ChemSpider 2D Image | Cyclo(L-Trp L-Pro) | C16H17N3O2

Cyclo(L-Trp L-Pro)

  • Molecular FormulaC16H17N3O2
  • Average mass283.325 Da
  • Monoisotopic mass283.132080 Da
  • ChemSpider ID157941
  • defined stereocentres - 2 of 2 defined stereocentres


More details:






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

Cyclo(L-Trp L-Pro)
(3S,8aS)-3-(1H-Indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazin-1,4-dion [German] [ACD/IUPAC Name]
(3S,8aS)-3-(1H-Indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione [ACD/IUPAC Name]
(3S,8aS)-3-(1H-Indol-3-ylméthyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione [French] [ACD/IUPAC Name]
brevianamide F
cyclo-(Trp-Pro)
cyclo-L-Trp-L-Pro
cyclo-L-tryptophanyl-L-proline
L-prolyl-L-tryptophan anhydride
L-tryptophyl-L-proline cyclic anhydride
More...
  • Miscellaneous
    • Chemical Class:

      A pyrrolopyrazine that is hexahydropyrrolo[1,2-<ital>a</ital>]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3<stereo>S</stereo>,8a<stereo>S</stereo>-diastereomer, obtai ned by formal cyclocondensation of <stereo>L</stereo>-tryptophan and <stereo>L</stereo>-proline). ChEBI CHEBI:64530

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

Density: 1.4±0.1 g/cm3
Boiling Point: 633.2±48.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 93.6±3.0 kJ/mol
Flash Point: 336.8±29.6 °C
Index of Refraction: 1.690
Molar Refractivity: 78.9±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.64
ACD/LogD (pH 5.5): 0.65
ACD/BCF (pH 5.5): 1.85
ACD/KOC (pH 5.5): 53.96
ACD/LogD (pH 7.4): 0.65
ACD/BCF (pH 7.4): 1.85
ACD/KOC (pH 7.4): 53.96
Polar Surface Area: 65 Å2
Polarizability: 31.3±0.5 10-24cm3
Surface Tension: 67.6±5.0 dyne/cm
Molar Volume: 206.5±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) =  0.37

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  544.98  (Adapted Stein & Brown method)
    Melting Pt (deg C):  233.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.11E-011  (Modified Grain method)
    Subcooled liquid VP: 1.96E-009 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):  7461
       log Kow used: 0.37 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9058.3 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.16E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.546E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.37  (KowWin est)
  Log Kaw used:  -11.676  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.046
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0876
   Biowin2 (Non-Linear Model)     :   0.9929
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3898  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7813  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1919
   Biowin6 (MITI Non-Linear Model):   0.0495
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1797
 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):  2.61E-007 Pa (1.96E-009 mm Hg)
  Log Koa (Koawin est  ): 12.046
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  11.5 
       Octanol/air (Koa) model:  0.273 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  0.956 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 233.9625 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.549 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.18E+004
      Log Koc:  4.072 

 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: 0.37 (estimated)

 Volatilization from Water:
    Henry LC:  5.16E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.91E+010  hours   (7.958E+008 days)
    Half-Life from Model Lake : 2.084E+011  hours   (8.681E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  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       0.000494        1.1          1000       
   Water     44.9            900          1000       
   Soil      55              1.8e+003     1000       
   Sediment  0.0883          8.1e+003     0          
     Persistence Time: 990 hr




                    

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