ChemSpider 2D Image | Vigabatrin | C6H11NO2


  • Molecular FormulaC6H11NO2
  • Average mass129.157 Da
  • Monoisotopic mass129.078979 Da
  • ChemSpider ID5463

More details:

Featured data source

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

(±)-4-Aminohexenoic acid
(R,S)-4-Amino-5-hexenoic acid
200-659-6 [EINECS]
270-929-6 [EINECS]
4-Amino-5-hexenoic acid [ACD/IUPAC Name]
4-Amino-5-hexensäure [German] [ACD/IUPAC Name]
4-Aminohex-5-enoic acid
5-Hexenoic acid, 4-amino- [ACD/Index Name]

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

5581 [DBID]
CHEBI:63638 [DBID]
0S931RNJ68 [DBID]
68506-86-5(60643-86-9) [DBID]
AIDS088550 [DBID]
AIDS-088550 [DBID]
C07500 [DBID]
CPP-109 [DBID]
D00535 [DBID]
DivK1c_006760 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Drug; Enzyme Inhibitor; Anticonvulsant; GABA Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2977
    • Safety:

      N03AG04 Wikidata Q421663
    • Target Organs:

      GABAR agonist TargetMol T0128
    • Chemical Class:

      A <locant>gamma</locant>-amino acid having a <locant>gamma</locant>-vinyl GABA structure. It is an irreversible inhibitor of <locant>gamma</locant>-aminobutyric 664 acid transaminase ChEBI CHEBI:63638
      A gamma-amino acid having a gamma-vinyl GABA structure. It is an irreversible inhibitor of gamma-aminobutyric 664 acid transaminase ChEBI, CHEBI:63638
    • Bio Activity:

      ABAT;GABA TargetMol T0128
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0868
      GABAA and A-rho Receptors Tocris Bioscience 808
      GABA-T inhibitor Tocris Bioscience 0808, 808
      Ion Channels Tocris Bioscience 808
      Ligand-gated Ion Channels Tocris Bioscience 808
      Neuroscience TargetMol T0128
      Others MedChem Express HY-15399
      Receptors & Transporters/Transporters/GABA uptake & transport Hello Bio HB0868
      Selective and irreversible GABA-T (transaminase) inhibitor. Inhibits GABA catabolism. Increases GABA levels in the brain and CSF while decreasing glutamate in a dose-dependent manner. Shows anticonvulsant and antidepressant actions. Hello Bio HB0868
      Selective GABA-T (transaminase) inhibitor. Anticonvulsant. Tocris Bioscience 0808, 808
      Selective, irreversible GABA-T (transaminase) inhibitor Hello Bio HB0868
      Vigabatrin(?-Vinyl-GABA; Sabril) is a structural analog of the inhibitory neurotransmitter ?-aminobutyric acid (GABA) that irreversibly inhibits the catabolism of GABA by GABA transaminase.; IC50 value:; Target: GABA transaminase; Clinical studies have shown that vigabatrin is superior to placebo in decreasing the frequency of infantile spasms. MedChem Express HY-15399
  • Gas Chromatography

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

Density: 1.1±0.1 g/cm3
Boiling Point: 277.7±28.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 56.8±6.0 kJ/mol
Flash Point: 121.7±24.0 °C
Index of Refraction: 1.483
Molar Refractivity: 34.6±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: -0.10
ACD/LogD (pH 5.5): -2.74
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.73
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 63 Å2
Polarizability: 13.7±0.5 10-24cm3
Surface Tension: 41.5±3.0 dyne/cm
Molar Volume: 121.3±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) =  -2.83
    Log Kow (Exper. database match) =  -2.16
       Exper. Ref:  Henczi,M et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  414.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  273.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.95E-009  (Modified Grain method)
    Subcooled liquid VP: 3.74E-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):  5.514e+004
       log Kow used: -2.16 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 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 :   1.30E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.142E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.16  (exp database)
  Log Kaw used:  -8.275  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  6.115
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9126
   Biowin2 (Non-Linear Model)     :   0.9492
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3028  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0902  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6091
   Biowin6 (MITI Non-Linear Model):   0.6205
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8657
 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):  0.000499 Pa (3.74E-006 mm Hg)
  Log Koa (Koawin est  ): 6.115
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00602 
       Octanol/air (Koa) model:  3.2E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.179 
       Mackay model           :  0.325 
       Octanol/air (Koa) model:  2.56E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  72.2863 E-12 cm3/molecule-sec
      Half-Life =     0.148 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.776 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   Fraction sorbed to airborne particulates (phi): 0.252 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9.165
      Log Koc:  0.962 

 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: -2.16 (expkow database)

 Volatilization from Water:
    Henry LC:  1.3E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.118E+006  hours   (2.133E+005 days)
    Half-Life from Model Lake : 5.584E+007  hours   (2.327E+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       0.00659         3.08         1000       
   Water     34.6            208          1000       
   Soil      65.4            416          1000       
   Sediment  0.0598          1.87e+003    0          
     Persistence Time: 384 hr


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