ChemSpider 2D Image | (-)-Deguelin | C23H22O6

(-)-Deguelin

  • Molecular FormulaC23H22O6
  • Average mass394.417 Da
  • Monoisotopic mass394.141632 Da
  • ChemSpider ID97058

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(-)-Deguelin
(-)-cis-Deguelin
(7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one
(7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-on [German] [ACD/IUPAC Name]
(7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one [ACD/IUPAC Name]
(7aS,13aS)-9,10-Diméthoxy-3,3-diméthyl-13,13a-dihydro-3H-chroméno[3,4-b]pyrano[2,3-h]chromén-7(7aH)-one [French] [ACD/IUPAC Name]
(7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one
3H-[1]Benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)- [ACD/Index Name]
3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-
3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS-cis)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C10417 [DBID]
KBio2_001524 [DBID]
KBio2_004092 [DBID]
KBio2_006660 [DBID]
KBio3_002083 [DBID]
KBioGR_002434 [DBID]
KBioSS_001524 [DBID]
NCGC00025288-01 [DBID]
SDCCGMLS-0066380.P001 [DBID]
SPBio_000236 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisom er). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. ChEBI CHEBI:4357

    • Compound Source:

      Linum usitatissimum PlantCyc CPD-12163
      rotenoid biosynthesis II PlantCyc CPD-12163

    • Bio Activity:

      Akt MedChem Express HY-13425
      Anticancer and antiviral agent; chemopreventive and pro-apoptotic Tocris Bioscience 1770
      Anticancer and antiviral agent; chemopreventive and pro-apoptotic. Inhibits phorbol ester-induced ornithine decarboxylase and NADH:ubiquinone oxidoreductase activities (IC50 values are 11 and 6.9 nM r espectively). Inhibits PI 3-kinase and reduces pAkt levels in pre-malignant and malignant human bronchial epithelial cells. Active in vivo. Tocris Bioscience 1770
      Anticancer and antiviral agent; chemopreventive and pro-apoptotic. Inhibits phorbol ester-induced ornithine decarboxylase and NADH:ubiquinone oxidoreductase activities (IC50 values are 11 and 6.9 nM respectively). Inhibits PI 3-kinase and reduces pAkt levels in pre-malignant and malignant human bronchial epithelial cells. Active in vivo. Tocris Bioscience 1770
      Apoptosis Tocris Bioscience 1770
      Apoptosis Inducers Tocris Bioscience 1770
      Cell Biology Tocris Bioscience 1770
      deguelin -> tephrosin PlantCyc CPD-12163
      Deguelin, a naturally occurring rotenoid, is known to be an Akt inhibitor and to have an anti-tumor effect on several cancers; decrease levels of phosphorylated Akt. MedChem Express
      Deguelin, a naturally occurring rotenoid, is known to be an Akt inhibitor and to have an anti-tumor effect on several cancers; decrease levels of phosphorylated Akt.; IC50 Value:; Target: Akt; Anti-cancer; in vitro: Deguelin in a dose and time dependent manner inhibited the growth of MDA-MB-231, MDA-MB-468, BT-549 and BT-20 cells [1]. MedChem Express HY-13425
      Deguelin, a naturally occurring rotenoid, is known to be an Akt inhibitor and to have an anti-tumor effect on several cancers; decrease levels of phosphorylated Akt.;IC50 Value:;Target: Akt; Anti-cancer;In vitro: Deguelin in a dose and time dependent manner inhibited the growth of MDA-MB-231, MDA-MB-468, BT-549 and BT-20 cells [1]. Deguelin administration causes a significant HNSCC cell death. Deguelin induces both cell apoptosis and autophagy by modulating multiple signaling pathways in cultured HNSCC cells. Deguelin inhibits Akt signaling, and down-regulates survivin and cyclin-dependent kinase 4 (Cdk4) expressions, by disrupting their association with heat shock protein-90 (Hsp-90). Deguelin induces ceramide production through de novo synthase pathway to promote HNSCC cell death. Importantly, increased ceramide level activates AMP-activated protein kinase (AMPK), which then directly phosphorylates Ulk1 and eventually leads to cell autophagy [2]. Deguelin inhibited the proliferat MedChem Express HY-13425
      PI3K/Akt/mTOR MedChem Express HY-13425
      PI3K/Akt/mTOR; MedChem Express HY-13425
      rot-2'-enonate + an oxidized electron acceptor + H+ -> deguelin + a reduced electron acceptor PlantCyc CPD-12163

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 560.1±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.3±3.0 kJ/mol
Flash Point: 244.7±30.2 °C
Index of Refraction: 1.584
Molar Refractivity: 105.1±0.3 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 5.03
ACD/LogD (pH 5.5): 4.72
ACD/BCF (pH 5.5): 2271.00
ACD/KOC (pH 5.5): 8789.76
ACD/LogD (pH 7.4): 4.72
ACD/BCF (pH 7.4): 2271.00
ACD/KOC (pH 7.4): 8789.76
Polar Surface Area: 63 Å2
Polarizability: 41.7±0.5 10-24cm3
Surface Tension: 43.2±3.0 dyne/cm
Molar Volume: 314.2±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) =  4.14

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  501.70  (Adapted Stein & Brown method)
    Melting Pt (deg C):  213.39  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.46E-010  (Modified Grain method)
    Subcooled liquid VP: 2.49E-008 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):  0.9711
       log Kow used: 4.14 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.015589 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.25E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.315E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.14  (KowWin est)
  Log Kaw used:  -11.668  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.808
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0969
   Biowin2 (Non-Linear Model)     :   0.9991
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7275  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.4201  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7695
   Biowin6 (MITI Non-Linear Model):   0.4924
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0089
 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):  3.32E-006 Pa (2.49E-008 mm Hg)
  Log Koa (Koawin est  ): 15.808
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.904 
       Octanol/air (Koa) model:  1.58E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.97 
       Mackay model           :  0.986 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 324.5764 E-12 cm3/molecule-sec
      Half-Life =     0.033 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.727 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec
      Half-Life =     0.546 Days (at 7E11 mol/cm3)
      Half-Life =     13.097 Hrs
   Fraction sorbed to airborne particulates (phi): 0.978 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3.075E+005
      Log Koc:  5.488 

 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 = 1.646 (BCF = 44.23)
       log Kow used: 4.14 (estimated)

 Volatilization from Water:
    Henry LC:  5.25E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.215E+010  hours   (9.228E+008 days)
    Half-Life from Model Lake : 2.416E+011  hours   (1.007E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              36.84  percent
    Total biodegradation:        0.37  percent
    Total sludge adsorption:    36.46  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       4.45e-006       0.746        1000       
   Water     3.92            4.32e+003    1000       
   Soil      93.7            8.64e+003    1000       
   Sediment  2.42            3.89e+004    0          
     Persistence Time: 8.23e+003 hr

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