ChemSpider 2D Image | Gliotoxin | C13H14N2O4S2

Gliotoxin

  • Molecular FormulaC13H14N2O4S2
  • Average mass326.391 Da
  • Monoisotopic mass326.039490 Da
  • ChemSpider ID5988

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(1R,7S,8S,11R)-7-Hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-dien-10,14-dion [German] [ACD/IUPAC Name]
(1R,7S,8S,11R)-7-Hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione [ACD/IUPAC Name]
(1R,7S,8S,11R)-7-Hydroxy-11-(hydroxyméthyl)-15-méthyl-12,13-dithia-9,15-diazatétracyclo[9.2.2.01,9.03,8]pentadéca-3,5-diène-10,14-dione [French] [ACD/IUPAC Name]
(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0¹,?.0³,?]pentadeca-3,5-diene-10,14-dione
(3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
[3R-(3a,5ab,6b,10aa)]-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
10H-3,10a-(Iminomethano)[1,2,4]dithiazino[4,3-a]indole-4,11(3H)-dione, 5a,6-dihydro-6-hydroxy-3-(hydroxymethyl)-12-methyl-, (3R,5aS,6S,10aR)- [ACD/Index Name]
200-835-2 [EINECS]
5L648PH06K
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

50675 [DBID]
CHEBI:5385 [DBID]
AI3-62383 [DBID]
AIDS086418 [DBID]
AIDS-086418 [DBID]
BRN 0050675 [DBID]
C10595 [DBID]
CCRIS 4025 [DBID]
NSC 102866 [DBID]
NSC102866 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. ChEBI CHEBI:5385, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5385

    • Bio Activity:

      Biochemicals & small molecules Hello Bio [HB4612]
      Cell process/Immunomodulation Hello Bio [HB4612]
      Enzymes Tocris Bioscience 2637
      Immunosuppressive agent Hello Bio [HB4612]
      Immunosuppressive agent; blocks phagocytosis, cytokine production and proliferation of T and B cells. Non-competitively inhibits chymotrypsin-like activity of 20S proteasome; prevents degradation of I ?B?, an endogenous blocker of NF-?B. Also inhibits farnesyltransferase and geranylgeranyltransferase I (IC50 values are 80 and 17 ?M respectively) and displays antitumor activity against breast cancer in vivo. Tocris Bioscience 2637
      Immunosuppressive agent; blocks phagocytosis, cytokine production and proliferation of T and B cells. Non-competitively inhibits chymotrypsin-like activity of 20S proteasome; prevents degradation of I?B?, an endogenous blocker of NF-?B. Also inhibits farnesyltransferase and geranylgeranyltransferase I (IC50 values are 80 and 17 ?M respectively) and displays antitumor activity against breast cancer in vivo. Tocris Bioscience 2637
      Immunosuppressive agent; blocks phagocytosis, cytokine production and proliferation of T and B cells. Non-competitively inhibits chymotrypsin-like activity of 20S proteasome; prevents degradation of IkappaBalpha, an endogenous blocker of NF-kappaB. Also inhibits farnesyltransferase and geranylgeranyltransferase I (IC50 values are 80 and 17 muM respectively) and displays antitumor activity against breast cancer in vivo. Tocris Bioscience 2637
      Inhibitor of 20S proteasome; immunosuppressant Tocris Bioscience 2637
      Proteases Tocris Bioscience 2637
      Proteasome Tocris Bioscience 2637

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

Density: 1.8±0.1 g/cm3
Boiling Point: 699.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±5.0 mmHg at 25°C
Enthalpy of Vaporization: 117.1±6.0 kJ/mol
Flash Point: 377.0±31.5 °C
Index of Refraction: 1.814
Molar Refractivity: 80.7±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 0.52
ACD/LogD (pH 5.5): 0.66
ACD/BCF (pH 5.5): 1.86
ACD/KOC (pH 5.5): 54.36
ACD/LogD (pH 7.4): 0.66
ACD/BCF (pH 7.4): 1.86
ACD/KOC (pH 7.4): 54.36
Polar Surface Area: 132 Å2
Polarizability: 32.0±0.5 10-24cm3
Surface Tension: 103.2±5.0 dyne/cm
Molar Volume: 186.5±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) =  2.90

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  544.31  (Adapted Stein & Brown method)
    Melting Pt (deg C):  233.29  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.32E-014  (Modified Grain method)
    Subcooled liquid VP: 2.3E-012 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):  28.46
       log Kow used: 2.90 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  70 mg/L (30 deg C)
        Exper. Ref:  SHIU,WY ET AL. (1990)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.0048e+005 mg/L
    Wat Sol (Exper. database match) =  70.00
       Exper. Ref:  SHIU,WY ET AL. (1990)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.39E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.992E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.90  (KowWin est)
  Log Kaw used:  -9.245  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.145
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9621
   Biowin2 (Non-Linear Model)     :   0.9273
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2652  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7397  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5649
   Biowin6 (MITI Non-Linear Model):   0.1410
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0179
 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):  3.07E-010 Pa (2.3E-012 mm Hg)
  Log Koa (Koawin est  ): 12.145
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.78E+003 
       Octanol/air (Koa) model:  0.343 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.965 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 457.5311 E-12 cm3/molecule-sec
      Half-Life =     0.023 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    16.832 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   100.000000 E-17 cm3/molecule-sec
      Half-Life =     0.011 Days (at 7E11 mol/cm3)
      Half-Life =     16.502 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 = 1.535 (BCF = 34.31)
       log Kow used: 2.90 (estimated)

 Volatilization from Water:
    Henry LC:  1.39E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  7.61E+007  hours   (3.171E+006 days)
    Half-Life from Model Lake : 8.301E+008  hours   (3.459E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               4.92  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.81  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       0.00867         0.185        1000       
   Water     20              900          1000       
   Soil      79.7            1.8e+003     1000       
   Sediment  0.365           8.1e+003     0          
     Persistence Time: 1.01e+003 hr

Click to predict properties on the Chemicalize site


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