ChemSpider 2D Image | (S)-(+)-Ibuprofen | C13H18O2

(S)-(+)-Ibuprofen

  • Molecular FormulaC13H18O2
  • Average mass206.281 Da
  • Monoisotopic mass206.130676 Da
  • ChemSpider ID36498
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

(S)-(+)-Ibuprofen
(+)-(S)-Ibuprofen
(+)-ibuprofen
(2S)-2-(4-Isobutylphenyl)propanoic acid [ACD/IUPAC Name]
(2S)-2-(4-Isobutylphenyl)propansäure [German] [ACD/IUPAC Name]
(2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
(2S)-2-[4-(2-Methylpropyl)phenyl]propionic acid
(S)-(+)-2-(4-isobutylphenyl)propanoic acid
(S)-4-Isobutyl-α-methylphenylacetic acid
(S)-a-Methyl-4-(2-methylpropyl)benzeneacetic acid
More...

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

375160_ALDRICH [DBID]
58635_FLUKA [DBID]
CHEBI:35706 [DBID]
D03715 [DBID]
EU-0100654 [DBID]
I106_SIGMA [DBID]
Lopac-I-106 [DBID]
Lopac-I-4883 [DBID]
NCGC00015529-01 [DBID]
NCGC00015529-02 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 076197
      P261; P262 Biosynth Q-200942
    • Target Organs:

      Plasminogen inhibitor;PPAR activator;COX inhibitor; Bcl-2 inhibitor;thrombomodulin TargetMol T0448
    • Chemical Class:

      Prostaglandin EU-OpenScreen [I-106]
    • Bio Activity:

      COX MedChem Express HY-78131A
      Cyclooxygenase Tocris Bioscience 2796
      Cyclooxygenase inhibitor (COX-1 > COX-2) Tocris Bioscience 2796
      Enzymes Tocris Bioscience 2796
      Immunology/Inflammation MedChem Express HY-78131A
      Immunology/Inflammation; MedChem Express HY-78131A
      Neuroscience;Angiogensis;Apoptosis TargetMol T0448
      Non-steroidal anti-inflammatory drug (NSAID) that inhibits cyclooxygenase 1 and cyclooxygenase 2 (IC50 values are 12 and 80 ?M respectively). Active isomer of ibuprofen. Tocris Bioscience 2796
      Oxygenases/Oxidases Tocris Bioscience 2796
      plasminogen;PPAR??; Prostaglandin G/H synthase ;Bcl-2, FABP;thrombomodulin;Cystic fibrosis transmembrane conductance regulator TargetMol T0448
      S(+)-Ibuprofen is capable of inhibiting cyclooxygenase (COX) at clinically relevant concentrations, R(-)-ibuprofen is not a COX inhibitor. MedChem Express
      S(+)-Ibuprofen is capable of inhibiting cyclooxygenase (COX) at clinically relevant concentrations, R(-)-ibuprofen is not a COX inhibitor.; IC50 Value: 13 uM (COX1); 370 uM (COX2) [1]; Target: COX1/2; The two enantiomers of ibuprofen are therefore different in terms of their pharmacological properties and may be regarded as two different 'drugs'. MedChem Express HY-78131A
      S(+)-Ibuprofen is capable of inhibiting cyclooxygenase (COX) at clinically relevant concentrations, R(-)-ibuprofen is not a COX inhibitor.;IC50 Value: 13 uM (COX1); 370 uM (COX2) [1];Target: COX1/2;The two enantiomers of ibuprofen are therefore different in terms of their pharmacological properties and may be regarded as two different 'drugs'. They also differ in terms of their metabolic profiles. ;In vitro: R(-)-ibuprofen becomes involved in pathways of lipid metabolism and is incorporated into triglycerides along with endogenous fatty acids. S(+)-Ibuprofen does not appear to become involved in these unusual metabolic reactions, which is why S(+)-ibuprofen is regarded as being metabolically 'cleaner' than racemic ibuprofen [2]. Cosolvents exponentially increased the solubility of both SIB and racIB, especially in the presence of PG and PEG 300. Glycerol was not very effective in increasing the aqueous solubilities of both compounds, whereas sorbitol solution had a minimal effect MedChem Express HY-78131A

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.0±0.1 g/cm3
Boiling Point: 319.6±11.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 59.3±3.0 kJ/mol
Flash Point: 216.7±14.4 °C
Index of Refraction: 1.519
Molar Refractivity: 60.8±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.72
ACD/LogD (pH 5.5): 2.25
ACD/BCF (pH 5.5): 16.17
ACD/KOC (pH 5.5): 122.42
ACD/LogD (pH 7.4): 0.45
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.95
Polar Surface Area: 37 Å2
Polarizability: 24.1±0.5 10-24cm3
Surface Tension: 38.1±3.0 dyne/cm
Molar Volume: 200.3±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) =  3.79
    Log Kow (Exper. database match) =  3.97
       Exper. Ref:  Avdeef,A (1997)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  323.11  (Adapted Stein & Brown method)
    Melting Pt (deg C):  94.22  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000186  (Modified Grain method)
    MP  (exp database):  76 deg C
    Subcooled liquid VP: 0.000567 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):  41.05
       log Kow used: 3.97 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  21 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  57.974 mg/L
    Wat Sol (Exper. database match) =  21.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.52E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.230E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.97  (exp database)
  Log Kaw used:  -5.207  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.177
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8314
   Biowin2 (Non-Linear Model)     :   0.8672
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9582  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7986  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1976
   Biowin6 (MITI Non-Linear Model):   0.1521
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0334
 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):  0.0756 Pa (0.000567 mm Hg)
  Log Koa (Koawin est  ): 9.177
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.97E-005 
       Octanol/air (Koa) model:  0.000369 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00143 
       Mackay model           :  0.00316 
       Octanol/air (Koa) model:  0.0287 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  11.8423 E-12 cm3/molecule-sec
      Half-Life =     0.903 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    10.838 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0023 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  394.3
      Log Koc:  2.596 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 3.97 (expkow database)

 Volatilization from Water:
    Henry LC:  1.52E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       5534  hours   (230.6 days)
    Half-Life from Model Lake : 6.049E+004  hours   (2520 days)

 Removal In Wastewater Treatment:
    Total removal:              28.72  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    28.40  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.977           21.7         1000       
   Water     20.5            360          1000       
   Soil      76.1            720          1000       
   Sediment  2.45            3.24e+003    0          
     Persistence Time: 572 hr




                    

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