ChemSpider 2D Image | Levodopa | C9H11NO4

Levodopa

  • Molecular FormulaC9H11NO4
  • Average mass197.188 Da
  • Monoisotopic mass197.068802 Da
  • ChemSpider ID5824
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(-)-dopa
(−)-dopa
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propansäure [German]
200-445-2 [EINECS]
2651
3,4-Dihydroxy-L-phenylalanine
3-Hydroxytyrosin [German] [ACD/IUPAC Name]
3-Hydroxytyrosine [ACD/IUPAC Name]
3-Hydroxytyrosine [French] [ACD/IUPAC Name]
59-92-7 [RN]
More...

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

46627O600J [DBID]
37830_FLUKA [DBID]
37840_FLUKA [DBID]
AIDS126624 [DBID]
AIDS-126624 [DBID]
bmse000322 [DBID]
C00355 [DBID]
CCRIS 3766 [DBID]
CHEBI:15765 [DBID]
D00059 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white crystalline powder Oxford University Chemical Safety Data (No longer updated) More details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

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 Oxford University Chemical Safety Data (No longer updated) More details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

      ORL-RAT LD50 1780 mg kg-1, IPR-RAT LD50 624 mg -1, IVN-RAT LD50 > 100 mg -1, IVN-MUS LD50 450 mg -1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      22 Alfa Aesar 41535, A11311
      36 Alfa Aesar 41535, A11311
      GHS07 Biosynth Q-201294
      H302 Alfa Aesar 41535, A11311
      H302; H315; H319; H335 Biosynth Q-201294
      Harmful and irritating. Possible irreversible damage risk Alfa Aesar A11311
      N04BA01 Wikidata Q300989
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-201294
      P264-P270-P301+P312-P330-P501a Alfa Aesar 41535, A11311
      Safety glasses. Oxford University Chemical Safety Data (No longer updated) More details
      TBC SynQuest 4657-1-S9
      Warning Alfa Aesar 41535, A11311
      Warning Biosynth Q-201294
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar A11311
      Xn Abblis Chemicals AB1009504
    • Chemical Class:

      amino acid Microsource [02300205]
      An optically active form of dopa having <stereo>L</stereo>-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease ChEBI CHEBI:15765, CHEBI:57504
    • Compound Source:

      Occurs in seedlings and pods of Vicia faba , in Mucuna pruriens, Sarothamnus scoparius, Stizolobium deeringianum, Stizolobium hassjoo, Aristolochia clematitis and other plants. Zerenex Molecular [ZBioX-0449]
      Vicia faba seedlings, Sarothamnus spp, & other palnts Microsource [02300205]
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 3788
      Antiparkinsonian Zerenex Molecular [ZBioX-0449]
      Dopamine precursor Tocris Bioscience 3788
      Dopamine Receptor MedChem Express HY-N0304
      Dopamine Receptors Tocris Bioscience 3788
      GPCR/G protein MedChem Express HY-N0304
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-N0304
      Immediate precursor of dopamine, produced by tyrosine hydroxylase. Displays antiParkinsonian activity. Tocris Bioscience 3788
      L-DOPA is a natural form of DOPA used in the treatment of Parkinson's disease. MedChem Express http://www.medchemexpress.com/Caftaric-acid.html, HY-N0304
      L-DOPA is a natural form of DOPA used in the treatment of Parkinson's disease. L-DOPA is the precursor of dopamine and product of tyrosine hydroxylase.;Target: Dopamine ReceptorL-DOPA (L-3,4-dihydroxyphenylalanine) is a chemical that is made and used as part of the normal biology of humans, some animals and plants. Some animals and humans make it via biosynthesis from the amino acid L-tyrosine. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine collectively known as catecholamines. L-DOPA can be manufactured and in its pure form is sold as apsychoactive drug with the INN levodopa; trade names include Sinemet, Parcopa, Atamet, Stalevo, Madopar, Prolopa, etc. As a drug it is used in the clinical treatment of Parkinson's disease and dopamine-responsive dystonia.L-DOPA crosses the protective blood-brain barrier, whereas dopamine itself cannot. Thus, L-DOPA is used to increase dopamine concentrations in the treatment of Park MedChem Express HY-N0304
      Non-selective Dopamine Tocris Bioscience 3788

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

Density: 1.5±0.1 g/cm3
Boiling Point: 448.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 74.5±3.0 kJ/mol
Flash Point: 225.0±28.7 °C
Index of Refraction: 1.655
Molar Refractivity: 49.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 5
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: -0.22
ACD/LogD (pH 5.5): -2.68
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.70
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 104 Å2
Polarizability: 19.5±0.5 10-24cm3
Surface Tension: 80.2±3.0 dyne/cm
Molar Volume: 134.3±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) =  -2.24
    Log Kow (Exper. database match) =  -2.39
       Exper. Ref:  Sangster (1993)
    Log Kow (Exper. database match) =  -2.74
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  419.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  295.15  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.56E-010  (Modified Grain method)
    MP  (exp database):  270 dec deg C
    Subcooled liquid VP: 1.26E-007 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):  3.201e+005
       log Kow used: -2.74 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  5000 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  3600 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996)
     Water Sol (Exper. database match) =  5000 mg/L (20 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.935e+005 mg/L
    Wat Sol (Exper. database match) =  5000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  3600.00
       Exper. Ref:  MERCK INDEX (1996)
    Wat Sol (Exper. database match) =  5000.00
       Exper. Ref:  BEILSTEIN

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.30E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.075E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.74  (exp database)
  Log Kaw used:  -16.275  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.535
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1665
   Biowin2 (Non-Linear Model)     :   0.9873
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1904  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0029  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3867
   Biowin6 (MITI Non-Linear Model):   0.2308
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7877
 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):  1.68E-005 Pa (1.26E-007 mm Hg)
  Log Koa (Koawin est  ): 13.535
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.179 
       Octanol/air (Koa) model:  8.41 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.866 
       Mackay model           :  0.935 
       Octanol/air (Koa) model:  0.999 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  96.6037 E-12 cm3/molecule-sec
      Half-Life =     0.111 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.329 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.9 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  160.6
      Log Koc:  2.206 

 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: -2.74 (expkow database)

 Volatilization from Water:
    Henry LC:  1.3E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.324E+014  hours   (2.635E+013 days)
    Half-Life from Model Lake : 6.899E+015  hours   (2.875E+014 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       2.6e-010        2.66         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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