ChemSpider 2D Image | Penicillamine | C5H11NO2S

Penicillamine

  • Molecular FormulaC5H11NO2S
  • Average mass149.211 Da
  • Monoisotopic mass149.051056 Da
  • ChemSpider ID5643
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

Penicillamine [INN] [Wiki]
(-)-penicillamine
(2S)-2-Amino-3-methyl-3-sulfanylbutansäure [German]
(D)-Penicillamine
(S)-Penicillamine
1121
200-148-8 [EINECS]
2219-30-9 [RN]
3,3-dimethylcysteine
3,3-Dimethyl-D(-)-cysteine
More...

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

196312_ALDRICH [DBID]
76398_FLUKA [DBID]
76400_FLUKA [DBID]
AIDS000443 [DBID]
AIDS-000443 [DBID]
BRN 1722374 [DBID]
C07418 [DBID]
CCRIS 2902 [DBID]
CCRIS 2904 [DBID]
D00496 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 6170 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      22-36/37/38 Alfa Aesar [B24710]
      26-36/37 Alfa Aesar [B24710]
      26-37 Alfa Aesar A11446
      36/37/38 Alfa Aesar A11446
      CAUTION: May be harmful if swallowed Alfa Aesar A11446
      H315-H319-H335 Alfa Aesar A11446
      Harmful/Irritant/Keep Cold SynQuest 8157-1-X0
      M01CC01 Wikidata Q421239
      P280g-P305+P351+P338 Alfa Aesar A11446
      Safety glasses, good ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      Toxic SynQuest 69591, 8157-1-X0
      Warning Alfa Aesar A11446
      WARNING: Irritates lungs, eyes, skin Alfa Aesar A11446
    • Target Organs:

      Chelator TargetMol T0983
    • Chemical Class:

      An optically active form of penicillamine having <stereo>D</stereo>-configuration. Pharmaceutical form (<stereo>L</stereo>-form is toxic) of chelating agent used to treat heavy metal poisoning. ChEBI CHEBI:7959
    • Bio Activity:

      Antiinflammatory; Zerenex Molecular [ZBioX-0452]
      Copper TargetMol T0983
      Others MedChem Express HY-B0300
      Others TargetMol T0983
      Penicillamine is the most characteristic degradation product of the penicillin antibiotics. MedChem Express http://www.medchemexpress.com/Etidronic-acid.html, HY-B0300
      Penicillamine is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.;Target: Penicillamine(Cuprimine, Depen) is used as an antirheumatic and as a chelating agent in Wilson's disease and is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activi MedChem Express HY-B0300

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

Density: 1.2±0.1 g/cm3
Boiling Point: 251.8±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 53.9±6.0 kJ/mol
Flash Point: 106.1±25.9 °C
Index of Refraction: 1.528
Molar Refractivity: 38.1±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.93
ACD/LogD (pH 5.5): -1.83
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.84
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 102 Å2
Polarizability: 15.1±0.5 10-24cm3
Surface Tension: 48.2±3.0 dyne/cm
Molar Volume: 123.8±3.0 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) =  -2.18
    Log Kow (Exper. database match) =  -1.78
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  360.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.69  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.99E-006  (Modified Grain method)
    MP  (exp database):  177 dec deg C
    Subcooled liquid VP: 7.53E-005 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):  2.156e+004
       log Kow used: -1.78 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.11e+005 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  38548 mg/L
    Wat Sol (Exper. database match) =  111000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.33E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.812E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.78  (exp database)
  Log Kaw used:  -8.419  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  6.639
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7191
   Biowin2 (Non-Linear Model)     :   0.7150
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0464  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9079  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5005
   Biowin6 (MITI Non-Linear Model):   0.3558
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5409
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.01 Pa (7.53E-005 mm Hg)
  Log Koa (Koawin est  ): 6.639
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000299 
       Octanol/air (Koa) model:  1.07E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0107 
       Mackay model           :  0.0233 
       Octanol/air (Koa) model:  8.55E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  70.9983 E-12 cm3/molecule-sec
      Half-Life =     0.151 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.808 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.017 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.272
      Log Koc:  0.797 

 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: -1.78 (expkow database)

 Volatilization from Water:
    Henry LC:  9.33E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.665E+006  hours   (3.194E+005 days)
    Half-Life from Model Lake : 8.362E+007  hours   (3.484E+006 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       0.0022          3.62         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0714          3.24e+003    0          
     Persistence Time: 577 hr




                    

Click to predict properties on the Chemicalize site





Feedback Form