ChemSpider 2D Image | (+)-rolipram | C16H21NO3

(+)-rolipram

  • Molecular FormulaC16H21NO3
  • Average mass275.343 Da
  • Monoisotopic mass275.152130 Da
  • ChemSpider ID139651

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(+)-rolipram
(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinon [German] [ACD/IUPAC Name]
(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone [ACD/IUPAC Name]
(4S)-4-[3-(Cyclopentyloxy)-4-méthoxyphényl]-2-pyrrolidinone [French] [ACD/IUPAC Name]
(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
(S)-(+)-Rolipram
(S)-ROLIPRAM
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, (4S)- [ACD/Index Name]
85416-73-5 [RN]
S-(+)-Rolipram
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

H6G4VMQ24K [DBID]
Lopac-R-6520 [DBID]
NCGC00015898-01 [DBID]
NCGC00016899-01 [DBID]
NCGC00024862-01 [DBID]
NCGC00024862-02 [DBID]
NCGC00024862-03 [DBID]
Tocris-0905 [DBID]
Tocris-1349 [DBID]
Tocris-1350 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      The (<stereo>S</stereo>)-enantiomer of rolipram. ChEBI CHEBI:59540
      The (S)-enantiomer of rolipram. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59540, CHEBI:59540

    • Bio Activity:

      (S)-(+)-Rolipram is a PDE4-inhibitor and an anti-inflammatory agent, less potent than its R enantiomer. MedChem Express
      (S)-(+)-Rolipram is a PDE4-inhibitor and an anti-inflammatory agent, less potent than its R enantiomer.; Target: PDE4B; PDE4D; Rolipram, a selective inhibitor of the cyclic AMP-specific phosphodiesterase (PDE IV). MedChem Express HY-B0392
      (S)-(+)-Rolipram is a PDE4-inhibitor and an anti-inflammatory agent, less potent than its R enantiomer.;Target: PDE4B; PDE4DRolipram, a selective inhibitor of the cyclic AMP-specific phosphodiesterase (PDE IV). Rolipram did not inhibit 5-lipoxygenase activity but did inhibit human monocyte production of leukotriene B4 (LTB4, IC50 3.5 microM). Rolipram inhibited arachidonic acid-induced inflammation in the mouse, while the low Km-cyclic-GMP PDE inhibitor. Rolipram had a modest effect on LTB4 production in the mouse, but markedly reduced LTB4-induced PMN infiltration [1]. In humans and animals rolipram produces thereby a variety of biological effects. These effects include attenuation of endogenous depression and inflammation in the central nervous system (CNS), both effects are of potential clinical relevance [2]. MedChem Express HY-B0392
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB2897
      Enzymes Tocris Bioscience 1350
      Enzymes/Phosphodiesterase/PDE4 Hello Bio HB2897
      Immunology/Inflammation MedChem Express HY-B0392
      Immunology/Inflammation; MedChem Express HY-B0392
      Less active enantiomer of the PDE4 inhibitor rolipram (Cat. No. 0905). (R)-(-)-Rolipram (Cat. No. 1349) also available. Tocris Bioscience 1350
      Less active enantiomer of the PDE4 inhibitor Rolipram. Racemate and R-enantiomer also available. Tocris Bioscience 1350
      Less potent enantiomer of Rolipram. Selective phosphodiesterase PDE4 inhibitor (IC<sub>50</sub> values are 0.58 and 0.75 ô‘M for membrane-bound PDE4 and cytosolic PDE4 respectively). Hello Bio HB2897
      Less potent enantiomer of Rolipram. Selective phosphodiesterase PDE4 inhibitor (IC<sub>50</sub> values are 0.58 and 0.75 µM for membrane-bound PDE4 and cytosolic PDE4 respectively). Hello Bio HB2897
      PDE4 MedChem Express HY-B0392
      PDE4 inhibitor. Less active enantiomer of rolipram (Cat. No. 0905) Tocris Bioscience 1350
      PDE4 inhibitor. Less potent enantiomer of Rolipram. Hello Bio HB2897
      Phosphodiesterases Tocris Bioscience 1350

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

Density: 1.2±0.1 g/cm3
Boiling Point: 472.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 73.6±3.0 kJ/mol
Flash Point: 239.7±28.7 °C
Index of Refraction: 1.552
Molar Refractivity: 76.2±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.43
ACD/LogD (pH 5.5): 1.72
ACD/BCF (pH 5.5): 12.02
ACD/KOC (pH 5.5): 206.42
ACD/LogD (pH 7.4): 1.72
ACD/BCF (pH 7.4): 12.02
ACD/KOC (pH 7.4): 206.42
Polar Surface Area: 48 Å2
Polarizability: 30.2±0.5 10-24cm3
Surface Tension: 43.5±3.0 dyne/cm
Molar Volume: 238.2±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) =  2.74

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  439.02  (Adapted Stein & Brown method)
    Melting Pt (deg C):  184.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.01E-008  (Modified Grain method)
    Subcooled liquid VP: 9.19E-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):  77.82
       log Kow used: 2.74 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  97.129 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.56E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.358E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.74  (KowWin est)
  Log Kaw used:  -9.643  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.383
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1451
   Biowin2 (Non-Linear Model)     :   0.9990
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3454  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7416  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5562
   Biowin6 (MITI Non-Linear Model):   0.5100
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5036
 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):  0.000123 Pa (9.19E-007 mm Hg)
  Log Koa (Koawin est  ): 12.383
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0245 
       Octanol/air (Koa) model:  0.593 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.469 
       Mackay model           :  0.662 
       Octanol/air (Koa) model:  0.979 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  75.0578 E-12 cm3/molecule-sec
      Half-Life =     0.143 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.710 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.566 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3895
      Log Koc:  3.591 

 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 = 1.410 (BCF = 25.71)
       log Kow used: 2.74 (estimated)

 Volatilization from Water:
    Henry LC:  5.56E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.747E+008  hours   (7.281E+006 days)
    Half-Life from Model Lake : 1.906E+009  hours   (7.943E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               4.00  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.89  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       9.65e-005       3.42         1000       
   Water     14.1            900          1000       
   Soil      85.7            1.8e+003     1000       
   Sediment  0.184           8.1e+003     0          
     Persistence Time: 1.72e+003 hr

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