Isoniazid C6H7N3O structure – Flashcards

Flashcard maker : Alicia Bennett

Molecular Formula C6H7N3O
Average mass 137.139 Da
Density 1.2±0.1 g/cm3
Boiling Point
Flash Point
Molar Refractivity 36.9±0.3 cm3
Polarizability 14.6±0.5 10-24cm3
Surface Tension 57.8±3.0 dyne/cm
Molar Volume 110.2±3.0 cm3
  • Experimental data
  • Predicted – ACD/Labs
  • Predicted – EPISuite
  • Predicted – ChemAxon
  • Predicted – Mcule
  • Experimental Physico-chemical Properties
    • Experimental Melting Point:

      172 °C TCI I0138
      169-174 °C Alfa Aesar
      171 °C Oxford University Chemical Safety Data (No longer updated) More details
      170 °C LKT Labs
      169-172 °C Merck Millipore 1669, 806753
      171.4 °C Jean-Claude Bradley Open Melting Point Dataset 16878, 17156, 21818, 28199
      172 °C Jean-Claude Bradley Open Melting Point Dataset 7364
      171 °C Jean-Claude Bradley Open Melting Point Dataset 13031, 15870, 8843
      169-174 °C Alfa Aesar A10583
      168-171 °C SynQuest 69243, 4H56-1-VD
      171-173 °C Oakwood 236758
      171-173 °C LabNetwork LN00221458
    • Experimental LogP:

      -0.887 Vitas-M STK086288
    • Experimental Flash Point:

      190 °C Oxford University Chemical Safety Data (No longer updated) More details
      250 °C LabNetwork LN00221458
    • Experimental Solubility:

      0.01 Egon Willighagen
      DMSO MedChem Express HY-B0329
      DMSO 28.2 mg/mL; Water 28.2 mg/mL MedChem Express HY-B0329
      Soluble 27 mg/mL in water, DMSO, methanol and ethanol. LKT Labs
  • Predicted Physico-chemical Properties
    • Predicted Melting Point:

      172 °C TCI
      172 °C TCI I0138
  • Miscellaneous
    • Appearance:

      white crystalline powder Oxford University Chemical Safety Data (No longer updated) More details
      WHITE POWDER NIH Clinical Collection
      White Solid Novochemy
    • Stability:

      Stable, but may be air or light sensitive. Combustible. Incompatible with strong oxidizing agents,chloral, aldehydes, iodine, ferric salts, hypochlorites. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-DOG LD50 50 mg kg-1, IVN-MUS LD50 149 mg kg-1, SCU-RAT LD50 329 mg kg-1, ORL-GPG LD50 255 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      20/21/22 Novochemy
      20/21/36/37/39 Novochemy
      22-36/37/38 Alfa Aesar A10583
      22-36/37/38-40 Alfa Aesar A10583
      26-36/37 Alfa Aesar A10583
      26-36/37-60 Alfa Aesar A10583
      GHS07; GHS09 Novochemy
      H301 H315 H319 H335 H351 LKT Labs
      H302-H315-H319-H335 Alfa Aesar A10583
      H332; H403 Novochemy
      Irritant SynQuest 4H56-1-VD, 69243
      P102; P210; P262; P270; P302+P352; P308+P313 Novochemy
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar A10583
      Safety glasses, gloves, good ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      Warning Alfa Aesar A10583
      Warning Novochemy
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar A10583
      Xn Abblis Chemicals AB1009474
      Xn Novochemy
    • Target Organs:

      Reductase inhibitor; Catalase-peroxidase TargetMol T0972
    • Compound Source:

      synthetic Microsource
    • Bio Activity:

      Antibacterial MedChem Express HY-B0329
      Anti-infection MedChem Express HY-B0329
      Anti-infection; MedChem Express HY-B0329
      Enzyme TargetMol T0972
      Isoniazid is an antibacterial agent used primarily as a tuberculostatic. MedChem Express
      Isoniazid is an antibacterial agent used primarily as a tuberculostatic.; Target: Antibacterial; Isoniazid is a prodrug and must be activated by a bacterial catalase-peroxidase enzyme that in M. MedChem Express HY-B0329
      Isoniazid is an antibacterial agent used primarily as a tuberculostatic.;Target: Antibacterial;Isoniazid is a prodrug and must be activated by a bacterial catalase-peroxidase enzyme that in M. tuberculosis is called KatG [1]. KatG couples the isonicotinic acyl with NADH to form isonicotinic acyl-NADH complex. This complex binds tightly to the enoyl-acyl carrier protein reductase known as InhA, thereby blocking the natural enoyl-AcpM substrate and the action of fatty acid synthase. This process inhibits the synthesis of mycolic acid, required for the mycobacterial cell wall. A range of radicals are produced by KatG activation of isoniazid, including nitric oxide, which has also been shown to be important in the action of another antimycobacterial prodrug PA-824 [2, 3]. Isoniazid is bactericidal to rapidly dividing mycobacteria, but is bacteriostatic if the mycobacteria are slow-growing [4]. MedChem Express HY-B0329
      NAPDH;Catalase-peroxidase TargetMol T0972
  • Gas Chromatography
    • Retention Index (Kovats):

      1431 (estimated with error: 83) NIST Spectra mainlib_228778, replib_65072, replib_190158, replib_290682, replib_379615
    • Retention Index (Normal Alkane):

      1582 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column type: Other; CAS no: 54853; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.584
Molar Refractivity: 36.9±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.89
ACD/LogD (pH 5.5): -0.64
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 10.66
ACD/LogD (pH 7.4): -0.63
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 10.76
Polar Surface Area: 68 Å2
Polarizability: 14.6±0.5 10-24cm3
Surface Tension: 57.8±3.0 dyne/cm
Molar Volume: 110.2±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) = -0.81
 Log Kow (Exper. database match) = -0.70
 Exper. Ref: Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
 Boiling Pt (deg C): 329.79 (Adapted Stein & Brown method)
 Melting Pt (deg C): 118.95 (Mean or Weighted MP)
 VP(mm Hg,25 deg C): 1.21E-005 (Modified Grain method)
 MP (exp database): 171.4 deg C
 Subcooled liquid VP: 0.000396 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): 1.669e+004
 log Kow used: -0.70 (expkow database)
 no-melting pt equation used
 Water Sol (Exper. database match) = 1.4e+005 mg/L (25 deg C)
 Exper. Ref: MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
 Wat Sol (v1.01 est) = 1e+006 mg/L
 Wat Sol (Exper. database match) = 140000.00
 Exper. Ref: MERCK INDEX (1996)

 ECOSAR Class Program (ECOSAR v0.99h):
 Class(es) found:

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
 Bond Method : 1.21E-014 atm-m3/mole
 Group Method: Incomplete
 Henrys LC [VP/WSol estimate using EPI values]: 1.308E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
 Log Kow used: -0.70 (exp database)
 Log Kaw used: -12.306 (HenryWin est)
 Log Koa (KOAWIN v1.10 estimate): 11.606
 Log Koa (experimental database): None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
 Biowin1 (Linear Model) : 0.5277
 Biowin2 (Non-Linear Model) : 0.3597
 Expert Survey Biodegradation Results:
 Biowin3 (Ultimate Survey Model): 2.6819 (weeks-months)
 Biowin4 (Primary Survey Model) : 3.6311 (days-weeks )
 MITI Biodegradation Probability:
 Biowin5 (MITI Linear Model) : -0.0695
 Biowin6 (MITI Non-Linear Model): 0.0000
 Anaerobic Biodegradation Probability:
 Biowin7 (Anaerobic Linear Model): 1.0954
 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): 0.0528 Pa (0.000396 mm Hg)
 Log Koa (Koawin est ): 11.606
 Kp (particle/gas partition coef. (m3/ug)):
 Mackay model : 5.68E-005 
 Octanol/air (Koa) model: 0.0991 
 Fraction sorbed to airborne particulates (phi):
 Junge-Pankow model : 0.00205 
 Mackay model : 0.00452 
 Octanol/air (Koa) model: 0.888 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
 Hydroxyl Radicals Reaction:
 OVERALL OH Rate Constant = 5.8373 E-12 cm3/molecule-sec
 Half-Life = 1.832 Days (12-hr day; 1.5E6 OH/cm3)
 Half-Life = 21.988 Hrs
 Ozone Reaction:
 No Ozone Reaction Estimation
 Fraction sorbed to airborne particulates (phi): 0.00329 (Junge,Mackay)
 Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
 Koc : 99.63
 Log Koc: 1.998 

 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: -0.70 (expkow database)

 Volatilization from Water:
 Henry LC: 1.21E-014 atm-m3/mole (estimated by Bond SAR Method)
 Half-Life from Model River: 5.666E+010 hours (2.361E+009 days)
 Half-Life from Model Lake : 6.182E+011 hours (2.576E+010 days)

 Removal In Wastewater Treatment:
 Total removal: 1.85 percent
 Total biodegradation: 0.09 percent
 Total sludge adsorption: 1.76 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 1.71e-007 44 1000 
 Water 46.3 900 1000 
 Soil 53.6 1.8e+003 1000 
 Sediment 0.0891 8.1e+003 0 
 Persistence Time: 974 hr


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