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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:46 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030583
Secondary Accession Numbers
  • HMDB30583
Metabolite Identification
Common NameSilibinin
Description3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one, also known as silibinin, belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety. Based on a literature review very few articles have been published on 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one.
Structure
Data?1563862007
Synonyms
ValueSource
SilibininKegg
SilybinKegg
FlavobinHMDB
Flavobin spofaHMDB
KarsilHMDB, MeSH
LegalonHMDB, MeSH
SilibinHMDB
Silibinin, innHMDB
SilibininaHMDB
SilibinineHMDB
SilibininumHMDB
SilimarinHMDB, MeSH
SilliverHMDB
Silybin (7ci)HMDB
SilybineHMDB
Silybum substance e6HMDB
Silymarin IHMDB
Silymarine IHMDB
CarsilMeSH, HMDB
2,3 DehydrosilybinMeSH, HMDB
2,3-DehydrosilybinMeSH, HMDB
Alepa forteMeSH, HMDB
Alepa-forteMeSH, HMDB
ArdeyhepanMeSH, HMDB
CefasilymarinMeSH, HMDB
Hepa merz silMeSH, HMDB
Hepa logesMeSH, HMDB
Hepa-merz silMeSH, HMDB
HepaBeschMeSH, HMDB
Hepar pascMeSH, HMDB
Hepar-pascMeSH, HMDB
HeparsyxMeSH, HMDB
HeplantMeSH, HMDB
LagosaMeSH, HMDB
Silibinin aMeSH, HMDB
Silibinin bMeSH, HMDB
SilymarinMeSH, HMDB
DurasilymarinMeSH, HMDB
Hepa-logesMeSH, HMDB
Legalon forteMeSH, HMDB
Silybin aMeSH, HMDB
Silybin bMeSH, HMDB
SilybininMeSH, HMDB
Chemical FormulaC25H22O10
Average Molecular Weight482.4362
Monoisotopic Molecular Weight482.121296924
IUPAC Name3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namesilymarin
CAS Registry Number22888-70-6
SMILES
COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O
InChI Identifier
InChI=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
InChI KeySEBFKMXJBCUCAI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFlavonolignans
Sub ClassNot Available
Direct ParentFlavonolignans
Alternative Parents
Substituents
  • Flavonolignan
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavanonol
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavan
  • Phenylbenzodioxane
  • 2-phenylbenzo-1,4-dioxane
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Chromane
  • Benzodioxane
  • Benzo-1,4-dioxane
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Para-dioxin
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point167 °CNot Available
Boiling Point793.03 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility77.36 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.232 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.093 g/LALOGPS
logP2.35ALOGPS
logP2.63ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
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
Polarizability48.13 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+210.4731661259
DarkChem[M-H]-210.92931661259
DeepCCS[M+H]+203.02630932474
DeepCCS[M-H]-200.6330932474
DeepCCS[M-2H]-233.51430932474
DeepCCS[M+Na]+208.93930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SilibininCOC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O5630.7Standard polar33892256
SilibininCOC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O4139.0Standard non polar33892256
SilibininCOC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O4561.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Silibinin,1TMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4593.3Semi standard non polar33892256
Silibinin,1TMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4592.2Semi standard non polar33892256
Silibinin,1TMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O4605.6Semi standard non polar33892256
Silibinin,1TMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O4624.0Semi standard non polar33892256
Silibinin,1TMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O4531.0Semi standard non polar33892256
Silibinin,2TMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4449.5Semi standard non polar33892256
Silibinin,2TMS,isomer #10COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O4413.2Semi standard non polar33892256
Silibinin,2TMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4476.0Semi standard non polar33892256
Silibinin,2TMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4382.6Semi standard non polar33892256
Silibinin,2TMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4400.1Semi standard non polar33892256
Silibinin,2TMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4403.1Semi standard non polar33892256
Silibinin,2TMS,isomer #6COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4417.7Semi standard non polar33892256
Silibinin,2TMS,isomer #7COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4332.3Semi standard non polar33892256
Silibinin,2TMS,isomer #8COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O4477.6Semi standard non polar33892256
Silibinin,2TMS,isomer #9COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O4352.9Semi standard non polar33892256
Silibinin,3TMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4363.0Semi standard non polar33892256
Silibinin,3TMS,isomer #10COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O4258.6Semi standard non polar33892256
Silibinin,3TMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4228.8Semi standard non polar33892256
Silibinin,3TMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4244.5Semi standard non polar33892256
Silibinin,3TMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4293.6Semi standard non polar33892256
Silibinin,3TMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4262.6Semi standard non polar33892256
Silibinin,3TMS,isomer #6COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4189.3Semi standard non polar33892256
Silibinin,3TMS,isomer #7COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4262.7Semi standard non polar33892256
Silibinin,3TMS,isomer #8COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4140.9Semi standard non polar33892256
Silibinin,3TMS,isomer #9COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4197.2Semi standard non polar33892256
Silibinin,4TMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C4188.3Semi standard non polar33892256
Silibinin,4TMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4170.8Semi standard non polar33892256
Silibinin,4TMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4058.7Semi standard non polar33892256
Silibinin,4TMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4114.7Semi standard non polar33892256
Silibinin,4TMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O4084.0Semi standard non polar33892256
Silibinin,5TMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C5C(=O)C4O[Si](C)(C)C)=CC=C3OC2CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C4037.5Semi standard non polar33892256
Silibinin,1TBDMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C4863.8Semi standard non polar33892256
Silibinin,1TBDMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4856.4Semi standard non polar33892256
Silibinin,1TBDMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O4846.1Semi standard non polar33892256
Silibinin,1TBDMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O4894.1Semi standard non polar33892256
Silibinin,1TBDMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O4847.1Semi standard non polar33892256
Silibinin,2TBDMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C4976.0Semi standard non polar33892256
Silibinin,2TBDMS,isomer #10COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O4970.5Semi standard non polar33892256
Silibinin,2TBDMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C5039.1Semi standard non polar33892256
Silibinin,2TBDMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C4953.1Semi standard non polar33892256
Silibinin,2TBDMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4958.1Semi standard non polar33892256
Silibinin,2TBDMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4920.6Semi standard non polar33892256
Silibinin,2TBDMS,isomer #6COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4965.5Semi standard non polar33892256
Silibinin,2TBDMS,isomer #7COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4868.9Semi standard non polar33892256
Silibinin,2TBDMS,isomer #8COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O4993.2Semi standard non polar33892256
Silibinin,2TBDMS,isomer #9COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O4891.4Semi standard non polar33892256
Silibinin,3TBDMS,isomer #1COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C5103.6Semi standard non polar33892256
Silibinin,3TBDMS,isomer #10COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O4984.8Semi standard non polar33892256
Silibinin,3TBDMS,isomer #2COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C4978.8Semi standard non polar33892256
Silibinin,3TBDMS,isomer #3COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4997.4Semi standard non polar33892256
Silibinin,3TBDMS,isomer #4COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO)=CC=C1O[Si](C)(C)C(C)(C)C5029.9Semi standard non polar33892256
Silibinin,3TBDMS,isomer #5COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C5028.7Semi standard non polar33892256
Silibinin,3TBDMS,isomer #6COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4898.5Semi standard non polar33892256
Silibinin,3TBDMS,isomer #7COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4989.8Semi standard non polar33892256
Silibinin,3TBDMS,isomer #8COC1=CC(C2OC3=CC(C4OC5=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4862.0Semi standard non polar33892256
Silibinin,3TBDMS,isomer #9COC1=CC(C2OC3=CC(C4OC5=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C5C(=O)C4O[Si](C)(C)C(C)(C)C)=CC=C3OC2CO[Si](C)(C)C(C)(C)C)=CC=C1O4900.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0455900000-36b82ae0b0aeac8e7ee02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Silibinin GC-MS (3 TMS) - 70eV, Positivesplash10-001i-0003009000-cbd9993c968c8b9331a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Silibinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin DI-ESI-qTof , Positive-QTOFsplash10-0a4i-0002090000-91ea766cf462829a92602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin DI-ESI-qTof , Negative-QTOFsplash10-00lr-0102900400-ed276357d0ccebb3d3702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin LC-ESI-qTof , Positive-QTOFsplash10-0f6t-2942100000-4792bc912cef07546d462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOFsplash10-001i-0002900000-811667e96533dac778b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOFsplash10-001i-0000900000-b2d2752da4d986f4e3af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOFsplash10-001i-0000900000-6fdb5df34264f81cc4ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin LC-ESI-TOF , negative-QTOFsplash10-001i-0003900000-1b715e5192005890816e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin , positive-QTOFsplash10-0f6t-2942100000-4792bc912cef07546d462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 20V, Negative-QTOFsplash10-001i-0001900000-c78b9a76622fdee660db2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 30V, Negative-QTOFsplash10-0udi-0754900000-293e8e3155acd47768702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 10V, Negative-QTOFsplash10-001i-0000900000-5462b344502c8958cbfe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 50V, Positive-QTOFsplash10-0gvk-0930000000-415706d7a9007d78d5852021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 10V, Positive-QTOFsplash10-001i-0100900000-991a30cf6721b9ec6ae22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 50V, Negative-QTOFsplash10-0udi-0930000000-f8d2ffdcbd89edcdce232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 40V, Negative-QTOFsplash10-0ufr-0941000000-0efa09253cf03f29f2872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 20V, Positive-QTOFsplash10-0i11-0922800000-53a9b5c1156fc75385732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 40V, Positive-QTOFsplash10-0f6t-0941000000-36232650400070cbb1582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Silibinin 30V, Positive-QTOFsplash10-0uea-0941300000-e59ac841aaab0eaba4ba2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 10V, Positive-QTOFsplash10-001i-0230900000-ff1d4c98753e257ea2352015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 20V, Positive-QTOFsplash10-0f79-0731900000-f0807aa0220a07f57ab82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 40V, Positive-QTOFsplash10-0uk9-0920000000-8b3e0a0d017c0e0cba9a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 10V, Negative-QTOFsplash10-001i-0101900000-dfaaf0e3e335ff1fdde52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 20V, Negative-QTOFsplash10-0i30-0622900000-6b3d60833f796db5d9852015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 40V, Negative-QTOFsplash10-0fui-1930000000-26f4134e3a2660dff1862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Silibinin 10V, Negative-QTOFsplash10-001i-0000900000-0b2b3bcd8db2872500de2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002476
KNApSAcK IDC00001003
Chemspider ID5024
KEGG Compound IDC07610
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1108841
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zi X, Zhang J, Agarwal R, Pollak M: Silibinin up-regulates insulin-like growth factor-binding protein 3 expression and inhibits proliferation of androgen-independent prostate cancer cells. Cancer Res. 2000 Oct 15;60(20):5617-20. [PubMed:11059749 ]
  2. Singh RP, Dhanalakshmi S, Agarwal C, Agarwal R: Silibinin strongly inhibits growth and survival of human endothelial cells via cell cycle arrest and downregulation of survivin, Akt and NF-kappaB: implications for angioprevention and antiangiogenic therapy. Oncogene. 2005 Feb 10;24(7):1188-202. [PubMed:15558015 ]
  3. Singh RP, Deep G, Blouin MJ, Pollak MN, Agarwal R: Silibinin suppresses in vivo growth of human prostate carcinoma PC-3 tumor xenograft. Carcinogenesis. 2007 Dec;28(12):2567-74. Epub 2007 Oct 4. [PubMed:17916909 ]
  4. Yoo HG, Jung SN, Hwang YS, Park JS, Kim MH, Jeong M, Ahn SJ, Ahn BW, Shin BA, Park RK, Jung YD: Involvement of NF-kappaB and caspases in silibinin-induced apoptosis of endothelial cells. Int J Mol Med. 2004 Jan;13(1):81-6. [PubMed:14654975 ]
  5. Zeng J, Sun Y, Wu K, Li L, Zhang G, Yang Z, Wang Z, Zhang D, Xue Y, Chen Y, Zhu G, Wang X, He D: Chemopreventive and chemotherapeutic effects of intravesical silibinin against bladder cancer by acting on mitochondria. Mol Cancer Ther. 2011 Jan;10(1):104-16. doi: 10.1158/1535-7163.MCT-10-0577. [PubMed:21220495 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .