ChemSpider 2D Image | 4-methyl-5-[(2S)-2-methyl-1,4-diazepan-1-ylsulfonyl]isoquinoline | C16H21N3O2S

4-methyl-5-[(2S)-2-methyl-1,4-diazepan-1-ylsulfonyl]isoquinoline

  • Molecular FormulaC16H21N3O2S
  • Average mass319.422 Da
  • Monoisotopic mass319.135437 Da
  • ChemSpider ID394969

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(S)-2-METHYL-1-[(4-METHYL-5-ISOQUINOLINE)SULFONYL]-HOMOPIPERAZINE
451462-58-1 [RN]
4-methyl-5-[(2S)-2-methyl-1,4-diazepan-1-ylsulfonyl]isoquinoline
4-Methyl-5-{[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl}isochinolin [German] [ACD/IUPAC Name]
4-Méthyl-5-{[(2S)-2-méthyl-1,4-diazépan-1-yl]sulfonyl}isoquinoléine [French] [ACD/IUPAC Name]
4-Methyl-5-{[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl}isoquinoline [ACD/IUPAC Name]
Isoquinoline, 5-[[(2S)-hexahydro-2-methyl-1H-1,4-diazepin-1-yl]sulfonyl]-4-methyl- [ACD/Index Name]
(S)-(+)-2-methyl-1-[(4-methyl-5-isoquinolinyl)sulfonyl]homopiperazine
(S)-(+)-2-METHYL-1-[(4-METHYL-5-ISOQUINOLYNYL)SULFONYL]HOMOPIPERAZINE
(S)-2-methyl-1-(4-methylisoquinoline-5-sulfonyl)-1,4-diazepane
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A member of the class of isoquinolines that is the sulfonamide formed by the formal condensation of the sulfo group of 4-methylisoquinoline-5-sulfonic acid with the 1-amino group of (<stereo>S</stereo >)-2-methyl-1,4-diazepane. ChEBI CHEBI:88220
      A member of the class of isoquinolines that is the sulfonamide formed by the formal condensation of the sulfo group of 4-methylisoquinoline-5-sulfonic acid with the 1-amino group of (S)-2-methyl-1,4-d iazepane. ChEBI CHEBI:88220

    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-15720
      Cell Cycle/DNA Damage; TGF-beta/Smad ; MedChem Express HY-15720
      H-1152, an isoquinolinesulfonamide derivative, is a more specific, stronger and membrane-permeable inhibitor of Rho-kinase with a Ki value of 1.6 nM, but poor inhibitor of other serine/threonine kinas es. MedChem Express
      H-1152, an isoquinolinesulfonamide derivative, is a more specific, stronger and membrane-permeable inhibitor of Rho-kinase with a Ki value of 1.6 nM, but poor inhibitor of other serine/threonine kinases.; IC50 Value: 1.6 nM (Ki Value) [1]; Target: ROCK; in vitro: H-1152 dose-dependently inhibited the phosphorylation of MARCKS in human neuroteratoma (NT-2) cells stimulated by Rho-activator lysophosphatidic acid (LPA), which was determined by phosphorylation site-specific antibody against phospho-Ser159 in MARCKS, whereas it hardly inhibited the phosphorylation stimulated by phorbol-12,13-dibutyrate (PDBu) [1]. MedChem Express HY-15720
      H-1152, an isoquinolinesulfonamide derivative, is a more specific, stronger and membrane-permeable inhibitor of Rho-kinase with a Ki value of 1.6 nM, but poor inhibitor of other serine/threonine kinases.;IC50 Value: 1.6 nM (Ki Value) [1];Target: ROCK;In vitro: H-1152 dose-dependently inhibited the phosphorylation of MARCKS in human neuroteratoma (NT-2) cells stimulated by Rho-activator lysophosphatidic acid (LPA), which was determined by phosphorylation site-specific antibody against phospho-Ser159 in MARCKS, whereas it hardly inhibited the phosphorylation stimulated by phorbol-12,13-dibutyrate (PDBu) [1]. Loss-of-function experiments in endothelial cells revealed that inhibition of ROCK I/II using the pharmacological inhibitor H-1152 and ROCK I/II-specific small-interfering RNAs resulted in a rise of VEGF-driven sprouting angiogenesis [3].;In vivo: Cumulative addition of H-1152 (0.001-3 microM) or Y-27632 [0.01-30 microM; (R)-(+)-trans-N-(4-pyridyl)-4-(1-aminoethyl)-cyclohexaneca MedChem Express HY-15720
      ROCK MedChem Express HY-15720

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

Density: 1.2±0.1 g/cm3
Boiling Point: 519.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 79.2±3.0 kJ/mol
Flash Point: 268.0±32.9 °C
Index of Refraction: 1.593
Molar Refractivity: 88.8±0.4 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.14
ACD/LogD (pH 5.5): -0.97
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.83
Polar Surface Area: 71 Å2
Polarizability: 35.2±0.5 10-24cm3
Surface Tension: 46.7±3.0 dyne/cm
Molar Volume: 262.2±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) =  2.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  476.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  201.56  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.48E-009  (Modified Grain method)
    Subcooled liquid VP: 1.08E-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):  1787
       log Kow used: 2.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  17590 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.69E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.481E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.03  (KowWin est)
  Log Kaw used:  -11.563  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.593
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8040
   Biowin2 (Non-Linear Model)     :   0.5399
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4429  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3616  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0305
   Biowin6 (MITI Non-Linear Model):   0.0053
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3557
 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):  1.44E-005 Pa (1.08E-007 mm Hg)
  Log Koa (Koawin est  ): 13.593
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.208 
       Octanol/air (Koa) model:  9.62 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.883 
       Mackay model           :  0.943 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 122.2110 E-12 cm3/molecule-sec
      Half-Life =     0.088 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.050 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.913 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.57E+004
      Log Koc:  4.818 

 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 = 0.860 (BCF = 7.252)
       log Kow used: 2.03 (estimated)

 Volatilization from Water:
    Henry LC:  6.69E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.564E+010  hours   (6.517E+008 days)
    Half-Life from Model Lake : 1.706E+011  hours   (7.11E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               2.27  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.18  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       7.57e-006       2.1          1000       
   Water     22.5            900          1000       
   Soil      77.4            1.8e+003     1000       
   Sediment  0.09            8.1e+003     0          
     Persistence Time: 1.44e+003 hr

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