ChemSpider 2D Image | (+)-Costunolide | C15H20O2

(+)-Costunolide

  • Molecular FormulaC15H20O2
  • Average mass232.318 Da
  • Monoisotopic mass232.146332 Da
  • ChemSpider ID4444782
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


More details:






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

(+)-Costunolide
(3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylen-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-on [German] [ACD/IUPAC Name]
(3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one [ACD/IUPAC Name]
(3aS,6E,10E,11aR)-6,10-Diméthyl-3-méthylène-3a,4,5,8,9,11a-hexahydrocyclodéca[b]furan-2(3H)-one [French] [ACD/IUPAC Name]
(3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
Costunolide [Wiki]
Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS,6E,10E,11aR)- [ACD/Index Name]
(10S,1R)-3,7-dimethyl-11-methylene-13-oxabicyclo[8.3.0]trideca-2,6-dien-12-one
(3aS,11aR)-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
(3aS,6E,10E)-3-Methylene-6,10-dimethyl-2,3,3aβ,4,5,8,9,11aα-octahydrocyclodeca[b]furan-2-one
More...

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

AIDS059915 [DBID]
AIDS-059915 [DBID]
C09382 [DBID]
NSC106404 [DBID]
  • Experimental Physico-chemical Properties
    • Experimental Solubility:

      Soluble to 100 mM in DMSO and to 50 mM in ethanol Tocris Bioscience 2483
      Soluble to 50 mM in DMSO and to 50 mM in ethanol Tocris Bioscience 2483
  • Miscellaneous
    • Chemical Class:

      A germacranolide with anthelminthic, antiparasitic and antiviral activities. ChEBI CHEBI:3900
    • Compound Source:

      Constit. of costus root (Saussurea lappa) and Artemisia balchanorum. Also from Talauma mexicana and Cosmos sulphureus Zerenex Molecular [ZBioX-0279]
    • Bio Activity:

      Enzymes Tocris Bioscience 2483
      Inhibitor of human telomerase activity Tocris Bioscience 2483
      Inhibitor of human telomerase activity (IC50 = 65 ?M in MCF-7 breast cancer cells). Suppresses proliferation and induces apoptosis in a variety of human tumor cell lines. Selectively blocks endothelia l cell proliferation induced by VEGF. Inhibits expression of iNOS and IL-1? and disrupts NF-?B activation. Displays anti-inflammatory, antifungal and antiviral properties. Tocris Bioscience 2483
      Inhibitor of human telomerase activity (IC50 = 65 ?M in MCF-7 breast cancer cells). Suppresses proliferation and induces apoptosis in a variety of human tumor cell lines. Selectively blocks endothelial cell proliferation induced by VEGF. Inhibits expression of iNOS and IL-1? and disrupts NF-?B activation. Displays anti-inflammatory, antifungal and antiviral properties. Tocris Bioscience 2483
      Inhibitor of human telomerase activity (IC50 = 65 muM in MCF-7 breast cancer cells). Suppresses proliferation and induces apoptosis in a variety of human tumor cell lines. Selectively blocks endothelial cell proliferation induced by VEGF. Inhibits expression of iNOS and IL-1beta and disrupts NF-kappaB activation. Displays anti-inflammatory, antifungal and antiviral properties. Tocris Bioscience 2483
      Polymerases Tocris Bioscience 2483
      Shows antimycobacterial activity Zerenex Molecular [ZBioX-0279]
      Telomerase Tocris Bioscience 2483

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

Density: 1.0±0.1 g/cm3
Boiling Point: 385.4±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 63.4±3.0 kJ/mol
Flash Point: 162.0±25.3 °C
Index of Refraction: 1.519
Molar Refractivity: 68.1±0.4 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 4.05
ACD/LogD (pH 5.5): 3.36
ACD/BCF (pH 5.5): 211.49
ACD/KOC (pH 5.5): 1607.10
ACD/LogD (pH 7.4): 3.36
ACD/BCF (pH 7.4): 211.49
ACD/KOC (pH 7.4): 1607.10
Polar Surface Area: 26 Å2
Polarizability: 27.0±0.5 10-24cm3
Surface Tension: 35.1±5.0 dyne/cm
Molar Volume: 224.5±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) =  4.10

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  354.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  90.02  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.39E-005  (Modified Grain method)
    Subcooled liquid VP: 0.000101 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):  9.376
       log Kow used: 4.10 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.3493 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.16E-004  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.792E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.10  (KowWin est)
  Log Kaw used:  -1.676  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.776
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8111
   Biowin2 (Non-Linear Model)     :   0.9779
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8260  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7415  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4941
   Biowin6 (MITI Non-Linear Model):   0.2901
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1535
 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):  0.0135 Pa (0.000101 mm Hg)
  Log Koa (Koawin est  ): 5.776
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000223 
       Octanol/air (Koa) model:  1.47E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00798 
       Mackay model           :  0.0175 
       Octanol/air (Koa) model:  1.17E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 201.2434 E-12 cm3/molecule-sec
      Half-Life =     0.053 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.638 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    87.137497 E-17 cm3/molecule-sec
      Half-Life =     0.013 Days (at 7E11 mol/cm3)
      Half-Life =     18.938 Min
   Fraction sorbed to airborne particulates (phi): 0.0127 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4059
      Log Koc:  3.608 

 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 = 2.455 (BCF = 284.8)
       log Kow used: 4.10 (estimated)

 Volatilization from Water:
    Henry LC:  0.000516 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      3.285  hours
    Half-Life from Model Lake :      163.6  hours   (6.818 days)

 Removal In Wastewater Treatment:
    Total removal:              44.71  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    32.19  percent
    Total to Air:               12.21  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0396          0.253        1000       
   Water     17              360          1000       
   Soil      80.3            720          1000       
   Sediment  2.69            3.24e+003    0          
     Persistence Time: 423 hr




                    

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