ChemSpider 2D Image | Thiolutin | C8H8N2O2S2

Thiolutin

  • Molecular FormulaC8H8N2O2S2
  • Average mass228.291 Da
  • Monoisotopic mass228.002716 Da
  • ChemSpider ID6608

More details:

Featured data source
The Merck Index Online

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

3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole
6-(Acetamido)-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one
87-11-6 [RN]
Acetamide, N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)- [ACD/Index Name]
acetopyrrothine
N-(4-Methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamid [German] [ACD/IUPAC Name]
N-(4-Methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide [ACD/IUPAC Name]
N-(4-Méthyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acétamide [French] [ACD/IUPAC Name]
Thiolutin [Wiki]
[87-11-6] [RN]
More...

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

02C005Q20B [DBID]
228.0027189 [DBID]
AIDS009894 [DBID]
AIDS-009894 [DBID]
BRN 0209485 [DBID]
NCI60_003708 [DBID]
NSC 3927 [DBID]
NSC3927 [DBID]
UNII:02C005Q20B [DBID]
UNII-02C005Q20B [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases. ChEBI CHEBI:156450

    • Bio Activity:

      Antibiotic; inhibits bacterial RNA polymerase. Inhibits adhesion of HUVEC cells to vitronectin (IC50 = 0.83 mM) and subsequently reduces paxillin levels. Suppresses tumor cell-induced angiogenesis. Tocris Bioscience 1567
      Bacterial RNA polymerase inhibitor Tocris Bioscience 1567
      Enzymes Tocris Bioscience 1567
      Polymerases Tocris Bioscience 1567
      RNA/DNA Polymerase Tocris Bioscience 1567

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

Density: 1.6±0.1 g/cm3
Boiling Point: 478.6±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 74.3±3.0 kJ/mol
Flash Point: 243.3±28.7 °C
Index of Refraction: 1.721
Molar Refractivity: 57.9±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 0.99
ACD/LogD (pH 5.5): 0.79
ACD/BCF (pH 5.5): 2.36
ACD/KOC (pH 5.5): 64.43
ACD/LogD (pH 7.4): 0.79
ACD/BCF (pH 7.4): 2.36
ACD/KOC (pH 7.4): 64.38
Polar Surface Area: 100 Å2
Polarizability: 23.0±0.5 10-24cm3
Surface Tension: 70.9±5.0 dyne/cm
Molar Volume: 146.5±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) =  -0.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  439.80  (Adapted Stein & Brown method)
    Melting Pt (deg C):  184.48  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.9E-008  (Modified Grain method)
    BP  (exp database):  200 @ 1 mm Hg deg C
    Subcooled liquid VP: 8.8E-007 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):  4580
       log Kow used: -0.56 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  210 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.9625e+005 mg/L
    Wat Sol (Exper. database match) =  210.00
       Exper. Ref:  MERCK INDEX (1996)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylamides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.37E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.246E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.56  (KowWin est)
  Log Kaw used:  -8.861  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.301
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0592
   Biowin2 (Non-Linear Model)     :   0.9942
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5863  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.9292  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2933
   Biowin6 (MITI Non-Linear Model):   0.0975
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5323
 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):  0.000117 Pa (8.8E-007 mm Hg)
  Log Koa (Koawin est  ): 8.301
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0256 
       Octanol/air (Koa) model:  4.91E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.48 
       Mackay model           :  0.672 
       Octanol/air (Koa) model:  0.00391 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 282.0696 E-12 cm3/molecule-sec
      Half-Life =     0.038 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.302 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.810000 E-17 cm3/molecule-sec
      Half-Life =     1.415 Days (at 7E11 mol/cm3)
      Half-Life =     33.956 Hrs
   Fraction sorbed to airborne particulates (phi): 0.576 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  138.9
      Log Koc:  2.143 

 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: -0.56 (estimated)

 Volatilization from Water:
    Henry LC:  3.37E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.625E+007  hours   (1.094E+006 days)
    Half-Life from Model Lake : 2.864E+008  hours   (1.193E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.00105         0.886        1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 966 hr

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