ChemSpider 2D Image | Silibinin | C25H22O10

Silibinin

  • Molecular FormulaC25H22O10
  • Average mass482.436 Da
  • Monoisotopic mass482.121307 Da
  • ChemSpider ID29263
  • defined stereocentres - 4 of 4 defined stereocentres


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Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-on [German] [ACD/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]-2,3-dihydro-4H-chromen-4-one [ACD/IUPAC Name]
(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-méthoxyphényl)-2-(hydroxyméthyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromén-4-one [French] [ACD/IUPAC Name]
[2R-[2a,3b,6(2R*,3R*)]]-2-[2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
22888-70-6 [RN]
245-302-5 [EINECS]
4H-1-Benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)- [ACD/Index Name]
Dura-Silymarin
SILIBININ A
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

33X338MNE4 [DBID]
AIDS003063 [DBID]
AIDS-003063 [DBID]
KBio3_002123 [DBID]
KBioGR_002481 [DBID]
NCGC00091057-01 [DBID]
NSC 651520 [DBID]
NSC651520 [DBID]
SDCCGMLS-0066916.P001 [DBID]
SPBio_001648 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07 Biosynth Q-100291
      H315; H319; H335 Biosynth Q-100291
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-100291
      Warning Biosynth Q-100291
    • Chemical Class:

      A flavonolignan isolated from milk thistle, <ital>Silybum marianum</ital>, that has been shown to exhibit antioxidant and antineoplastic activities. ChEBI CHEBI:9144
      flavan Microsource [01505256]
    • Drug Status:

      INN Microsource [01505256]
    • Compound Source:

      Silybum marianum Microsource [01505256]
    • Bio Activity:

      Others MedChem Express HY-13748
      Silibinin, an effective anti-cancer and chemopreventive agent, has been shown to exert multiple effects on cancer cells, including inhibition of both cell proliferation and migration. MedChem Express
      Silibinin, an effective anti-cancer and chemopreventive agent, has been shown to exert multiple effects on cancer cells, including inhibition of both cell proliferation and migration.; IC50 value:; Target: anticancer; in vitro: silibinin significantly induced the expression of the non-steroidal anti-inflammatory drug-activated gene-1 (NAG-1) in both p53 wild-type and p53-null cancer cell lines, suggesting that silibinin-induced NAG-1 up-regulation is p53-independent manner.Silibinin up-regulates early growth response-1 (EGR-1) expression [1]. MedChem Express HY-13748
      Silibinin, an effective anti-cancer and chemopreventive agent, has been shown to exert multiple effects on cancer cells, including inhibition of both cell proliferation and migration.;IC50 value:;Target: anticancer;In vitro: silibinin significantly induced the expression of the non-steroidal anti-inflammatory drug-activated gene-1 (NAG-1) in both p53 wild-type and p53-null cancer cell lines, suggesting that silibinin-induced NAG-1 up-regulation is p53-independent manner.Silibinin up-regulates early growth response-1 (EGR-1) expression [1]. silibinin induced cell death in human breast cancer cell lines MCF7 and MDA-MB-231. Silibinininduced cell death was attenuated by antioxidants, N-acetylcysteine (NAC) and Trolox, suggesting that the effect of silibinin was dependent on generation of reactive oxygen species (ROS) [2]. SIL treatment resulted in a dose- and time-dependent inhibition of HCC cell viability, SIL exhibited strong antitumor activity, as evidenced not only by reductions i MedChem Express HY-13748

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.5±0.1 g/cm3
Boiling Point: 793.0±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 121.0±3.0 kJ/mol
Flash Point: 274.5±26.4 °C
Index of Refraction: 1.684
Molar Refractivity: 120.0±0.3 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: 2.59
ACD/LogD (pH 5.5): 2.26
ACD/BCF (pH 5.5): 30.56
ACD/KOC (pH 5.5): 399.50
ACD/LogD (pH 7.4): 1.77
ACD/BCF (pH 7.4): 9.91
ACD/KOC (pH 7.4): 129.64
Polar Surface Area: 155 Å2
Polarizability: 47.6±0.5 10-24cm3
Surface Tension: 73.1±3.0 dyne/cm
Molar Volume: 315.9±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.94

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  712.02  (Adapted Stein & Brown method)
    Melting Pt (deg C):  311.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.1E-021  (Modified Grain method)
    Subcooled liquid VP: 6.76E-018 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  77.36
       log Kow used: 1.94 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  310.67 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.63E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.364E-023 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.94  (KowWin est)
  Log Kaw used:  -22.176  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.116
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.7172
   Biowin2 (Non-Linear Model)     :   0.9999
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3671  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.8159  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8114
   Biowin6 (MITI Non-Linear Model):   0.4680
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9920
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  9.01E-016 Pa (6.76E-018 mm Hg)
  Log Koa (Koawin est  ): 24.116
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.33E+009 
       Octanol/air (Koa) model:  3.21E+011 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 290.4263 E-12 cm3/molecule-sec
      Half-Life =     0.037 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.517 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9622
      Log Koc:  3.983 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = -0.694 (BCF = 0.2021)
       log Kow used: 1.94 (estimated)

 Volatilization from Water:
    Henry LC:  1.63E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  7.89E+020  hours   (3.287E+019 days)
    Half-Life from Model Lake : 8.607E+021  hours   (3.586E+020 days)

 Removal In Wastewater Treatment:
    Total removal:               2.19  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.10  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       5.13e-006       0.884        1000       
   Water     24.1            900          1000       
   Soil      75.8            1.8e+003     1000       
   Sediment  0.0871          8.1e+003     0          
     Persistence Time: 1.39e+003 hr




                    

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