ChemSpider 2D Image | LENAMPICILLIN | C21H23N3O7S

LENAMPICILLIN

  • Molecular FormulaC21H23N3O7S
  • Average mass461.488 Da
  • Monoisotopic mass461.125671 Da
  • ChemSpider ID59083

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(2S,5R,6R)-6-{[(2R)-2-Amino-2-phénylacétyl]amino}-3,3-diméthyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate de (5-méthyl-2-oxo-1,3-dioxol-4-yl)méthyle [French] [ACD/IUPAC Name]
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate [ACD/IUPAC Name]
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl-(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylat [German] [ACD/IUPAC Name]
[2S-[2a,5a,6b(S*)]]-6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, (2S,5R,6R)- [ACD/Index Name]
6-[D(-)-a-Aminophenylacetamido]penicillanic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester
86273-18-9 [RN]
8M568DM08K
Ampicillin (5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl Ester
LENAMPICILLIN [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5467 [DBID]
KB 1585 [DBID]
Kbt 1585 [DBID]
KBT-1585 [DBID]
  • Miscellaneous

    • Chemical Class:

      A penicillanic acid ester that is the (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of ampicillin. It is a prodrug of ampicillin. ChEBI CHEBI:135748

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

Density: 1.5±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.654
Molar Refractivity: 114.3±0.4 cm3
#H bond acceptors: 10
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: 2.22
ACD/LogD (pH 5.5): 0.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 8.80
ACD/LogD (pH 7.4): 1.37
ACD/BCF (pH 7.4): 6.23
ACD/KOC (pH 7.4): 122.39
Polar Surface Area: 163 Å2
Polarizability: 45.3±0.5 10-24cm3
Surface Tension: 70.2±5.0 dyne/cm
Molar Volume: 311.9±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):  759.91  (Adapted Stein & Brown method)
    Melting Pt (deg C):  334.01  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.27E-018  (Modified Grain method)
    Subcooled liquid VP: 4.05E-015 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):  576.4
       log Kow used: 0.40 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.8745e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters
       Benzyl Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.77E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.338E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.40  (KowWin est)
  Log Kaw used:  -12.946  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.346
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2203
   Biowin2 (Non-Linear Model)     :   0.9992
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0455  (months      )
   Biowin4 (Primary Survey Model) :   3.7165  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1564
   Biowin6 (MITI Non-Linear Model):   0.0041
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6050
 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):  5.4E-013 Pa (4.05E-015 mm Hg)
  Log Koa (Koawin est  ): 13.346
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.56E+006 
       Octanol/air (Koa) model:  5.45 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 211.6773 E-12 cm3/molecule-sec
      Half-Life =     0.051 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.606 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec
      Half-Life =     0.084 Days (at 7E11 mol/cm3)
      Half-Life =      2.015 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    :  5196
      Log Koc:  3.716 

 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: 0.40 (estimated)

 Volatilization from Water:
    Henry LC:  2.77E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.541E+011  hours   (1.892E+010 days)
    Half-Life from Model Lake : 4.953E+012  hours   (2.064E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  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       0.0469          0.757        1000       
   Water     54.1            1.44e+003    1000       
   Soil      45.7            2.88e+003    1000       
   Sediment  0.108           1.3e+004     0          
     Persistence Time: 743 hr

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