ChemSpider 2D Image | Protopine | C20H19NO5

Protopine

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

More details:



Featured data source



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

130-86-9 [RN]
204-999-6 [EINECS]
4,6,7,14-Tetrahydro-5-methylbis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one
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]
MFCD00022322
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

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
    • Toxicity:

      Organic Compound; Amine; Ester; Food Toxin; Plant Toxin; Metabolite; Natural Compound Toxin, Toxin-Target Database T3D4015
    • Chemical Class:

      A dibenzazecine alkaloid isolated from <ital>Fumaria vaillantii</ital>. ChEBI CHEBI:16415
      A dibenzazecine alkaloid isolated from Fumaria vaillantii. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16415
    • Compound Source:

      Amborella trichopoda PlantCyc PROTOPINE
      Aquilegia coerulea PlantCyc PROTOPINE
      Arabidopsis halleri PlantCyc PROTOPINE
      Arabidopsis thaliana col PlantCyc PROTOPINE
      Asparagus officinalis PlantCyc PROTOPINE
      Brassica napus PlantCyc PROTOPINE
      Brassica oleracea var. oleracea PlantCyc PROTOPINE
      Camptotheca acuminata PlantCyc PROTOPINE
      Citrus sinensis PlantCyc PROTOPINE
      Linum usitatissimum PlantCyc PROTOPINE
      Lotus japonicus PlantCyc PROTOPINE
      Malus domestica PlantCyc PROTOPINE
      Medicago truncatula PlantCyc PROTOPINE
      Petunia axillaris PlantCyc PROTOPINE
      Ricinus communis PlantCyc PROTOPINE
      Rosa chinensis PlantCyc PROTOPINE
      sanguinarine and macarpine biosynthesis PlantCyc PROTOPINE
      Solanum lycopersicum PlantCyc PROTOPINE
      Triticum aestivum PlantCyc PROTOPINE
      Vitis vinifera PlantCyc PROTOPINE
      Zea mays subsp. mays PlantCyc PROTOPINE
    • Bio Activity:

      (S)-cis-N-methylstylopine + NADPH + oxygen -> protopine + NADP+ + H2O PlantCyc PROTOPINE
      Others MedChem Express HY-N0793
      protopine + NADPH + H+ + oxygen -> 6-hydroxyprotopine + NADP+ + H2O PlantCyc PROTOPINE
      protopine + NADPH + oxygen + H+ -> 6-hydroxyprotopine + NADP+ + H2O PlantCyc PROTOPINE
      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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