ChemSpider 2D Image | Cefcapene | C17H19N5O6S2

Cefcapene

  • Molecular FormulaC17H19N5O6S2
  • Average mass453.493 Da
  • Monoisotopic mass453.077667 Da
  • ChemSpider ID4940731
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


More details:



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

(6R-(6a,7b(Z)))-3-(((aminocarbonyl)oxy)methyl)-7-((2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl)amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-2-pentenamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Carbamate (Ester)
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-pentenoyl]amino}-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carbonsäure [German] [ACD/IUPAC Name]
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-pentenoyl]amino}-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ACD/IUPAC Name]
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)pent-2-enoyl]amino}-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
135889-00-8 [RN]
4D5D3422MW
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-penten-1-yl]amino]-8-oxo-, (6R,7R)- [ACD/Index Name]
7006
Acide (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-pentenoyl]amino}-3-[(carbamoyloxy)méthyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ène-2-carboxylique [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

S 1106 [DBID]
S 1006 [DBID]
  • Miscellaneous
    • Chemical Class:

      A cephalosporin compound having (carbamoyloxy)methyl and <element>N</element>-[(2<stereo>Z</stereo>)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino side-groups. It is used (generally as the corresponn ding pivaloyloxymethyl ester prodrug) as an oral antibacterial. ChEBI CHEBI:131729

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

Density: 1.6±0.1 g/cm3
Boiling Point: 936.0±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 142.7±3.0 kJ/mol
Flash Point: 519.9±34.3 °C
Index of Refraction: 1.715
Molar Refractivity: 109.1±0.4 cm3
#H bond acceptors: 11
#H bond donors: 6
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 2
ACD/LogP: -0.16
ACD/LogD (pH 5.5): -3.34
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.20
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 231 Å2
Polarizability: 43.2±0.5 10-24cm3
Surface Tension: 95.8±5.0 dyne/cm
Molar Volume: 277.7±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) =  -0.40

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  736.24  (Adapted Stein & Brown method)
    Melting Pt (deg C):  322.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.69E-018  (Modified Grain method)
    Subcooled liquid VP: 1.77E-014 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):  151.2
       log Kow used: -0.40 (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:
       Aromatic Amines-acid
       Esters-acid
       Acrylamides-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.11E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.035E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.40  (KowWin est)
  Log Kaw used:  -25.343  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.943
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8704
   Biowin2 (Non-Linear Model)     :   0.8452
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2715  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0751  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2455
   Biowin6 (MITI Non-Linear Model):   0.0006
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6284
 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):  2.36E-012 Pa (1.77E-014 mm Hg)
  Log Koa (Koawin est  ): 24.943
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.27E+006 
       Octanol/air (Koa) model:  2.15E+012 
   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 = 154.7646 E-12 cm3/molecule-sec
      Half-Life =     0.069 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.829 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    21.043749 E-17 cm3/molecule-sec
      Half-Life =     0.054 Days (at 7E11 mol/cm3)
      Half-Life =      1.307 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    :  443.1
      Log Koc:  2.647 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  4.496E-003  L/mol-sec
  Kb Half-Life at pH 8:       4.885  years  
  Kb Half-Life at pH 7:      48.853  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.40 (estimated)

 Volatilization from Water:
    Henry LC:  1.11E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.123E+024  hours   (4.68E+022 days)
    Half-Life from Model Lake : 1.225E+025  hours   (5.106E+023 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       2.05e-012       0.731        1000       
   Water     46.2            900          1000       
   Soil      53.7            1.8e+003     1000       
   Sediment  0.089           8.1e+003     0          
     Persistence Time: 976 hr




                    

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