ChemSpider 2D Image | DEHYDROCOSTUS LACTONE | C15H18O2

DEHYDROCOSTUS LACTONE

  • Molecular FormulaC15H18O2
  • Average mass230.302 Da
  • Monoisotopic mass230.130676 Da
  • ChemSpider ID65938

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

DEHYDROCOSTUS LACTONE
(-)-dehydrocostus lactone
(3aS,6aR,9aR,9bS)-3,6,9-Trimethylendecahydroazuleno[4,5-b]furan-2(3H)-on [German] [ACD/IUPAC Name]
(3aS,6aR,9aR,9bS)-3,6,9-Triméthylènedécahydroazuléno[4,5-b]furan-2(3H)-one [French] [ACD/IUPAC Name]
(3aS,6aR,9aR,9bS)-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3H)-one
(3AS,6AR,9AR,9BS)-3,6,9-TRIMETHYLIDENE-DODECAHYDROAZULENO[4,5-B]FURAN-2-ONE
(3aS,6aR,9aR,9bS)-3,6,9-Tris(methylene)decahydroazuleno[4,5-b]furan-2(3H)-one [ACD/IUPAC Name]
(3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one
[3aS-(3aα,6aα,9aα,9bβ)]-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one
477-43-0 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

71TRF5K040 [DBID]
4733740 [DBID]
AIDS070708 [DBID]
AIDS-070708 [DBID]
C09387 [DBID]
UNII:71TRF5K040 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      Others TargetMol T2833

    • Chemical Class:

      An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in whic h the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding <locant>gamma</locant>-lactone. ChEBI CHEBI:244418
      An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in whic h the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:244418, CHEBI:244418

    • Bio Activity:

      Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea lappa. MedChem Express
      Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea lappa.; IC50 value:; Target:; In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. MedChem Express HY-N0591
      Dehydrocostus Lactone is a major sesquiterpene lactone isolated from the roots of Saussurea lappa.;IC50 value:;Target:;In vitro: Dehydrocostus Lactone promoted apoptosis with increased activation of caspases 8, 9, 7, 3, enhanced PARP cleavage, decreased Bcl-xL expression and increased levels of Bax, Bak, Bok, Bik, Bmf, and t-Bid. We have demonstrated that Dehydrocostus Lactone inhibits cell growth and induce apoptosis in DU145 cells [1]. Dehydrocostus Lactone inhibits NF-kappaB activation by preventing TNF-alpha-induced degradation and phosphorylation of its inhibitory protein I-kappaB alpha in human leukemia HL-60 cells and that dehydrocostus lactone renders HL-60 cells susceptible to TNF-alpha-induced apoptosis by enhancing caspase-8 and caspase-3 activities [2]. Dehydrocostus Lactone inhibited the production of NO in lipopolysaccharide (LPS)-activated RAW 264.7 cells by suppressing inducible nitric oxide synthase enzyme expression.;In vivo: Dehydrocostus Lactone decreased the T MedChem Express HY-N0591
      Others MedChem Express HY-N0591
      Others TargetMol T2833

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

Density: 1.1±0.1 g/cm3
Boiling Point: 383.7±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 63.2±3.0 kJ/mol
Flash Point: 161.2±25.3 °C
Index of Refraction: 1.536
Molar Refractivity: 65.8±0.4 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 3.40
ACD/LogD (pH 5.5): 3.43
ACD/BCF (pH 5.5): 238.77
ACD/KOC (pH 5.5): 1752.91
ACD/LogD (pH 7.4): 3.43
ACD/BCF (pH 7.4): 238.77
ACD/KOC (pH 7.4): 1752.91
Polar Surface Area: 26 Å2
Polarizability: 26.1±0.5 10-24cm3
Surface Tension: 35.9±5.0 dyne/cm
Molar Volume: 210.8±5.0 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) =  3.31

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  343.38  (Adapted Stein & Brown method)
    Melting Pt (deg C):  99.20  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.59E-005  (Modified Grain method)
    Subcooled liquid VP: 0.000189 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):  45.13
       log Kow used: 3.31 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.6573 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.63E-004  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.411E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.31  (KowWin est)
  Log Kaw used:  -2.176  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.486
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8121
   Biowin2 (Non-Linear Model)     :   0.9785
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8304  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7444  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5365
   Biowin6 (MITI Non-Linear Model):   0.2540
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2445
 Ready Biodegradability Prediction:   YES

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.0252 Pa (0.000189 mm Hg)
  Log Koa (Koawin est  ): 5.486
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000119 
       Octanol/air (Koa) model:  7.52E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00428 
       Mackay model           :  0.00943 
       Octanol/air (Koa) model:  6.01E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 133.6322 E-12 cm3/molecule-sec
      Half-Life =     0.080 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.960 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     3.537500 E-17 cm3/molecule-sec
      Half-Life =     0.324 Days (at 7E11 mol/cm3)
      Half-Life =      7.775 Hrs
   Fraction sorbed to airborne particulates (phi): 0.00686 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4143
      Log Koc:  3.617 

 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 = 1.849 (BCF = 70.65)
       log Kow used: 3.31 (estimated)

 Volatilization from Water:
    Henry LC:  0.000163 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:          7  hours
    Half-Life from Model Lake :      203.6  hours   (8.484 days)

 Removal In Wastewater Treatment:
    Total removal:              15.86  percent
    Total biodegradation:        0.15  percent
    Total sludge adsorption:     8.88  percent
    Total to Air:                6.83  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.223           1.54         1000       
   Water     20.5            360          1000       
   Soil      78.7            720          1000       
   Sediment  0.621           3.24e+003    0          
     Persistence Time: 420 hr

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