ChemSpider 2D Image | 3-(1-(4-chlorobenzyl)-3-t-butylthio-5-isopropylindol-2-yl)-2,2-dimethylpropanoic acid | C27H34ClNO2S

3-(1-(4-chlorobenzyl)-3-t-butylthio-5-isopropylindol-2-yl)-2,2-dimethylpropanoic acid

  • Molecular FormulaC27H34ClNO2S
  • Average mass472.082 Da
  • Monoisotopic mass471.199890 Da
  • ChemSpider ID2885052

More details:

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

1-((4-Chlorophenyl)methyl)-3-((1,1-dimethylethyl)thio)-α,α-dimethyl-5-(1-methylethyl)-1H-indole-2-propanoic acid
1-[(4-Chlorophenyl)methyl]-3-[(1,1-dimethylethyl)thio]-a,a-dimethyl-5-(1-methylethyl)-1H-Indole-2-propanoic acid
118414-82-7 [RN]
1H-Indole-2-propanoic acid, 1-((4-chlorophenyl)methyl)-3-((1,1-dimethylethyl)thio)-α,α-dimethyl-5-(1-methylethyl)-
1H-Indole-2-propanoic acid, 1-[(4-chlorophenyl)methyl]-3-[(1,1-dimethylethyl)thio]-α,α-dimethyl-5-(1-methylethyl)- [ACD/Index Name]
3-(1-(4-chlorobenzyl)-3-t-butylthio-5-isopropylindol-2-yl)-2,2-dimethylpropanoic acid
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
3-[3-(tert-Butylsulfanyl)-1-(4-chlorobenzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
3-{1-(4-Chlorbenzyl)-5-isopropyl-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropansäure [German] [ACD/IUPAC Name]
3-{1-(4-Chlorobenzyl)-5-isopropyl-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropanoic acid [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

080626SQ8C [DBID]
L 663536 [DBID]
MK 886 [DBID]
MK-886 [DBID]
NCGC00025106-01 [DBID]
Tocris-1311 [DBID]
UNII:080626SQ8C [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A member of the class of indoles that is 1<element>H</element>-indole substituted by a isopropyl group at position 5, a <ital>tert</ital>-butylsulfanediyl group at position 3, a 4-chlorobenzyl group a t position 1 and a 2-carboxy-2-methylpropyl group at position 2. It acts as an inhibitor of arachidonate 5-lipoxygenase. ChEBI CHEBI:75390
      A member of the class of indoles that is 1H-indole substituted by a isopropyl group at position 5, a tert-butylsulfanediyl group at position 3, a 4-chlorobenzyl group a; t position 1 and a 2-carboxy-2 -methylpropyl group at position 2. It acts as an inhibitor of arachidonate 5-lipoxygenase. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75390
      A member of the class of indoles that is 1H-indole substituted by a isopropyl group at position 5, a tert-butylsulfanediyl group at position 3, a 4-chlorobenzyl group at position 1 and a 2-carboxy-2-m ethylpropyl group at position 2. It acts as an inhibitor of arachidonate 5-lipoxygenase. ChEBI CHEBI:75390

    • Bio Activity:

      An inhibitor of leukotriene biosynthesis (IC50 = 3 nM in human polymorphonuclear leukocytes). Acts by inhibiting 5-lipoxygenase-activating protein (FLAP) (IC50 = 30 nM for inhibition of [125I]-L-691,6 78 photoaffinity labelling). Also moderately potent PPAR? antagonist (IC50 = 0.5-1 ?M). Orally active in vivo. Tocris Bioscience 1311
      An inhibitor of leukotriene biosynthesis (IC50 = 3 nM in human polymorphonuclear leukocytes). Acts by inhibiting 5-lipoxygenase-activating protein (FLAP) (IC50 = 30 nM for inhibition of [125I]-L-691,678 photoaffinity labelling). Also moderately potent PPAR? antagonist (IC50 = 0.5-1 ?M). Orally active in vivo. Tocris Bioscience 1311
      An inhibitor of leukotriene biosynthesis (IC50 = 3 nM in human polymorphonuclear leukocytes). Acts by inhibiting 5-lipoxygenase-activating protein (FLAP) (IC50 = 30 nM for inhibition of [125I]-L-691,678 photoaffinity labelling). Also moderately potent PPARalpha antagonist (IC50 = 0.5-1 muM). Orally active in vivo. Tocris Bioscience 1311
      Enzymes Tocris Bioscience 1311
      Inhibitor of 5-lipoxygenase-activating protein (FLAP) Tocris Bioscience 1311
      Lipoxygenase Tocris Bioscience 1311
      Oxygenases/Oxidases Tocris Bioscience 1311

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

Density: 1.1±0.1 g/cm3
Boiling Point: 614.6±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 95.9±3.0 kJ/mol
Flash Point: 325.5±31.5 °C
Index of Refraction: 1.575
Molar Refractivity: 137.2±0.5 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 1
ACD/LogP: 8.21
ACD/LogD (pH 5.5): 7.05
ACD/BCF (pH 5.5): 85495.91
ACD/KOC (pH 5.5): 68742.22
ACD/LogD (pH 7.4): 5.26
ACD/BCF (pH 7.4): 1362.64
ACD/KOC (pH 7.4): 1095.62
Polar Surface Area: 68 Å2
Polarizability: 54.4±0.5 10-24cm3
Surface Tension: 38.4±7.0 dyne/cm
Molar Volume: 415.2±7.0 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) =  9.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  575.69  (Adapted Stein & Brown method)
    Melting Pt (deg C):  247.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.2E-012  (Modified Grain method)
    Subcooled liquid VP: 3.16E-010 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):  1.921e-005
       log Kow used: 9.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.8186e-005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.88E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.880E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  9.54  (KowWin est)
  Log Kaw used:  -9.929  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.469
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1545
   Biowin2 (Non-Linear Model)     :   0.0006
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7400  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9429  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4305
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4834
 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):  4.21E-008 Pa (3.16E-010 mm Hg)
  Log Koa (Koawin est  ): 19.469
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  71.2 
       Octanol/air (Koa) model:  7.23E+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 = 207.3849 E-12 cm3/molecule-sec
      Half-Life =     0.052 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.619 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  5.392E+006
      Log Koc:  6.732 

 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: 9.54 (estimated)

 Volatilization from Water:
    Henry LC:  2.88E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.417E+008  hours   (1.84E+007 days)
    Half-Life from Model Lake : 4.819E+009  hours   (2.008E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              94.03  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.26  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       0.00362         1.24         1000       
   Water     0.695           4.32e+003    1000       
   Soil      43.8            8.64e+003    1000       
   Sediment  55.5            3.89e+004    0          
     Persistence Time: 1.18e+004 hr

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