ChemSpider 2D Image | Exiguamine A | C25H26N5O6

Exiguamine A

  • Molecular FormulaC25H26N5O6
  • Average mass492.503 Da
  • Monoisotopic mass492.187775 Da
  • ChemSpider ID17214271

  • Charge - Charge

    defined stereocentres - 1 of 1 defined stereocentres

More details:

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(4R)-9'-(2-Aminoethyl)-5'-hydroxy-1,3,3',3'-tetramethyl-2,5,8',12'-tetraoxo-1',2',3',8',11',12'-hexahydrospiro[imidazolidine-4,7'-pyrrolo[3',2':5,6]chromeno[3,4-f]indol[3]ium] [ACD/IUPAC Name]
Exiguamine A
Spiro[imidazolidine-4,7'-[7H]pyrano[3,2-e:5,4-f']diindolium], 9'-(2-aminoethyl)-1',2',3',8',11',12'-hexahydro-5'-hydroxy-1,3,3',3'-tetramethyl-2,5,8',12'-tetraoxo-, (4R)- [ACD/Index Name]
(4R)-9'-(2-aminoethyl)-5'-hydroxy-1,3,3',3'-tetramethyl-2,5,8',12'-tetraoxo-1',2',3',8',11',12'-hexahydrospiro[imidazolidine-4,7'-pyrano[3,2-e:5,4-f']diindol[3]ium]
10747312 [Beilstein]
  • Miscellaneous

    • Chemical Class:

      An alkaloid isolated from the marine sponge Neopetrosia exigua which acts as a potent inhibitor of indoleamine 2,3-dioxygenase. ChEBI CHEBI:50655

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

Density:
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction:
Molar Refractivity:
#H bond acceptors: 11
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: -2.67
ACD/LogD (pH 5.5): -4.18
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.78
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 146 Å2
Polarizability:
Surface Tension:
Molar Volume:

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -2.84

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  917.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.18E-025  (Modified Grain method)
    Subcooled liquid VP: 2.65E-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):  1.042e+004
       log Kow used: -2.84 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.1096 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Imides
       Phenols
       Vinyl/Allyl Ethers
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.86E-038  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.222E-029 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.84  (KowWin est)
  Log Kaw used:  -35.395  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  32.555
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8537
   Biowin2 (Non-Linear Model)     :   0.2327
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7267  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9623  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1907
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1304
 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):  3.53E-019 Pa (2.65E-021 mm Hg)
  Log Koa (Koawin est  ): 32.555
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.49E+012 
       Octanol/air (Koa) model:  8.81E+019 
   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 = 259.6657 E-12 cm3/molecule-sec
      Half-Life =     0.041 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.658 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec
      Half-Life =     0.546 Days (at 7E11 mol/cm3)
      Half-Life =     13.097 Hrs
   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    :  1340
      Log Koc:  3.127 

 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: -2.84 (estimated)

 Volatilization from Water:
    Henry LC:  9.86E-038 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.318E+034  hours   (5.491E+032 days)
    Half-Life from Model Lake : 1.438E+035  hours   (5.99E+033 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       9.49e-016       0.919        1000       
   Water     53.9            4.32e+003    1000       
   Soil      46              8.64e+003    1000       
   Sediment  0.106           3.89e+004    0          
     Persistence Time: 1.51e+003 hr

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