ChemSpider 2D Image | Mycothiol | C17H30N2O12S

Mycothiol

  • Molecular FormulaC17H30N2O12S
  • Average mass486.491 Da
  • Monoisotopic mass486.151947 Da
  • ChemSpider ID10193006

  • defined stereocentres - 12 of 12 defined stereocentres

More details:

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

(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-Pentahydroxycyclohexyl 2-[(N-acetyl-L-cysteinyl)amino]-2-deoxy-α-D-glucopyranoside [ACD/IUPAC Name]
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-Pentahydroxycyclohexyl-2-[(N-acetyl-L-cysteinyl)amino]-2-desoxy-α-D-glucopyranosid [German] [ACD/IUPAC Name]
(2R)-2-Acetamido-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}tetrahydro-2H-pyran-3-yl]-3-sulfanylpropanamide
192126-76-4 [RN]
2-[(N-Acétyl-L-cystéinyl)amino]-2-désoxy-α-D-glucopyranoside de (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyle [French] [ACD/IUPAC Name]
Mycothiol [Wiki]
α-D-Glucopyranoside, (1α,2α,3α,4β,5α,6β)-2,3,4,5,6-pentahydroxycyclohexyl 2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy- [ACD/Index Name]
(2R)-2-acetamido-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]-3-sulfanylpropanamide
1-D-<i>myo<;/i>-inosityl-2-(<i>N</i&gt;-acetylcysteinyl)amido-2-deoxy-&α;-D-glucopyranoside
1D-1-O-[2-(N-acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-myo-inositol
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  • Miscellaneous

    • Chemical Class:

      A pseudodisaccharide, 1<stereo>D</stereo>-<ital>myo</ital>-inosityl-<stereo>alpha</stereo>-<stereo>D</stereo>-glucopyranoside, in which the hydroxy group at the 2-position of the glucose moiety is rep laced by an (<element>N</element>-acetyl-<stereo>L</stereo>-cysteinyl)amido group. ChEBI CHEBI:16768
      A pseudodisaccharide, 1D-myo-inosityl-alpha-D-glucopyranoside, in which the hydroxy group at the 2-position of the glucose moiety is rep; laced by an (N-acetyl-L-cysteinyl)amido group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16768
      A pseudodisaccharide, 1D-myo-inosityl-alpha-D-glucopyranoside, in which the hydroxy group at the 2-position of the glucose moiety is replaced by an (N-acetyl-L-cysteinyl)amido group. ChEBI CHEBI:16768

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

Density: 1.7±0.1 g/cm3
Boiling Point: 862.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 142.4±6.0 kJ/mol
Flash Point: 475.2±34.3 °C
Index of Refraction: 1.657
Molar Refractivity: 107.6±0.4 cm3
#H bond acceptors: 14
#H bond donors: 10
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: -1.13
ACD/LogD (pH 5.5): -2.30
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.34
ACD/LogD (pH 7.4): -2.31
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.32
Polar Surface Area: 277 Å2
Polarizability: 42.6±0.5 10-24cm3
Surface Tension: 99.8±5.0 dyne/cm
Molar Volume: 292.4±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) =  -5.20

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  853.53  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.2E-027  (Modified Grain method)
    Subcooled liquid VP: 1.13E-023 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: -5.20 (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:
       Thiols(mercaptans)

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.39E-030  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.408E-033 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -5.20  (KowWin est)
  Log Kaw used:  -27.465  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.265
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.5114
   Biowin2 (Non-Linear Model)     :   0.9725
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2781  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.5728  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9956
   Biowin6 (MITI Non-Linear Model):   0.0709
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4885
 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):  1.51E-021 Pa (1.13E-023 mm Hg)
  Log Koa (Koawin est  ): 22.265
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.99E+015 
       Octanol/air (Koa) model:  4.52E+009 
   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 = 212.9753 E-12 cm3/molecule-sec
      Half-Life =     0.050 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.603 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  13.41
      Log Koc:  1.128 

 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: -5.20 (estimated)

 Volatilization from Water:
    Henry LC:  8.39E-030 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.539E+026  hours   (6.413E+024 days)
    Half-Life from Model Lake : 1.679E+027  hours   (6.996E+025 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       7.41e-005       1.21         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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