ChemSpider 2D Image | Pregabalin | C8H17NO2

Pregabalin

  • Molecular FormulaC8H17NO2
  • Average mass159.226 Da
  • Monoisotopic mass159.125931 Da
  • ChemSpider ID4589156
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(3S)-3-(Aminomethyl)-5-methylhexanoic acid [ACD/IUPAC Name]
(3S)-3-(Aminomethyl)-5-methylhexansäure [German] [ACD/IUPAC Name]
(S)-(+)-3-aminomethyl-5-methylhexanoic acid
(S)-3-(Aminomethyl)-5-methylhexanoic acid
(S)-3-Aminomethyl-5-methyl-hexanoic acid
(S)-3-Isobutyl GABA
148553-50-8 [RN]
55JG375S6M
7643
Acide (3S)-3-(aminométhyl)-5-méthylhexanoïque [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CI 1008 [DBID]
D02716 [DBID]
HSDB 2898 [DBID]
PD 144723 [DBID]
TOS-BB-0910 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      off-white crystalline powder Mole-Sci.Tech [mole86034]
    • Safety:

      5 Axon Medchem 1823
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1823
      IRRITANT Matrix Scientific 076200
      N03AX16 Wikidata Q412174
      no pictogram Axon Medchem 1823
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1823
      Sold for research purposes under agreement from Pfizer Inc. Tocris Bioscience 3775
      Warning Axon Medchem 1823
    • Target Organs:

      Calcium Channel inhibitor TargetMol T0350
    • Chemical Class:

      A <locant>gamma</locant>-amino acid that is <locant>gamma</locant>-aminobutyric acid (GABA) carrying an isobutyl substitutent at the <locant>beta</locant>-position (the <stereo>S</stereo>-enantiomer). Binds with high affinity to the <greek>alpha</greek><smallsub>2</smallsub>-<greek>delta</greek> site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. ChEBI CHEBI:64356
    • Drug Status:

      Approved BIONET-Key Organics KS-5378
    • Bio Activity:

      Anticonvulsant and antiepileptic; also used to treat neuropathic pain. Binds with high affinity and selectivity to the ?2? subunit of voltage-sensitive Ca2+ channels and modulates their activity. Disp lays anxiolytic-like activity in ethological and conflict models of anxiety. Analog of GABA (Cat. No. 0344). Tocris Bioscience 3775
      Anticonvulsant and antiepileptic; also used to treat neuropathic pain. Binds with high affinity and selectivity to the ?2? subunit of voltage-sensitive Ca2+ channels and modulates their activity. Displays anxiolytic-like activity in ethological and conflict models of anxiety. Analog of GABA (Cat. No. 0344). Tocris Bioscience 3775
      Anticonvulsant and antiepileptic; also used to treat neuropathic pain. Binds with high affinity and selectivity to the alpha2delta subunit of voltage-sensitive Ca2+ channels and modulates their activity. Displays anxiolytic-like activity in ethological and conflict models of anxiety. Analog of GABA (Cat. No. 0344). Tocris Bioscience 3775
      Anticonvulsant; selectively binds the ?2? subunit of voltage-sensitive calcium channels Tocris Bioscience 3775
      Anticonvulsant; selectively binds the alpha2delta subunit of voltage-sensitive calcium channels Tocris Bioscience 3775
      Calcium Channel MedChem Express HY-17414
      Calcium Channel TargetMol T0350
      Calcium Channels Tocris Bioscience 3775
      Ion Channels Tocris Bioscience 3775
      Membrane Tranporter/Ion Channel MedChem Express HY-17414
      Membrane Tranporter/Ion Channel; MedChem Express HY-17414
      Membrane Transporter/Ion Channel TargetMol T0350
      Pregabalin(CI-1008; PD-144723) is a GABA analogue and binds with high affinity and selectivity to the ?2? subunit of voltage-sensitive Ca2+ channels and modulates their activity. MedChem Express HY-17414
      Voltage-gated Calcium Channels Tocris Bioscience 3775

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

Density: 1.0±0.1 g/cm3
Boiling Point: 274.0±23.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 56.4±6.0 kJ/mol
Flash Point: 119.5±22.6 °C
Index of Refraction: 1.465
Molar Refractivity: 44.1±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.12
ACD/LogD (pH 5.5): -1.76
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.75
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 63 Å2
Polarizability: 17.5±0.5 10-24cm3
Surface Tension: 37.9±3.0 dyne/cm
Molar Volume: 159.6±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) =  -1.78

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  431.31  (Adapted Stein & Brown method)
    Melting Pt (deg C):  282.51  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.02E-009  (Modified Grain method)
    Subcooled liquid VP: 1.42E-006 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):  1.963e+004
       log Kow used: -1.78 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.9364e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.08E-010  atm-m3/mole
   Group Method:   6.89E-011  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.156E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.78  (KowWin est)
  Log Kaw used:  -7.900  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  6.120
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8983
   Biowin2 (Non-Linear Model)     :   0.9242
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2363  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0469  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5006
   Biowin6 (MITI Non-Linear Model):   0.4767
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7873
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000189 Pa (1.42E-006 mm Hg)
  Log Koa (Koawin est  ): 6.120
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0158 
       Octanol/air (Koa) model:  3.24E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.364 
       Mackay model           :  0.559 
       Octanol/air (Koa) model:  2.59E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.8095 E-12 cm3/molecule-sec
      Half-Life =     0.262 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.145 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.462 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  27.38
      Log Koc:  1.437 

 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: -1.78 (estimated)

 Volatilization from Water:
    Henry LC:  6.89E-011 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 1.072E+007  hours   (4.468E+005 days)
    Half-Life from Model Lake :  1.17E+008  hours   (4.874E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.00366         6.29         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0714          3.24e+003    0          
     Persistence Time: 577 hr




                    

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