ChemSpider 2D Image | Eseroline | C13H18N2O

Eseroline

  • Molecular FormulaC13H18N2O
  • Average mass218.295 Da
  • Monoisotopic mass218.141907 Da
  • ChemSpider ID106485

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(-)-Eseroline
(3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol [ACD/IUPAC Name]
(3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol [German] [ACD/IUPAC Name]
(3aS,8aR)-1,3a,8-Triméthyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol [French] [ACD/IUPAC Name]
(3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol
Eseroline [Wiki]
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)- [ACD/Index Name]
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS-cis)-
(3AS,8AR)-1,3A,8-TRIMETHYL-1H,2H,3H,3AH,8H,8AH-PYRROLO[2,3-B]INDOL-5-OL
(3aS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Q22H41O18D [DBID]
  • Miscellaneous

    • Chemical Class:

      A pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-<ital>b</ital>]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physosti gmine and causes neuronal cell death by a mechanism involving loss of cell ATP. ChEBI CHEBI:48845
      A pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physosti; gmine and c auses neuronal cell death by a mechanism involving loss of cell ATP. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48845

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

Density: 1.2±0.1 g/cm3
Boiling Point: 366.3±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 63.7±3.0 kJ/mol
Flash Point: 189.6±26.5 °C
Index of Refraction: 1.598
Molar Refractivity: 64.1±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 1.26
ACD/LogD (pH 5.5): -1.08
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.56
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 15.59
Polar Surface Area: 27 Å2
Polarizability: 25.4±0.5 10-24cm3
Surface Tension: 44.4±3.0 dyne/cm
Molar Volume: 188.0±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) =  0.21

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  340.10  (Adapted Stein & Brown method)
    Melting Pt (deg C):  123.83  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.04E-006  (Modified Grain method)
    Subcooled liquid VP: 1E-005 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):  2.338e+004
       log Kow used: 0.21 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  39623 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.25E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.278E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.21  (KowWin est)
  Log Kaw used:  -7.292  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.502
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2079
   Biowin2 (Non-Linear Model)     :   0.0058
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1550  (months      )
   Biowin4 (Primary Survey Model) :   2.9328  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1935
   Biowin6 (MITI Non-Linear Model):   0.0275
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.1750
 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):  0.00133 Pa (1E-005 mm Hg)
  Log Koa (Koawin est  ): 7.502
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00225 
       Octanol/air (Koa) model:  7.8E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0752 
       Mackay model           :  0.153 
       Octanol/air (Koa) model:  0.000623 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 412.0733 E-12 cm3/molecule-sec
      Half-Life =     0.026 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    18.689 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.985000 E-17 cm3/molecule-sec
      Half-Life =     1.163 Days (at 7E11 mol/cm3)
      Half-Life =     27.923 Hrs
   Fraction sorbed to airborne particulates (phi): 0.114 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  141.2
      Log Koc:  2.150 

 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: 0.21 (estimated)

 Volatilization from Water:
    Henry LC:  1.25E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  6.92E+005  hours   (2.884E+004 days)
    Half-Life from Model Lake :  7.55E+006  hours   (3.146E+005 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       0.0113          0.609        1000       
   Water     50.2            1.44e+003    1000       
   Soil      49.6            2.88e+003    1000       
   Sediment  0.0992          1.3e+004     0          
     Persistence Time: 1.01e+003 hr

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