ChemSpider 2D Image | D-(−)-ampicillin | C16H19N3O4S

D-(−)-ampicillin

  • Molecular FormulaC16H19N3O4S
  • Average mass349.405 Da
  • Monoisotopic mass349.109619 Da
  • ChemSpider ID6013
  • defined stereocentres - 4 of 4 defined stereocentres


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D-(−)-ampicillin
(2S,5R,6R)-6-{(E)-[(2R)-2-Amino-1-hydroxy-2-phenylethyliden]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsäure [German] [ACD/IUPAC Name]
(2S,5R,6R)-6-{(E)-[(2R)-2-Amino-1-hydroxy-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid [ACD/IUPAC Name]
(2S,5R,6R)-6-{[(2R)-2-Amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsäure [German] [ACD/IUPAC Name]
(2S,5R,6R)-6-{[(2R)-2-Amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid [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
1339
200-709-7 [EINECS]
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(1E,2R)-2-amino-1-hydroxy-2-phenylethylidene]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- [ACD/Index Name]
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

A9393_SIGMA [DBID]
AIDS029735 [DBID]
AIDS-029735 [DBID]
AY 6108 [DBID]
AY-6108 [DBID]
BA 7305 [DBID]
Bayer 5427 [DBID]
BRL 1341 [DBID]
BRL-1341 [DBID]
C06574 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J01CA01 Wikidata Q244150
      S01AA19 Wikidata Q244150
    • Target Organs:

      Antibiotic TargetMol T0814L
    • Chemical Class:

      A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group. ChEBI CHEBI:28971
    • Bio Activity:

      Ampicillin is an orally active broad-spectrum antibiotic. MedChem Express
      Ampicillin is an orally active broad-spectrum antibiotic.; Target: Antibacterial; Ampicillin is an antibiotic useful for the treatment of a number of bacterial infections. MedChem Express HY-B0522
      Ampicillin is an orally active broad-spectrum antibiotic.;Target: AntibacterialAmpicillin is an antibiotic useful for the treatment of a number of bacterial infections. It is a beta-lactam antibiotic that is part of the aminopenicillin family and is roughly equivalent to its successor, amoxicillin in terms of spectrum and level of activity. Belonging to the penicillin group of beta-lactam antibiotics, ampicillin is able to penetrate Gram-positive and some Gram-negative bacteria. It differs from penicillin G, or benzylpenicillin, only by the presence of an amino group. That amino group helps the drug penetrate the outer membrane of Gram-negative bacteria. Ampicillin acts as an irreversible inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their cell walls. It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis. Ampicillin has received FDA approval for its mechanism of action. From Wikip MedChem Express HY-B0522
      Antibacterial MedChem Express HY-B0522
      Anti-infection MedChem Express HY-B0522
      Anti-infection; MedChem Express HY-B0522
      Microbiology & Virology TargetMol T0814L
      PBPs TargetMol T0814L

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

Density: 1.5±0.1 g/cm3
Boiling Point: 683.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 105.4±3.0 kJ/mol
Flash Point: 367.4±31.5 °C
Index of Refraction: 1.675
Molar Refractivity: 89.9±0.4 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.35
ACD/LogD (pH 5.5): -1.59
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.38
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 138 Å2
Polarizability: 35.7±0.5 10-24cm3
Surface Tension: 74.3±5.0 dyne/cm
Molar Volume: 239.3±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) =  1.45
    Log Kow (Exper. database match) =  1.35
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  622.61  (Adapted Stein & Brown method)
    Melting Pt (deg C):  324.85  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.84E-013  (Modified Grain method)
    MP  (exp database):  198 deg C
    Subcooled liquid VP: 1.89E-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):  439.3
       log Kow used: 1.35 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.01e+004 mg/L (21 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  7560 mg/L (21 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  10100.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  7560.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.39E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.972E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.35  (exp database)
  Log Kaw used:  -15.010  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.360
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1722
   Biowin2 (Non-Linear Model)     :   0.9948
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5175  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0348  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2775
   Biowin6 (MITI Non-Linear Model):   0.0175
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5365
 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):  2.52E-009 Pa (1.89E-011 mm Hg)
  Log Koa (Koawin est  ): 16.360
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.19E+003 
       Octanol/air (Koa) model:  5.62E+003 
   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 = 103.3219 E-12 cm3/molecule-sec
      Half-Life =     0.104 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.242 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    :  534.4
      Log Koc:  2.728 

 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: 1.35 (expkow database)

 Volatilization from Water:
    Henry LC:  2.39E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.579E+013  hours   (1.908E+012 days)
    Half-Life from Model Lake : 4.995E+014  hours   (2.081E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               1.94  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.84  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       9.83e-007       2.48         1000       
   Water     35.6            900          1000       
   Soil      64.3            1.8e+003     1000       
   Sediment  0.0837          8.1e+003     0          
     Persistence Time: 1.14e+003 hr




                    

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