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(3R,4S)-293B

Molecular FormulaC₁₅H₂₀N₂O₄S
Average mass324.395 Da
Monoisotopic mass324.114380 Da
ChemSpider ID108704

- 2 of 2 defined stereocentres

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Names and Synonyms

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

(-)-Chromanol 293B

(-)-[3R,4S]-Chromanol 293B

(3R,4S)-293B

163163-23-3 [RN]

163163-24-4 [RN]

Chromanol 293B

Ethanesulfonamide, N-[(3R,4S)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl- [ACD/Index Name]

MFCD06798368 [MDL number]

N-[(3R,4S)-6-Cyan-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-4-yl]-N-methylethansulfonamid [German] [ACD/IUPAC Name]

N-[(3R,4S)-6-Cyano-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-4-yl]-N-methylethanesulfonamide [ACD/IUPAC Name]

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N-[(3R,4S)-6-Cyano-3-hydroxy-2,2-diméthyl-3,4-dihydro-2H-chromén-4-yl]-N-méthyléthanesulfonamide [French] [ACD/IUPAC Name]

rel-N-[(3R,4S)-6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methylethanesulfonamide

trans-N-[6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl-ethanesulfonamide

(-)-(3R,4S)-CHROMANOL 293B

(3R,4S)-293B

(3R,4S)-Ethanesulfonic acid (6-cyano-3-hydroxy-2,2-dimethyl-chroman-4-yl)-methyl-amide

[163163-24-4] [RN]

N-[(3R,4S)-6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methylethanesulfonamide

293B cpd

6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dimethylchromane

CHEMBL434045

chromanol 239B

chromanol 239B|LS-185874

Chromanol 293B [3R,4S]-(-)-

Chromanol293B

ES-0008

Ethanesulfonamide, N-((3R,4S)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-N-methyl-, rel-

Ethanesulfonamide, N-[(3R,4S)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl-, rel-

Ethanesulfonamide,N-[(3R,4S)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl-

Ethanesulfonic acid ((3R,4S)-6-cyano-3-hydroxy-2,2-dimethyl-chroman-4-yl)-methyl-amide (relative stereochemistry)

https://www.ebi.ac.uk/chembl/compound_reportcard/CHEMBL434045/

LS-185874

MFCD06799499 [MDL number]

N-((3R,4S)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methylethanesulfonamide

N-[(3R,4S)-6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methylethanesulfonamide

N-[(3R,4S)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl-rel-ethanesulfonamide

N-[(3R,4S)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-4-yl]-N-methylethanesulfonamide

N-[(3R,4S)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl]-N-methylethane-1-sulfonamide

N-[(3R,4S)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl]-N-methylethanesulfonamide

rel-N-[(3R,4S)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl-ethanesulfonamide

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Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Experimental Physico-chemical Properties

Enantiomer that selectively inhibits the slow component of delayed rectifier K+ current (IKs). Block is use-dependent and 7-fold more potent than the (+)-(3S,4R) enantiomer (IC50 values are 1.36 and 9 .6 ?M respectively). Has negligible inhibitory action at KV11.1 (hERG) channels (IC50 > 30 ?M). Racemate Chromanol 293B (Cat. No. 1412) also available. Tocris Bioscience 1475

Enantiomer that selectively inhibits the slow component of delayed rectifier K+ current (IKs). Block is use-dependent and 7-fold more potent than the (+)-(3S,4R) enantiomer (IC50 values are 1.36 and 9.6 ?M respectively). Has negligible inhibitory action at KV11.1 (hERG) channels (IC50 > 30 ?M). Racemate Chromanol 293B (Cat. No. 1412) also available. Tocris Bioscience 1475

Enantiomer that selectively inhibits the slow component of delayed rectifier K+ current (IKs). Block is use-dependent and 7-fold more potent than the (+)-(3S,4R) enantiomer (IC50 values are 1.36 and 9.6 muM respectively). Has negligible inhibitory action at KV11.1 (hERG) channels (IC50 > 30 muM). Racemate also available. Tocris Bioscience 1475

Enantiomer that selectively inhibits the slow component of delayed rectifier K+ current (IKs). Block is use-dependent and 7-fold more potent than the (+)-(3S,4R) enantiomer (IC50 values are 1.36 and 9.6 muM respectively). Has negligible inhibitory action at KV11.1 (hERG) channels (IC50 > 30 muM). Racemate Chromanol 293B (Cat. No. 1412) also available. Tocris Bioscience 1475

IKs blocker. Enantiomer of Chromanol 293B (Cat. No. 1412) Tocris Bioscience 1475

Ion Channels Tocris Bioscience 1475

Potassium Channels Tocris Bioscience 1475

Selective delayed rectifier K+ current (IKs) inhibitor (IC50 = 1.36 µM). Enantiomer of Chromanol 293B; more potent than the (+)-(3S,4R) enantiomer (IC50 = 9.6 µM). Shows an open channel time-dependent block. Hello Bio HB1076

Voltage-Gated Potassium Channels Tocris Bioscience 1475

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

Density:	1.3±0.1 g/cm³
Boiling Point:	474.1±55.0 °C at 760 mmHg
Vapour Pressure:	0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization:	77.7±3.0 kJ/mol
Flash Point:	240.6±31.5 °C
Index of Refraction:	1.592
Molar Refractivity:	82.3±0.4 cm³
#H bond acceptors:	6
#H bond donors:	1
#Freely Rotating Bonds:	4
#Rule of 5 Violations:	0

ACD/LogP:	2.02
ACD/LogD (pH 5.5):	1.83
ACD/BCF (pH 5.5):	14.59
ACD/KOC (pH 5.5):	237.03
ACD/LogD (pH 7.4):	1.83
ACD/BCF (pH 7.4):	14.59
ACD/KOC (pH 7.4):	237.03
Polar Surface Area:	99 Å²
Polarizability:	32.6±0.5 10^-24cm³
Surface Tension:	59.9±5.0 dyne/cm
Molar Volume:	243.0±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) =  1.07

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  464.22  (Adapted Stein & Brown method)
    Melting Pt (deg C):  195.89  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.62E-011  (Modified Grain method)
    Subcooled liquid VP: 2.27E-009 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):  586.3
       log Kow used: 1.07 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3426.4 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.35E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.635E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.07  (KowWin est)
  Log Kaw used:  -12.017  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.087
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0068
   Biowin2 (Non-Linear Model)     :   0.9909
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2896  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3676  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3211
   Biowin6 (MITI Non-Linear Model):   0.0532
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3066
 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):  3.03E-007 Pa (2.27E-009 mm Hg)
  Log Koa (Koawin est  ): 13.087
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.91 
       Octanol/air (Koa) model:  3 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  65.8011 E-12 cm3/molecule-sec
      Half-Life =     0.163 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.951 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  95.48
      Log Koc:  1.980 

 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 = 0.123 (BCF = 1.326)
       log Kow used: 1.07 (estimated)

 Volatilization from Water:
    Henry LC:  2.35E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.487E+010  hours   (1.87E+009 days)
    Half-Life from Model Lake : 4.895E+011  hours   (2.04E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.89  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.80  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       0.000153        3.9          1000       
   Water     39.8            900          1000       
   Soil      60.1            1.8e+003     1000       
   Sediment  0.0854          8.1e+003     0          
     Persistence Time: 1.07e+003 hr

Click to predict properties on the Chemicalize site

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(3R,4S)-293B

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