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

(+)-Alantolactone

  • Molecular FormulaC15H20O2
  • Average mass232.318 Da
  • Monoisotopic mass232.146332 Da
  • ChemSpider ID65564

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(+)-Alantolactone
(+)-Alantolactone.
(3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylen-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-on [German] [ACD/IUPAC Name]
(3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one [ACD/IUPAC Name]
(3aR,5S,8aR,9aR)-5,8a-Diméthyl-3-méthylène-3a,5,6,7,8,8a,9,9a-octahydronaphto[2,3-b]furan-2(3H)-one [French] [ACD/IUPAC Name]
(3AR,5S,8AR,9AR)-5,8A-DIMETHYL-3-METHYLIDENE-2H,3H,3AH,5H,6H,7H,8H,8AH,9H,9AH-NAPHTHO[2,3-B]FURAN-2-ONE
(3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one
[3aR-(3aa,5b,8ab,9aa)]-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one
208-899-3 [EINECS]
3aR,5S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylene-naphtho[2,3-b]furan-2(3H)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

M7GSN5Q1M6 [DBID]
NSC 93131 [DBID]
AI3-31147 [DBID]
AIDS014287 [DBID]
AIDS-014287 [DBID]
C09289 [DBID]
CHEBI:2540 [DBID]
KBio2_000777 [DBID]
KBio2_003345 [DBID]
KBio2_005913 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      Others TargetMol T2896

    • Chemical Class:

      A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-<ital>b</ital>]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at positio n 3. ChEBI CHEBI:2540
      A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at positio; n 3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2540
      A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3. ChEBI CHEBI:2540

    • Bio Activity:

      Alantolactone(Alant camphor) is a sesquiterpene lactone; has potential activity against triple-negative breast cancer MDA-MB-231 cells by suppressing the signal transducer and activator of transcripti on 3 (STAT3) signaling pathway. MedChem Express
      Alantolactone(Alant camphor) is a sesquiterpene lactone; has potential activity against triple-negative breast cancer MDA-MB-231 cells by suppressing the signal transducer and activator of transcription 3 (STAT3) signaling pathway.; IC50 value:; Target: STAT3 inhibitor; in vitro: Alantolactone effectively suppressed both constitutive and inducible STAT3 activation at tyrosine 705. MedChem Express HY-N0038
      Antiproliferative; induces activin/Smad3 signaling Tocris Bioscience 4490
      BMP and Other Activin Receptors Tocris Bioscience 4490
      Enzyme-Linked Receptors Tocris Bioscience 4490
      JAK/STAT Signaling MedChem Express HY-N0038
      JAK/STAT Signaling; MedChem Express HY-N0038
      Others TargetMol T2896
      Receptor Serine/Threonine Kinases (RSTKs) Tocris Bioscience 4490
      Sesquiterpene lactone. Induces activin/SMAD3 signaling and disrupts Cripto-1/activin receptor type II A interaction. Displays antiproliferative activity in human colon adenocarcinoma HCT-8 cells. Tocris Bioscience 4490
      STAT MedChem Express HY-N0038

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

Density: 1.1±0.1 g/cm3
Boiling Point: 275.0±0.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.5 mmHg at 25°C
Enthalpy of Vaporization: 51.3±3.0 kJ/mol
Flash Point: 111.5±18.2 °C
Index of Refraction: 1.534
Molar Refractivity: 66.4±0.4 cm3
#H bond acceptors: 2
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 3.69
ACD/LogD (pH 5.5): 3.74
ACD/BCF (pH 5.5): 408.09
ACD/KOC (pH 5.5): 2572.67
ACD/LogD (pH 7.4): 3.74
ACD/BCF (pH 7.4): 408.09
ACD/KOC (pH 7.4): 2572.67
Polar Surface Area: 26 Å2
Polarizability: 26.3±0.5 10-24cm3
Surface Tension: 37.2±5.0 dyne/cm
Molar Volume: 213.5±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) =  3.27
    Log Kow (Exper. database match) =  3.38
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  343.57  (Adapted Stein & Brown method)
    Melting Pt (deg C):  104.16  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00239  (Modified Grain method)
    MP  (exp database):  76 deg C
    BP  (exp database):  275 deg C
    Subcooled liquid VP: 0.00728 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):  38.39
       log Kow used: 3.38 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.0873 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.19E-004  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.903E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.38  (exp database)
  Log Kaw used:  -2.048  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.428
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6272
   Biowin2 (Non-Linear Model)     :   0.8876
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6139  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5881  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5680
   Biowin6 (MITI Non-Linear Model):   0.3421
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0677
 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):  0.971 Pa (0.00728 mm Hg)
  Log Koa (Koawin est  ): 5.428
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.09E-006 
       Octanol/air (Koa) model:  6.58E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.000112 
       Mackay model           :  0.000247 
       Octanol/air (Koa) model:  5.26E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 117.7956 E-12 cm3/molecule-sec
      Half-Life =     0.091 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.090 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.531250 E-17 cm3/molecule-sec
      Half-Life =     0.134 Days (at 7E11 mol/cm3)
      Half-Life =      3.224 Hrs
   Fraction sorbed to airborne particulates (phi): 0.000179 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3749
      Log Koc:  3.574 

 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 = 1.903 (BCF = 79.91)
       log Kow used: 3.38 (expkow database)

 Volatilization from Water:
    Henry LC:  0.000219 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       5.63  hours
    Half-Life from Model Lake :      189.2  hours   (7.885 days)

 Removal In Wastewater Treatment:
    Total removal:              18.69  percent
    Total biodegradation:        0.15  percent
    Total sludge adsorption:     9.93  percent
    Total to Air:                8.60  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.103           1.3          1000       
   Water     13              900          1000       
   Soil      86.2            1.8e+003     1000       
   Sediment  0.71            8.1e+003     0          
     Persistence Time: 889 hr

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