ChemSpider 2D Image | (2S)-2-[(3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid | C22H36O5

(2S)-2-[(3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid

  • Molecular FormulaC22H36O5
  • Average mass380.518 Da
  • Monoisotopic mass380.256287 Da
  • ChemSpider ID7826644

  • defined stereocentres - 11 of 11 defined stereocentres

More details:

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

(2S)-2-[(3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid [ACD/IUPAC Name]
(2S)-2-[(3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]propansäure [German] [ACD/IUPAC Name]
Acide (2S)-2-[(3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-3,7,12-trihydroxy-10,13-diméthylhexadécahydro-1H-cyclopenta[a]phénanthrén-17-yl]propanoïque [French] [ACD/IUPAC Name]
(2S)-2-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aS)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]propanoic acid
(2S)-2-[(1S,2S,5R,7S,9R,10R,11S,14R,15S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]propanoic acid
(2S)-2-[(1S,2S,5R,7S,9R,10R,11S,14R,15S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]propanoic acid
24-dinor-3α,7α,12α-trihydroxy-5β-cholan-22-oic acid
Bisnorcholic acid
Dinorcholic acid

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

LMST04050005 [DBID]
  • Miscellaneous

    • Chemical Class:

      A bile acid that is 24-dinor-5beta-cholan-22-oic acid bearing three hydroxy substituents at positions 3alpha, 7alpha and 12alpha. ChEBI CHEBI:145219

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

Density: 1.2±0.1 g/cm3
Boiling Point: 565.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 97.5±6.0 kJ/mol
Flash Point: 309.7±26.6 °C
Index of Refraction: 1.568
Molar Refractivity: 102.0±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.72
ACD/LogD (pH 5.5): 0.52
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 17.31
ACD/LogD (pH 7.4): -1.28
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 98 Å2
Polarizability: 40.4±0.5 10-24cm3
Surface Tension: 52.9±3.0 dyne/cm
Molar Volume: 311.8±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) =  2.53

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  521.36  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.92E-014  (Modified Grain method)
    Subcooled liquid VP: 3.8E-012 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):  68.6
       log Kow used: 2.53 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15491 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.93E-013  atm-m3/mole
   Group Method:   1.99E-021  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.131E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.53  (KowWin est)
  Log Kaw used:  -10.922  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.452
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7474
   Biowin2 (Non-Linear Model)     :   0.1365
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7785  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7658  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5681
   Biowin6 (MITI Non-Linear Model):   0.0504
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1764
 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):  5.07E-010 Pa (3.8E-012 mm Hg)
  Log Koa (Koawin est  ): 13.452
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.92E+003 
       Octanol/air (Koa) model:  6.95 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.998 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  58.3744 E-12 cm3/molecule-sec
      Half-Life =     0.183 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.199 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    :  342.2
      Log Koc:  2.534 

 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: 2.53 (estimated)

 Volatilization from Water:
    Henry LC:  2.93E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.898E+009  hours   (1.624E+008 days)
    Half-Life from Model Lake : 4.252E+010  hours   (1.772E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               3.18  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.08  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       0.287           4.4          1000       
   Water     24.1            360          1000       
   Soil      75.4            720          1000       
   Sediment  0.176           3.24e+003    0          
     Persistence Time: 523 hr

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