ChemSpider 2D Image | cefaloram | C18H18N2O6S

cefaloram

  • Molecular FormulaC18H18N2O6S
  • Average mass390.410 Da
  • Monoisotopic mass390.088562 Da
  • ChemSpider ID62165

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

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

(6R,7R)-3-((Acetyloxy)methyl)-8-oxo-7-((phenylacetyl)amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carbonsäure [German] [ACD/IUPAC Name]
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ACD/IUPAC Name]
(6R,7R)-3-[(ACETYLOXY)METHYL]-8-OXO-7-(2-PHENYLACETAMIDO)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID
212-725-1 [EINECS]
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-phenylacetyl)amino]-, (6R,7R)- [ACD/Index Name]
859-07-4 [RN]
Acide (6R,7R)-3-(acétoxyméthyl)-8-oxo-7-[(2-phénylacétyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ène-2-carboxylique [French] [ACD/IUPAC Name]
cefaloram [INN]
cefaloramum [Latin] [INN]
More...

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

1723 [DBID]
  • Miscellaneous

    • Chemical Class:

      A cephalosporin derivative with potent antibacterial activity which binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzym es involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division, inactivation of which interferes with the cross-linkage of peptidogl ycan chains necessary for bacterial cell wall strength and rigidity, resulting in the weakening of the bacterial cell wall and causing cell lysis. ChEBI CHEBI:192380

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

Density: 1.5±0.1 g/cm3
Boiling Point: 742.8±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.6 mmHg at 25°C
Enthalpy of Vaporization: 113.7±3.0 kJ/mol
Flash Point: 403.0±32.9 °C
Index of Refraction: 1.660
Molar Refractivity: 96.9±0.4 cm3
#H bond acceptors: 8
#H bond donors: 2
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 1.77
ACD/LogD (pH 5.5): -1.53
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.46
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 138 Å2
Polarizability: 38.4±0.5 10-24cm3
Surface Tension: 72.8±5.0 dyne/cm
Molar Volume: 262.5±5.0 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) =  0.34
    Log Kow (Exper. database match) =  0.20
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  628.13  (Adapted Stein & Brown method)
    Melting Pt (deg C):  272.45  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.55E-014  (Modified Grain method)
    Subcooled liquid VP: 1.35E-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):  116
       log Kow used: 0.20 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  46237 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.21E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.129E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.20  (exp database)
  Log Kaw used:  -14.882  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.082
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.4116
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6800  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.2462  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4087
   Biowin6 (MITI Non-Linear Model):   0.0766
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4165
 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):  1.8E-009 Pa (1.35E-011 mm Hg)
  Log Koa (Koawin est  ): 15.082
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.67E+003 
       Octanol/air (Koa) model:  296 
   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 = 120.9908 E-12 cm3/molecule-sec
      Half-Life =     0.088 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.061 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   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    :  261.1
      Log Koc:  2.417 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.467E-001  L/mol-sec
  Kb Half-Life at pH 8:      23.141  days   
  Kb Half-Life at pH 7:     231.410  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.20 (expkow database)

 Volatilization from Water:
    Henry LC:  3.21E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.604E+013  hours   (1.502E+012 days)
    Half-Life from Model Lake : 3.931E+014  hours   (1.638E+013 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       5.59e-005       1.35         1000       
   Water     45.4            900          1000       
   Soil      54.5            1.8e+003     1000       
   Sediment  0.0885          8.1e+003     0          
     Persistence Time: 986 hr

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