ChemSpider 2D Image | Valproic acid | C8H16O2

Valproic acid

  • Molecular FormulaC8H16O2
  • Average mass144.211 Da
  • Monoisotopic mass144.115036 Da
  • ChemSpider ID3009

More details:

Featured data source
The Merck Index Online

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

200-659-6 [EINECS]
263-770-9 [EINECS]
2-n-Propylpentanoic acid
2-Propylpentanoic acid [ACD/IUPAC Name]
2-Propylpentansäure [German] [ACD/IUPAC Name]
2-Propylvaleric Acid
99-66-1 [RN]
Acide 2-propylpentanoïque [French] [ACD/IUPAC Name]
Acide valproique [French] [INN]
Acido valproico [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

UNII-614OI1Z5WI [DBID]
YV7875000 [DBID]
614OI1Z5WI [DBID]
A-44090 [DBID]
Abbott 44090 [DBID]
AI3-10500 [DBID]
AIDS057177 [DBID]
AIDS-057177 [DBID]
BRN 1750447 [DBID]
CHEBI:39867 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Drug; Food Toxin; Enzyme Inhibitor; Anticonvulsant; Antimanic Agent; GABA Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2558

    • Safety:

      53-45 Alfa Aesar A12962
      61-22-34 Alfa Aesar A12962
      8 Alfa Aesar A12962
      Danger Alfa Aesar A12962
      DANGER: CORROSIVE, burns skin and eyes Alfa Aesar A12962
      H360D-H314-H302 Alfa Aesar A12962
      N03AG01 Wikidata Q240642
      P201-P309-P310 Alfa Aesar A12962

    • Chemical Class:

      A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:39867, CHEBI:39867

    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-10585
      Cell Cycle/DNA Damage; MedChem Express HY-10585
      HDAC MedChem Express HY-10585
      Valproic acid, a histone deacetylase (HDAC) inhibitor (IC50=10 uM in Hela cell, 24h) has an anticancer effect. MedChem Express
      Valproic acid, a histone deacetylase (HDAC) inhibitor (IC50=10 uM in Hela cell, 24h) has an anticancer effect.; IC50 Value: 10 uM (Hela, 24h) [1]; Target: HDAC; in vitro: Valproic acid had the effect on the growth and death of HeLa cervical cancer cells in relation to reactive oxygen species (ROS) and glutathione (GSH). MedChem Express HY-10585
  • Gas Chromatography

    • Retention Index (Kovats):

      1109 (estimated with error: 51) NIST Spectra mainlib_343602, replib_334915, replib_245952, replib_231899

    • Retention Index (Normal Alkane):

      1098.8 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 12 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 290 C; Start time: 1 min; CAS no: 99661; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Neill, G.P.; Davies, N.W.; McLean, S., Automated screening procedure using gas chromatography-mass spectrometry for identification of drugs after their extraction from biological samples, J. Chromatogr., 565, 1991, 207-224.) NIST Spectra nist ri
      1084 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 130 C; End T: 290 C; End time: 10 min; Start time: 1 min; CAS no: 99661; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Sharp, M.E., A rapid screening procedure for acidic and neutral drugs in blood by high resolution gas chromatography, J. Anal. Toxicol., 11, 1987, 8-11.) NIST Spectra nist ri
      1116 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 15 K/min; Start T: 80 C; End T: 295 C; End time: 8 min; Start time: 1 min; CAS no: 99661; Active phase: SE-54; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Friel, P.N.; Logan, B.K.; Formoso, E.J., GC-MS analysis and post-mortem distribution of felbamate in humans, J. Epilepsy, 10, 1997, 283-286.) NIST Spectra nist ri

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

Density: 0.9±0.1 g/cm3
Boiling Point: 220.0±0.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 50.3±6.0 kJ/mol
Flash Point: 111.1±0.0 °C
Index of Refraction: 1.435
Molar Refractivity: 40.6±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.72
ACD/LogD (pH 5.5): 1.89
ACD/BCF (pH 5.5): 10.52
ACD/KOC (pH 5.5): 113.71
ACD/LogD (pH 7.4): 0.10
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.84
Polar Surface Area: 37 Å2
Polarizability: 16.1±0.5 10-24cm3
Surface Tension: 31.8±3.0 dyne/cm
Molar Volume: 155.6±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) =  2.96
    Log Kow (Exper. database match) =  2.75
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  234.20  (Adapted Stein & Brown method)
    Melting Pt (deg C):  37.72  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0847  (Modified Grain method)
    BP  (exp database):  222 deg C
    Subcooled liquid VP: 0.11 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):  894.6
       log Kow used: 2.75 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2000 mg/L (20 deg C)
        Exper. Ref:  RIEMENSCHNEIDER (1986)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1861.5 mg/L
    Wat Sol (Exper. database match) =  2000.00
       Exper. Ref:  RIEMENSCHNEIDER (1986)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.00E-006  atm-m3/mole
   Group Method:   3.62E-006  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.797E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.75  (exp database)
  Log Kaw used:  -3.911  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  6.661
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7516
   Biowin2 (Non-Linear Model)     :   0.8326
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2451  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0252  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6121
   Biowin6 (MITI Non-Linear Model):   0.7602
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8018
 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):  14.7 Pa (0.11 mm Hg)
  Log Koa (Koawin est  ): 6.661
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.05E-007 
       Octanol/air (Koa) model:  1.12E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  7.39E-006 
       Mackay model           :  1.64E-005 
       Octanol/air (Koa) model:  9E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   8.1796 E-12 cm3/molecule-sec
      Half-Life =     1.308 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    15.692 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1.19E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  24.06
      Log Koc:  1.381 

 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: 2.75 (expkow database)

 Volatilization from Water:
    Henry LC:  3.62E-006 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River:      195.5  hours   (8.144 days)
    Half-Life from Model Lake :       2233  hours   (93.04 days)

 Removal In Wastewater Treatment:
    Total removal:               4.24  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.93  percent
    Total to Air:                0.20  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       2.2             31.4         1000       
   Water     25.6            360          1000       
   Soil      71.9            720          1000       
   Sediment  0.272           3.24e+003    0          
     Persistence Time: 466 hr

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