ChemSpider 2D Image | Rolipram | C16H21NO3

Rolipram

  • Molecular FormulaC16H21NO3
  • Average mass275.343 Da
  • Monoisotopic mass275.152130 Da
  • ChemSpider ID4913

More details:






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

(±)-Rolipram
(R,S)-Rolipram
262-771-1 [EINECS]
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]- [ACD/Index Name]
4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinon [German] [ACD/IUPAC Name]
4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone [ACD/IUPAC Name]
4-[3-(Cyclopentyloxy)-4-méthoxyphényl]-2-pyrrolidinone [French] [ACD/IUPAC Name]
4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
4362
61413-54-5 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS025486 [DBID]
AIDS-025486 [DBID]
Bio2_000076 [DBID]
Bio2_000556 [DBID]
BRN 1588548 [DBID]
D01783 [DBID]
EU-0101072 [DBID]
KBio2_000076 [DBID]
KBio2_002644 [DBID]
KBio2_005212 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1212
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1212
      IRRITANT Matrix Scientific 065356
      no pictogram Axon Medchem 1212
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1212
      Warning Axon Medchem 1212
    • Chemical Class:

      A member of the lclass of pyrrolidin-2-ones that is pyrrolidin-2-one bearing a 3-(cyclopentyloxy)-4-methoxyphenyl substituent at the 4-position. It is a type IV-specific phosphodiesterase (PDE4) inhi bitor. ChEBI CHEBI:104872
    • Drug Status:

      pre-clinical BIONET-Key Organics KS-1400
    • Compound Source:

      synthetic; ZK-62711 Microsource [01505683]
    • Bio Activity:

      Enzymes Tocris Bioscience 905
      Immunology/Inflammation MedChem Express HY-16900
      Immunology/Inflammation; Metabolic Enzyme/Protease; MedChem Express HY-16900
      PDE4 MedChem Express HY-16900
      PDE4 inhibitor Tocris Bioscience 0905, 905
      Phosphodiesterases Tocris Bioscience 905
      Rolipram(SB95952; ZK62711) is a selective inhibitor of phosphodiesterases PDE 4, especially of the subtype PDE 4B (IC50=130nM), IC50 for PDE4D is 240 nM. MedChem Express http://www.medchemexpress.com/4-Azido-L-phenylalanine-hydrochloride.html, HY-16900
      Rolipram(SB95952; ZK62711) is a selective inhibitor of phosphodiesterases PDE 4, especially of the subtype PDE 4B (IC50=130nM), IC50 for PDE4D is 240 nM. ;IC50 Value: 130 nM (PDE4B); 240 nM (PDE4D) [1];Target: PDE4;In vitro: Rolipram, inhibited immunopurified PDE4B and PDE4D activities similarly, with IC(50) values of approx. 130 nM and 240 nM respectively. In contrast, rolipram inhibited immunopurified PDE4A activity with a dramatically lower IC(50) value of around 3 nM. Rolipram increased phosphorylation of cAMP-response-element-binding protein (CREB) in U937 cells in a dose-dependent fashion, which implied the presence of both high affinity (IC(50) value approx. 1 nM) and low affinity (IC(50) value approx. 120 nM) components. Rolipram dose-dependently inhibited the interferon-gamma (IFN-gamma)-stimulated phosphorylation of p38 mitogen-activated protein (MAP) kinase in a simple monotonic fashion with an IC(50) value of approx. 290 nM [1]. MKP-1 expression was enhanced by rolipram MedChem Express HY-16900
      Selective inhibitor of cAMP phosphodiesterase (PDE4) (IC50 = 2.0 ?M). Discriminates between two conformational states of PDE4 isoenzymes. Separate isomers (R)-(-)-Rolipram and (S)-(+)-Rolipram are ava ilable (Cat. Nos. 1349 and 1350 respectively). Tocris Bioscience 0905
      Selective inhibitor of cAMP phosphodiesterase (PDE4) (IC50 = 2.0 ?M). Discriminates between two conformational states of PDE4 isoenzymes. Separate isomers (R)-(-)-Rolipram and (S)-(+)-Rolipram are available (Cat. Nos. 1349 and 1350 respectively). Tocris Bioscience 905
      Selective inhibitor of cAMP phosphodiesterase (PDE4) (IC50 = 2.0 muM). Discriminates between two conformational states of PDE4 isoenzymes. R-enantiomer and S-enantiomer also available. Tocris Bioscience 905
      Selective inhibitor of cAMP phosphodiesterase (PDE4) (IC50 = 2.0 muM). Discriminates between two conformational states of PDE4 isoenzymes. Separate isomers (R)-(-)-Rolipram and (S)-(+)-Rolipram are available (Cat. Nos. 1349 and 1350 respectively). Tocris Bioscience 905

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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