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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015537
Secondary Accession Numbers
  • HMDB15537
Metabolite Identification
Common NameProbucol
DescriptionProbucol is only found in individuals that have used or taken this drug. It is a drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).Probucol lowers serum cholesterol by increasing the fractional rate of low-density lipoprotein (LDL) catabolism in the final metabolic pathway for cholesterol elimination from the body. Additionally, probucol may inhibit early stages of cholesterol biosynthesis and slightly inhibit dietary cholesterol absorption. Recent information suggests that probucol may inhibit the oxidation and tissue deposition of LDL cholesterol, thereby inhibiting atherogenesis. It appears to inhibits ABCA1-mediated cellular lipid efflux.
Structure
Data?1582753307
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 Weight516.842
Monoisotopic Molecular Weight516.30957216
IUPAC Name2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
Traditional Nameprobucol
CAS Registry Number23288-49-5
SMILES
CC(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 Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.2e-05 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+220.54231661259
DarkChem[M-H]-218.76931661259
DeepCCS[M+H]+232.55830932474
DeepCCS[M-H]-230.16330932474
DeepCCS[M-2H]-263.34130932474
DeepCCS[M+Na]+238.47130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProbucolCC(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)C3551.6Standard polar33892256
ProbucolCC(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)C3547.7Standard non polar33892256
ProbucolCC(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)C3362.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Probucol,1TMS,isomer #1CC(C)(SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1)SC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C(C)(C)C)=C13301.9Semi standard non polar33892256
Probucol,2TMS,isomer #1CC(C)(SC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C(C)(C)C)=C1)SC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C(C)(C)C)=C13353.0Semi standard non polar33892256
Probucol,1TBDMS,isomer #1CC(C)(SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1)SC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)C)=C13530.4Semi standard non polar33892256
Probucol,2TBDMS,isomer #1CC(C)(SC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)C)=C1)SC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)C)=C13807.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Probucol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uki-0090250000-bea4462f54c2e521b6862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Probucol GC-MS (2 TMS) - 70eV, Positivesplash10-0002-2055019000-30fa34699e923dce7d7a2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 10V, Positive-QTOFsplash10-014r-0050090000-8055cc2880de3aa85f232016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 20V, Positive-QTOFsplash10-00kr-1190350000-8282024214cf3b54f3582016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 40V, Positive-QTOFsplash10-0a4r-2290000000-85de6b8949af9e5047282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 10V, Negative-QTOFsplash10-014i-0020090000-19b668dd13894848b8d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 20V, Negative-QTOFsplash10-016r-0080190000-f8b67c1f43ff76bc30d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 40V, Negative-QTOFsplash10-000i-0190000000-a5edd080c63083d43b952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 10V, Positive-QTOFsplash10-014i-0000290000-9741161cfe44930e32a02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 20V, Positive-QTOFsplash10-0ldr-0110950000-7a7628d0a216ce8324ea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 40V, Positive-QTOFsplash10-0pc1-1951010000-3a329c91fac683b63bd42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 10V, Negative-QTOFsplash10-00kr-0000960000-04f6058c5a25b66d3efe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 20V, Negative-QTOFsplash10-014r-0000960000-18c8b152adb145f78acf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Probucol 40V, Negative-QTOFsplash10-00e9-0001900000-fd2b811cb419d25d47f72021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01599 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01599 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01599
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4743
KEGG Compound IDC07373
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProbucol
METLIN IDNot Available
PubChem Compound4912
PDB IDNot Available
ChEBI ID8427
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
References
  1. Jeon SM, Park YB, Kwon OS, Huh TL, Lee WH, Do KM, Park T, Choi MS: Vitamin E supplementation alters HDL-cholesterol concentration and paraoxonase activity in rabbits fed high-cholesterol diet: comparison with probucol. J Biochem Mol Toxicol. 2005;19(5):336-46. [PubMed:16292755 ]
General function:
Involved in ATP binding
Specific function:
cAMP-dependent and sulfonylurea-sensitive anion transporter. Key gatekeeper influencing intracellular cholesterol transport
Gene Name:
ABCA1
Uniprot ID:
O95477
Molecular weight:
254299.9
References
  1. Favari E, Zanotti I, Zimetti F, Ronda N, Bernini F, Rothblat GH: Probucol inhibits ABCA1-mediated cellular lipid efflux. Arterioscler Thromb Vasc Biol. 2004 Dec;24(12):2345-50. Epub 2004 Oct 28. [PubMed:15514211 ]
  2. Yamamoto A: A uniqe antilipidemic drug--probucol. J Atheroscler Thromb. 2008 Dec;15(6):304-5. Epub 2008 Dec 11. [PubMed:19075491 ]
  3. de la Llera-Moya M, Drazul-Schrader D, Asztalos BF, Cuchel M, Rader DJ, Rothblat GH: The ability to promote efflux via ABCA1 determines the capacity of serum specimens with similar high-density lipoprotein cholesterol to remove cholesterol from macrophages. Arterioscler Thromb Vasc Biol. 2010 Apr;30(4):796-801. doi: 10.1161/ATVBAHA.109.199158. Epub 2010 Jan 14. [PubMed:20075420 ]
  4. Sirtori CR, Manzoni C, Lovati MR: Mechanisms of lipid-lowering agents. Cardiology. 1991;78(3):226-35. [PubMed:1868500 ]
  5. Shichiri M, Takanezawa Y, Rotzoll DE, Yoshida Y, Kokubu T, Ueda K, Tamai H, Arai H: ATP-binding cassette transporter A1 is involved in hepatic alpha-tocopherol secretion. J Nutr Biochem. 2010 May;21(5):451-6. doi: 10.1016/j.jnutbio.2009.02.002. Epub 2009 May 7. [PubMed:19427182 ]
  6. Arakawa R, Tsujita M, Iwamoto N, Ito-Ohsumi C, Lu R, Wu CA, Shimizu K, Aotsuka T, Kanazawa H, Abe-Dohmae S, Yokoyama S: Pharmacological inhibition of ABCA1 degradation increases HDL biogenesis and exhibits antiatherogenesis. J Lipid Res. 2009 Nov;50(11):2299-305. doi: 10.1194/jlr.M900122-JLR200. Epub 2009 May 20. [PubMed:19458386 ]