ChemSpider 2D Image | Protopine | C20H19NO5

Protopine

  • Molecular FormulaC20H19NO5
  • Average mass353.369 Da
  • Monoisotopic mass353.126312 Da
  • ChemSpider ID4799

More details:



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130-86-9 [RN]
204-999-6 [EINECS]
4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one
7-Methyl-6,8,9,16-tetrahydro[1,3]dioxolo[5,6]benzo[1,2-c][1,3]dioxolo[4,5]benzo[1,2-g]azecin-15(7H)-on
7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-on [German] [ACD/IUPAC Name]
7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one [ACD/IUPAC Name]
7-Méthyl-6,8,9,16-tétrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azécin-15(7H)-one [French] [ACD/IUPAC Name]
Bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one, 6,8,9,16-tetrahydro-7-methyl- [ACD/Index Name]
Protopine [Wiki]
UIW569HT35
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

. [DBID]
AI3-62909 [DBID]
AIDS040935 [DBID]
AIDS-040935 [DBID]
C05189 [DBID]
CHEBI:16415 [DBID]
HSDB 3527 [DBID]
NCGC00017389-01 [DBID]
NSC11440 [DBID]
TNP00339 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A dibenzazecine alkaloid isolated from <ital>Fumaria vaillantii</ital>. ChEBI CHEBI:16415
    • Bio Activity:

      Others MedChem Express HY-N0793
      Protopine, an isoquinoline alkaloid contained in plants in northeast Asia. MedChem Express
      Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.; IC50 Value:; Target:; In vitro: Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. MedChem Express HY-N0793
  • Gas Chromatography
    • Retention Index (Kovats):

      2943 (estimated with error: 174) NIST Spectra mainlib_287490, replib_121191, replib_337234, replib_128622
      2730 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 12 m; Column type: Capillary; Heat rate: 30 K/min; Start T: 100 C; End T: 310 C; End time: 8 min; Start time: 3 min; CAS no: 130869; Active phase: Cross-Linked Methylsilicone; Carrier gas: He; Phase thickness: 0.33 um; Data type: Kovats RI; Authors: Paul, L.D.; Maurer, H.H., Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry, J. Chromatogr. B, 789, 2003, 43-57.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      2730 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 12 m; Column type: Capillary; Heat rate: 30 K/min; Start T: 100 C; End T: 310 C; End time: 8 min; Start time: 3 min; CAS no: 130869; Active phase: Cross-Linked Methylsilicone; Carrier gas: He; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Paul, L.D.; Springer, D.; Staack, R.F.; Kraemer, T.; Maurer, H.H., Cytochrome P450 isoenzymes involved in rat liver microsomal metabolism of californine and protopine, Eur. J. Pharmacol., 485, 2004, 69-79.) NIST Spectra nist ri

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

Density: 1.3±0.1 g/cm3
Boiling Point: 547.5±49.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 82.7±3.0 kJ/mol
Flash Point: 284.9±29.8 °C
Index of Refraction: 1.613
Molar Refractivity: 93.0±0.3 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 3.76
ACD/LogD (pH 5.5): 0.63
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.72
ACD/LogD (pH 7.4): 2.33
ACD/BCF (pH 7.4): 24.98
ACD/KOC (pH 7.4): 237.23
Polar Surface Area: 57 Å2
Polarizability: 36.9±0.5 10-24cm3
Surface Tension: 50.5±3.0 dyne/cm
Molar Volume: 266.9±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) =  -0.47

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  467.76  (Adapted Stein & Brown method)
    Melting Pt (deg C):  197.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.71E-009  (Modified Grain method)
    Subcooled liquid VP: 1.78E-007 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):  1.484e+005
       log Kow used: -0.47 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.11E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.515E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.47  (KowWin est)
  Log Kaw used:  -11.680  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.210
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.4751
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9798  (months      )
   Biowin4 (Primary Survey Model) :   3.0056  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0374
   Biowin6 (MITI Non-Linear Model):   0.0048
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3637
 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):  2.37E-005 Pa (1.78E-007 mm Hg)
  Log Koa (Koawin est  ): 11.210
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.126 
       Octanol/air (Koa) model:  0.0398 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.82 
       Mackay model           :  0.91 
       Octanol/air (Koa) model:  0.761 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 461.1158 E-12 cm3/molecule-sec
      Half-Life =     0.023 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    16.701 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =  2053.525146 E-17 cm3/molecule-sec
      Half-Life =     0.001 Days (at 7E11 mol/cm3)
      Half-Life =      0.804 Min
   Fraction sorbed to airborne particulates (phi): 0.865 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.500 (BCF = 3.162)
       log Kow used: -0.47 (estimated)

 Volatilization from Water:
    Henry LC:  5.11E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.157E+010  hours   (8.987E+008 days)
    Half-Life from Model Lake : 2.353E+011  hours   (9.804E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.0131       1000       
   Water     49.3            1.44e+003    1000       
   Soil      50.6            2.88e+003    1000       
   Sediment  0.0961          1.3e+004     0          
     Persistence Time: 1.17e+003 hr




                    

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