ChemSpider 2D Image | alvaradoin E | C22H22O9

alvaradoin E

  • Molecular FormulaC22H22O9
  • Average mass430.405 Da
  • Monoisotopic mass430.126373 Da
  • ChemSpider ID20568101

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

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

(5S)-1-O-Acetyl-5-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydro-9-anthracenyl]-α-L-lyxopyranose [German] [ACD/IUPAC Name]
(5S)-1-O-Acetyl-5-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydro-9-anthracenyl]-α-L-lyxopyranose [ACD/IUPAC Name]
(5S)-1-O-Acétyl-5-[(9S)-4,5-dihydroxy-2-méthyl-10-oxo-9,10-dihydro-9-anthracényl]-α-L-lyxopyranose [French] [ACD/IUPAC Name]
alvaradoin E
α-L-Lyxopyranose, 5-C-[(9S)-9,10-dihydro-4,5-dihydroxy-2-methyl-10-oxo-9-anthracenyl]-, 1-acetate, (5S)- [ACD/Index Name]
(10S)-C-(1-O-acetyl)-β-L-lyxopyranosyl-1,8-dihydroxy-3-methylanthracen-9(10H)-one
(5S)-1-O-acetyl-5-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-α-L-lyxopyranose
  • Miscellaneous

    • Chemical Class:

      A <element>C</element>-glycosyl compound that is 1,8-dihydroxy-3-methylanthracen-9(10<element>H</element>)-one substituted by a (1-<element>O</element>-acetyl)-<stereo>alpha</stereo>-<stereo>L</stereo >-lyxopyranosyl moiety at position 10 via a <element>C</element>-glycosidic linkage (the 10<stereo>S</stereo> stereoisomer). It is isolated from the leaves of <ital>Alvaradoa haitiensis</ital> and exh ibits cytotoxicity against human oral epidermoid carcinoma. ChEBI CHEBI:65390
      A C-glycosyl compound that is 1,8-dihydroxy-3-methylanthracen-9(10H)-one substituted by a (1-O-acetyl)-alpha-L-lyxopyranosyl moiety at position 10 via a C-glycosidic linkage (the 10S stereoisomer). It is isolated from the leaves of Alvaradoa haitiensis and exhibits cytotoxicity against human oral epidermoid carcinoma. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65390, CHEBI:65390

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

Density: 1.6±0.1 g/cm3
Boiling Point: 655.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 101.4±3.0 kJ/mol
Flash Point: 229.6±25.0 °C
Index of Refraction: 1.705
Molar Refractivity: 104.9±0.4 cm3
#H bond acceptors: 9
#H bond donors: 5
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 3.74
ACD/LogD (pH 5.5): 3.08
ACD/BCF (pH 5.5): 128.02
ACD/KOC (pH 5.5): 1115.27
ACD/LogD (pH 7.4): 2.60
ACD/BCF (pH 7.4): 42.20
ACD/KOC (pH 7.4): 367.64
Polar Surface Area: 154 Å2
Polarizability: 41.6±0.5 10-24cm3
Surface Tension: 91.2±5.0 dyne/cm
Molar Volume: 269.9±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) =  1.46

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  641.72  (Adapted Stein & Brown method)
    Melting Pt (deg C):  278.80  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.14E-019  (Modified Grain method)
    Subcooled liquid VP: 3.26E-016 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):  33.12
       log Kow used: 1.46 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.9163e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.49E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.789E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.46  (KowWin est)
  Log Kaw used:  -18.846  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.306
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1934
   Biowin2 (Non-Linear Model)     :   0.9683
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8000  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7544  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6419
   Biowin6 (MITI Non-Linear Model):   0.1001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1059
 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):  4.35E-014 Pa (3.26E-016 mm Hg)
  Log Koa (Koawin est  ): 20.306
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.9E+007 
       Octanol/air (Koa) model:  4.97E+007 
   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 = 275.2751 E-12 cm3/molecule-sec
      Half-Life =     0.039 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.976 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    :  34.14
      Log Koc:  1.533 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.079E+000  L/mol-sec
  Kb Half-Life at pH 8:       7.433  days   
  Kb Half-Life at pH 7:      74.333  days   

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = -0.416 (BCF = 0.3835)
       log Kow used: 1.46 (estimated)

 Volatilization from Water:
    Henry LC:  3.49E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.48E+017  hours   (1.45E+016 days)
    Half-Life from Model Lake : 3.797E+018  hours   (1.582E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.96  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.87  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       0.000396        0.933        1000       
   Water     29.7            360          1000       
   Soil      70.3            720          1000       
   Sediment  0.0691          3.24e+003    0          
     Persistence Time: 646 hr

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