Silybin (CED0004595)

Record Information
Version1.0
Creation Date2016-05-22 03:59:55 UTC
Update Date2026-05-14 19:04:51 UTC
Accession NumberCHEM017188
Identification
Common NameSilybin
ClassSmall Molecule
Description
Silybin is an organic compound with the formula C25H22O10 and an average molecular weight of 482.44 g/mol. Silybin belongs to the flavonolignans, a class of lignans, neolignans and related compounds within the organic compounds. In biological contexts, the compound acts as an antioxidant (PMC10975324, PMC2767273) and an iron chelator (PMC12630495). It serves as an inhibitor of the protein Polyunsaturated fatty acid 5-lipoxygenase (ALOX5) and has a therapeutic effect on inflammation (PMC9117022). Industrially, silybin is utilized as a softener and conditioner. The compound is found in or released from 20 recorded sources across several sectors. These include healthcare, pharmaceuticals and veterinary products via medical devices; energy, oil and gas through lubricants; and textiles, leather and furnishings, specifically carpets, rugs, and synthetic textiles. It is also present in household cleaning and consumer products, such as soap detergents, tobacco smoke filters, and perfumes within detergents and soaps. Within the food, food processing and cookware sector, it is associated with food preservation, food packaging, the preparation of vinegar, and fermentation processes for beer. Additionally, it is found in electrical and electronic equipment, including batteries, capacitors, printed circuit boards, cell phones, and wires and cables, among two other sectors. Recorded exposure routes for silybin include oral, inhalation, and touch.
Contaminant Type
  • PFAS
Chemical Structure
Synonyms
ValueSource
FlavobinChEBI
KarsilChEBI
SilibininaChEBI
SilibinineChEBI
SilibininumChEBI
SilybinChEBI
SilymarinChEBI
Silymarin IKegg
LegalonKegg
Silybin bMeSH
Hepar pascMeSH
ArdeyhepanMeSH
CefasilymarinMeSH
Hepa-merz silMeSH
Hepa-logesMeSH
Legalon forteMeSH
Silibinin bMeSH
2,3 DehydrosilybinMeSH
Silibinin aMeSH
Hepar-pascMeSH
LagosaMeSH
SilybininMeSH
Silybin aMeSH
HeplantMeSH
Alepa forteMeSH
Alepa-forteMeSH
HepaBeschMeSH
2,3-DehydrosilybinMeSH
DurasilymarinMeSH
SilibinMeSH
Hepa logesMeSH
HeparsyxMeSH
Hepa merz silMeSH
SilibininMeSH
HepatosMeSH
Chemical FormulaC25H22O10
Average Molecular Mass482.441 g/mol
Monoisotopic Mass482.121 g/mol
CAS Registry Number22888-70-6
IUPAC Name(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namesilibinin
SMILES[H][C@@]1(OC2=C(O[C@@H]1CO)C=CC(=C2)[C@@]1([H])OC2=C(C(O)=CC(O)=C2)C(=O)[C@@H]1O)C1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
InChI KeySEBFKMXJBCUCAI-HKTJVKLFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • 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 Solubility0.093 g/LALOGPS
logP2.35ALOGPS
logP2.63ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.75ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.29 m³·mol⁻¹ChemAxon
Polarizability48.41 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-0gvk-2952100000-c3d2a818a44f51b39801Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ue9-0943800000-af015f0adf79e0968a5aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gvk-2952100000-c3d2a818a44f51b39801Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f7k-0931200000-a04a951f896c0248d2feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0230900000-300bc825bbe98458b2bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-0741900000-d501c9b910b2d5fdab53Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-0920000000-fa7604cbd3962727b9f7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0101900000-89dc501a9aa86eeb6450Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0wpi-0632900000-9280d934e31287af1255Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fs9-1930000000-cb4cf324a6790d4133c7Not 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
2055.0Log mg/kg[1200:3700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC9117022
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal 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
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)0.233548
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)0.0778492
Click to view 3D structureMonocarboxylate transporter 8P36021HumansPredicted (SEA)0.0778492
Click to view 3D structureSolute carrier organic anion transporter family member 2B1O94956HumansPredicted (SEA)0.155698
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)13.7015
Click to view 3D structureTyrosinaseO42713Agaricus bisporusPredicted (SEA)0.155698
Click to view 3D structureATP-dependent translocase ABCB1P21447Mus musculusPredicted (SEA)0.544945
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)59.4768
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)27.3251
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)44.7633
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)54.3388
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)20.0851
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)24.6782
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)385.821
Pyruvate kinase PKM structureClick to view 3D structurePyruvate kinase PKMP14618HumansPredicted (SEA)4.98235
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)29.5827
Xanthine dehydrogenase/oxidase structureClick to view 3D structureXanthine dehydrogenase/oxidaseP47989HumansPredicted (SEA)9.73115
Cytochrome P450 1A1 structureClick to view 3D structureCytochrome P450 1A1P04798HumansPredicted (SEA)29.1935
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)547.047
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)95.8324
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)151.183
Click to view 3D structureArginaseO96394Leishmania amazonensisPredicted (SEA)5.60514
Click to view 3D structure72 kDa type IV collagenaseP33436Rattus norvegicusPredicted (SEA)1.24559
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)12.4559
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)65.3933
Concentrations
Not Available
External Links
DrugBank IDDB09298
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001003
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSilibinin
Chemspider IDNot Available
ChEBI ID9144
PubChem Compound ID31553
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22086675
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22555054
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22899727
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23073223
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23357565
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23402882