ChemSpider 2D Image | Ursodeoxycholic acid | C24H40O4

Ursodeoxycholic acid

  • Molecular FormulaC24H40O4
  • Average mass392.572 Da
  • Monoisotopic mass392.292664 Da
  • ChemSpider ID29131
  • defined stereocentres - 10 of 10 defined stereocentres


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(3a,5b,7b)-3,7-dihydroxy-cholan-24-oic acid
(3a,5b,7b)-3,7-Dihydroxycholan-24-oic Acid
(3a,5b,7b,8x)-3,7-dihydroxycholan-24-oic acid
(3α,5β,7β)-3,7-Dihydroxycholan-24-oic acid [ACD/IUPAC Name]
(3α,5β,7β)-3,7-Dihydroxycholan-24-säure [German] [ACD/IUPAC Name]
(3α,5β,7β,8ξ,20R)-3,7-Dihydroxycholan-24-oic acid [ACD/IUPAC Name]
(3α,5β,7β,8ξ,20R)-3,7-Dihydroxycholan-24-säure [German] [ACD/IUPAC Name]
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentansäure [German]
128-13-2 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 3219888 [DBID]
C07880 [DBID]
CCRIS 5502 [DBID]
CHEBI:9907 [DBID]
D00734 [DBID]
e2 [DBID]
LMST04010033 [DBID]
MLS000028461 [DBID]
NCI60_028904 [DBID]
NSC 657950 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A05AA02 Wikidata Q241374
      P261; P262 Biosynth U-9000
    • Target Organs:

      Biliation inhibitor TargetMol T0700
    • Chemical Class:

      A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstone s. ChEBI CHEBI:9907
    • Therapeutical Effect:

      Cholagogues and Choleretics Sean Ekins
    • Drug Status:

      approved BIONET-Key Organics KS-5243
    • Bio Activity:

      Bile salt export pump TargetMol T0700
      Metabolism TargetMol T0700
      Others MedChem Express HY-13771
      Ursodiol reduces cholesterol absorption and is used to dissolve gallstones. MedChem Express
      Ursodiol reduces cholesterol absorption and is used to dissolve gallstones.; Target: Others; Ursodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. MedChem Express HY-13771
      Ursodiol reduces cholesterol absorption and is used to dissolve gallstones.;Target: Ursodiol, also known as ursodeoxycholic acid and the abbreviation UDCA, is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery. The drug is very expensive, however, and if the patient stops taking it, the gallstones tend to recur if the condition that gave rise to their formation does not change. For these reasons, it has not supplanted surgical treatment by cholecystectomy.Ursodeoxycholic acid is currently the only established drug for the treatment of chronic cholestatic liver diseases. It has cytoprotective, anti-apoptotic, membrane stabilizing, anti-oxidative and immunomodulatory effects. Prolonged administration of ursodeoxycholic acid in patients with primary biliary cirrhosis (PBC) is associated with survival benefi MedChem Express HY-13771

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

Density: 1.1±0.1 g/cm3
Boiling Point: 547.1±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.3 mmHg at 25°C
Enthalpy of Vaporization: 95.0±6.0 kJ/mol
Flash Point: 298.8±19.7 °C
Index of Refraction: 1.543
Molar Refractivity: 109.7±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.66
ACD/LogD (pH 5.5): 2.94
ACD/BCF (pH 5.5): 64.54
ACD/KOC (pH 5.5): 403.10
ACD/LogD (pH 7.4): 1.14
ACD/BCF (pH 7.4): 1.03
ACD/KOC (pH 7.4): 6.44
Polar Surface Area: 78 Å2
Polarizability: 43.5±0.5 10-24cm3
Surface Tension: 46.0±3.0 dyne/cm
Molar Volume: 347.9±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) =  5.06
    Log Kow (Exper. database match) =  3.00
       Exper. Ref:  Roda,A et al. (1990)
    Log Kow (Exper. database match) =  4.15
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  508.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  216.44  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.85E-012  (Modified Grain method)
    MP  (exp database):  119 deg C
    Subcooled liquid VP: 3.29E-011 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):  2.414
       log Kow used: 4.15 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  20 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  89.9 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  53.216 mg/L
    Wat Sol (Exper. database match) =  20.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  89.90
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.41E-011  atm-m3/mole
   Group Method:   1.62E-016  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.238E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.15  (exp database)
  Log Kaw used:  -9.239  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.389
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5829
   Biowin2 (Non-Linear Model)     :   0.0417
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5919  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6189  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4772
   Biowin6 (MITI Non-Linear Model):   0.0446
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4166
 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):  4.39E-009 Pa (3.29E-011 mm Hg)
  Log Koa (Koawin est  ): 13.389
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  684 
       Octanol/air (Koa) model:  6.01 
   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 =  52.7948 E-12 cm3/molecule-sec
      Half-Life =     0.203 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.431 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    :  681.2
      Log Koc:  2.833 

 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: 4.15 (expkow database)

 Volatilization from Water:
    Henry LC:  1.41E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.227E+007  hours   (3.428E+006 days)
    Half-Life from Model Lake : 8.975E+008  hours   (3.74E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              37.35  percent
    Total biodegradation:        0.38  percent
    Total sludge adsorption:    36.97  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       0.0988          4.86         1000       
   Water     13.7            900          1000       
   Soil      81.6            1.8e+003     1000       
   Sediment  4.6             8.1e+003     0          
     Persistence Time: 1.4e+003 hr




                    

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