ChemSpider 2D Image | chloramphenicol | C11H12Cl2N2O5

chloramphenicol

  • Molecular FormulaC11H12Cl2N2O5
  • Average mass323.129 Da
  • Monoisotopic mass322.012329 Da
  • ChemSpider ID5744
  • defined stereocentres - 2 of 2 defined stereocentres


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

(-)-Chloramphenicol
(1E)-2,2-Dichlor-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propanyl]ethanimidsäure [German] [ACD/IUPAC Name]
(1E)-2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propanyl]ethanimidic acid [ACD/IUPAC Name]
[R-(R*,R*)]-2,2-Dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide
2,2-Dichlor-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propanyl]acetamid [German] [ACD/IUPAC Name]
2,2-Dichlor-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamid
2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propanyl]acetamide [ACD/IUPAC Name]
2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophényl)-2-propanyl]acétamide [French] [ACD/IUPAC Name]
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxyméthyl)-2-(4-nitrophényl)éthyl]acétamide [French]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:17698 [DBID]
U 6062 [DBID]
23276_FLUKA [DBID]
442513_SUPELCO [DBID]
46110_RIEDEL [DBID]
AI3-25003 [DBID]
AIDS019445 [DBID]
AIDS-019445 [DBID]
AIDS110811 [DBID]
AIDS-110811 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      45-63 Alfa Aesar B20841
      53-20-36/37-45 Alfa Aesar B20841
      Danger Alfa Aesar B20841
      Danger Biosynth C-3307
      GHS08 Biosynth C-3307
      H350 Biosynth C-3307
      H350-H361 Alfa Aesar B20841
      Harmful/Carcinogenic/Teratogenic/Light Sensitive SynQuest 4656-5-Y2, 63265
      IRRITANT Matrix Scientific 058319
      P201; P308+P313 Biosynth C-3307
      P281-P201-P202-P308+P313-P405-P501a Alfa Aesar B20841
      T Abblis Chemicals AB1009524
    • Bio Activity:

      Antibacterial MedChem Express HY-B0239
      Anti-infection MedChem Express HY-B0239
      Anti-infection; MedChem Express HY-B0239
      Chloramphenicol is a broad-spectrum antibiotic. MedChem Express
      Chloramphenicol is a broad-spectrum antibiotic.; Target: Antibacterial; Chloramphenicol is a bacteriostatic drug that stops bacterial growth by inhibiting protein synthesis. MedChem Express HY-B0239
      Chloramphenicol is a broad-spectrum antibiotic.;Target: AntibacterialChloramphenicol is a bacteriostatic drug that stops bacterial growth by inhibiting protein synthesis. Chloramphenicol prevents protein chain elongation by inhibiting the peptidyl transferase activity of the bacterial ribosome. It specifically binds to A2451 and A2452 residues in the 23S rRNA of the 50S ribosomal subunit, preventing peptide bond formation. While chloramphenicol and the macrolide class of antibiotics both interact with ribosomes, chloramphenicol is not a macrolide. It directly interferes with substrate binding, whereas macrolides sterically block the progression of the growing peptide [1, 2]. MedChem Express HY-B0239
  • Gas Chromatography
    • Retention Index (Normal Alkane):

      2310 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 56757; 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
    • Retention Index (Linear):

      2310 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.8 m; Column type: Packed; Heat rate: 8 K/min; Start T: 130 C; End T: 290 C; End time: 8 min; Start time: 2 min; CAS no: 56757; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 19, 1981, 219-226.) NIST Spectra nist ri

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

Density: 1.5±0.1 g/cm3
Boiling Point: 644.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 100.0±3.0 kJ/mol
Flash Point: 343.8±31.5 °C
Index of Refraction: 1.612
Molar Refractivity: 72.6±0.3 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 1.02
ACD/LogD (pH 5.5): 1.02
ACD/BCF (pH 5.5): 3.51
ACD/KOC (pH 5.5): 85.50
ACD/LogD (pH 7.4): 1.02
ACD/BCF (pH 7.4): 3.51
ACD/KOC (pH 7.4): 85.46
Polar Surface Area: 115 Å2
Polarizability: 28.8±0.5 10-24cm3
Surface Tension: 66.1±3.0 dyne/cm
Molar Volume: 208.8±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) =  0.92
    Log Kow (Exper. database match) =  1.14
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  508.10  (Adapted Stein & Brown method)
    Melting Pt (deg C):  216.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.75E-012  (Modified Grain method)
    MP  (exp database):  150.5 deg C
    Subcooled liquid VP: 3.32E-011 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):  388.5
       log Kow used: 1.14 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2500 mg/L (25 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.4859e+005 mg/L
    Wat Sol (Exper. database match) =  2500.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.29E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.915E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.14  (exp database)
  Log Kaw used:  -16.029  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.169
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5935
   Biowin2 (Non-Linear Model)     :   0.0538
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2349  (months      )
   Biowin4 (Primary Survey Model) :   3.5363  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0145
   Biowin6 (MITI Non-Linear Model):   0.0013
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3640
 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):  4.43E-009 Pa (3.32E-011 mm Hg)
  Log Koa (Koawin est  ): 17.169
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  678 
       Octanol/air (Koa) model:  3.62E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  30.9744 E-12 cm3/molecule-sec
      Half-Life =     0.345 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.144 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1 (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 = -0.472 (BCF = 0.3371)
       log Kow used: 1.14 (expkow database)

 Volatilization from Water:
    Henry LC:  2.29E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.596E+014  hours   (1.915E+013 days)
    Half-Life from Model Lake : 5.014E+015  hours   (2.089E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.81  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       1.55e-007       8.29         1000       
   Water     41.3            1.44e+003    1000       
   Soil      58.6            2.88e+003    1000       
   Sediment  0.0915          1.3e+004     0          
     Persistence Time: 1.33e+003 hr




                    

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