ChemSpider 2D Image | dihydrobetulinic acid | C30H50O3

dihydrobetulinic acid

  • Molecular FormulaC30H50O3
  • Average mass458.716 Da
  • Monoisotopic mass458.376007 Da
  • ChemSpider ID58804

  • defined stereocentres - 10 of 10 defined stereocentres

More details:

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

(3β)-3-Hydroxylupan-28-oic acid [ACD/IUPAC Name]
(3β)-3-Hydroxylupan-28-säure [German] [ACD/IUPAC Name]
25488-53-3 [RN]
Acide (3β)-3-hydroxylupan-28-oïque [French] [ACD/IUPAC Name]
dihydrobetulinic acid
Lupan-28-oic acid, 3-hydroxy-, (3β)- [ACD/Index Name]
(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid
(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
20,29-dihydrobetulinic acid
3-Hydroxylupan-28-oic acid, (3β)
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS005861 [DBID]
AIDS-005861 [DBID]
  • Miscellaneous

    • Chemical Class:

      A pentacyclic triterpenoid that is lupane having a 3<stereo>beta</stereo>-hydroxy and 28-carboxy substituents. Isolated from the leaves of <ital>Syzygium claviflorum</ital>, it exhibits anti-HIV and a ntileishmanial activity. ChEBI CHEBI:65485
      A pentacyclic triterpenoid that is lupane having a 3beta-hydroxy and 28-carboxy substituents. Isolated from the leaves of Syzygium claviflorum, it exhibits anti-HIV and a; ntileishmanial activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65485
      A pentacyclic triterpenoid that is lupane having a 3beta-hydroxy and 28-carboxy substituents. Isolated from the leaves of Syzygium claviflorum, it exhibits anti-HIV and antileishmanial activity. ChEBI CHEBI:65485

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

Density: 1.1±0.1 g/cm3
Boiling Point: 547.5±23.0 °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: 299.0±19.1 °C
Index of Refraction: 1.526
Molar Refractivity: 133.7±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 9.18
ACD/LogD (pH 5.5): 7.28
ACD/BCF (pH 5.5): 123362.38
ACD/KOC (pH 5.5): 86956.67
ACD/LogD (pH 7.4): 5.47
ACD/BCF (pH 7.4): 1952.31
ACD/KOC (pH 7.4): 1376.16
Polar Surface Area: 58 Å2
Polarizability: 53.0±0.5 10-24cm3
Surface Tension: 39.4±3.0 dyne/cm
Molar Volume: 435.4±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) =  8.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  519.46  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.69  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.73E-013  (Modified Grain method)
    Subcooled liquid VP: 4.73E-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):  0.00154
       log Kow used: 8.00 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.043504 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 :   9.31E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.462E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.00  (KowWin est)
  Log Kaw used:  -7.420  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.420
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1591
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6494  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9337  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2519
   Biowin6 (MITI Non-Linear Model):   0.0070
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.2018
 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):  6.31E-009 Pa (4.73E-011 mm Hg)
  Log Koa (Koawin est  ): 15.420
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  476 
       Octanol/air (Koa) model:  646 
   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 =  43.0540 E-12 cm3/molecule-sec
      Half-Life =     0.248 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.981 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    :  2.913E+005
      Log Koc:  5.464 

 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 = 1.000 (BCF = 10)
       log Kow used: 8.00 (estimated)

 Volatilization from Water:
    Henry LC:  9.31E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.347E+006  hours   (5.612E+004 days)
    Half-Life from Model Lake : 1.469E+007  hours   (6.122E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              94.02  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.24  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       0.0187          5.96         1000       
   Water     0.719           4.32e+003    1000       
   Soil      42.6            8.64e+003    1000       
   Sediment  56.7            3.89e+004    0          
     Persistence Time: 1.14e+004 hr

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