ChemSpider 2D Image | H-89 | C20H20BrN3O2S

H-89

  • Molecular FormulaC20H20BrN3O2S
  • Average mass446.361 Da
  • Monoisotopic mass445.045959 Da
  • ChemSpider ID395827
  • Double-bond stereo - Double-bond stereo


More details:






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

127243-85-0 [RN]
5-Isoquinolinesulfonamide, N-[2-[[(2E)-3-(4-bromophenyl)-2-propen-1-yl]amino]ethyl]- [ACD/Index Name]
N-(2-{[(2E)-3-(4-Bromophényl)-2-propén-1-yl]amino}éthyl)-5-isoquinoléinesulfonamide [French] [ACD/IUPAC Name]
N-(2-{[(2E)-3-(4-Bromophenyl)-2-propen-1-yl]amino}ethyl)-5-isoquinolinesulfonamide [ACD/IUPAC Name]
N-(2-{[(2E)-3-(4-bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide
N-(2-{[(2E)-3-(4-Bromphenyl)-2-propen-1-yl]amino}ethyl)-5-isochinolinsulfonamid [German] [ACD/IUPAC Name]
N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
(E)-N-(2-((3-(4-bromophenyl)allyl)amino)ethyl)isoquinoline-5-sulfonamide
[127243-85-0]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

M876330O56 [DBID]
AIDS108022 [DBID]
AIDS-108022 [DBID]
Bio1_000301 [DBID]
Bio1_000790 [DBID]
Bio1_001279 [DBID]
Bio2_000384 [DBID]
Bio2_000864 [DBID]
CBiol_002015 [DBID]
H 89 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of <element>N</element><s mallsup>1</smallsup>-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. ChEBI CHEBI:47495
    • Bio Activity:

      H 89 is a potent and selective inhibitor of cyclic AMP-dependent protein kinase (protein kinase A) with IC50 of 48 nM; weak inhibition on PKG, PKC, CK1, CK2 and kinases.;IC50 value: 48 nM [1];Target: PKA inhibitor;In vitro: H-89 inhibits protein kinase A, in competitive fashion against ATP. To examine the role of protein kinase A in neurite outgrowth of PC12 cells, H-89 was applied along with nerve growth factor (NGF), forskolin, or dibutyryl cAMP. Pretreatment with H-89 led to a dose-dependent inhibition of the forskolin-induced protein phosphorylation, with no decrease in intracellular cyclic AMP levels in PC12D cells, and the NGF-induced protein phosphorylation was not not inhibited. H-89 also significantly inhibited the forskolin-induced neurite outgrowth from PC12D cells [1]. In intact single fibres of the flexor digitorum longus (FDB) muscle of the mouse, 1-3 microM H-89 had no noticeable effect on action-potential-mediated Ca2+ transients. Higher concentrations (4-10 MedChem Express HY-15979
      H 89 is a potent and selective inhibitor of cyclic AMP-dependent protein kinase (protein kinase A) with IC50 of 48 nM; weak inhibition on PKG, PKC, CK1, CK2 and others kinases. MedChem Express
      H 89 is a potent and selective inhibitor of cyclic AMP-dependent protein kinase (protein kinase A) with IC50 of 48 nM; weak inhibition on PKG, PKC, CK1, CK2 and others kinases.; IC50 value: 48 nM [1]; Target: PKA inhibitor; in vitro: H-89 inhibits protein kinase A, in competitive fashion against ATP. MedChem Express HY-15979
      PKA MedChem Express HY-15979
      Protein Tyrosine Kinase/RTK MedChem Express HY-15979
      Protein Tyrosine Kinase/RTK; MedChem Express HY-15979

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

Density: 1.4±0.1 g/cm3
Boiling Point: 639.7±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 94.5±3.0 kJ/mol
Flash Point: 340.7±34.3 °C
Index of Refraction: 1.653
Molar Refractivity: 113.7±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 3.03
ACD/LogD (pH 5.5): 1.27
ACD/BCF (pH 5.5): 1.56
ACD/KOC (pH 5.5): 11.02
ACD/LogD (pH 7.4): 2.95
ACD/BCF (pH 7.4): 76.24
ACD/KOC (pH 7.4): 538.25
Polar Surface Area: 79 Å2
Polarizability: 45.1±0.5 10-24cm3
Surface Tension: 56.8±3.0 dyne/cm
Molar Volume: 310.7±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) =  3.84

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  564.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.90  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.63E-012  (Modified Grain method)
    Subcooled liquid VP: 6.03E-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):  8.463
       log Kow used: 3.84 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  85.252 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.32E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.825E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.84  (KowWin est)
  Log Kaw used:  -13.468  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.308
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5785
   Biowin2 (Non-Linear Model)     :   0.0199
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1012  (months      )
   Biowin4 (Primary Survey Model) :   3.0935  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1729
   Biowin6 (MITI Non-Linear Model):   0.0014
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0100
 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):  8.04E-008 Pa (6.03E-010 mm Hg)
  Log Koa (Koawin est  ): 17.308
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  37.3 
       Octanol/air (Koa) model:  4.99E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 152.4255 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 160.0255 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.842 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.802 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.825000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     4.030 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.015 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.974E+006
      Log Koc:  6.295 

 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 = 2.254 (BCF = 179.6)
       log Kow used: 3.84 (estimated)

 Volatilization from Water:
    Henry LC:  8.32E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.487E+012  hours   (6.195E+010 days)
    Half-Life from Model Lake : 1.622E+013  hours   (6.758E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              23.33  percent
    Total biodegradation:        0.27  percent
    Total sludge adsorption:    23.06  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       9.39e-006       1.19         1000       
   Water     8.69            1.44e+003    1000       
   Soil      89.5            2.88e+003    1000       
   Sediment  1.76            1.3e+004     0          
     Persistence Time: 2.89e+003 hr




                    

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