ChemSpider 2D Image | Droxidopa | C9H11NO5

Droxidopa

  • Molecular FormulaC9H11NO5
  • Average mass213.187 Da
  • Monoisotopic mass213.063721 Da
  • ChemSpider ID83927
  • defined stereocentres - 2 of 2 defined stereocentres


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

(βR)-β,3-Dihydroxy-L-tyrosin [German] [ACD/IUPAC Name]
(βR)-β,3-Dihydroxy-L-tyrosine [ACD/IUPAC Name]
(βR)-β,3-Dihydroxy-L-tyrosine [French] [ACD/IUPAC Name]
223-480-5 [EINECS]
24A0V01WKS
3916-18-5 [RN]
6120
J7A92W69L7
L-threo 3,4-Dihydroxyphenylserine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Dops [DBID] [Trade name]
L-DOPS [DBID]
SM-5688 [DBID]
BRN 2852792 [DBID]
SM 5688 [DBID]
ZINC01482049 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-201050
    • Chemical Class:

      A serine derivative that is <stereo>L</stereo>-serine substituted at the <stereo>beta</stereo>-position by a 3,4-dihydroxyphenyl group. A prodrug for noradrenalone, it is used for treatment of neuroge nic orthostatic hypotension ChEBI CHEBI:31524
    • Bio Activity:

      Droxidopa(L-DOPS, SM5688) is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline); capable of crossing the prot ective blood–brain barrier MedChem Express
      Droxidopa(L-DOPS, SM5688) is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline); capable of crossing the protective blood?brain barrier; IC50 value: ; Target: ; The acute administration of droxidopa in PVL and BDL rats caused a significant and maintained increase in arterial pressure and mesenteric arterial resistance, with a significant decrease of mesenteric arterial and portal blood flow, without changing portal pressure and renal blood flow [1]. MedChem Express HY-13458
      Droxidopa(L-DOPS, SM5688) is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline); capable of crossing the protective blood?brain barrier;IC50 value: ;Target: ;The acute administration of droxidopa in PVL and BDL rats caused a significant and maintained increase in arterial pressure and mesenteric arterial resistance, with a significant decrease of mesenteric arterial and portal blood flow, without changing portal pressure and renal blood flow [1]. L-threo-dihydroxyphenyslerine (Droxidopa) is a pro-drug which has a structure similar to noradrenaline, but with a carboxyl group. It has no pressor effects in this form. It can be administered orally, unlike noradrenaline, and after absorption is converted by the enzyme dopa decarboxylase into noradrenaline thus increasing levels of the neurotransmitter which is identical to endogenous noradrenaline [2]. MedChem Express HY-13458
      Others MedChem Express HY-13458

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

Density: 1.6±0.1 g/cm3
Boiling Point: 549.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.3±3.0 kJ/mol
Flash Point: 286.3±30.1 °C
Index of Refraction: 1.692
Molar Refractivity: 50.8±0.3 cm3
#H bond acceptors: 6
#H bond donors: 6
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: -0.95
ACD/LogD (pH 5.5): -3.56
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.58
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 124 Å2
Polarizability: 20.1±0.5 10-24cm3
Surface Tension: 98.2±3.0 dyne/cm
Molar Volume: 132.6±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) =  -2.78

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  451.83  (Adapted Stein & Brown method)
    Melting Pt (deg C):  299.92  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.58E-012  (Modified Grain method)
    Subcooled liquid VP: 5.36E-009 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):  2.877e+005
       log Kow used: -2.78 (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 Alcohols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.77E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.466E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.78  (KowWin est)
  Log Kaw used:  -20.710  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.930
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2629
   Biowin2 (Non-Linear Model)     :   0.9907
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3898  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.1778  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5462
   Biowin6 (MITI Non-Linear Model):   0.4317
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0753
 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):  7.15E-007 Pa (5.36E-009 mm Hg)
  Log Koa (Koawin est  ): 17.930
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.2 
       Octanol/air (Koa) model:  2.09E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.993 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 101.3682 E-12 cm3/molecule-sec
      Half-Life =     0.106 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.266 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.995 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: -2.78 (estimated)

 Volatilization from Water:
    Henry LC:  4.77E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.792E+019  hours   (7.467E+017 days)
    Half-Life from Model Lake : 1.955E+020  hours   (8.146E+018 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       6.33e-013       2.53         1000       
   Water     34.5            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr




                    

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