ChemSpider 2D Image | Obeticholic acid | C26H44O4

Obeticholic acid

  • Molecular FormulaC26H44O4
  • Average mass420.625 Da
  • Monoisotopic mass420.323975 Da
  • ChemSpider ID394730
  • defined stereocentres - 11 of 11 defined stereocentres


More details:






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

(3α,5β,6α,7α,8ξ)-6-Ethyl-3,7-dihydroxycholan-24-oic acid [ACD/IUPAC Name]
(3α,5β,6α,7α,8ξ)-6-Ethyl-3,7-dihydroxycholan-24-säure [German] [ACD/IUPAC Name]
459789-99-2 [RN]
6α-ethyl-chenodeoxycholic acid
9084
Acide (3α,5β,6α,7α,8ξ)-6-éthyl-3,7-dihydroxycholan-24-oïque [French] [ACD/IUPAC Name]
Cholan-24-oic acid, 6-ethyl-3,7-dihydroxy-, (3α,5β,6α,7α,8ξ)- [ACD/Index Name]
Obeticholic acid [Wiki]
(3α,5β,6α,7α)-6-ethyl-3,7-dihydroxy-cholan-24-oic acid
(4R)-4-[(1S,2S,5R,7S,8R,9R,10S,11S,14R,15R)-8-ethyl-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

0462Z4S4OZ [DBID]
INT-747 [DBID]
C15636 [DBID]
INT747 [DBID]
UNII:0462Z4S4OZ [DBID]
UNII-0462Z4S4OZ [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      Farnesoid X receptor TargetMol T1789
    • Chemical Class:

      A dihydroxy-5<stereo>beta</stereo>-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6<stereo>alpha</stereo>-position. A semi-synthetic bile acid which acts a s a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis. ChEBI CHEBI:43602
      A dihydroxy-5beta-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6alpha-position. A semi-synthetic bile acid which acts a; s a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:43602
    • Bio Activity:

      Biochemicals & small molecules/Agonists & activators Hello Bio [HB3731]
      FXR MedChem Express HY-12222
      FXR TargetMol T1789
      INT-747(Obeticholic acid; 6-ECDCA) is a potent and selective FXR agonist(EC50=99 nM) endowed with anticholestatic activity. MedChem Express
      INT-747(Obeticholic acid; 6-ECDCA) is a potent and selective FXR agonist(EC50=99 nM) endowed with anticholestatic activity.; IC50 value: 99 nM(EC50) [1]; Target: FXR agonist; in vitro: The exposure of rat hepatocytes to 1 microM 6-ECDCA caused a 3- to 5-fold induction of small heterodimer partner (Shp) and bile salt export pump (bsep) mRNA and 70 to 80% reduction of cholesterol 7alpha-hydroxylase (cyp7a1), oxysterol 12beta-hydroxylase (cyp8b1), and Na(+)/taurocholate cotransporting peptide (ntcp) [2].; in vivo: In vivo administration of 6-ECDCA protects against cholestasis induced by E(2)17alp ha [2]. MedChem Express HY-12222
      INT-747(Obeticholic acid; 6-ECDCA) is a potent and selective FXR agonist(EC50=99 nM) endowed with anticholestatic activity.;IC50 value: 99 nM(EC50) [1];Target: FXR agonist;In vitro: The exposure of rat hepatocytes to 1 microM 6-ECDCA caused a 3- to 5-fold induction of small heterodimer partner (Shp) and bile salt export pump (bsep) mRNA and 70 to 80% reduction of cholesterol 7alpha-hydroxylase (cyp7a1), oxysterol 12beta-hydroxylase (cyp8b1), and Na(+)/taurocholate cotransporting peptide (ntcp) [2].;In vivo: In vivo administration of 6-ECDCA protects against cholestasis induced by E(2)17alpha [2]. high salt (HS) diet significantly increased systemic blood pressure. In addition, HS diet downregulated tissue DDAH expression while INT-747 protected the loss in DDAH expression and enhanced insulin sensitivity compared to vehicle controls [3]. Rats were gavaged with INT-747 or vehicle during 10 days after bile-duct ligation and then were assessed for changes in gut permeability, BTL, an MedChem Express HY-12222
      Metabolism TargetMol T1789
      Others MedChem Express HY-12222
      Potent and selective FXR agonist Hello Bio [HB3731]
      Potent and selective FXR agonist (EC50= 99nM). Induces SHP in HSCs to suppress TIMP-1 expression. Apoptosis inducer. Protects against liver fibrosis development in rat in vivo. Displays anticholeretic activity in rat in vivo. Promotes preadipocyte differentiation. Regulates adipogenesis and insulin signaling in vivo. Inhibits vascular smooth muscle cell inflammation and migration. Hello Bio [HB3731]
      Receptors & Transporters/Nuclear hormone/Farnesoid X Hello Bio [HB3731]

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

Density: 1.1±0.1 g/cm3
Boiling Point: 562.9±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 97.2±6.0 kJ/mol
Flash Point: 308.3±19.7 °C
Index of Refraction: 1.530
Molar Refractivity: 119.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 5.68
ACD/LogD (pH 5.5): 3.61
ACD/BCF (pH 5.5): 206.75
ACD/KOC (pH 5.5): 927.55
ACD/LogD (pH 7.4): 1.81
ACD/BCF (pH 7.4): 3.30
ACD/KOC (pH 7.4): 14.82
Polar Surface Area: 78 Å2
Polarizability: 47.2±0.5 10-24cm3
Surface Tension: 42.5±3.0 dyne/cm
Molar Volume: 385.4±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) =  5.96

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  528.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  225.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.39E-014  (Modified Grain method)
    Subcooled liquid VP: 7.65E-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):  0.04564
       log Kow used: 5.96 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.0124 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 :   2.48E-011  atm-m3/mole
   Group Method:   3.88E-016  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  6.536E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.96  (KowWin est)
  Log Kaw used:  -8.994  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.954
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5696
   Biowin2 (Non-Linear Model)     :   0.0284
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5299  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5784  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4363
   Biowin6 (MITI Non-Linear Model):   0.0221
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3107
 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):  1.02E-009 Pa (7.65E-012 mm Hg)
  Log Koa (Koawin est  ): 14.954
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.94E+003 
       Octanol/air (Koa) model:  221 
   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 =  56.3080 E-12 cm3/molecule-sec
      Half-Life =     0.190 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.279 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    :  2222
      Log Koc:  3.347 

 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 = 0.750 (BCF = 5.623)
       log Kow used: 5.96 (estimated)

 Volatilization from Water:
    Henry LC:  2.48E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.842E+007  hours   (2.017E+006 days)
    Half-Life from Model Lake : 5.282E+008  hours   (2.201E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              91.98  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    91.21  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       0.0679          4.56         1000       
   Water     4.1             900          1000       
   Soil      38.8            1.8e+003     1000       
   Sediment  57              8.1e+003     0          
     Persistence Time: 2.55e+003 hr




                    

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