ChemSpider 2D Image | Pyochelin I | C14H16N2O3S2

Pyochelin I

  • Molecular FormulaC14H16N2O3S2
  • Average mass324.418 Da
  • Monoisotopic mass324.060242 Da
  • ChemSpider ID16738332

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

Pyochelin I
(2R,4R)-2-[(4R)-2-(2-Hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-carbonsäure [German] [ACD/IUPAC Name]
(2R,4R)-2-[(4R)-2-(2-Hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid [ACD/IUPAC Name]
4-Thiazolidinecarboxylic acid, 2-[(4R)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolyl]-3-methyl-, (2R,4R)- [ACD/Index Name]
79236-62-7 [RN]
Acide (2R,4R)-2-[(4R)-2-(2-hydroxyphényl)-4,5-dihydro-1,3-thiazol-4-yl]-3-méthyl-1,3-thiazolidine-4-carboxylique [French] [ACD/IUPAC Name]
Pyochelin
(2R,4R)-2-((R)-2-(2-Hydroxyphenyl)-4,5-dihydrothiazol-4-yl)-3-methylthiazolidine-4-carboxylic acid
(4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid
69772-54-9 [RN]

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

488 [DBID]
  • Miscellaneous

    • Chemical Class:

      A pyochelin that has <stereo>R</stereo>-stereochemistry at the thioaminal centre; the diastereoisomer with <stereo>S</stereo>-stereochemistry at this centre is pyochelin II. <ital>Pseudomonas aerugino sa</ital> produces a mixture of pyochelin I (major) and pyochelin II (minor) via condensation of salicylic acid and two molecules of cysteine. The enantiomeric compounds, <ital>enant</ital>-pyochelin I and II, are produced by <ital>Pseudomonas fluorescens</ital>. ChEBI CHEBI:67183
      A pyochelin that has R-stereochemistry at the thioaminal centre; the diastereoisomer with S-stereochemistry at this centre is pyochelin II. Pseudomonas aerugino; sa produces a mixture of pyochelin I ( major) and pyochelin II (minor) via condensation of salicylic acid and two molecules of cysteine. The enantiomeric compounds, enant-pyochelin ; I and II, are produced by Pseudomonas fluorescens. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:67183
      A pyochelin that has R-stereochemistry at the thioaminal centre; the diastereoisomer with S-stereochemistry at this centre is pyochelin II. Pseudomonas aeruginosa produces a mixture of pyochelin I (ma jor) and pyochelin II (minor) via condensation of salicylic acid and two molecules of cysteine. The enantiomeric compounds, enant-pyochelin I and II, are produced by Pseudomonas fluorescens. ChEBI CHEBI:67183

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.6±0.1 g/cm3
Boiling Point: 558.2±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 88.4±3.0 kJ/mol
Flash Point: 291.4±32.9 °C
Index of Refraction: 1.746
Molar Refractivity: 84.4±0.5 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.28
ACD/LogD (pH 5.5): -0.88
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.33
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 124 Å2
Polarizability: 33.5±0.5 10-24cm3
Surface Tension: 66.0±7.0 dyne/cm
Molar Volume: 208.0±7.0 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) =  0.05

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  520.49  (Adapted Stein & Brown method)
    Melting Pt (deg C):  309.94  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.2E-013  (Modified Grain method)
    Subcooled liquid VP: 9.73E-010 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):  259.8
       log Kow used: 0.05 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  391.88 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 :   4.12E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.019E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.05  (KowWin est)
  Log Kaw used:  -14.774  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.824
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5763
   Biowin2 (Non-Linear Model)     :   0.0937
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6484  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5169  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0176
   Biowin6 (MITI Non-Linear Model):   0.0042
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5542
 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):  1.3E-007 Pa (9.73E-010 mm Hg)
  Log Koa (Koawin est  ): 14.824
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  23.1 
       Octanol/air (Koa) model:  164 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 246.0874 E-12 cm3/molecule-sec
      Half-Life =     0.043 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.522 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  7193
      Log Koc:  3.857 

 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: 0.05 (estimated)

 Volatilization from Water:
    Henry LC:  4.12E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  2.56E+013  hours   (1.066E+012 days)
    Half-Life from Model Lake : 2.792E+014  hours   (1.163E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       1.26e-006       1.04         1000       
   Water     45.7            900          1000       
   Soil      54.2            1.8e+003     1000       
   Sediment  0.0887          8.1e+003     0          
     Persistence Time: 983 hr

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