ChemSpider 2D Image | CROTALINE | C16H23NO6


  • Molecular FormulaC16H23NO6
  • Average mass325.357 Da
  • Monoisotopic mass325.152527 Da
  • ChemSpider ID9044
  • defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source

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

(3R,4R,5R,13aR,13bR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizin-2,6(3H)-dion [German] [ACD/IUPAC Name]
(3R,4R,5R,13aR,13bR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione [ACD/IUPAC Name]
(3R,4R,5R,13aR,13bR)-4,5-Dihydroxy-3,4,5-triméthyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundécino[2,3,4-gh]pyrrolizine-2,6(3H)-dione [French] [ACD/IUPAC Name]
2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)- [ACD/Index Name]
315-22-0 [RN]
MFCD00084656 [MDL number]

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

48732 [DBID]
73077K8HYV [DBID]
A 6080 [DBID]
AIDS002694 [DBID]
AIDS-002694 [DBID]
BRN 0048732 [DBID]
C10350 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      TGF-beta/Smad inhibitor TargetMol T2803
    • Chemical Class:

      alkaloid Microsource [01502252]
    • Drug Status:

      experimental Microsource [01502252]
    • Compound Source:

      Alkaloid from Crotalaria retusa, Crotalaria spectabilis, Crotalaria aegyptiaca, Crotalaria burhia and Lindelofia spectabilis (Leguminosae, Boraginaceae) Zerenex Molecular [ZBioX-0288]
      Crotalaria spp Microsource [01502252]
    • Bio Activity:

      Hepatotoxin; Zerenex Molecular [ZBioX-0288]
      Immunology/Inflammation TargetMol T2803
      TGF-beta TargetMol T2803

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

Density: 1.4±0.1 g/cm3
Boiling Point: 537.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.2 mmHg at 25°C
Enthalpy of Vaporization: 93.6±6.0 kJ/mol
Flash Point: 278.7±30.1 °C
Index of Refraction: 1.586
Molar Refractivity: 80.3±0.4 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: -0.37
ACD/LogD (pH 5.5): -0.33
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 8.16
ACD/LogD (pH 7.4): 0.28
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 33.09
Polar Surface Area: 96 Å2
Polarizability: 31.8±0.5 10-24cm3
Surface Tension: 59.3±5.0 dyne/cm
Molar Volume: 239.4±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) =  -1.18

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  502.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  213.94  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.53E-013  (Modified Grain method)
    MP  (exp database):  197 dec deg C
    Subcooled liquid VP: 4.87E-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):  9.019e+005
       log Kow used: -1.18 (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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.35E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.574E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.18  (KowWin est)
  Log Kaw used:  -10.258  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.078
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3679
   Biowin2 (Non-Linear Model)     :   0.7065
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0815  (months      )
   Biowin4 (Primary Survey Model) :   3.2414  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6057
   Biowin6 (MITI Non-Linear Model):   0.2023
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2375
 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):  6.49E-009 Pa (4.87E-011 mm Hg)
  Log Koa (Koawin est  ): 9.078
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  462 
       Octanol/air (Koa) model:  0.000294 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.023 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 123.5571 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.039 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   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    :  10
      Log Koc:  1.000 

 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: -1.18 (estimated)

 Volatilization from Water:
    Henry LC:  1.35E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.823E+008  hours   (3.259E+007 days)
    Half-Life from Model Lake : 8.534E+009  hours   (3.556E+008 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       0.0282          0.489        1000       
   Water     55.2            1.44e+003    1000       
   Soil      44.6            2.88e+003    1000       
   Sediment  0.107           1.3e+004     0          
     Persistence Time: 753 hr


Click to predict properties on the Chemicalize site