ChemSpider 2D Image | 2,5-S,S'-dicysteinyldopa | C15H21N3O8S2

2,5-S,S'-dicysteinyldopa

  • Molecular FormulaC15H21N3O8S2
  • Average mass435.473 Da
  • Monoisotopic mass435.076996 Da
  • ChemSpider ID164364
  • defined stereocentres - 3 of 3 defined stereocentres


More details:






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

2,5-Bis{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-3-hydroxy-L-tyrosin [German] [ACD/IUPAC Name]
2,5-Bis{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-3-hydroxy-L-tyrosine [ACD/IUPAC Name]
2,5-Bis{[(2R)-2-amino-2-carboxyéthyl]sulfanyl}-3-hydroxy-L-tyrosine [French] [ACD/IUPAC Name]
2,5-S,S'-dicysteinyldopa
L-Tyrosine, 2,5-bis[[(2R)-2-amino-2-carboxyethyl]thio]-3-hydroxy- [ACD/Index Name]
(2R)-2-AMINO-3-({6-[(2S)-2-AMINO-2-CARBOXYETHYL]-4-{[(2R)-2-AMINO-2-CARBOXYETHYL]SULFANYL}-2,3-DIHYDROXYPHENYL}SULFANYL)PROPANOIC ACID
2,5-S,S-dicysteinyl-3,4-dihydroxyphenylalanine
2,5-S,S-Dicysteinyldopa
3-(2,5-S,S-dicysteinyl-3,4-dihydroxyphenyl)alanine
57954-84-4 [RN]
More...
  • Miscellaneous
    • Chemical Class:

      An <stereo>L</stereo>-tyrosine derivative that is <stereo>L</stereo>-DOPA in which the hydrogens at positions 2 and 5 on the phenyl ring are replaced by cysteinyl groups. Found in the urine of patient s with melanoma. ChEBI CHEBI:84298
      An L-tyrosine derivative that is L-DOPA in which the hydrogens at positions 2 and 5 on the phenyl ring are replaced by cysteinyl groups. Found in the urine of patient; s with melanoma. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:84298

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

Density: 1.7±0.1 g/cm3
Boiling Point: 718.2±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 110.2±3.0 kJ/mol
Flash Point: 388.2±32.9 °C
Index of Refraction: 1.747
Molar Refractivity: 103.3±0.4 cm3
#H bond acceptors: 11
#H bond donors: 11
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 2
ACD/LogP: -1.32
ACD/LogD (pH 5.5): -4.74
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -5.01
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 281 Å2
Polarizability: 40.9±0.5 10-24cm3
Surface Tension: 122.4±5.0 dyne/cm
Molar Volume: 254.2±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) =  -5.23

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  744.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  342.64  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.08E-021  (Modified Grain method)
    Subcooled liquid VP: 2.1E-017 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):  1e+006
       log Kow used: -5.23 (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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.55E-037  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.911E-027 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -5.23  (KowWin est)
  Log Kaw used:  -34.730  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  29.500
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.5061
   Biowin2 (Non-Linear Model)     :   0.9888
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4419  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.5169  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0878
   Biowin6 (MITI Non-Linear Model):   0.0026
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.4269
 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):  2.8E-015 Pa (2.1E-017 mm Hg)
  Log Koa (Koawin est  ): 29.500
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.07E+009 
       Octanol/air (Koa) model:  7.76E+016 
   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 = 333.8416 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.068 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   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    :  2.429E+005
      Log Koc:  5.385 

 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: -5.23 (estimated)

 Volatilization from Water:
    Henry LC:  4.55E-037 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.685E+033  hours   (1.119E+032 days)
    Half-Life from Model Lake : 2.929E+034  hours   (1.221E+033 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       2.05e-018       0.769        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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