ChemSpider 2D Image | Piperlongumine | C17H19NO5

Piperlongumine

  • Molecular FormulaC17H19NO5
  • Average mass317.336 Da
  • Monoisotopic mass317.126312 Da
  • ChemSpider ID553441

  • Double-bond stereo - Double-bond stereo

More details:

Featured data source
The Merck Index Online

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

(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
(E)-Piplartine
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinon [German] [ACD/IUPAC Name]
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone [ACD/IUPAC Name]
1-[(2E)-3-(3,4,5-Triméthoxyphényl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone [French] [ACD/IUPAC Name]
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one
2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]- [ACD/Index Name]
20069-09-4 [RN]
More...

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

C10166 [DBID]
Prestwick_399 [DBID]
Prestwick0_000604 [DBID]
Prestwick1_000604 [DBID]
SPBio_002727 [DBID]
  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Compound Source:

      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from The Merck Index Online]
      Piper tuberculatum (Piperaceae) Susan Richardson [Structure found in ChemSpider, confirmed from The Merck Index Online]

    • Bio Activity:

      Apoptosis Tocris Bioscience 4396
      Apoptosis Inducers Tocris Bioscience 4396
      Cell Biology Tocris Bioscience 4396
      Induces apoptosis; increases p53 and ROS levels in cancer cells Tocris Bioscience 4396
      Induces cell death and increases the level of reactive oxygen species (ROS) in cancer cells with both wild-type and normal p53. Also inhibits the growth of spontaneous malignant breast tumors in mice. Displays little effect on normal cells. Rapidly depletes androgen receptor expression in human prostate cancer cells via a ROS-dependent, proteasome-mediated mechanism. Tocris Bioscience 4396
      Induces cell death and increases the level of reactive oxygen species (ROS) in cancer cells with both wild-type and normal p53. Also inhibits the growth of spontaneous malignant breast tumors in mice. Displays little effect on normal cells. Rapidly depletes androgen receptor expression in human prostate cancer cells via a ROS-dependent, proteasome-mediated mechanism. Tocris Bioscience 4396
  • Gas Chromatography

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

Density: 1.2±0.1 g/cm3
Boiling Point: 475.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 73.9±3.0 kJ/mol
Flash Point: 241.4±28.7 °C
Index of Refraction: 1.581
Molar Refractivity: 86.4±0.3 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.34
ACD/LogD (pH 5.5): 1.63
ACD/BCF (pH 5.5): 10.16
ACD/KOC (pH 5.5): 182.92
ACD/LogD (pH 7.4): 1.63
ACD/BCF (pH 7.4): 10.16
ACD/KOC (pH 7.4): 182.92
Polar Surface Area: 65 Å2
Polarizability: 34.3±0.5 10-24cm3
Surface Tension: 47.9±3.0 dyne/cm
Molar Volume: 259.4±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) =  1.14

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  492.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  208.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.81E-010  (Modified Grain method)
    Subcooled liquid VP: 4.31E-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):  1030
       log Kow used: 1.14 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  80.967 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.25E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.950E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.14  (KowWin est)
  Log Kaw used:  -11.036  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.176
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9922
   Biowin2 (Non-Linear Model)     :   0.9948
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3235  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6212  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4356
   Biowin6 (MITI Non-Linear Model):   0.1441
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4064
 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):  5.75E-006 Pa (4.31E-008 mm Hg)
  Log Koa (Koawin est  ): 12.176
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.522 
       Octanol/air (Koa) model:  0.368 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.95 
       Mackay model           :  0.977 
       Octanol/air (Koa) model:  0.967 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 247.2357 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 249.8957 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.519 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.514 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.187500 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     3.237500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    12.573 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     8.495 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.963 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3110
      Log Koc:  3.493 

 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 = 0.179 (BCF = 1.509)
       log Kow used: 1.14 (estimated)

 Volatilization from Water:
    Henry LC:  2.25E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.635E+009  hours   (1.931E+008 days)
    Half-Life from Model Lake : 5.057E+010  hours   (2.107E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.81  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       8.31e-005       0.959        1000       
   Water     38.9            900          1000       
   Soil      61              1.8e+003     1000       
   Sediment  0.085           8.1e+003     0          
     Persistence Time: 1.08e+003 hr

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