ChemSpider 2D Image | Semicochliodinol A | C27H22N2O4

Semicochliodinol A

  • Molecular FormulaC27H22N2O4
  • Average mass438.475 Da
  • Monoisotopic mass438.157959 Da
  • ChemSpider ID416436

More details:

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

2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-(1H-indol-3-yl)-6-[5-(3-methyl-2-buten-1-yl)-1H-indol-3-yl]- [ACD/Index Name]
2,5-Dihydroxy-3-(1H-indol-3-yl)-6-[5-(3-methyl-2-buten-1-yl)-1H-indol-3-yl]-1,4-benzochinon [German] [ACD/IUPAC Name]
2,5-Dihydroxy-3-(1H-indol-3-yl)-6-[5-(3-methyl-2-buten-1-yl)-1H-indol-3-yl]-1,4-benzoquinone [ACD/IUPAC Name]
2,5-Dihydroxy-3-(1H-indol-3-yl)-6-[5-(3-méthyl-2-butén-1-yl)-1H-indol-3-yl]-1,4-benzoquinone [French] [ACD/IUPAC Name]
Semicochliodinol A
2,5-dihydroxy-3-(1H-indol-3-yl)-6-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

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

AIDS082017 [DBID]
AIDS-082017 [DBID]
  • Miscellaneous

    • Chemical Class:

      A bisindole alkaloid that is quinone bearing hydroxy substituents at positions 2 and 5 and two indol-3-yl groups at positions 3 and 6, one of which is carrying a prenyl group at position 5. Isolated f rom the culture broth of <ital>Chrysosporium merdarium</ital>, it acts as an inhibitor of HIV-1 protease and EGF-R protein tyrosine kinase. ChEBI CHEBI:66461
      A bisindole alkaloid that is quinone bearing hydroxy substituents at positions 2 and 5 and two indol-3-yl groups at positions 3 and 6, one of which is carrying a prenyl group at position 5. Isolated f rom the culture broth of Chrysosporium merdarium, it acts as an inhibitor of HIV-1 protease and EGF-R protein tyrosine kinase. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66461, CHEBI:66461

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

Density: 1.5±0.1 g/cm3
Boiling Point: 766.8±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 117.1±3.0 kJ/mol
Flash Point: 417.5±32.9 °C
Index of Refraction: 1.787
Molar Refractivity: 127.1±0.3 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.64
ACD/LogD (pH 5.5): 0.49
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.15
ACD/LogD (pH 7.4): -0.53
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 106 Å2
Polarizability: 50.4±0.5 10-24cm3
Surface Tension: 82.8±3.0 dyne/cm
Molar Volume: 301.0±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) =  4.89

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  721.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  315.91  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.77E-021  (Modified Grain method)
    Subcooled liquid VP: 3.32E-018 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):  0.009172
       log Kow used: 4.89 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.543e-006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.60E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.113E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.89  (KowWin est)
  Log Kaw used:  -13.832  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.722
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9246
   Biowin2 (Non-Linear Model)     :   0.2123
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4303  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3610  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0093
   Biowin6 (MITI Non-Linear Model):   0.0043
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8955
 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):  4.43E-016 Pa (3.32E-018 mm Hg)
  Log Koa (Koawin est  ): 18.722
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.78E+009 
       Octanol/air (Koa) model:  1.29E+006 
   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 = 315.3360 E-12 cm3/molecule-sec
      Half-Life =     0.034 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.422 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    47.199997 E-17 cm3/molecule-sec
      Half-Life =     0.024 Days (at 7E11 mol/cm3)
      Half-Life =     34.963 Min
   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    :  3342
      Log Koc:  3.524 

 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 = 3.063 (BCF = 1156)
       log Kow used: 4.89 (estimated)

 Volatilization from Water:
    Henry LC:  3.6E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.406E+012  hours   (1.419E+011 days)
    Half-Life from Model Lake : 3.715E+013  hours   (1.548E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              73.92  percent
    Total biodegradation:        0.65  percent
    Total sludge adsorption:    73.26  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       0.0118          0.34         1000       
   Water     12.6            900          1000       
   Soil      64.7            1.8e+003     1000       
   Sediment  22.7            8.1e+003     0          
     Persistence Time: 1.35e+003 hr

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