3,5-dichloro-2-hydroxyphenyl)sulfanyl]phenol
Traditional Namebitin
SMILESOC1=C(SC2=C(O)C(Cl)=CC(Cl)=C2)C=C(Cl)C=C1Cl
InChI IdentifierInChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
InChI KeyJFIOVJDNOJYLKP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassAryl thioethers
Direct ParentDiarylthioethers
Alternative Parents
Substituents
  • Diarylthioether
  • 1,3-dichlorobenzene
  • 4-halophenol
  • 2-halophenol
  • 2-chlorophenol
  • 4-chlorophenol
  • Thiophenol ether
  • Chlorobenzene
  • Halobenzene
  • Phenol
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Benzenoid
  • Sulfenyl compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP6.12ALOGPS
logP5.97ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.92 m³·mol⁻¹ChemAxon
Polarizability31.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0aor-0319000000-435a514099cbd5198501Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0900000000-684715f22d6e281ceb85Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0900000000-f1f9ecff11b990a79e9bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0900000000-c7ff76fb8e23902d9da0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0109000000-3a73c9a59c804e137c76Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03kc-0900000000-8ef5e3d659c81e67ae2aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-022i-2900000000-e4a0e278b9a2e67380a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03kc-0900000000-36cb9c1d601dab6970a4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-022i-2900000000-58c9d055e731de6ae0daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0209000000-aff65a21aef363fc90c6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-894168ccc4396cacbb73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-159b93778441331acb03Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-8307400ffa40e9a68249Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0109000000-684d16a2f39a2ea46a45Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1901000000-1dc626bf9e6509dd3387Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0209000000-d5fce7281e8b969c8497Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0209000000-86d0032836270302c58bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1942000000-a641fd0d439b9383ece7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-2b3095a2931d5865ad23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-1749000000-100437b9f8f4f2a74e15Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-9800000000-22ac5226dad083ff8c6eNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
32.0Log mg/kg[20:57]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)69.2858
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)99.3356
Click to view 3D structureThromboxane-A synthaseP24557HumansPredicted (SEA)1.63483
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)286.952
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)86.0234
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)276.754
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)177.263
Click to view 3D structureEnvelope glycoprotein gp160Q6QLK5Human immunodeficiency virus 1Predicted (SEA)0.0778492
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)140.518
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)75.0467
Click to view 3D structureCalpain-2 catalytic subunitP43367Sus scrofaPredicted (SEA)6.92858
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)75.7473
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)61.8901
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)42.6614
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)58.3869
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)6.15009
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)83.2208
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)38.4575
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)26.5466
GTP-binding protein Rheb structureClick to view 3D structureGTP-binding protein RhebQ15382HumansPredicted (SEA)0.778492
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)253.866
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)129.074
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)132.889
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)101.204
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)240.632
Concentrations
Not Available
External Links
DrugBank IDDB04813
HMDB IDHMDB0249278
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBithionol
Chemspider ID2313
ChEBI ID3131
PubChem Compound IDNot Available
Kegg Compound IDC07967
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17129675
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24495391