ChemSpider 2D Image | Tilivalline | C20H19N3O2

Tilivalline

  • Molecular FormulaC20H19N3O2
  • Average mass333.384 Da
  • Monoisotopic mass333.147736 Da
  • ChemSpider ID113792

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(11S,11aS)-9-Hydroxy-11-(1H-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-on [German] [ACD/IUPAC Name]
(11S,11aS)-9-Hydroxy-11-(1H-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one [ACD/IUPAC Name]
(11S,11aS)-9-Hydroxy-11-(1H-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazépin-5-one [French] [ACD/IUPAC Name]
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0³,?]tetradeca-1(14),10,12-trien-2-one
5H-Pyrrolo[2,1-c][1,4]benzodiazepin-5-one, 1,2,3,10,11,11a-hexahydro-9-hydroxy-11-(1H-indol-3-yl)-, (11S,11aS)- [ACD/Index Name]
80279-24-9 [RN]
Tilivalline
(6S,6aS)-4-hydroxy-6-(1H-indol-3-yl)-5,6,6a,7,8,9-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0(3,7)]tetradeca-1(10),11,13-trien-2-one
5H-Pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 1,2,3,10,11,11a-hexahydro-9-hydroxy-11(1H-indol-3-yl)-, (11S-cis)-
  • Miscellaneous

    • Chemical Class:

      A pyrrolobenzodiazepine that is (11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine substituted by an oxo group at position 5, by a hydroxy group at position 9, and by a 1H-indol-3-y l group at position 11S. It is a natural product discovered in Klebsiella oxytoca which is the causative toxin in antibiotic associated hemorrhagic colitis. It exhibits a microtubule-stabilizing activ ity that leads to mitotic arrest in the host cells. ChEBI CHEBI:156292

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

Density: 1.4±0.1 g/cm3
Boiling Point: 649.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 99.3±3.0 kJ/mol
Flash Point: 346.8±31.5 °C
Index of Refraction: 1.760
Molar Refractivity: 95.8±0.4 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 0.94
ACD/LogD (pH 5.5): 2.07
ACD/BCF (pH 5.5): 21.90
ACD/KOC (pH 5.5): 316.85
ACD/LogD (pH 7.4): 2.07
ACD/BCF (pH 7.4): 21.88
ACD/KOC (pH 7.4): 316.54
Polar Surface Area: 68 Å2
Polarizability: 38.0±0.5 10-24cm3
Surface Tension: 79.2±5.0 dyne/cm
Molar Volume: 232.7±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) =  1.96

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  565.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  243.35  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.29E-013  (Modified Grain method)
    Subcooled liquid VP: 5.32E-011 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):  165.7
       log Kow used: 1.96 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  17.738 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.92E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.063E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.96  (KowWin est)
  Log Kaw used:  -18.795  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.755
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6810
   Biowin2 (Non-Linear Model)     :   0.4919
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3296  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5035  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1189
   Biowin6 (MITI Non-Linear Model):   0.0058
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9798
 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):  7.09E-009 Pa (5.32E-011 mm Hg)
  Log Koa (Koawin est  ): 20.755
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  423 
       Octanol/air (Koa) model:  1.4E+008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 267.6271 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.776 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.033E+004
      Log Koc:  4.781 

 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 = 0.808 (BCF = 6.428)
       log Kow used: 1.96 (estimated)

 Volatilization from Water:
    Henry LC:  3.92E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.727E+017  hours   (1.136E+016 days)
    Half-Life from Model Lake : 2.975E+018  hours   (1.24E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               2.21  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.12  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       1.04e-009       0.959        1000       
   Water     23.8            900          1000       
   Soil      76.1            1.8e+003     1000       
   Sediment  0.0876          8.1e+003     0          
     Persistence Time: 1.4e+003 hr

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