ChemSpider 2D Image | (+)-S,S-Ethambutol | C10H24N2O2

(+)-S,S-Ethambutol

  • Molecular FormulaC10H24N2O2
  • Average mass204.310 Da
  • Monoisotopic mass204.183777 Da
  • ChemSpider ID13433
  • defined stereocentres - 2 of 2 defined stereocentres


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(+)-S,S-Ethambutol
(+)-(S,S)-2,2'-(1,2-Ethylenediimino)-di-1-butanol
(+)-2,2'-(Ethylenediimino)di-1-butanol
(+)-ethambutol
(2S,2'S)-2,2'-(1,2-Ethandiyldiimino)di(1-butanol) [German] [ACD/IUPAC Name]
(2S,2'S)-2,2'-(1,2-Ethanediyldiimino)di(1-butanol) [ACD/IUPAC Name]
(2S,2'S)-2,2'-(1,2-Éthanediyldiimino)di(1-butanol) [French] [ACD/IUPAC Name]
(2S,2'S)-2,2'-(Ethane-1,2-diyldiimino)dibutan-1-ol
(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diol
(S,S)-ethambutol
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS007655 [DBID]
AIDS-007655 [DBID]
AIDS032284 [DBID]
AIDS-032284 [DBID]
AIDS088822 [DBID]
AIDS-088822 [DBID]
C06984 [DBID]
DivK1c_000561 [DBID]
KBio1_000561 [DBID]
KBio2_001538 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J04AK02 Wikidata Q412318
    • Chemical Class:

      An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (<stereo>S</stereo>,<stereo>S</stereo>-co nfiguration). It is a bacteriostatic antimycobacterial drug, effective against <ital>Mycobacterium tuberculosis</ital> and some other mycobacteria. It is used (as the dihydrochloride salt) in combinat ion with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of <ital>M. tuberculosis</ital> are readily produced if ethambutol is used alone. ChEBI CHEBI:4877
    • Bio Activity:

      Antibacterial MedChem Express HY-B0535
      Anti-infection MedChem Express HY-B0535
      Anti-infection; MedChem Express HY-B0535
      Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases. MedChem Express
      Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.; Target: Antibacterial; Ethambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. MedChem Express HY-B0535
      Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.;Target: AntibacterialEthambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. In M. smegmatis, Ethambutol inhibits synthesis of arabinan completely and inhibits AG synthesis most likely as a consequence of this; more than 50% of the cell arabinan is released from the bacteria following Ethambutol treatment, whereas no galactan is released. Ethambutol main targets against embB gene product in M. avium. Ethambutol induces 60% changes in the embB gene in M. tuberculosis resistant mutants [1]. Ethambutol is effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of the M. aviumcomplex (MAC) are sensitive to Ethambutol. [1] Ethambutol is potency against M. tu MedChem Express HY-B0535

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

Density: 1.0±0.1 g/cm3
Boiling Point: 345.3±22.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 68.3±6.0 kJ/mol
Flash Point: 113.7±12.9 °C
Index of Refraction: 1.478
Molar Refractivity: 58.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: -0.05
ACD/LogD (pH 5.5): -3.35
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 65 Å2
Polarizability: 23.2±0.5 10-24cm3
Surface Tension: 38.1±3.0 dyne/cm
Molar Volume: 207.0±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) =  -0.41

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  334.27  (Adapted Stein & Brown method)
    Melting Pt (deg C):  96.43  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.82E-006  (Modified Grain method)
    MP  (exp database):  88 deg C
    Subcooled liquid VP: 7.32E-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):  9.488e+005
       log Kow used: -0.41 (estimated)
       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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.65E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.157E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.41  (KowWin est)
  Log Kaw used:  -11.826  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.416
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2754
   Biowin2 (Non-Linear Model)     :   0.9897
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1165  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8984  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6891
   Biowin6 (MITI Non-Linear Model):   0.6184
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1213
 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):  0.000976 Pa (7.32E-006 mm Hg)
  Log Koa (Koawin est  ): 11.416
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00307 
       Octanol/air (Koa) model:  0.064 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0999 
       Mackay model           :  0.197 
       Octanol/air (Koa) model:  0.837 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 212.9135 E-12 cm3/molecule-sec
      Half-Life =     0.050 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.603 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.149 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: -0.41 (estimated)

 Volatilization from Water:
    Henry LC:  3.65E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.293E+010  hours   (9.554E+008 days)
    Half-Life from Model Lake : 2.501E+011  hours   (1.042E+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       9.42e-007       1.21         1000       
   Water     38.8            360          1000       
   Soil      61.1            720          1000       
   Sediment  0.0712          3.24e+003    0          
     Persistence Time: 580 hr




                    

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