ChemSpider 2D Image | epicylindrospermopsin | C15H21N5O7S

epicylindrospermopsin

  • Molecular FormulaC15H21N5O7S
  • Average mass415.422 Da
  • Monoisotopic mass415.116180 Da
  • ChemSpider ID102932

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

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

(2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)(hydroxy)methyl]-3-methyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacenaphthylen-4-yl hydrogen sulfate [ACD/IUPAC Name]
(2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)(hydroxy)methyl]-3-methyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacenaphthylen-4-ylhydrogensulfat [German] [ACD/IUPAC Name]
2,4(1H,3H)-Pyrimidinedione, 6-[(S)-hydroxy[(2aS,3R,4S,5aS,7R)-2a,3,4,5,5a,6,7,8-octahydro-3-methyl-4-(sulfooxy)-2H-1,8,8b-triazaacenaphthylen-7-yl]methyl]- [ACD/Index Name]
265652-18-4 [RN]
6-[(S)-Hydroxy[(2aS,3R,4S,5aS,7R)-2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy)-1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]-2,4(1H,3H)-pyrimidinedione
7-epicyclindrospermopsin
7-epi-cylindrospermopsin
epicylindrospermopsin
Hydrogénosulfate de (2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-dioxo-1,2,3,6-tétrahydro-4-pyrimidinyl)(hydroxy)méthyl]-3-méthyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacénaphtylén-4-yle [French] [ACD/IUPAC Name]
(-)-Epicyclindrospermopsin
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  • Miscellaneous

    • Chemical Class:

      A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1<element>H</element>-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-t etrahydropyrimidin-4-yl)(hydroxy)methyl groups, respectively (the 2a<stereo>S</stereo>,3<stereo>R</stereo>,4<stereo>S</stereo>,5a<stereo>S</stereo>,7<stereo>R</stereo> stereoisomer in which the carbon bearing the hydroxy group has <stereo>S</stereo> configuration). It is a cyanotoxin produced by several species of freshwater cyanobacteria, such as <ital>Aphanizomenon ovalisporum</ital>. ChEBI CHEBI:88049
      A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-t; etrahydropyrimidi n-4-yl)(hydroxy)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon; bearing the hydroxy group has S configuration). It is a cyanotoxin produced by several species of f reshwater cyanobacteria, such as Aphanizomenon ovalisporum. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88049
      A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin- 4-yl)(hydroxy)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon bearing the hydroxy group has S configuration). It is a cyanotoxin produced by several species of fresh water cyanobacteria, such as Aphanizomenon ovalisporum. ChEBI CHEBI:88049

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

Density: 2.0±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.858
Molar Refractivity: 92.0±0.5 cm3
#H bond acceptors: 12
#H bond donors: 5
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: -1.22
ACD/LogD (pH 5.5): -4.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.27
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 178 Å2
Polarizability: 36.5±0.5 10-24cm3
Surface Tension: 97.5±7.0 dyne/cm
Molar Volume: 204.6±7.0 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) =  -5.17

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  806.65  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.9E-025  (Modified Grain method)
    Subcooled liquid VP: 4.05E-021 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):  1e+006
       log Kow used: -5.17 (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
       Imides
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.90E-030  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.318E-031 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -5.17  (KowWin est)
  Log Kaw used:  -28.110  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.940
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7085
   Biowin2 (Non-Linear Model)     :   0.1452
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4411  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3778  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2853
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4871
 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):  5.4E-019 Pa (4.05E-021 mm Hg)
  Log Koa (Koawin est  ): 22.940
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.56E+012 
       Octanol/air (Koa) model:  2.14E+010 
   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 = 178.6596 E-12 cm3/molecule-sec
      Half-Life =     0.060 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.718 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   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    :  425.6
      Log Koc:  2.629 

 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: -5.17 (estimated)

 Volatilization from Water:
    Henry LC:  1.9E-030 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.281E+026  hours   (2.617E+025 days)
    Half-Life from Model Lake : 6.852E+027  hours   (2.855E+026 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       1.86e-008       1.36         1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr

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