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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
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, (4S)- [ACD/Index Name]
85416-73-5 [RN]
(+)-rolipram; (S)-(+)-rolipram; S-rolipram
(+)-Rolipram;(S)-Rolipram
More...

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]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1432
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1432
      no pictogram Axon Medchem 1432
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1432
      Warning Axon Medchem 1432
    • 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
    • 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]
      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

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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