ChemSpider 2D Image | neosaxitoxin | C10H17N7O5

neosaxitoxin

  • Molecular FormulaC10H17N7O5
  • Average mass315.286 Da
  • Monoisotopic mass315.129120 Da
  • ChemSpider ID19975931

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

[(3aS,4R,10aS)-2-Amino-5,10,10-trihydroxy-6-imino-3a,4,5,6,9,10-hexahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate [ACD/IUPAC Name]
[(3aS,4R,10aS)-2-Amino-5,10,10-trihydroxy-6-imino-3a,4,5,6,9,10-hexahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methylcarbamat [German] [ACD/IUPAC Name]
1H,10H-Pyrrolo[1,2-c]purine-10,10-diol, 4-[[(aminocarbonyl)oxy]methyl]octahydro-5-hydroxy-2,6-diimino-, (3aS,4R,10aS)- [ACD/Index Name]
64296-20-4 [RN]
Carbamate de [(3aS,4R,10aS)-2-amino-5,10,10-trihydroxy-6-imino-3a,4,5,6,9,10-hexahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]méthyle [French] [ACD/IUPAC Name]
neosaxitoxin
neo-Saxitoxin
[(3aS,4R,10aS)-2-amino-5,10,10-trihydroxy-6-imino-3a,4,5,6,9,10-hexahydro-3H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
[(4R,10aS,10bS)-2-amino-5,10,10-trihydroxy-6-imino-3H,4H,5H,6H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
[(4R,10aS,10bS)-2-amino-5,10,10-trihydroxy-6-imino-3H,4H,8H,9H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6YRL8BWD9H [DBID]
S0170_SIGMA [DBID]
UNII:6YRL8BWD9H [DBID]
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Amide; Food Toxin; Marine Toxin; Metabolite; Animal Toxin; Natural Compound Toxin, Toxin-Target Database T3D4023

    • Chemical Class:

      A pyrrolopurine that is saxitoxin carrying a hydroxy substituent on the nitrogen atom at position 5. It is a sodium channel blocker that is undergoing clinical trials as a prolonged-duration local ane sthetic. ChEBI CHEBI:167561

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

Density: 2.3±0.1 g/cm3
Boiling Point: 625.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.1 mmHg at 25°C
Enthalpy of Vaporization: 106.1±6.0 kJ/mol
Flash Point: 332.0±34.3 °C
Index of Refraction: 1.972
Molar Refractivity: 66.6±0.5 cm3
#H bond acceptors: 12
#H bond donors: 9
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 2
ACD/LogP: -2.32
ACD/LogD (pH 5.5): -5.94
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -6.16
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 191 Å2
Polarizability: 26.4±0.5 10-24cm3
Surface Tension: 152.0±7.0 dyne/cm
Molar Volume: 135.8±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) =  -3.71

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  635.73  (Adapted Stein & Brown method)
    Melting Pt (deg C):  276.00  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.94E-019  (Modified Grain method)
    Subcooled liquid VP: 5.24E-016 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):  7.13e+005
       log Kow used: -3.71 (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
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.55E-032  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.218E-025 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.71  (KowWin est)
  Log Kaw used:  -29.730  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  26.020
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3086
   Biowin2 (Non-Linear Model)     :   0.0195
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0292  (months      )
   Biowin4 (Primary Survey Model) :   3.2781  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0233
   Biowin6 (MITI Non-Linear Model):   0.0086
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0325
 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):  6.99E-014 Pa (5.24E-016 mm Hg)
  Log Koa (Koawin est  ): 26.020
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.29E+007 
       Octanol/air (Koa) model:  2.57E+013 
   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 = 203.3002 E-12 cm3/molecule-sec
      Half-Life =     0.053 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.631 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.602E-005  L/mol-sec
  Kb Half-Life at pH 8:     332.653  years  
  Kb Half-Life at pH 7:    3326.534  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -3.71 (estimated)

 Volatilization from Water:
    Henry LC:  4.55E-032 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.289E+028  hours   (9.535E+026 days)
    Half-Life from Model Lake : 2.497E+029  hours   (1.04E+028 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       1.76e-015       1.26         1000       
   Water     49.5            1.44e+003    1000       
   Soil      50.4            2.88e+003    1000       
   Sediment  0.0962          1.3e+004     0          
     Persistence Time: 1.17e+003 hr

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