Probucol (CED0004765)

Record Information
Version1.0
Creation Date2016-05-22 05:09:26 UTC
Update Date2026-08-22 10:42:53 UTC
Accession NumberCHEM018322
Identification
Common NameProbucol
ClassSmall Molecule
Description
Probucol belongs to the phenylpropanes, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 516.84 g/mol, Probucol is a heavy molecule with the chemical formula C31H48O2S2. It functions as a biological antioxidant (PMC13440557, PMC4271727, PMC5989656, PMC7648605). In terms of health effects, the compound is used as a treatment for coronary artery disease (PMC4271727) and has a therapeutic effect on atherosclerosis (PMC11086401). Its protein targets include Liver carboxylesterase 1 (CES1) and the Phospholipid-transporting ATPase ABCA1, which it inhibits. Probucol is found in or released from ten recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as a lipid modifying agent. It is also associated with food preservation and fermentation processes for beer. Other recorded sources include household cleaning and consumer products, such as perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is linked to electrical and electronic equipment, specifically antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, and electrically stimulated smoking devices. The recorded route of exposure for this compound is oral.
Contaminant Type
  • Tertiary butyl phenols
Chemical Structure
Synonyms
ValueSource
Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptoleChEBI
BiphenabidChEBI
BisbidChEBI
BisphenabidChEBI
DH-581ChEBI
LesterolChEBI
LorelcoChEBI
LurselleChEBI
ProbucolumChEBI
SerterolChEBI
SuperlipidChEBI
4,4'-(Isopropylidenedithio)bis(2, 6-di-tert-butylphenol)HMDB
4,4'-(Isopropylidenedithio)bis(2,6-di-tert-butylphenol)HMDB
4,4'-(Isopropylidenedithio)bis[2, 6-di-tert-butylphenol]HMDB
Acetone, bis (3,5-di-tert-butyl-4-hydroxyphenyl) mercaptoleHMDB
Acetone, bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptoleHMDB
Almirall brand OF probucolHMDB
PanavirHMDB
Aventis brand OF probucolHMDB
Hoechst brand OF probucolHMDB
Chemical FormulaC31H48O2S2
Average Molecular Mass516.842 g/mol
Monoisotopic Mass516.310 g/mol
CAS Registry Number23288-49-5
IUPAC Name2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
Traditional Nameprobucol
SMILESCC(C)(SC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C)SC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
InChI IdentifierInChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3
InChI KeyFYPMFJGVHOHGLL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aryl thioether
  • Thiophenol ether
  • Alkylarylthioether
  • Phenol
  • Dithioketal
  • Thioacetal
  • Sulfenyl compound
  • Thioether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • 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 Roles
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 Solubility4.2e-05 g/LALOGPS
logP8.92ALOGPS
logP10.57ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity159.26 m³·mol⁻¹ChemAxon
Polarizability62.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0uki-0090250000-bea4462f54c2e521b686Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-2055019000-30fa34699e923dce7d7aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0050090000-8055cc2880de3aa85f23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-1190350000-8282024214cf3b54f358Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-2290000000-85de6b8949af9e504728Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0020090000-19b668dd13894848b8d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-0080190000-f8b67c1f43ff76bc30d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0190000000-a5edd080c63083d43b95Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000290000-9741161cfe44930e32a0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ldr-0110950000-7a7628d0a216ce8324eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pc1-1951010000-3a329c91fac683b63bd4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0000960000-04f6058c5a25b66d3efeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0000960000-18c8b152adb145f78acfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00e9-0001900000-fd2b811cb419d25d47f7Not 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
8986.0Log mg/kg[5100:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
atherosclerosishas_therapeutic_effect_onNot AvailablePMC11086401
coronary artery diseaseis_treatment_forNot AvailablePMC4271727
Exposure Sources
Source IDSourceSectorReference
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
491Industrial manufacturing & chemical processingNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care 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
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP12527Rattus norvegicusPredicted (SEA)10.9767
Click to view 3D structureProstaglandin G/H synthase 2Q05769Mus musculusPredicted (SEA)5.52729
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)13.2344
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)57.9977
NAD-dependent protein deacylase sirtuin-5, mitochondrial structureClick to view 3D structureNAD-dependent protein deacylase sirtuin-5, mitochondrialQ9NXA8HumansPredicted (SEA)0.0778492
Serine protease hepsin structureClick to view 3D structureSerine protease hepsinP05981HumansPredicted (SEA)84.9335
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)125.571
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)885.301
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)455.496
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 1P04191Oryctolagus cuniculusPredicted (SEA)4.12601
Tyrosinase structureClick to view 3D structureTyrosinaseP14679HumansPredicted (SEA)59.7882
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)387.689
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 2P11507Rattus norvegicusPredicted (SEA)7.23998
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)3090.07
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)4651.18
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 3Q93084HumansPredicted (SEA)3.26967
CDGSH iron-sulfur domain-containing protein 1 structureClick to view 3D structureCDGSH iron-sulfur domain-containing protein 1Q9NZ45HumansPredicted (SEA)62.2015
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)5315.23
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)6258.22
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)2968.86
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)5881.74
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)3987.05
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)4470.73
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)6671.29
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)3735.67
Concentrations
Not Available
External Links
DrugBank IDDB01599
HMDB IDHMDB0015537
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProbucol
Chemspider ID4743
ChEBI ID8427
PubChem Compound ID4912
Kegg Compound IDC07373
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22305809
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23107872
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23167559
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23334712
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23363981
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23378294
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23443157
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23741215