ChemSpider 2D Image | 23-hydroxyursolic acid | C30H48O4

23-hydroxyursolic acid

  • Molecular FormulaC30H48O4
  • Average mass472.700 Da
  • Monoisotopic mass472.355255 Da
  • ChemSpider ID10208541
  • defined stereocentres - 11 of 11 defined stereocentres


More details:






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

(3β)-3,23-Dihydroxyurs-12-en-28-oic acid [ACD/IUPAC Name]
(3β)-3,23-Dihydroxyurs-12-en-28-säure [German] [ACD/IUPAC Name]
23-hydroxyursolic acid
Acide (3β)-3,23-dihydroxyurs-12-én-28-oïque [French] [ACD/IUPAC Name]
Urs-12-en-28-oic acid, 3,23-dihydroxy-, (3β)- [ACD/Index Name]
(1S,2R,4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
2-deoxyasiatic acid
3β,23-dihydroxyurs-12-en-28-oic acid
94414-19-4 [RN]
CHEMBL523622
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  • Miscellaneous
    • Chemical Class:

      A pentacyclic triterpenoid that is ursolic acid substituted by an additional hydroxy group at position 23. It has been isolated from <ital>Lagerstroemia speciosa</ital> and <ital>Juglans sinensis</ita l>. ChEBI CHEBI:67896
      A pentacyclic triterpenoid that is ursolic acid substituted by an additional hydroxy group at position 23. It has been isolated from Lagerstroemia speciosa and Juglans sinensis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:67896

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

Density: 1.1±0.1 g/cm3
Boiling Point: 592.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.8 mmHg at 25°C
Enthalpy of Vaporization: 101.5±6.0 kJ/mol
Flash Point: 326.4±26.6 °C
Index of Refraction: 1.568
Molar Refractivity: 135.1±0.4 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 7.36
ACD/LogD (pH 5.5): 6.21
ACD/BCF (pH 5.5): 19016.97
ACD/KOC (pH 5.5): 22501.60
ACD/LogD (pH 7.4): 4.41
ACD/BCF (pH 7.4): 300.19
ACD/KOC (pH 7.4): 355.20
Polar Surface Area: 78 Å2
Polarizability: 53.5±0.5 10-24cm3
Surface Tension: 49.2±5.0 dyne/cm
Molar Volume: 413.0±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) =  6.86

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  571.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  246.00  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.22E-015  (Modified Grain method)
    Subcooled liquid VP: 3.04E-013 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):  0.003677
       log Kow used: 6.86 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.4696 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 :   3.53E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.064E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.86  (KowWin est)
  Log Kaw used:  -8.841  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.701
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0070
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7785  (months      )
   Biowin4 (Primary Survey Model) :   3.0430  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4576
   Biowin6 (MITI Non-Linear Model):   0.0170
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7512
 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):  4.05E-011 Pa (3.04E-013 mm Hg)
  Log Koa (Koawin est  ): 15.701
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.4E+004 
       Octanol/air (Koa) model:  1.23E+003 
   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 = 131.4756 E-12 cm3/molecule-sec
      Half-Life =     0.081 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.976 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   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    :  1.75E+004
      Log Koc:  4.243 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.86 (estimated)

 Volatilization from Water:
    Henry LC:  3.53E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.606E+007  hours   (1.503E+006 days)
    Half-Life from Model Lake : 3.934E+008  hours   (1.639E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              93.77  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.00  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       0.0125          1.28         1000       
   Water     1.63            1.44e+003    1000       
   Soil      31.6            2.88e+003    1000       
   Sediment  66.7            1.3e+004     0          
     Persistence Time: 4.58e+003 hr




                    

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