ChemSpider 2D Image | Cefatrizine | C18H18N6O5S2

Cefatrizine

  • Molecular FormulaC18H18N6O5S2
  • Average mass462.503 Da
  • Monoisotopic mass462.078003 Da
  • ChemSpider ID4918615
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



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

(6R,7R)-7-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carbonsäure [German] [ACD/IUPAC Name]
(6R,7R)-7-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ACD/IUPAC Name]
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
[6R-[6a,7b(R*)]]-7-[[Amino-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
257-324-2 [EINECS]
3839
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(1H-1,2,3-triazol-5-ylthio)methyl]-, (6R,7R)- [ACD/Index Name]
64217-62-5 [RN]
7-[D-a-Amino-a-(4-hydroxyphenyl)-acetamido]-3-(1,2,3-triazol-4(5)-ylthiomethyl)-3-cepbem-4-carboxylic Acid
8P4W949T8K
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BLS 640 [DBID]
SKF 60771 [DBID]
D02406 [DBID]
  • Miscellaneous
    • Chemical Class:

      A cephalosporin compound having (1<element>H</element>-1,2,3-triazol-4-ylsulfanyl)methyl and [(2<stereo>R</stereo>)-2-amino-2-(4-hydroxyphenyl)]acetamido side-groups. An antibacterial drug first prepa red in the 1970s, it has more recently been found to be an inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which is known to regulate apoptosis, autophagy and ER stress in many types of hu man cancers. ChEBI CHEBI:131730

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

Density: 1.7±0.1 g/cm3
Boiling Point: 948.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 144.6±3.0 kJ/mol
Flash Point: 527.2±34.3 °C
Index of Refraction: 1.794
Molar Refractivity: 113.2±0.4 cm3
#H bond acceptors: 11
#H bond donors: 6
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: 0.11
ACD/LogD (pH 5.5): -3.52
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.01
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 225 Å2
Polarizability: 44.9±0.5 10-24cm3
Surface Tension: 120.5±5.0 dyne/cm
Molar Volume: 266.4±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) =  -1.21

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  834.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.7E-022  (Modified Grain method)
    Subcooled liquid VP: 8.71E-019 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):  2505
       log Kow used: -1.21 (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-acid
       Phenols-acid
       Benzyl Amines-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.71E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.130E-026 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.21  (KowWin est)
  Log Kaw used:  -25.155  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.945
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2900
   Biowin2 (Non-Linear Model)     :   0.9889
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5141  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0599  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0065
   Biowin6 (MITI Non-Linear Model):   0.0016
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3141
 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):  1.16E-016 Pa (8.71E-019 mm Hg)
  Log Koa (Koawin est  ): 23.945
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.58E+010 
       Octanol/air (Koa) model:  2.16E+011 
   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 = 196.6153 E-12 cm3/molecule-sec
      Half-Life =     0.054 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.653 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
   Reaction With Nitrate Radicals May Be Important!
   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    :  4.528E+004
      Log Koc:  4.656 

 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: -1.21 (estimated)

 Volatilization from Water:
    Henry LC:  1.71E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.363E+023  hours   (3.068E+022 days)
    Half-Life from Model Lake : 8.033E+024  hours   (3.347E+023 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       7.78e-008       0.966        1000       
   Water     46.4            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0891          8.1e+003     0          
     Persistence Time: 973 hr




                    

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